Explore every episode of the podcast Run the Numbers

In this episode of Run the Numbers, CJ sits down with Todd McElhatton, CFO of Zuora, for a deep cut on pricing, packaging, and value in the age of AI. They dig into how companies are figuring out whether to charge for AI at all, why token-based budgets are starting to sit alongside headcount budgets, and why AI may be increasing — not decreasing — the value of deep expertise.

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SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics.

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

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LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: linkedin.com/in/todd-mcelhatton-2140761

Company: www.zuora.com

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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TIMESTAMPS:

0:00 Intro

1:15 Meet Todd

2:24 Debating Price

7:33 Is Software "Going Headless"?

9:18 Is AI Increasing the Value of Experts

9:58 Hiring Specialists vs. Generalists

16:49 Rethinking the Budget Envelope

26:56 Time to Value

31:20 Forward-Deployed Engineers

35:20 Parallels Between On-Prem-to-Cloud

36:10 Rethinking Strategy

37:07 Avoiding the Sunk Cost Trap

38:58 The Art of Pivoting

40:12 VMware

41:31 Experimenting With AI

42:33 What Private Boards Bring

43:13 Short-Term Pain

43:45 One-Way Doors vs. Two-Way Doors

44:57Long-Ass Lightning Round

45:04 Biggest Career Mistake

45:36 Advice45:56 Finance Tech Stack

46:43 The Craziest Thing Expense

#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #Zuora #GoingPrivate

CJ sits down with Lauren Dillard, CFO of LiveRamp, whose path to the CFO seat ran through investor relations, communications, and even a year as interim CMO. They dig into why storytelling and influence matter as much as technical finance chops, how LiveRamp tore down and rebuilt its entire commercial model — collapsing 25+ usage metrics into 5 and inventing the "token" along the way.

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SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

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LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/lauren-russi-dillard-25502424/

Company: https://www.liveramp.com

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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TIMESTAMPS:

0:00 Cold Open

1:18 Intro

1:29 Meet Lauren Dillard

4:48 Lauren's Path to CFO

5:06 The "Wrong" Career Move

7:48 Why Storytelling Matters

9:41 Turning the Answer Into Action

10:33 People Plus AI

14:50 Pricing Is a Strategy Exercise

16:43 Rebuilding a Commercial Model

22:29 Simplifying Quote-to-Cash

23:29 Where the "Token" Came From

28:48 Selling a New Pricing Model

29:27 Balancing New Logos

30:17 Upmarket or Downmarket?

34:17 Where Finance and HR Disagree

36:07 The Biggest Mistake

38:23 Will It Make the Boat Go Faster?

42:27 Lessons from the NBA

44:25 Lauren's Biggest Misstep

46:27 Finance Tech Stack

47:42 Craziest Expense

#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #MasterworksArt #ContextEngineering

Nscale just filed its S-1 to go public on the NYSE — and it might be the wildest IPO filing of the year. This UK-based "NeoCloud" is only 2 years old, is gross margin negative, started life as a crypto miner, and has somehow locked up over $100 billion in contracted value from Anthropic and Microsoft. CJ breaks down the entire S-1 line by line: what a NeoCloud actually is, how Nscale's "power to token" strategy works, why Nvidia shows up as its supplier, investor, guarantor, AND customer, and whether this is a durable business or a well-timed arbitrage on the AI compute shortage.

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SPONSORS:

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

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LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Company: https://www.nscale.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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TIMESTAMPS:

0:00 Cold Open

0:53 Intro: Nscale Files to Go Public

2:40 WTF Is a NeoCloud?

4:11 The 5 Layers of the AI Stack

5:55 Landlord vs. Hotel: Nscale's Two Businesses

7:21 How Take-or-Pay Contracts Work

8:28 Sponsor Break

11:43 Breaking Down the Financials

15:37 What's a Contract Actually Worth?

18:45 Is This Just Nvidia Vendor Financing?

20:58 Sponsor Break

22:54 Medium-Term Arbitrage or Durable Company?

24:30 5 Potential Red Flags

27:08 How Does the CEO Get Paid?

28:04 Who's on the Board?

28:26 Is This the CoreWeave of the UK?

31:09 Miscellaneous Filing Oddities

33:31 Final Take

#Nscale #IPO #NeoCloud #S1Breakdown #AIInfrastructure

In today’s Run the Numbers, CJ sits down with Blake Saunders, founder and managing director at Core Advisors (an investment bank focused on media) and founder of The Joint, to go deep on how media companies actually make money — and how that's changing fast.

If you're anywhere near advertising, media, or content monetization, this one's a masterclass.

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SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

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LINKS:

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: linkedin.com/in/blakesaunders

Company: https://coreadvs.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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TIMESTAMPS:

0:00 Cold Open and Intro

1:17 Welcome Back: Meet Blake Saunders

3:11 What Does "Media" Even Mean Today?

3:24 AI and LLMs

6:13 How Media Companies Make Money

7:32 Subscriptions vs. Ads vs. Events

8:54 Why Events Are the Riskiest Ad Dollar

9:48 B2B vs. B2C

14:25 Why Advertising Gets Such a Bad Rap

17:58 The Hulu Paradox

20:50 Built to Hold vs. Built to Sell

27:10 Content Decay and the Monetization Mismatch

29:08 Are IP Libraries Becoming Valuable

34:39 How Big-Name Podcast Deals Get Structured

37:50 Bundling, Unbundling, and Subscription Fatigue

39:08 The Bending Spoons Trade

40:20 Inside a Private Equity Value Creation Plan

41:56 The Content-to-Commerce Playbook

44:50 How Narrative-Driven Is Media M&A?

46:49 7 Moments a Deal Feels Dead

49:00 Farewell

CJ sits down with multi-time CFO Rick Smith, founder of Bonfire Advisory and author of Six Months to the Sale, to break down what actually happens when you sell a company. They cover why buyers value some businesses on ARR and others on EBITDA (and why being slightly profitable can hurt you), how to negotiate banker fees, what buyers find when they dig into your balance sheet, and why every cap table Rick inherits is wrong.

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SPONSORS:

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: linkedin.com/in/rick-smith-906939

Company: https://www.linkedin.com/company/bonfire-advisory

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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TIMESTAMPS:

1:21 Meet Rick Smith and "Six Months to the Sale"
2:44 Why Teach M&A Through Fiction
4:26 CEO/CFO Tension
7:08 Botching the Announcement
8:15 How Staff Really React
9:18 When Personal Life Collides With a Deal
13:50 ARR vs. EBITDA
17:58 What to Optimize Before a Sale
18:50 Churn and Contract Renewal
20:43 Strategics vs. PE
27:46 Investment Banker Fee Structures
29:09 What's Negotiable
29:56 The Realtor Problem
34:53 Big 4 vs. Regional Firms for Audit and QoE
35:47 Negotiating Accounting Fees
37:47 Deferred Revenue
41:23 Warrants, Options, and Carta Cleanup
44:02 QSBS: What CFOs Need to Know
45:28 Quality of Earnings: Who Pays and Why
47:44 What a QoE Actually Digs Into
51:22 Why Deal Momentum Is So Hard to Stop
53:47 The Waterfall
58:19 Who Keeps Their Job
61:31 Why Selling CFOs Feel Intimidated
62:56 Prospect Theory
65:28 Where to Find the Book

#RunTheNumbersPodcast #MandA #CFOLife #SellingACompany #QualityOfEarnings

CJ Gustafson sits down with Nigel Glenday, CFO and COO of Masterworks, to talk about how AI is actually changing day-to-day finance work. They cover why context matters more than model choice, how Nigel runs a dozen Claude Code terminal sessions at once, and how his team solved a 300,000 K-1 problem with Python instead of a $300K tool. Plus: a detour into the 2026 art market and what securitizing fine art teaches you about scarcity and pricing power.

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SPONSORS:

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: linkedin.com/in/nglenday

Company: https://www.masterworks.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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RELATED EPISODES:

Nigel's Previous Episode: ⁠⁠⁠https://www.youtube.com/watch?v=zfmqwIzM0P4&t=9s⁠⁠⁠

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TIMESTAMPS:

2:04 The Dinner Story: AI as Leverage

7:27 AI and the Value of Human-Curated Creativity

12:16 Why Context Beats Intelligence

14:11 What "Context" Actually Means for AI

16:50 Building a Knowledge Map

18:50 Why CFOs Are Uniquely Positioned to Encode Context

21:36 Making Data Cheap to Access

28:55 Claude Code Over the Web App

30:49 Building "The A-Team"

35:24 Solving 300,000 K-1s with AI and Python

42:26 Asking Better Questions Segment

42:50 Adopting Campfire

44:20 When Human Writing Beats AI

#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #MasterworksArt #ContextEngineering

How did Oura turn a tiny piece of wearable hardware into a $1.4 billion business? CJ breaks down the numbers behind Oura’s IPO filing and the surprisingly powerful business model hiding behind the ring.

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SPONSORS:

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

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LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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TIMESTAMPS:

0:00 Oura Files S1

2:24 Key Revenue Stats

3:35 Revenue Per Ring

4:14 Gross Margin Breakdown

5:31 The Weird $924M "Net Loss"

6:11 Adjusted EBITDA and Cash Position

7:20 Headcount and Bankers

11:01 What Oura Actually Does

13:46 Go-to-Market Channels

15:57 Why Oura Rejects the "Fitness Tracker" Label

16:49 Who's Actually Buying It

21:26 Global Penetration Is Still Low

21:54 The $84M Battery Problem

22:56 Aggressive Growth Spend

24:16 Samsung's Patent Complaint

25:00 The Sleep Accuracy Class Action

25:17 Former CEO Lawsuit

25:52 Customer Concentration Risk

26:31 Supply Chain and Tariff Exposure

27:07 Clean Governance, No Material Weaknesses

27:20 The Cap Table

27:44 Oura's Massive Stock Buybacks

29:29 The RSU Vesting Mechanics

30:34 Tax Withholding on Settlement

31:07 Valuation: $16B at 11x Revenue

31:34 Who Do You Comp Oura To

32:34 Miscellaneous Filing Details

33:14 Final Take

In this episode of Run the Numbers, CJ sits down with Matt Hedberg, a sell-side equity analyst at RBC who has covered software for more than 20 years. They break down how AI compares to the cloud transition, why traditional software moats are changing, what separates management teams that will actually capitalize on AI, and why cash, customer relationships, data, and technical leadership matter more than ever.

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SPONSORS:

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

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LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/matt-hedberg/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RBC Capital Markets: This content is based on information available at the time it was recorded, and is for informational purposes only. It is not an offer to buy or sell, or a solicitation, and no recommendations are implied. It is outside the scope of this communication, to consider whether it is suitable for you, and your financial objectives. For Required Conflicts Disclosures, see: https://www.rbccm.com/GLDisclosure/PublicWeb/DisclosureLookup.aspx?entityId=1. For Disclaimer, see: https:/www.rbccm.com/en/policies-disclaimers.page.

In this episode of Run the Numbers, CJ sits down with leadership coach and former Akamai executive Andy Ellis. They break down why being indispensable can actually hurt your career, why managers shouldn’t automatically replace someone who leaves, how hero-villain thinking leads to bad decisions, and what great delegation and leadership actually look like.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/csoandy/

Company: https://www.csoandy.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Jero and Villain Stories

1:43 Welcome to Run the Numbers

2:53 Andy's Book: 1% Leadership

7:44 Rule 1: Don't Replace People Immediately

14:04 Rule 2: Don't Become Indispensable

16:02 How Andy Learned to Speak Finance

22:35 Rule 3: Don't Tell Yourself Hero/Villain Stories

26:59 The 5K Race Mindset Shift

31:01 Rule 4: Don't Overspecify Delegation

35:59 Rule 5: Don't Obsess Over Your Strengths

38:23 The Six Leadership Disciplines

43:45 The Vendor Rebuff Email

47:45 Why Leaders Avoid Saying No

50:28 Story: The Guinness Bartender Promotion

53:52 When Metrics Get Gamed

54:11 Asking Better Questions Segment

59:07 Where to Get the Book

In this episode of Run the Numbers, CJ sits down with Jay Ritter. They break down what Apple, Nvidia, the dot-com boom, and today’s AI giants can teach us about IPOs, why companies leave money on the table on day one, why firms stay private longer, and what the data actually says about long-term IPO performance.

—

SPONSORS:

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/jay-ritter-1323861/

Company: https://www.ufl.edu/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

3:10 Meet Jay Ritter, Mr. IPO

4:02 The Original 1983 Question

5:08 PCs, Internet, and AI Compared

9:36 Network Effects

14:46 Sitzfleisch: Outlasting the Field

16:10 Where Have All the IPOs Gone

23:29 IPOs as Relationship-Building

26:31 Why Investors Tolerate Founder Control

29:16 Dual-Class Stock's Origins

30:21 How Jay's Thinking Evolved

31:36 Why Boards Don't Get Angry

34:39 Banks' Real Client: Institutions

37:08 Book Building

38:56 Why Direct Listings Haven't Taken Over

39:57 What Goldman Is Really Selling

41:57 Sentiment vs. Long-Term Performance

43:13 Does Staying Private Help Society

49:35 Asking Better Questions with EY

52:12 Are Markets Efficient

CJ sits down with Rebecca Schwartz of Tabs, Fred Havemeyer of Fleet AI, and Rahul Rekhi of Rogo for a live conversation about what it actually takes to build an AI-native company.

—

SPONSORS:

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

https://www.tabs.com/

https://fleetai.com/

https://www.rogo.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

1:16 Welcome to Run the Numbers

3:17 Meet the Panel: Rebecca, Fred, Rahul

9:52 How Rogo Found PMF

13:47 How Tabs Found PMF

14:51 Growth Rates: Headcount and Revenue

16:23 The Real Hiring Constraint

17:21 What "Forward Deployed" Actually Means

18:53 What's Blocking AI Adoption Now

20:19 How Sales Hiring Has Changed

24:34 How Go-to-Market Has Changed

25:28 Pricing Models: Then vs. Now

28:18 Tabs' Pricing Evolution

29:20 What the Finance Team Looks Like

31:00 How Far You Can Push Outsourced Accounting

32:43 Managing AI Gross Margins

35:07 The North Star Metric for AI Companies

37:02 Token Spend vs. Per-Seat Pricing

39:34 Asking Better Questions: What Counts as ARR

41:38 Biggest Bug in Cash to Collections

43:05 Closing Advice for Founders

In this episode of Run the Numbers, CJ sits down with Wisam Hirzalla, Head of Product at Stripe Billing, to trace the full journey of a dollar—from product packaging and pricing through quoting, contracts, billing, tax, collections, and revenue recognition.

—

SPONSORS:

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/wisam-hirzalla-9b20a91/

Company: https://stripe.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 What Drives Billing Downstream

1:41 Welcome to Run the Numbers

2:37 Wisam's Path to "Queen of Billing"

4:55 What Head of Billing at Stripe Entails

5:45 Defining Quote-to-Cash

7:50 Layer 1: Pricing and Packaging Mistakes

14:46 Pricing Models Rising Because of AI

18:11 Layer 2: Inside a Quote

19:27 Why Enterprise Deals Get So Messy

24:38 Layer 3: Contracting

27:21 Layer 4: Billing

30:15 Why Usage-Based Billing Is So Complex

34:51 Tokens as a Pricing Unit

36:57 Billing's Move Out of the ERP

39:53 Layer 5: Provisioning and Entitlements

43:36 Layer 6: Tax

44:27 Layer 7: Getting Paid

48:18 Layer 8: RevRec

50:52 When Billing Stopped Being Back Office

51:47 Asking Better Questions Segment

52:28 Will AI Replace Finance Jobs

Front CFO & COO Meredith Finn joins CJ to explain why finance leaders are taking on more of the operator’s job. They break down the CFO-COO dual mandate, how Front funds new bets inside a mature SaaS business, why AI requires more coordination than simply handing everyone new tools, and how finance teams should think about the growing cost of AI.

—

SPONSORS:

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/meredithfinn1/

Company: https://front.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Adam Swiecicki - CFO of Rippling

https://youtu.be/JyGJVpmZNac

Aurélien Nolf - CFO of Navan

https://youtu.be/siwzJSRXAvY

—

TIMESTAMPS:

0:00 The CFO/COO Dual Mandate

1:45 Welcome to Run the Numbers

2:52 Front's In-House Podcast Studio

3:41 Meredith's Investment Thesis on Front

7:21 The "Portfolio Career" Analogy

8:35 What She Had to Unlearn as an Operator

13:13 Books on Strategy vs. Execution

16:17 When a CFO Should Also Be COO

18:27 What the COO Hat Actually Covers

20:20 Where the Two Roles Conflict

25:42 Budgeting for AI Token Costs

29:16 Using Internal Usage as a Benchmark

35:40 Funding a Series A Bet Inside a Series D Company

38:04 Sizing Bets: Core, Adjacent, Moonshot

40:04 The Secret to Re-Accelerating Growth

41:46 Going Deeper, Not Wider

43:18 What the Pricing Overhaul Taught Her

47:30 Why Customer P&L Matters

50:11 Lightning Round Begins

51:32 Advice to Her Younger Self

52:33 Front's Finance Tool Stack

53:21 Craziest Expense Ever

#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #SaaSGrowth

In this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology. Claire also shares how she builds teams around her weaknesses, what small businesses actually want from AI, and why she views diversity as a business performance decision.

—

SPONSORS:

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/claire-bramley-133b7174/

Company: https://www.xero.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

3:00 Xero and CJ's History With It

4:12 Xero's Size and Scale Today

5:10 The Expanding CFO Role

7:06 Hiring Experts You're Not

8:47 Imposter Syndrome

11:00 Getting Better at Asking Questions

15:04 Asking the "Stupid Question"

16:21 Finance as the Corporate Junk Drawer

17:48 The Trial Period Idea

18:24 Tripwires: Leading Indicators for CFOs

25:35 AI Hype vs. Main Street Reality

26:44 What Small Business Owners Actually Want

28:45 What Big Corps Underestimate

31:10 Trust as a Competitive Moat

33:45 Why the Line Is Thinner for Small Biz

35:12 AI Inside Claire's Finance Team

37:23 AI for Investor Relations

39:28 Diversity as Capital Allocation

42:07 A Decision Diversity Changed

44:45 Lightning Round Begins

46:06 Advice to Her Younger Self

48:49 Craziest Expense Ever

#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #WomenInFinance

On this episode of Run the Numbers, CJ and Ben trace corporate private jets from Sam Walton’s scrappy two-seater to Alex Karp’s $17 million jet bill. They break down when flying private actually makes business sense, how jets hit the balance sheet, the tax and accounting implications, what companies disclose to investors, and when executive travel crosses the line from productivity tool to corporate excess.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Jersey Mike’s IPO: The $4.2B Sandwich Machine

https://youtu.be/ZL6AbqHI-0g

—

TIMESTAMPS:

0:00 Fly Like a G6

0:29 $17M on jets: Alex Karp guess

1:16 Sam Walton starts it all

2:49 The yellow legal pads

4:37 Walmart Aviation founded (1968)

5:14 Piston to Bombardier jets

6:51 Walmart's modern jet fleet

8:13 Where it hides in SEC filings

9:25 SEC Reg S-K Item 402

13:37 Gulfport Energy scandal

14:42 Tyco: Kozlowski & Schwartz

16:57 When jets are actually useful

17:55 P&L vs. balance sheet treatment

18:40 PP&E and depreciation basics

19:04 Off-balance-sheet leases

19:28 The chartering loophole

19:54 "Uber Jet" fractional ownership

23:14 How activists hunt jet spend

23:36 Flight registries & tail numbers

24:13 Jack Sweeney vs. Elon Musk

25:00 What top companies spend

25:18 Walmart's fleet is #1

26:17 Charter vs. lease vs. own

29:02 Should we care? 3 angles

30:06 Angle 2: opportunity cost

30:59 Angle 3: company size

31:42 General Electric's shadow jet

32:50 Back to Alex Karp

34:02 Credits

#RunTheNumbersPodcast #PrivateJets #CorporateFinance #ExecutivePerks #CFOLife

On this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster. They cover building AI fluency, combining FP&A with BI, monetizing vertical software, integrating acquisitions, and the leadership lessons Richard carried from entrepreneurship.

—

SPONSORS:

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/richardharem/

Company: https://rapidsos.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

3:10 What RapidSOS does

4:59 CJ’s own car accident

5:33 What's broken about 911

6:50 Who's the actual customer

7:46 How RapidSOS monetizes

10:13 Sponsors — Pulley | Rillet | Maximor

13:27 Too much data, too much noise

16:35 Data pollution and trust

18:24 The data stack early on

19:25 Should BI have come sooner?

20:45 The framework: questions to decisions

22:43 Building a data culture

23:58 Sponsors — Brex | Anrok | RightRev

26:51 Bottoms-up vs. top-down AI

28:42 Inspiration, not training

32:24 The three-phase AI progression

33:31 Founding an AV company at 8

35:37 Giving people room to grow

38:12 Depending on heroes

39:55 Working under founder personalities

41:23 Do startups undervalue what they sell

42:48 A price hike, zero churn

43:24 Signs you're underpricing

44:57 Lightning round

45:03 Screwed up: refreshed data before a demo

47:15 Advice to younger self

47:41 Finance software stack

48:37 Craziest expense: personal gas

49:29 Credits

On this episode of Run the Numbers, CJ sits down with Plaid CFO Seun Sodipo. Seun explains how her team is using AI to improve speed, accuracy, and ambition; why finance leaders need both bottom-up experimentation and top-down direction; and how she approaches planning, network effects, and building a durable company.

—

SPONSORS:

RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/seun-sodipo-1498b580/

Company: https://plaid.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

2:12 What Plaid does

3:53 How Plaid makes money

7:04 Eight months in, not new anymore

8:57 Sponsors — RightRev | Pulley | Rillet

11:48 Career path: Stripe, Glossier, Plaid

14:32 Evaluating durability from the outside

15:36 Rising expectations and AI

17:23 Top-down vs. bottoms-up AI adoption

20:06 Sponsors — Maximor | Brex | Anrok

23:20 Coolest AI use case: sorting physical mail

25:21 How her questions have changed

27:11 AI should make you think deeper

27:51 Finance AI Day explained

31:23 A four-month journey to usable tools

32:22 How AI changed her leadership style

33:19 Skills that matter more now

36:22 The Objective, Strategy, Tactics framework

39:56 What planning reveals about an org

41:36 Sequential vs. parallel planning

45:38 Measuring the value of a network

47:33 What people underestimate about Plaid

48:56 Lightning round

48:56 Screwed up: the reversed page order

49:39 Advice to younger self

50:32 Finance software stack

51:43 Craziest expense: the photo shoots

52:20 Credits

On this special episode of Run the Numbers, CJ Gustafson revisits standout moments from past conversations with Alex Immerman, Curt Sigfstead, Daniel Kang, Adam Ante, and David Laptor. Together, their advice reveals how great CFOs earn trust, challenge founders, speak up when the data says something is wrong, and become true strategic partners without relying on the power of the purse strings.

—

SPONSORS:

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

3:27 Alex Immerman's favorite CFO interview question

4:54 What a weak answer looks like

5:26 When the hard calls actually matter

6:37 Walt and Roy Disney

7:36 Liked even when making unpopular calls

8:43 Sponsors — Anrok | RightRev | Pulley

11:35 Curt from Clio: ego in the bottom drawer

13:52 CFO as supporting cast

15:10 Backbone vs. ego: when to use each

16:23 Daniel Kang: don't use the purse strings as power

17:36 Earn the seat, don't demand it

18:52 Money is one arrow, not the whole quiver

20:39 Sponsors — Rillet | Maximor | Brex

23:54 Adam Ante: finance people pigeonhole themselves

26:46 The CFO can sit in any meeting

27:30 First 90 days: listen before suggesting

28:46 David Laptor: listen, observe, think, speak

30:50 Build a culture where speaking up is welcomed

31:51 Curt from Clio: don't come in as a know-it-all

33:08 Earn trust through curiosity

33:46 Beware of all-green dashboards

35:28 What would CJ say to Ballmer?

37:14 Parting thoughts from Ben

38:00 Credits

On this episode of Run the Numbers, CJ sits down with Datadog SVP of FP&A AJ Ljubich to break down the four stages of a world-class finance team.

—

SPONSORS:

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/aj-ljubich-cfa-727ab912/

Company: https://www.datadoghq.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

2:42 FP&A as a product team

4:53 The five pillars of AJ's team

6:39 How far FP&A has come

7:33 How do you know you're doing a good job?

10:20 FP&A as the dashboard, not the engine

10:20 Sponsors — Brex | Anrok | RightRev

13:18 The four-stage FP&A maturity model

16:00 Can you reach all four stages at Series B?

16:45 Why AJ holds weekly forecast meetings

18:24 How often to actually change the forecast

21:42 Sponsors — Pulley | Rillet | Maximor

24:49 Single source of truth: still on the vision board

26:12 AI and the self-serve data risk

26:21 CAC payback over LTV to CAC

29:39 Inside sales vs. enterprise payback comparison

31:47 Finance as the yes, but people

34:02 FP&A vs. IR: which is harder?

36:14 How IR makes you a better FP&A leader

37:19 Is the IR profile shifting?

42:01 IPOs are branding events, not finish lines

43:27 The Datadog IPO during the WeWork meltdown

45:15 Career philosophy: do great work where you are

49:52 Datadog didn't have a role for AJ when he started

52:16 Lightning round

52:24 Screwed up: forgot the currency guy

54:37 Finance software stack

56:16 Advice to younger self

57:13 Credits

On this episode of Run the Numbers, CJ sits down with Dave McClure and Aman Verjee of Practical VC to talk about the evolution of startup investing — from the PayPal mafia and Founders Fund era to 500 Startups, YC-style scale, and today’s secondary market.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guests:https://www.linkedin.com/in/davemcclure/https://www.linkedin.com/in/aman-verjee/

Company:https://practicalvc.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

3:00 Writing as a distribution strategy

5:17 How Dave's blog led to Founders Fund

7:24 Aman: writing at PayPal and law school

9:29 PayPal: the red pen of David Sacks

11:44 Sponsors — Rillet | Maximor | Brex

14:59 500 Startups: the original thesis

16:22 The volume strategy: more shots on goal

18:44 Twilio, Lyft, Sendgrid, Credit Karma

20:15 60x returns: right place, right time

23:07 Sponsors — Anrok | RightRev | Pulley

25:58 Accelerator ecosystem evolution

28:42 500 vs. YC: scale as a weapon

32:52 Globalizing the accelerator model

35:04 Seed to secondaries: how it happened

37:00 Scratching their own itch for liquidity

38:10 The secondary market explained

40:50 Types of secondaries

43:29 Why would a VC sell a winner?

46:07 Managing DPI as a late-stage manager

47:02 The five horse framework

49:15 Skipping the J curve

51:44 Imperfect information as a feature

55:22 Landmines: fraud, mismarked valuations

57:00 VCs lie about valuations three ways

57:58 Forward contracts and counterparty risk

1:00:29 Credits

On this episode of Run the Numbers, CJ breaks down Cumberland Farms’ IPO filing and the surprising business behind it.

—

SPONSORS:

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

2:57 Key metrics

4:28 Europe now out-earns America

5:01 $5.8B debt at 8x leverage

6:20 TLDR: snacks, gas, borrowed money

7:58 Fuel vs. inside: the gross profit photo finish

8:58 COCO, CONCO, and OTHER explained

10:57 Sponsors — Maximor | Brex | Anrok

14:02 Why scale matters: four reasons

16:02 The US convenience store market

17:42 EVs: long the birth rate

18:05 Back to the debt

19:10 The sale leaseback

20:24 Sponsors — RightRev | Pulley | Rillet

23:26 Does the deleveraging math work?

24:27 The growth thesis

25:06 600–700 stores become Cumberland Farms

26:16 The chicken fryer ROI

27:00 Coffee and loyalty: 6M members in 13 months

28:15 Red flag 1: five-for-five COSO failures

28:41 Red flag 2: entire C-suite is new

29:04 Red flag 3: lending to their own parent

29:42 Red flag 4: Big Tobacco funds loyalty

29:57 Red flag 5: foreign issuer, Cayman charter

30:10 Red flag 6: one supplier is 31% of costs

30:32 Red flag 7: balance sheet is stale

30:45 Cap table: TDR Capital and the Issa brothers

31:55 Casey's vs. ARCO

33:47 Goldman got bumped

34:08 Massachusetts banned the pump clip until 2015

34:57 No health insurance disclosure for 16K US workers

35:30 Robert Swan (ex-Intel CEO) is on the board

36:08 Credits

In this episode of Run the Numbers, CJ sits down with Rogo president Rahul Rekhi to unpack what AI actually changes in investment banking and finance. They dig into token economics, why adoption without ROI is a trap, how vertical AI wins, and why domain expertise still matter.

—

SPONSORS:

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/rahulrekhi/

Company: https://www.rogo.ai/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

A CFO Explains the Stock Exchanges

https://youtu.be/pooOE6ZNGR4

A CFO Explains Marketplaces

https://youtu.be/LpbH9GpBrSY

—

TIMESTAMPS:

0:00 Preview and Intro

2:44 Why finance was first to verticalize AI

6:28 What the president title means at Rogo

9:55 Sponsors — Pulley | Rillet | Maximor

13:02 The problem Rogo is solving

16:16 Token maxing is not transformation

17:43 Why ROI is so hard to measure

19:39 Sponsors — Brex | Anrok | RightRev

22:37 ROI is business-unit specific

24:03 Budgeting tokens like a benefits load

25:00 AI incentives aren't aligned to efficiency

26:26 The model broker function

32:03 Not all token spend is equal

37:14 Who owns AI efficiency?

40:59 The forward deployed banker

43:00 Domain expertise: the Interstellar analogy

49:21 Lightning round

49:28 Screwed up: DCF error in a live deal

51:13 Will new grads have the spidey sense?

53:03 Meeting Pope Francis

55:04 Fact-checking jobs numbers at the White House

57:39 Advice to younger self

59:21 Credits

On this episode of Run the Numbers, CJ breaks down Jersey Mike’s S-1 and the franchise machine behind more than $4 billion in sandwich sales. He explains how an asset-light royalty model works, why franchise economics can be so powerful, what Blackstone saw in the business, and what the filing reveals about growth, margins, and the real money behind the subs.

—

SPONSORS:

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Sell $4B in subs, own none of the stores

0:33 Origin story: Peter Cancro buys a sub shop at 17

1:47 It's a royalty business

2:42 Key metrics

6:07 What you're actually buying

6:42 The three revenue streams

7:19 The franchisee's P&L

10:00 Sponsors — RightRev | Pulley | Rillet

13:02 Corporate P&L: 47% EBITDA margins

13:33 The Blackstone math

14:38 $2.1B whole business securitization

15:09 Full EBITDA bridge

16:00 The CEO buying back the 2%

17:10 Red flag 1: Up-C structure

18:11 Red flag 2: tax receivable agreement

18:45 Red flag 3: controlled company governance

19:05 Red flag 4: sponsor already took $500M

19:29 Red flag 5: charitable donations added back

20:13 Red flag 6: cheap debt maturing in 2029

20:52 Sponsors — Maximor | Brex | Anrok

23:56 Valuation: $10–12B

24:32 Peer comparison

25:27 How do you underwrite $12B?

25:58 Misc: quantum attack on the provolone

26:28 The hidden 53rd week

26:57 No drive-thru is a feature

27:13 Verdict

27:56 Credits

#RunTheNumbersPodcast #IPO #Investing #BusinessStrategy #FinanceLeadership

What actually prepares someone to become a CFO? CJ revisits Erin Callan’s short, brutal run as Lehman Brothers CFO and pulls lessons from past guests on operational reps, simple communication, fast-moving bad news, budget mistakes, and why great finance leaders can’t just report the numbers, they have to shape them.

—

SPONSORS:

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Steve Isom

https://youtu.be/a4lEdrgFW5E

Jake Kornreich

https://youtu.be/GKo0B1w4bo4

Manu Diwakar

https://youtu.be/J0J4Rfne54E

Dan Bettes

https://youtu.be/b4w_OHpSNNw

Alan Imberman

https://youtu.be/UD9lYhkfA6U

—

TIMESTAMPS:

0:00 Erin Callan: Lehman's CFO Set up to Fail

5:48 Steve Isom: broadcaster vs. team captain

9:37 Be in rhythm with the business

11:15 Sponsors — Anrok | RightRev | Pulley

14:07 Jake Kornreich: title vs. impact

18:23 Get into the room where decisions are made

22:08 Sponsors — Rillet | Maximor | Brex

25:23 Dan Betts: don't church it up

27:11 The higher up you go, the simpler it gets

29:04 Dan Betts: the many faces of EBITDA

30:39 Understand what success means to them

32:07 Jake Kornreich: the $5M budget bust

33:04 Bad news travels fast

35:01 Alan Imberman: the $100K coffee tab

38:15 ROI on perks

40:25 Alan Imberman: long-term vs. short-term investors

43:28 Would you take the Lehman job?

45:44 Credits

#RunTheNumbersPodcast #CFO #FinanceLeadership #StartupGrowth #FinanceHistory

In this episode of Run the Numbers, CJ goes live from Rillet Recon with Dana Decker (VP of Finance at Opendoor), AJ Ljubich (SVP, FP&A at Datadog), and Micah Richard (Principal, AI at PwC) to unpack how finance teams are actually using AI.

—

SPONSORS:

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guests:

https://www.linkedin.com/in/aj-ljubich-cfa-727ab912/

https://www.linkedin.com/in/dana-decker/

https://www.linkedin.com/in/micah-richard-64a53238/

Companies:

https://www.datadoghq.com/

https://www.opendoor.com/

https://www.pwc.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

2:27 Panel intros: AJ, Micah, Dana

4:00 FP&A a year ago vs. today

6:45 Opendoor: default-to-AI company

7:40 Leadership being in the weeds

8:30 Building a daily P&L view with Claude

9:39 Sponsors — Brex | Anrok | RightRev

12:38 Forecasting at Datadog: consumption model

14:20 AI picks up seasonality, misses customer context

15:10 Semantic layer and blessed queries

16:35 Self-serve data: how far can you go?

20:10 Best-in-class adoption: build over buy

20:23 Sponsors — Pulley | Rillet | Maximor

23:30 Does a 2-year head start matter?

24:10 Build vs. buy criteria haven't changed

25:10 Evaluating vendor roadmaps

26:20 Procurement shifting toward build

28:00 Data access controls and RBAC

31:00 Token usage: haves and have-nots

32:50 Encouraging tokens across the org

34:40 ROI metrics haven't changed

35:45 90-day advice: just start

36:55 Leadership has to pull the red tape

38:05 Get the data right first

39:07 Credits

In this episode of Run the Numbers, CJ breaks down Lime’s S-1 as the scooter company heads toward the public markets. He gets into the $1.8B valuation, Wayne Ting’s turnaround playbook, Lime’s unit economics, the post-Covid recovery, and the debt wall that may be forcing the IPO window open.

—

SPONSORS:

SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

SpaceX S1 Breakdown

https://youtu.be/AARjbTO8FKo

—

TIMESTAMPS:

0:00 Intro

1:48 What Lime does

2:47 Phoenix rising from the ashes

3:53 Revenue: $887M, 29% growth

6:38 Gross margin and the depreciation trick

7:53 Adjusted EBITDA: $218M, up 42%

8:27 Why the net loss got bigger

9:54 Sponsors — SpendHound | Brex | Aleph

13:08 Revenue per vehicle per day

13:42 Marketing: only 2% of revenue

14:01 Subscription mix: 28% and rising

14:25 The debt: $821M but most converts

15:37 The turnaround story

16:42 What Wayne found taking over

17:31 The three numbers he locked in on

18:05 The warehouse overhaul

19:31 Sponsors — RightRev | Rillet | EY

22:33 The debt deep dive

23:20 Why the net loss widened

24:27 Post-IPO: nearly debt free

25:07 Why more scooters make each scooter worth more

28:43 How a scooter pays for itself

30:43 The swappable battery

32:39 Is this a real moat?

34:14 Red flag 1: going concern

35:11 Red flag 2: depreciation change before IPO

36:11 Red flag 3: permits can disappear

36:32 Red flag 4: Uber is everything

37:24 Red flag 5: vehicles catch fire

37:56 Valuation: under 2x revenue

39:55 Comps: between Lyft and Uber

40:55 Bull vs. bear

41:52 Legal name is Neutron Holdings

42:47 Credits

On this episode of Run the Numbers, CJ sits down with Confluent CFO Rohan Sivaram to talk goal setting, prioritization, consumption-based pricing, hybrid zero-based budgeting, and the frameworks finance leaders use to scale companies. Rohan shares why he carries his 12-month goals with him, how he evaluates opportunities through TAM, technology, and team, and why usage-based pricing changes the entire operating model.

—

SPONSORS:

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/rohan-sivaram-69007b7/

Company: https://www.confluent.io/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

A CFO Explains Marketplaces

https://youtu.be/LpbH9GpBrSY

—

TIMESTAMPS:

0:00 Preview and Intro

2:26 Writing down 12-month goals and carrying them

6:33 Rule of 168: 168 hours a week

7:36 Delegation and calendar management

9:25 Learning to say no: cultural shift

11:32 Sponsors — EY | SpendHound | Brex

14:29 Joining Confluent: the state of the company

16:57 Building blocks of a budgeting process

19:46 Execute, learn, adapt

21:59 Healthy tension in the planning cycle

22:26 Sponsors — Aleph | RightRev | Rillet

25:46 What is hybrid zero-based budgeting?

30:37 Moving from subscription to consumption pricing

32:22 Why this was a one-way door

33:56 New metrics required in a consumption business

35:28 Evaluating job opportunities: the three T's

37:39 Networking and reciprocity

39:54 Lightning round

40:04 Screwed up: free cash flow sign error

42:03 Advice to younger self: take more risks

42:38 Finance software stack

43:00 AI tools the team has built

43:44 Credits

In this episode of Run the Numbers, CJ sits down with Jake Kornreich, CFO of CoLab and former CFO of Own, live from the New York Stock Exchange. Jake breaks down the six-part framework behind Own’s $2.1B sale to Salesforce, why “control your destiny” matters, how CFOs should think about IPO readiness, board communication, share price theater, and why great finance leaders operate beyond the spreadsheet.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/jake-kornreich/

Company: https://www.colabsoftware.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

TIMESTAMPS:

0:00 Preview and Intro

2:20 First stock

3:28 Benefits of going public today

5:42 Come-up: chief of staff to CFO

6:31 Running HR like a sales org

8:32 Control your destiny

9:24 Synergies with Salesforce

10:09 Sponsors — Rillet | EY | SpendHound

13:10 Do your own ROI due diligence

14:40 Share price equals entertainment

16:26 Disciplined execution

17:45 Performance, not stories

19:24 Activist investors and the acquirer's board

20:13 Write the memo for the other side

20:45 Sponsors — Brex | Aleph | RightRev

24:02 Triangulate your way to success

25:18 Your board takes snapshots, you run the movie

26:21 Knowing when to sell

27:16 Valuation limits your exit options

27:38 Stakeholder comms during the acquisition

29:58 CFO as operator, not just function

31:31 What is CoLab?

32:09 Why Jake joined post-Series C

33:50 Personal product market fit for CFOs

35:27 Lightning round

35:42 Screwed up: $5M budget error

36:17 Advice to younger self

36:41 Finance software stack

37:34 Culture of expense discipline

38:22 Credits

In this episode of Run the Numbers, CJ sits down with Dan Bettes, CFO of SoundCloud, at the New York Stock Exchange. Dan breaks down how SoundCloud operates as a two-sided music marketplace, how he thinks about liquidity between fans and creators, and why great finance leaders need to make forecasting feel owned by the business

—

SPONSORS:

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/danielbettes/

Company: https://soundcloud.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

2:17 First stock: a Vanguard index fund

3:13 Most memorable IPO: Groupon

4:54 Benefits of going public have changed

5:47 SoundCloud and the music industry

7:21 Three eras: physical, streaming, creator platform

8:49 Streaming unbundled the album

10:03 Artists don't need labels anymore

11:40 Sponsors — Aleph | RightRev | Rillet

15:00 SoundCloud's two-sided business model

16:23 Touring replaced the album

17:17 First metric every morning: net adds

18:31 DAU vs. MAU: it's a funnel

19:14 Viral moments and exogenous pops

20:10 LTV and the subscription funnel

21:38 Sponsors — EY | SpendHound | Brex

24:35 Tops-down vs. bottoms-up: reconcile both

26:21 Revenue is an output

27:45 Handling forecast deviation

29:24 How often to reforecast

30:23 The final boss: indirect cash flow statement

33:09 Cash vs. EBITDA fluency

35:04 Plain English and the power of reps

36:52 Tailor the message to the audience

37:45 Lightning round

37:45 Screwed up: miscounted corn at a banquet

38:41 Lean into discomfort

39:55 Craziest expense: a post-flight massage

40:17 Credits

In this episode of Run the Numbers, CJ breaks down Bending Spoons’ F-1 filing and the acquisition machine behind AOL, Evernote, Vimeo, Eventbrite, and more. He unpacks the company’s playbook: buy under-optimized digital businesses, transform operations, raise prices, reinvest earnings, and repeat — while asking the core question: how much was built, and how much was bought?

—

SPONSORS:

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 What is Bending Spoons?

1:03 The Internet's attic: the portfolio

3:11 The metrics rundown

5:44 Revenue: $1.3B, 95% growth

6:04 82% of growth was bought, not built

6:29 Gross margin: 66%

6:50 Subscription mix and NRR

7:33 Net income: basically zero

8:00 Cash: $741M, debt: $4.4B

8:35 Revenue per employee: $2.57M

9:39 Sponsors — RightRev | Rillet | EY

12:42 Organic growth is mostly price hikes

13:50 A house of adjustments

14:54 Add-backs bigger than the profit

15:22 The reorganization line: cost of firing

19:21 Sponsors — SpendHound | Brex | Aleph

22:51 Does the playbook actually work?

23:07 Evernote: the proof point

23:45 Romini: the growth proof point

24:10 AI in three directions at once

25:45 The debt engine

27:50 Red flag 1: material accounting weaknesses

28:38 Red flag 2: pro forma numbers come with a confession

29:00 Red flag 3: App Store dependency

29:11 Red flag 4: no long-term contracts

29:30 Red flag 5: foreign private issuer

29:52 Red flag 6: they've never sold anything

30:19 Cap table and board

31:07 Valuation: 14–18x

33:00 Bull vs. bear case

33:55 Miscellaneous: the S1 is already stale

35:25 Credits

CJ Gustafson sits down with Marten Abrahamsen, CFO of Vercel, at the NYSE to talk about running finance inside a hypergrowth AI company. They cover AI use cases in finance, rev rec, forecasting, KPI dashboards, PLG, consumption pricing, and Marten’s “speeding tickets vs. parking tickets” framework for moving fast without losing control.

—

SPONSORS:

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/martenabrahamsen/

Company: http://vercel.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Speeding tickets vs. parking tickets

3:21 Visa IPO in the financial crisis

5:09 Going public has changed

6:45 Private market: 22–24 trillion

9:03 More or fewer public companies?

9:48 Sponsors — Brex | Aleph | RightRev

13:04 KPI dashboard on your phone

14:12 Revenue flux via Slack and Notion

15:37 RevRec tool: green, yellow, red

17:56 V0 is a job requirement

19:43 Speeding tickets vs. parking tickets

20:33 Sponsors — Rillet | EY | SpendHound

23:49 Very few one-way doors

25:02 Finance in hypergrowth

25:39 Three-scenario planning

27:00 Honest with the board

31:00 PLG + consumption at Vercel

33:32 What Marten checks every morning

34:03 Why RPO doesn't work here

35:36 Holiday usage is up

37:10 ICP shifted to solo developer

39:22 Capital allocation in a fast market

41:32 Growth compounds; margin can't

43:22 SaaS gross margins: spicy take

44:24 Cash-burning AI: 2026 vs. 2021

47:29 Are some hypergrowth cos destroying value?

50:00 Lightning round

50:11 Bank of Ireland mix-up

51:10 Don't punt problems forward

52:04 Finance software stack

52:38 Expensed an oven

53:12 Credits

In this episode of Run the Numbers, CJ breaks down how stock exchanges became the operating system of modern capitalism. From ship captains raising voyage money, to the Dutch East India Company’s first tradable shares, to coffee house traders, the Buttonwood Agreement, market crashes, Robinhood, and GameStop, this is the story of how markets turned ownership into something liquid, global, and very, very human.

—

SPONSORS:

SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

—

RELATED EPISODES:

A CFO Explains Secondaries

https://youtu.be/pENvBuXhGuk

A CFO Explains the Diamond Industry

https://youtu.be/fPrho7hvykA

A CFO Explains Marketplaces

https://youtu.be/LpbH9GpBrSY

—

TIMESTAMPS:

0:00 The First IPO, and Why It Changed Everything

2:50 Coffee, Buttonwood Trees, and the First Insider Trading Scandal

6:31 The Railroads Built Your Month-End Close

10:17 Sponsors — SpendHound | Brex | Aleph

13:47 Buying Stocks on Credit, and How That Ended

18:13 Merrill Lynch Goes to the Suburbs, and the Paper Almost Wins

21:44 Sponsors — RightRev | Rillet | EY

24:47 NASDAQ, Pets.com, and the Most Expensive Sock Puppet in History

28:49 The Phone in Your Pocket Democratized Everything, For Better or Worse

33:03 The Stock Market Was Never Really About Stocks

36:47 Credits

#RunTheNumbersPodcast #FinanceHistory #StockMarket #Investing #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Ryan Roccon, CFO of Zapier, to cover AI hiring standards, automating month-end close, measuring ROI on AI spend, and why determinism still beats agents most of the time.

—

SPONSORS:

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj

Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/ryanroccon/

Company: https://zapier.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Ryan’s First Appearance

https://youtu.be/VIZ_RzfV78I

Chris Byington, Head of Data @ Superhuman

https://youtu.be/ydH38JnWfww

—

TIMESTAMPS:

0:00 Preview and intro

2:11 Ryan's scope at Zapier

3:17 Why the finance guy runs ecosystems

6:19 AI is a required hire competency

6:46 The four levels: unacceptable to transformative

8:48 How Zapier tests for it

11:50 Favorite interview question

13:06 Sponsors — EY | SpendHound | Brex

16:18 AI changes the hiring profile

17:07 Support becomes customer-facing engineering

18:44 Where AI beats deterministic Zaps

21:00 80-90% of builds are deterministic

22:41 Sponsors — Aleph | RightRev | Rillet

26:00 Month end close on Zaps

27:40 Time saved is a leading indicator

29:53 AI token costs: COGS or investment?

31:51 Performance issue or measurement issue?

33:41 Partner ARR: chasing the wrong thing

35:56 Build around what changes the decision

37:17 The initiative sizing coach

40:00 Escalate on magnitude, not certainty

41:55 The 9,000 integration story

44:02 M&A process and minimum model

46:19 Cash vs. stock: incentive alignment

48:06 CFO's role in M&A: show up early

49:18 Credits

In this episode of Run the Numbers, CJ sits down with Aurélien Nolf, CFO of Navan, to unpack how to pre-align before budgeting, how to think about portfolio construction inside a company, when to fund or kill internal bets, how IR is becoming more connected to FP&A, and where AI actually works inside finance teams.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/aureliennolf5b716412/

Company: https://navan.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

1:21 Welcome and guest intro

3:06 100-mile ultramarathon at Lake Tahoe

4:47 Resource allocation lessons from EA

6:41 Bucketing bets: proven, intuition, moonshots

7:43 Pre-alignment before budgeting

9:58 The 70/20/10 framework

10:35 Sponsors — Rillet | EY | SpendHound

13:51 The common trap: chasing everything

16:16 Lyft: $1B burning to $1B profitable

18:11 Killing projects without crushing morale

19:24 TAM as the planning foundation

20:57 Navan's TAM: managed vs. unmanaged

22:15 Sponsors — Brex | Aleph | RightRev

25:48 Why go after the unmanaged segment

28:24 Not all TAM dollars are equal

29:26 How IR is evolving

30:45 Why FP&A and IR belong together

31:54 Metrics: disclose vs. guide

34:04 Use internal metrics externally

35:12 Communicating bad news to the market

39:22 Earnings prep: the black book

40:04 AI in finance: can't vibe code compliance

41:31 Ava handles 55% of interactions

43:08 AI ROI: same framework as anything else

44:02 Why finance hasn't had its AI moment

44:46 Lightning round

44:56 Screwed up: wrong investor meeting

45:23 Sunday planning ritual

46:42 Advice to younger self

47:29 Finance software stack

48:34 Craziest expense: curtains at the hotel laundry

49:17 Credits

In this episode of Run the Numbers, CJ breaks down SpaceX’s S-1, unpacking what the filing reveals about Starlink, xAI, X, common control accounting, revenue, losses, CapEx, and Elon Musk’s Mars-linked compensation structure.

—

SPONSORS:

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics
Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

—

LINKS: 

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 SpaceX S1 breakdown

0:50 Elon's Mars colony comp plan

2:03 Common control accounting: SpaceX + xAI + X

3:04 What SpaceX actually does

3:43 How reusable rockets work

4:24 Launch cost curve: foundation of everything

5:49 Launch services: $8B, 85% of global launches

6:44 Starlink: $11.4B, 63% EBITDA margins

7:36 xAI and X: burning $1B/month

8:22 Sponsors — RightRev | Rillet | EY

11:18 Colossus and orbital AI thesis

11:41 Revenue, segments and CapEx breakdown

14:54 RPO: $28.4B backlog

15:18 Starlink subscribers and ARPU decline

16:01 Target valuation: $1.5–1.75 trillion

16:47 Starlink deep dive

18:05 International pricing strategy

21:38 The consolidated entity problem

22:28 Related party section: nine pages

22:32 Sponsors — SpendHound | Brex | Aleph

26:15 Valor Equity: $20B in equipment leases

27:05 Tesla cross-ownership and Terrafab

28:23 R&D: $8.6B, 46% of revenue

30:33 Starship: key risk and growth linchpin

31:41 Red flag 1: CEO comp tied to Mars colony

32:22 Red flag 2: Musk concentration risk

32:49 Red flag 3: Cursor option — $10B downside

33:36 Red flag 4: X advertising is shrinking

34:06 IPO structure and SPCX ticker

34:50 30% retail allocation, no lockups

35:44 S&P 500 inclusion forces buying within 15 days

37:54 Valuation: 60–70x forward revenue

38:43 Peer comparison

39:44 What you're buying at $1.5T

40:53 CFO comp: the only sane plan in the filing

41:25 Bitcoin on the balance sheet

41:57 Credits

In this episode of Run the Numbers, CJ sits down with ParkerGale Operating Partner Paul Stansik to break down five ways CFOs can help build a better sales engine: making the budget mean something, improving forecasting, sharpening metrics, getting involved in key RevOps moments, and building real trust with sales.

—

SPONSORS:

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/paulstansik/

Company: https://www.parkergale.com/

Hello Operator: https://hellooperator.substack.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Is a weekly martini ARR? | with Dave Kellogg

https://youtu.be/Yb1lUQLJ6qw

—

TIMESTAMPS:

All verified. Here are the timestamps:

0:00 Preview and intro

2:27 Parker Gale and Paul's role

3:52 Topic: how CFOs build a better sales engine

6:21 1: Make the budget mean something

8:11 Budget segmentation and cleaving the business

10:54 Sponsors — Aleph | RightRev | Rillet

14:08 2: Help emphasize forecasting

17:23 Forecasting as non-threatening co-construction

19:37 Sponsors — EY | SpendHound | Brex

23:06 3: Lend a hand with data and metrics

25:32 Walking sales through NDR levers

27:16 Metrics tied to exit readiness

28:00 4: Get involved in a few RevOps spots

29:04 Pricing, proposals, and quoting

31:22 Kill your SKUs

32:51 Selling with certainty: quote formatting

34:26 CFO letter for enterprise deals

37:37 5: Build a great relationship with sales

37:59 You can't fix a secret

39:23 EQ over IQ for finance leaders

40:41 Recap: all five tips

42:11 Credits

#RunTheNumbersPodcast #CFO #SalesStrategy #FinanceLeadership #RevenueOperations

In this episode of Run the Numbers, CJ sits down with Figure Technologies CFO Macrina Kgil to break down how Figure’s business model works, why traditional lending remains so bloated, and how speed in origination and funding flows through financial performance. They also cover stablecoins, blockchain as invisible infrastructure, AI in accounting, and scaling finance with fewer than 35 people.

—

SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/macrina/

Company: https://www.figure.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

3:10 Working for a CEO who's a former CFO

5:00 What Figure does and how it makes money

6:57 Blockchain's first commercial use case

8:17 50%+ margins, path to 60%

9:23 Sponsors — Brex | Aleph | RightRev

12:56 HELOC origination: 45 days to 5 days

14:26 Where the lending system is bloated

15:56 Credit and liquidity as core risks

17:06 Blockchain makes the marketplace transparent

18:10 Risk as a fintech CFO

19:49 Sponsors — Rillet | EY | SpendHound

22:58 Crypto on the balance sheet

24:12 Blockchain becomes invisible like cloud

25:44 Stablecoins explained

27:47 YLDS: Figure's yield-bearing stablecoin

29:02 Crawl, walk, run stablecoin strategy

34:32 IPO process: what got easier

35:03 What got harder: testing the waters

37:12 Blockchain KPIs and investor conversations

38:21 Finance team: 130 people down to 35

40:00 SEC engagement: storytelling not financials

40:49 IPO advice: pick durable KPIs

42:05 First earnings after IPO: don't miss

43:13 AI automation goal: 60% by 2026

46:11 Director of Finance Transformation hire

47:40 30-60-90 for the transformation role

48:58 Long-Ass Lightning Round

52:20 Credits

Cerebras is going public with the largest commercial chip ever built, $510M in 2025 revenue, and a $24.6B backlog mostly tied to OpenAI. CJ breaks down the company’s wafer-scale AI bet, why inference changed the story, the strange customer-investor-lender relationships behind the IPO, and the big question: is Cerebras the next NVIDIA-style infrastructure winner, or a concentrated hardware company with a very expensive cloud pivot?

—

SPONSORS:

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

0:59 Cerebras: the dinner plate chip

3:56 Why chip size matters for AI

5:26 Old vs. new AI: inference is the bottleneck

7:30 Revenue: 20x in 3 years

7:49 Sponsors — SpendHound | Brex | Aleph

11:33 Gross margin

12:02 Net income: the one-time accounting trick

12:41 Operating cash flow whipsaw

13:24 RPO: $24.6B backlog

13:58 Customer concentration: the UAE entities

18:06 Sponsors — RightRev | Rillet | EY

21:05 Cloud revenue: the inverse SaaS story

22:23 Cloud gross margin collapse

23:53 G42 warrants for pennies

29:14 The OpenAI warrant: Funky Town

31:08 $40B market cap milestone

31:36 R&D and S&M breakdown

33:15 Balance sheet and cash burn

35:59 Red flag 1: accounting weaknesses

36:37 Red flag 2: one foundry, no supply deal

37:28 Red flag 3: UAE geopolitical risk

38:10 Red flag 4: cloud is unproven

39:02 Cap table: founders diluted

40:43 Voting control: Class A, B, and N

41:15 Valuation: 10–13x forward revenue

41:48 Peer comparison

43:47 CEO's prior issues

46:10 Credits

Nothing said or created by this podcast is business or investment advice

#RunTheNumbersPodcast #IPO #Semiconductors #AIStrategy #FinanceLeadership

David Bell, co-founder of Idea Farm Ventures and early investor behind Warby Parker, Harry’s, and Diapers.com, and CJ break down how consumer investing works. They cover why durable consumer companies require more than clean unit economics, how to apply SaaS-style thinking to businesses without contracts, and why the best opportunities often live in boring gray space.

—

SPONSORS:

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

—

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/david-bell-086820/

Company: https://www.ideafarmventures.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

3:16 Edge: economics and psychology

5:21 Best ideas in boring gray space

5:41 Functional, emotional, and symbolic value

7:08 Grüns gummies and divisibility

9:02 Sponsors — EY | SpendHound | Brex

12:31 Ideation: personal pain vs. market analysis

13:17 Diapers.com and the Starbucks origin story

16:00 Warby Parker: asking why

16:33 LTV to CAC in D2C

18:02 Retention math: 85 to 90% can double LTV

19:00 Milkman and recurring vs. reoccurring

20:42 Trust economics

22:38 Warby stores boost online sales

22:58 Sponsors — Aleph | RightRev | Rillet

26:12 Away store as advertising

27:46 Warby discovery: dots on a map

30:10 Home try-on word of mouth value

32:09 D2C unit economics mistakes

34:55 Innovating on distribution

35:50 Touchland in Sephora: right channel, right signal

37:00 Capital allocation: margin and low CAC first

39:18 Sequencing: people, brand, then inventory

40:58 Product vs. brand: the 8x10 thought experiment

42:23 Consumer monetization shifts

45:45 The gravity framework

50:32 Isolation principle: most underused lever

52:36 Working backwards from exit at day zero

57:23 What if your business isn't venture scale?

59:32 Book plug: Founders Gold

1:00:25 Credits

CJ turns the mic on the people behind Mostly Media for a special behind-the-scenes episode of Run the Numbers. Michelle, Callie, Sarah, Matthew, Ben, and Steve share what it’s like building the company, scaling media, talent, sales, production, and operations, and dealing with CJ’s scooter lore, calendar quirks, and chaos along the way.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

2:44 Show intro: meet the Mostly Media team

3:37 Michelle Finn: accounting and ops

4:28 Parts Tech days: CJ's first CFO role

7:21 How the newsletter convinced Michelle to join

9:02 Sponsors — Rillet | EY | SpendHound

12:11 Callie Spillane: talent director

13:17 Callie's background: HubSpot, Sneak, Superhuman

13:40 Why Callie was hard to hire

15:37 Snyk hypergrowth: 150 to 1,500 people

16:59 Zero to one vs. one to ten

18:20 9 of 20 roles filled: how it's going

23:24 Sponsors — Brex | Aleph | RightRev

26:58 Sarah Bousquet: media op

27:45 Stay at home mom to ops lead

33:48 CJ's schedule: American Psycho

34:43 Matthew Mozzocchi: sales and partnerships

35:41 Going full time with a newborn

36:20 Product market fit signal

38:07 Fewer, bigger bets on creators

41:00 Podcast is the air game, newsletter is the ground game

43:56 Ben Hillman and Steve Cerasoli: production

47:46 Media in service of a product vs. the product itself

48:37 Run the Numbers vs. Mostly Growth

51:25 Where are we in three years?

52:40 Credits

#RunTheNumbersPodcast #CreatorEconomy #MediaBusiness #Entrepreneurship #ContentBusiness

In this episode of Run the Numbers, CJ Gustafson breaks down the diamond industry as a business model: how De Beers controlled supply, engineered demand, and built one of the most powerful pricing machines in history. From the Central Selling Organization to “A Diamond Is Forever” to the rise of lab-grown diamonds, this episode unpacks monopolies, scarcity, pricing power, and what happens when technology forces transparency.

—

SPONSORS:

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Why Uber Drivers Can’t Escape the 30% Cut

https://youtu.be/LpbH9GpBrSY

—

TIMESTAMPS:

All verified. Here are the timestamps:

0:00 Blood Diamond

1:55 Show intro

2:15 Diamond history: ancient India and riverbed origins

3:56 Brazil supply shock and the mining era

4:39 De Beers: Cecil Rhodes and the PE rollup

6:47 Sponsors — RightRev | Rillet | EY

9:49 The Central Selling Organization (CSO)

10:39 The site system: invite-only, take-it-or-leave-it auctions

12:22 Diamonds are more abundant than gold

13:01 NW Ayer, Bernays, and engineering demand

14:17 "A Diamond is Forever" campaign

15:13 Lab grown diamonds: 20% of US purchases

16:32 De Beers collapses: $3.1B operating loss

17:18 Sponsors — SpendHound | Brex | Aleph

21:07 Lesson 1: Rollups are powered by capital

21:39 Lesson 2: Distribution beats mining

22:11 Lesson 3: Artificial scarcity unravels

22:55 Lesson 4: Price opacity is a temporary moat

23:39 Lesson 5: Demand engineering

24:30 Lesson 6: The real product was risk smoothing

26:30 Credits

#RunTheNumbersPodcast #BusinessStrategy #FinanceHistory #Pricing #Monopoly

In this episode of Run the Numbers, CJ Gustafson sits down with Angela Chen, former CFO of The North Face and Mars Veterinary Health, to unpack how finance leaders build and scale iconic consumer brands. Angela shares how to measure brand equity, why the CFO should act as an architect of growth, and how capital, talent, and strategy connect inside a scaling business. They also get into humanistic leadership, consumer-margin tradeoffs, and what a 39-cent Taco Bell taco can teach finance teams about growth.

—

SPONSORS:

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/angelachensf/

Company: https://sku.is/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

RELATED EPISODES:

Minted’s CFO: Half the Year Happens in One Month

https://youtu.be/hD4-exunKMo

—

TIMESTAMPS:

0:00 Preview and intro

2:45 Measuring brand equity

5:09 CFO as architect of growth

7:11 Connecting money, ideas, and talent

7:52 North Face vs. Mars: where to invest

10:52 Sponsors — Aleph | RightRev | Rillet

14:14 Scaling North Face 5x without diluting the brand

16:31 From technical brand to lifestyle brand

19:30 Quality of revenue

21:49 Seasonality and Q4 concentration

24:01 Sponsors — EY | SpendHound | Brex

27:14 Retailers shouldn't own factories

31:30 Supply chain and 18-month product cycles

33:23 Humanistic leadership in finance

34:32 Purpose and profit are mutually reinforcing

36:15 Purpose vs. profit in public companies

38:05 Playing to Win framework

39:47 Operational cadence and the gas gauge

43:02 Killing bad projects: the battery jacket story

44:16 Taco Bell and 39-cent margins

47:10 Lightning round

47:36 Screwed up: hiring on credentials

48:27 Advice to younger self: network is the work

50:07 Craziest expense story: snowcat ski trip

50:50 Credits

In this episode of Run the Numbers, CJ sits down with PSG Managing Director Chris Nesbitt to unpack how great deals are actually found, how investment decisions are really made, and why narrative often matters more than most investors admit. They also dig into forecasting, boardroom authenticity, simple vs. complex models, and the roles of market, product, and leadership in driving outcomes.

—

SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/christophersnesbitt/

Company: https://psgequity.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

2:44 PSG origin story

4:01 Growth to 30B AUM

5:07 Strategy: small software at scale

5:50 Vertical SaaS treasure hunting

8:10 Ministry Brands: software meets payments

9:28 Sponsors — Brex | Aleph | RightRev

12:46 Early M&A work and rollup strategy

15:52 Sourcing is more competitive now

18:28 Smoke signals and relationship sourcing

21:22 Does brand get you in the room?

22:15 Authenticity as a sourcing edge

22:52 Sponsors — Rillet | EY | SpendHound

26:09 Brand name of investor or deal partner?

27:44 Investors are narrative driven animals

29:18 Market, product, then execution

31:26 Danger of falling in love with the narrative

33:40 Operator AI pivot story: GRC company

34:51 Keep it simple: one tab, five key inputs

39:21 Forecasting confidence beyond 12-18 months

41:51 What makes a useful board meeting

45:01 Build vs. buy: the payments decision

47:45 ARR vs. EBITDA multiples

50:30 Lightning round

50:34 Board materials: send 3 days in advance

51:03 LTV to CAC and cap software debates

51:32 First deal at PSG

52:35 What young investors get wrong

54:04 Credits

In this episode of Run the Numbers, CJ sits down with Manu Diwakar, CFO of Virta Health, to unpack why health tech breaks traditional SaaS thinking. They get into the realities of running a business where outcomes matter, half the company are medical professionals, and efficiency can’t come at the expense of care. It’s a conversation about sustainable scaling, smarter reinvestment, and building for durability over hype.

—

SPONSORS:

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/manu-diwakar-1aa578/

Company: https://www.virtahealth.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

1:18 Welcome and guest intro

3:02 What sector is health tech?

4:34 Virta go to market explained

7:01 B2B to B2C model

9:00 Value based care and ROI guarantees

9:18 Half the company are medical professionals

10:36 Sponsors — SpendHound | Brex | Aleph

14:03 Annual planning process

16:42 Shape of the curve

17:33 TAM: metabolic health is massive

20:45 Fee for service vs. value based care

24:16 Sponsors — RightRev | Rillet | EY

27:24 Unique costs of health tech: billing, compliance

30:54 Corporate practice of medicine

31:44 North star: members under management

32:43 The flywheel: $250 charge, $500 saved

33:28 Early stage CFO job is easy

35:28 Bad habits baked in during high growth

38:02 Choosing not to profit vs. not turning a profit

41:15 Running a VC-backed business for sustainability

42:07 People, tech and process framework

44:31 Hiring philosophy: hard work, learning, curiosity

48:26 Athletes vs. experts in hiring

50:03 Clock hands interview question

50:49 Lightning round

51:09 Screwed up: having hard conversations late

51:57 Advice to younger self

52:15 Finance software stack

52:42 Craziest expense story

53:47 Credits

In this episode of Run the Numbers, CJ sits down with Praveer Melwani, CFO of Figma, to unpack the financial model behind one of tech’s most iconic product-led companies. They cover viral growth, forecasting without a traditional sales pipeline, AI credit pricing, margin tradeoffs, and the metric Praveer believes matters most in the long run: free cash flow per share.

—

SPONSORS:

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/praveer-melwani/

Company: https://www.figma.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

1:21 Welcome and guest intro

2:55 From banking to Dropbox to Figma

5:04 Inflection points: building trust early

8:36 TAM expansion thinking

10:31 Sponsors — EY | SpendHound | Brex

13:38 Two-thirds of Figma users aren't designers

14:36 Forecasting product led growth

16:22 Cohorts and NDR discovery

17:39 LTV to CAC philosophy

18:57 Product signals for account expansion

20:22 How Figma achieved hypergrowth with 90%+ margins

22:14 AI expands TAM: time to hit the gas

23:22 AI credit pricing model

24:50 Sponsors — Aleph | RightRev | Rillet

28:13 Outcome based pricing consideration

29:00 Where AI margins settle: gross profit dollars

30:08 Free cash flow per share as north star

31:04 NDR and pricing volatility

32:13 Bundled vs. unbundled seats

34:50 Being engaged in sales to understand admin pain

35:17 IPO day experience

36:27 Keeping employees focused beyond the stock price

37:19 Employee stock pressure and lockup reality

39:37 Kitchen cabinet of advisors

41:44 How to ask better questions of advisors

41:47 Lightning round

41:50 Advice to younger self

42:47 Finance software stack

44:09 Claude WTF moment: forecasting model throughput

45:13 Craziest expense story: the haircut

45:59 Credits

In this episode of Run the Numbers, CJ sits down with Wealthfront CFO Alan Imberman to unpack automation as a strategy, the compounding power of retention and trust, and how to balance elite profitability with continued investment. They also discuss why Wealthfront went public earlier than many peers and what’s really happening in fintech right now.

—

SPONSORS:

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/alan-imberman-cfa-aab2371/

Company: https://www.wealthfront.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

1:37 Welcome and guest intro

3:11 Wealthfront overview

4:38 Automation as core philosophy

6:50 55K clients per support rep example

7:45 90% gross margins and $1M revenue per employee

8:46 Optimization vs. exploration framework

9:58 Data flywheel: the Path product

10:43 Cash account insight from customer data

11:26 Home lending insight from wire data

13:33 Sponsors — Rillet | EY | SpendHound

16:45 Product led growth and referrals

18:11 Incentives vs. paid marketing

20:46 Compounding philosophy and 120% NDR

22:07 Long term thinking vs. public market pressure

22:40 No guidance decision

26:26 Sponsors — Brex | Aleph | RightRev

29:44 Serving the wealth builder: 80/20 in wealth management

31:45 Decision to go public at $339M revenue

33:46 Does size matter for IPOs?

34:46 Fintech's moment: Chime, Klarna, Circle

36:49 Non-monetary benefits of going public

38:30 Memos over slides

40:31 Hedge fund early career: spreading 10-Ks in Excel

46:45 Don't lose the forest for the trees in modeling

48:31 Lightning round

48:43 Screwed up: de-annualizing a fee rate

49:55 Advice to younger self

50:32 Finance software stack

51:14 Craziest expense story: $100K coffee tab

53:11 Credits

#RunTheNumbersPodcast #CFO

On this week’s Run the Numbers, CJ sits down with Steve Isom of Bloomerang to break down what a “strategic CFO” really is. They cover the shift from reporting to operating, why customer orgs drive SaaS value, and how AI is reshaping the finance role. 

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SPONSORS:

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

—

LINKS: 

Steve on LinkedIn: linkedin.com/in/steveisomjr

Company: https://bloomerang.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview

1:25 Intro

2:55 Welcome Steve Isom

3:13 CFO to COO promotion

5:02 Having a pulse on every function

6:51 Defining "strategic CFO"

7:19 Tying strategy to value creation

9:27 Being embedded in the rhythm of the business

10:55 Finance leaders as commentators vs. team captains

12:25 Sponsors — RightRev | Rillet | EY

15:33 Killing projects as a core skill

18:14 Activity doesn't equal impact

19:16 Project Steve killed

20:39 Taking over the customer org at Bloomerang

22:18 Why acquisition is a cash-losing exercise

23:07 LTV lives post-sale

24:39 Most vulnerable area: customer success

25:24 Ruthless CSM segmentation

26:30 Nonprofits don't think about your software

29:21 Sponsors — Spendhound | Brex | Aleph

32:43 CFO running ops

35:52 Metrics vs. humans

37:18 Skip levels and what they reveal

39:01 Incentives drive the wrong outcomes

40:22 Customer-introduced delays as a key sub-metric

40:27 Unit economics become tangible when you're accountable

42:17 Going deep on AI

45:13 Motivating your team to experiment with AI

46:02 AI for personal projects

47:05 Resource allocation in a vibe-coding world

48:42 Does AI efficiency just mean more work?

50:32 What excites Steve about the future of finance leadership

52:08 Finance leaders who don't use AI won't get hired

52:13 Credits

#RunTheNumbersPodcast #CFO #StrategicFinance #SaaSFinance #FinanceLeadership #CFOtoCOO

Secondaries aren’t a niche anymore — they’re the main event. In 2025, the secondary market hit $233B, outpacing IPOs 5:1. This episode breaks down how we got here, why companies stay private longer, and how employees, investors, and CFOs actually navigate liquidity. From Facebook’s wild west to structured tenders and continuation vehicles — this is the new playbook.

—

SPONSORS:

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

Slacker Stuff: https://www.slackerstuff.com/

—

RELATED EPISODES:

IPOs Are Being Replaced

https://youtu.be/oGuZf83pdRE

The $10T Question: Who Needs Wall Street?" | Scott Voss

https://youtu.be/szCIZmTs3SQ

Driving revenue without selling | Greg Henry of 1Password

https://youtu.be/f5FsNoG8A3E

Finance vs. Marketing: Who’s Really Right About ROI? | Brandon Sullivan

https://youtu.be/ivcht5N7uRQ

Do the things spreadsheets can’t do | SeatGeek’s Teddy Collins

https://youtu.be/jn0L5KkmMI4

—

TIMESTAMPS:

0:00 The $233B market replacing IPOs

2:57 What is a secondary?

4:24 The dot-com hangover

5:48 The wild west era

8:58 Sponsors — Aleph | RightRev | Rillet

12:21 Why companies stay private longer

13:56 The three stakeholders

18:57 When is it too early?

20:42 How to run one of these things

23:57 Sponsors — EY | SpendHound | Brex

27:04 Not all shares are created equal

31:08 The good, the bad, and the ugly

34:23 GP-led continuation vehicles

36:19 The whole game changed

37:34 Credits

#RunTheNumbersPodcast #PrivateMarkets #SecondaryMarkets #VentureCapital #CFO

In this episode of Run the Numbers, CJ sits down with Glenn Schiffman, CFO of Fanatics. They break down the economics of sports IP, how Fanatics approaches CAC, LTV, and capital allocation across merchandising, collectibles, and betting, and the negotiation lessons Glenn learned from decades in investment banking and leading finance at IAC.

—

SPONSORS:

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/glenn-h-s-51440521/

Company: https://www.fanaticsinc.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and intro

1:13 Welcome and guest intro

2:38 Football at Duke and college businesses

5:40 Predecessor to DoorDash story

7:10 IP monetization explained

9:22 All deals are snowflakes

10:36 Partnership KPIs

13:21 Sponsors — Brex | Aleph | RightRev

16:40 Buy, bet, collect: CAC and LTV

17:15 Single view of the fan

18:39 Multi-business customers spend 4.7x

20:32 Fanatics credit card launch

22:13 AI for personalization

23:01 DTC vs. wholesale margin profiles

24:05 Budgeting process

26:07 Infinite vs. finite: focus on revenue

26:37 Sponsors — Rillet | EY | SpendHound

29:47 Starve your losers, feed your winners

32:58 Capital compounding: revenue, EBITDA, FCF

33:56 Buybacks at IAC

37:02 First negotiation at Lehman

39:17 Outlasting the other side

39:56 Listening in negotiations

40:03 Long-Ass Lightning Round

44:25 Credits

#RunTheNumbersPodcast #CFO #SportsCommerce #CapitalAllocation #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Kunal Agarwal, CFO of Gorgias, to unpack how AI is reshaping pricing and operations. They discuss outcome-based pricing, how to forecast LLM-driven costs, and why order-to-cash isn’t just back-office plumbing—it can be a true growth lever when designed correctly.

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SPONSORS:

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

—

LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Guest: https://www.linkedin.com/in/agarwalk/

Company: https://www.gorgias.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

—

TIMESTAMPS:

0:00 Preview and Intro

2:14 PE to venture incubator

4:39 Operational empathy from zero-to-one

4:45 First paying user feeling

5:40 Jet ski customer support story

8:49 Hanging with IC sales reps

12:24 Sponsors — Tabs | Abacum | Brex

15:44 Finance as the decision engine

17:36 Gorgias overview

20:20 Pricing structure and iteration

22:11 Outcome based / resolution pricing

24:48 AI success rate as key metric

25:33 Sponsors — Metronome | RightRev | Rillet

28:57 Pricing value split — $1 per resolution

31:17 Vertical specificity as AI moat

33:27 Managing LLM costs

35:41 Falling token costs and model mix

39:28 Order to cash as growth engine

43:31 Auditing order to cash at 25M ARR

44:09 Manual choke points

46:32 Learning density over titles

48:30 SurveyMonkey as the most formative period

50:07 Lightning round

50:17 Listening to respond vs. listening to learn

51:04 Advice to younger self

52:02 Finance software stack

52:45 Cortex — internal AI decision tool

54:21 Craziest expense story

54:52 Credits