Explorez tous les épisodes du podcast Run the Numbers
| Titre | Date | Durée | |
|---|---|---|---|
| “It’s Not Zero”: The CFO Rule for AI Forecasting | Dan Griggs | 29 Jan 2026 | 00:46:50 | |
In this episode of Run the Numbers, CJ sits down with Intercom CFO Dan Griggs to discuss pricing and forecasting in the AI era. Dan shares the “it’s not zero” rule, the logic behind Fin’s $0.99 pricing, and how to bet on AI without blowing up the core business. — 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 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 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 — LINKS: Dan on LinkedIn: https://www.linkedin.com/in/dan-griggs-0970181/ Intercom: https://www.intercom.com/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brown — TIMESTAMPS: 00:00:00 Cold Open 00:01:03 Dan Griggs and Intercom’s AI Pivot 00:02:45 Ice Cream to SaaS 00:04:19 Learning the Business 00:06:26 Operational Reality and Forecasts 00:08:00 “It’s Not Zero” Forecasting 00:10:09 Scenario Planning and Ambiguity 00:11:23 Sponsors — Brex | Metronome | RightRev 00:14:43 Mental Models for Metrics 00:16:15 Mental Math for Forecasts 00:17:28 Core CFO Ratios 00:19:13 Intercom’s Burn-the-Boats Moment 00:20:53 AI as an Existential Bet 00:22:21 SaaS Categories AI Can Replace 00:23:04 Why Finance Lags on AI 00:23:39 Sponsors — Rillet | Tabs | Abacum 00:27:05 Why Fin Uses Outcome Pricing 00:28:59 The $0.99 Resolution Tradeoff 00:30:46 Why Support Work Varies 00:32:01 AI Resolution Unit Economics 00:33:08 Model Choice as Costs Fall 00:35:19 Domain-Specific vs Generic LLMs 00:36:08 Selling Against the Core 00:38:50 Founder vs Professional CEOs 00:41:47 Hiring Mistakes and Instincts 00:44:28 Intercom’s Finance Stack 00:45:49 Craziest Expense Request | |||
| How finance shows its value beyond being the “no” department | Maria Izurieta | 26 Jan 2026 | 00:53:14 | |
In this episode of Run the Numbers, CJ sits down with Maria Izurieta, CFO of Huntress, to unpack what it really means to lead finance as a connective tissue across the organization. Drawing on experience across VC-backed, PE-owned, and public companies, Maria shares how she balances impact versus perfection, builds trust through small wins, and helps teams move from transactional finance to insight-driven decision making. They dig into data transparency, centralized BI, partnering with sales and marketing on revenue, and why the best CFOs unblock friction instead of becoming the “no” department — all while bringing a deeply people-first lens to scale. — SPONSORS: 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 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 — LINKS: Maria on LinkedIn: https://www.linkedin.com/in/maria-izurieta-909a3b/ Company: https://www.huntress.com/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: How the Best CFOs Lead Without Being the CEO | Ken Stillwell — TIMESTAMPS: 00:00:00 Preview and Intro 00:01:01 Maria’s Background 00:03:09 People-First Team Building 00:05:16 People, Process, Systems at Scale 00:07:13 Removing Friction Outside Finance 00:09:15 Data Transparency & Decision-Making 00:11:06 Sponsors — Abacum | Brex | Metronome 00:14:22 Forward-Deployed Data 00:16:21 Centralized Data vs. Silos 00:19:23 Finance as Data Steward 00:21:08 Cost-to-Price Feedback Loop 00:22:35 Curiosity Builds Credibility 00:23:43 Sponsors — RightRev | Rillet | Tabs 00:27:12 Trust First, Then Impact 00:30:27 Celebrating Small Wins 00:31:21 From Transactions to Insights 00:33:00 CFO at the Revenue Table 00:34:32 Educating the Org on Metrics 00:36:21 Customer-Level Margin Reality 00:37:13 Using Facts to Change Decisions 00:38:27 Ownership Mindset in Growth Companies 00:39:10 VC vs. PE vs. Public CFO Tradeoffs 00:41:02 Operating Inside Constraints 00:42:18 Finding Your Stage Fit 00:44:17 Building a Personal Advisor Network 00:46:43 Visibility and Women in Leadership 00:47:44 Work–Life Integration, Not Balance 00:48:45 Lightning Round: Biggest Mistake 00:50:10 Advice to Younger Self 00:51:36 Finance Tech Stack 00:52:01 Craziest Expense Story 00:52:44 Credits #RunTheNumbersPodcast #CFOLeadership #ScalingCompanies #DataDrivenDecisions #ExecutiveLeadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Inside the Economics of Independent Creators | Mostly Growth | 27 Dec 2025 | 00:40:43 | |
Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowth Mostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102 Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3 In this year-end episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman reflect on what it actually takes to build a modern media business around newsletters and podcasts. They unpack CJ’s first year going full-time, comparing creative intuition versus metric-driven operating styles, and discuss what content truly drives growth. The conversation also covers distribution dynamics, the emotional reality of unsubscribes and burnout, and closes with a candid look at monetization, team building, and the tradeoffs between simplicity and scale. — SPONSORS: Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics 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 — LINKS: Mostly Metrics: https://www.mostlymetrics.com CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Growth Unhinged: https://www.growthunhinged.com/ Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/ Slacker Stuff: https://www.slackerstuff.com/ Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/ https://www.growthunhinged.com/p/deep-research-for-gtm https://www.growthunhinged.com/p/2025-state-of-b2b-gtm-report https://www.mostlymetrics.com/p/presenting-the-state-of-the-agentic-financial-stack https://www.mostlymetrics.com/p/the-great-ai-arr-illusion https://www.mostlymetrics.com/p/presenting-the-2025-tech-stack-report https://www.mostlymetrics.com/p/download-the-annual-planning-bible https://www.growthunhinged.com/p/how-to-sell-annual-plans https://www.growthunhinged.com/p/get-recommended-by-chatgpt https://www.growthunhinged.com/p/gtm-vibecoding-ideas https://www.growthunhinged.com/p/how-to-use-ai-agents-for-marketing — RELATED EPISODES: We get roasted for swag and drop some GTM gold Do vanity plates bring serious business? Pricing in the Real World: Babies, Bots, and Billing — TIMESTAMPS: 00:00:00 Preview and Intro 00:01:52 Sponsors — Pulley | Metronome 00:04:12 Action Figure Swag and Year-in-Review Setup 00:05:47 Going Full-Time and the First-Year Reality Check 00:07:24 Writing Schedules, Creative Work, and Time Optimization 00:09:16 Writing Speed, Craft, and the Myth That Time Equals Quality 00:10:51 Perfectionism vs. Throughput in Newsletter Writing 00:13:03 Creator Burnout, Motivation, and Engagement Anxiety 00:14:08 Playing the Long Game vs. Obsessing Over Metrics 00:15:42 Best Work of the Year and High-Leverage Content Bets 00:17:55 Big Research Reports as Career-Defining Projects 00:19:19 When Memes Outperform Deep Work 00:19:52 LinkedIn Algorithms vs. Content Quality 00:20:51 Writing for the Feed vs. Writing to Think 00:22:03 Optimizing LinkedIn Profiles for Credibility 00:23:47 Subscriber Growth, Audience Quality, and Churn Reality 00:27:20 Reports and Research as Growth Engines 00:28:37 Tactical “How-To” Content That Actually Converts 00:30:21 Tactical Value Beats Sounding Smart 00:30:40 Building a Team and Scaling Beyond a Solopreneur 00:32:05 Simplicity vs. Scale in Early Business Decisions 00:35:37 Avoiding Boredom and Shiny Object Syndrome 00:37:12 Balancing Writing, Consulting, and Energy 00:37:54 Making the Leap Financially as a Creator 00:39:01 Subscriptions vs. Advertising as the Real Business Model #MostlyGrowthPodcast #CreatorEconomy #IndependentCreator #NewsletterBusiness #YearInReview This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| The High-Stakes World of Consumer Marketplaces: John Connolly on Trends, Metrics, & Myths | 03 Apr 2025 | 00:48:31 | |
In this episode, CJ sits down with John Connolly, Managing Director at Spectrum Equity, to explore the evolution of consumer investing. They discuss how investor sentiment toward consumer companies has shifted over the past 15 years and why traditional SaaS metrics like net dollar retention (NDR) don’t always apply in this space. John explains what signals indicate a strong consumer business, whether brand or product wins in the long run, and how consumer companies have adapted their monetization strategies over the last decade. Plus, John shares the story behind Spectrum Equity’s investment in Teachers Pay Teachers and the craziest thing he’s ever done to land a deal. If you're looking for an ERP, head to NetSuite: https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. — SPONSORS: Subscript is a modern billing and revenue recognition platform designed for SaaS finance teams that need flexibility and accuracy. From automated invoicing and dunning to compliant, transparent revenue recognition and real-time analytics, Subscript eliminates manual work, reduces errors, and gives you a single source of truth for all your financial data. Book a free demo at subscript.com. Rippling Spend is a spend management solution that handles your entire company’s spending in one unified system. It enables you to bring your corporate cards, expense management, bill pay, and more into one place to achieve real-time visibility and uniquely granular control with automated policy controls across every type of spend. Get a demo to see how much time your org would save at rippling.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. From spotting hidden optimization opportunities to automating painful procurement workflows and giving you the best market data to turn vendor negotiations in your favor, Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:32) Sponsor – Subscript | Rippling Spend | Vanta (06:04) The Evolution of Investing and Defensibility (08:50) Cooling Investor Appetite for Consumer Businesses (10:13) Efficiency Metrics for Consumer Businesses (12:24) How To Navigate Retention and Churn (14:12) Sponsor – Tropic | NetSuite | Planful (17:47) When Churn Is Necessary (19:15) Increasing TAM in Consumer Businesses (21:13) The Most Important Metric: Funnel Health (24:08) Celebrity Partnerships as a Competitive Mode (25:05) Why Brand Is Even More Important in B2C Than B2B (26:25) The Strongest Brands John Has Invested In (28:23) Changes in How Companies Monetize Over the Past Decade (29:52) Using the Supply Side To Bring You Demand (34:02) How COVID-19 Wreaked Havoc on Consumer Trends (38:11) Evaluating Consumer Businesses (39:04) The Craziest Thing John Has Done To Win a Deal (40:56) How To Pitch to Bootstrapped Founders (43:00) The Revolutionary Teachers Pay Teachers Marketplace (46:18) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Stripe rips, Plaid falls, and Wiz gets PAID... State of the Private Markets (March) | 29 Mar 2025 | 00:11:37 | |
On this episode of Run the Numbers we’ll cover the state of the private tech markets. * Did Google overpay for Wiz? * Stripe’s valuation is (nearly) back up to their COVID high water mark * Plaid shares fall in secondary market * Figma is growing into it’s valuation * The Rippling and Deel (hilarious) controversy You can get this in written form at mostlymetrics.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| The Startup Shutdown Playbook: How to Succeed in Closing a Company | 27 Mar 2025 | 01:03:23 | |
While few plan for the demise of their startup, it’s something that many face. In this episode, CJ is joined by Dori Yona, co-founder and CEO of SimpleClosure, to unpack the financial, legal, and emotional complexities of shutting down a company. Dori explains the options available when a company is running out of cash, what bankruptcy actually means, and the importance of budgeting for the end. The conversation covers acqui-hires, dissolution, returning capital to investors, hidden liabilities, legal pitfalls, tax implications, and more. Dori breaks down the differences between shutting down corporations versus LLCs and the timelines involved. They also discuss how to break the news to investors and why perseverance is sometimes overrated. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. — SPONSORS: Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) @DoriYona https://x.com/doriyona (Dori) LINKS: SimpleClosure: SimpleClosure.com LinkedIn: https://www.linkedin.com/in/dori-yona-b8369877/ Email dori@simpleclosure.com — TIMESTAMPS: (00:00) Preview and Intro (01:44) Sponsor – Tropic | NetSuite | RightRev (05:32) The Inspiration Behind SimpleClosure (08:25) Three Scenarios When a Company Is Running Out of Cash (11:32) The Complications of Shutting Down a Business After Selling It (13:38) What Bankruptcy Actually Means and the Different Types (16:34) Sponsor – Planful | Brex | Vanta (20:16) Giving Money Back to Investors and the Pref Stack (24:31) How To Budget for a Shutdown (27:15) The Time It Takes To Shut Down a Business (29:24) SimpleClosure’s Business Model: Serving Customers That Churn (32:00) The Velocity of SimpleClosure’s Transactions (36:09) What “Piercing the Corporate Veil” Means (41:27) Shutting Down Corporations Versus LLCs (45:36) The Seasonal Nature of Startups Shutting Down (47:49) Communicating a Shutdown to Your Investors (54:35) Knowing When To Persevere and When To Move On (59:53) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| The Art of Stacking S-Curves: Olo’s Winning Vertical SaaS Strategy with CFO Peter Benevides | 24 Mar 2025 | 01:02:54 | |
In this episode, CJ is joined by Peter Benevides, CFO of Olo, a leading vertical SaaS company powering digital ordering, payments, and guest engagement solutions for popular restaurant brands. Peter explains how Olo successfully expanded into payments and used this as a strategic advantage. He breaks down how the company stacks S-curves through continued product expansion and adoption, and how this enables them to increase revenue without increasing the take-rate. The conversation also covers pricing strategy and how Olo balances subscription and consumption-based models. Peter also sheds light on what it's like selling into franchise businesses and lessons learned from other vertical SaaS companies like Veeva. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:53) Sponsor – NetSuite | RightRev | Planful (05:24) An Introduction to Olo (08:34) Reaching Larger and Smaller Enterprises (10:34) The Focus on Guest-Facing Technology (13:22) The Evolution of Payments at Olo (16:38) Sponsor – Brex | Vanta | Tropic (20:33) The Card-Not-Present Offering and Fraud (23:50) Knowing Who Your Guest Is and Olo’s Extended Value Prop (32:04) Stacking S-Curves (33:30) Increasing Revenue Without Increasing the Take-Rate (36:27) How the Payments Module Makes Other Products Stickier (37:39) Advice to CFOs Looking to Add Payments (39:11) Pricing Subscription and Consumption-Based Products (42:35) Forecasting and the Predictability of This Model (44:43) Vertical Software Company Case Study: Veeva (49:06) Working with Franchises (53:42) Long-Ass Lightning Round: Planning for the Future (56:16) Advice to Younger Self (58:48) Finance Software Stack (59:24) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Klarna IPO: S1 Breakdown | 22 Mar 2025 | 00:27:08 | |
Klarna, the Swedish fintech powerhouse, is going public on the NYSE (ticker: KLAR).This marks a major moment for the Buy Now, Pay Later (BNPL) space. This IPO will test whether investors believe BNPL is a smarter alternative to credit cards—or another form of subprime lending in disguise.A few years ago, Klarna was worth $46B in private markets. Now? It’s eyeing a $15B-$20B valuation—a stark reminder of how fintech sentiment has shifted in a world of higher interest rates.7 Key Themes:1️⃣ Klarna is going public at a fraction of its peak valuation.2️⃣ AI-driven cost cutting (automated customer service, AI-powered CRM) is improving margins.3️⃣ Klarna’s banking license is an advantage, but deposit growth is slowing.4️⃣ The US is now Klarna’s largest market, but credit losses there are rising.5️⃣ Klarna is morphing into an advertising & payments platform (ads = 6% of revenue).6️⃣ Internal controls raise red flags (issues with user access, revenue recognition, and credit loss estimates).7️⃣ Insiders & VCs have already cashed out >$800M pre-IPO.Valuation Debate:🚀 Bull case: Klarna transitions into a broader fintech platform, scaling ads and banking services.🏛️ Base case: Klarna remains a profitable BNPL, but growth slows due to regulation.📉 Bear case: Klarna gets valued like a consumer lender, with rising credit losses and shrinking margins.Klarna’s IPO will be a key test for fintech. If it pops, it could reopen the IPO window for names like Chime, Revolut, and (maybe someday) Stripe.Does Klarna deserve a premium multiple, or is it just a fancy lender?Let’s hear it—bull or bear? 🐂📉Get the full breakdown on the IPO at mostlymetrics.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Red Flags & Big Wins: Lucas Swisher on What Makes Coatue Say Yes (or No) to an Investment | 20 Mar 2025 | 00:55:58 | |
In this episode, CJ interviews Lucas Swisher, Co-Lead of Growth Investing and Software Investing at Coatue, to explore how one of tech’s most influential investment firms navigates both public and private markets. Lucas explains Coatue’s evolution—from hedge fund origins to a powerhouse in venture capital—and how the company balances short-term public market pressures and long-term private investments. The conversation takes a dive deep into data-driven decision-making and how Coatue’s proprietary Mosaic platform provides an edge while still leaving room for human intuition. They also discuss the firm’s investment philosophy, what differentiates them from other investment companies, and why they choose to have such a concentrated portfolio of investments. Lucas sheds light on how they evaluate the sustainability of a small software company's unit economics, the most important metric that they look at, and other important factors and red flags that often get overlooked when choosing where to invest. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:18) Sponsor – RightRev | Planful | Brex (06:15) Lucas’s Role at Coatue (07:58) The Evolution of Coatue’s Investment Strategy (11:36) Growth-Stage Private Assets Versus Public Markets (14:18) Balancing Short-Term Public Investing and Long-Term Patience of Private Markets (16:07) Sponsor – Vanta | Tropic | NetSuite (19:50) The Service Business at the Core of Coatue’s Growth Investing (22:08) Coatue’s Mosaic Platform and Due Diligence (26:29) How Mosaic Helps Coatue Get to No Faster (28:05) Creating a Concentrated Portfolio of Investments (30:40) Coatue’s Edge Versus Firms with Other Investment Philosophies (37:20) How the Best Investment Firms Differentiate Themselves (41:14) Assessing the Sustainability of a Small Software Company’s Unit Economics (44:12) Evaluating Enterprise SaaS Versus Consumer Software (46:21) The Next Buyer Scenario (48:53) Prediction for Coatue’s Future Structure and Strategy (50:34) What Growth Stage Companies Should Look for in an Investor (52:29) Advice for the Next Generation of Investors This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| 21 Million Customers: The Two Keys to Long-Term Tech Success with GoDaddy CFO Mark McCaffrey | 17 Mar 2025 | 00:55:47 | |
Mark McCaffrey, the CFO of GoDaddy, joins CJ to talk about the evolution of one of the most recognizable brands on the internet from domain registration to a full-service platform for small businesses. Mark sheds light on GoDaddy’s role in the entrepreneurial micro-startup ecosystem and how, after 21 years, GoDaddy has grown to 21 million customers. He describes the trends he’s identified in the formation of micro businesses, their adoption of AI, their survival rates, and why churn caused by failing small businesses doesn’t affect GoDaddy as much as you think it would. He also talks about the metrics that matter, what he tracks, what he discloses, and how he uses this to pursue customers with intent. He also explains how to not lose sight of the micro when the macro is so big, and lists the two things every company in the tech industry needs to do to achieve long-term success. Spoiler: one has to do with customer relationships. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:54) Sponsor – Planful | Brex | Vanta (06:16) GoDaddy and the Entrepreneurial Micro-Startup Ecosystem (07:40) The Origins of the GoDaddy Name (09:08) GoDaddy’s Business Model and its Evolution (11:45) The Strategic High Ground of Starting with the Domain (12:58) Definition of a Micro-Business (15:32) Sponsor – Tropic | NetSuite | RightRev (19:15) The Mostly Metrics Domain Name (21:50) Unsuccessful Businesses and Churn at GoDaddy (27:07) Surprises from GoDaddy’s Data (29:20) Customer Trends in Openness to AI (30:45) Determining Which Metrics Matter and Which to Disclose (34:31) Pursuing Customers with Intent (35:44) When and How Mark Introduces a New Metric (38:25) ARR Versus Bookings (39:25) Retention Trends (41:06) Two Things to Do in the Tech Industry for Long-Term Success (45:47) How the Power of Relationships Led Mark to GoDaddy (49:08) Long-Ass Lightning Round: Excel Spreadsheets (49:44) Three Rules for Every Young Professional (51:02) Finance Software Stack (52:11) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| The Business of Mostly Metrics. Part I. | 15 Mar 2025 | 00:14:32 | |
Welcome to the first episode on The Business of Mostly Metrics. The CFO became a CEO. Pretty wild. The CEO of me. During this series we’ll cover the following topics: * Writing your story in reverse, which is what today is about * How I lost $209,640 of my own money trying to start a marketplace business * Quitting a job to be able to keep writing, leaving a million dollars of equity on the table, and getting my first CFO job * Decoding my timeline from 0 to 50,000 subscribers and the tactics I used along the way to keep stacking wins * How I monetize my business across sponsorships, paid subscriptions, and events * Starting the podcast and climbing the guest ladder * Where this might all go next * And if you’re,, lucky I’ll tell you how much this business makes So let’s go back through all these things that I’ve done to get to this point. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Taking Criticism Like a Pro: Airtable's Ambereen Toubassy on Investor Feedback and Curiosity | 13 Mar 2025 | 00:59:41 | |
Ambereen Toubassy, the CFO of Airtable, has experience as an advisor, an investor, and an operator. In this episode, she joins CJ to talk about how this experience informs her role as a CFO. The two delve into the complexities of navigating investor feedback and how to take criticism without getting defensive. They also discuss how to build the right advisory network, red flags to watch for, and the importance of scaffolding your weaknesses with external expertise. The episode also highlights the value of specificity in the role of a finance leader. Ambereen shares insights from her extensive career, including her time at Quibi, explaining what she learned from this moonshot idea that didn’t work out as hoped and her approach to balancing fiduciary duties with the human side of leadership. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how MUFG is the largest bank in Japan and a global banking powerhouse with a focus on empowering Growth and Middle Market stage companies in North America and Europe. MUFG provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. The bank combines its global capabilities with deep operational understanding to help companies accelerate their growth trajectory. Contact group head Bob Blee at bblee@us.mufg.jp to find out more. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:25) Sponsor – Brex | Vanta | Tropic (06:55) What Ambereen Has Learned from Being an Investor (10:53) Dealing with Investor Feedback (18:09) Sponsor – MUFG | NetSuite | RightRev | Planful (22:54) Tips for Not Taking Feedback Personally (24:12) When to Bring Founders into Meetings with Investors (25:52) Scaffolding Your Weaknesses (30:59) Whether or Not to Pay More for Great Advisors (34:12) How to Identify the Right Banker or Consultant (35:13) Banker and Consultant Red Flags to Watch Out For (39:11) “In the Particular Is Contained the Universal” (42:42) How the Specific Plays a Role in the Job of a Finance Leader (46:46) Quibi, the Moonshot Idea That Didn’t Land as Planned (50:16) Fiduciary Responsibility When Things Don’t Go as Planned (55:00) Long-Ass Lightning Round: A Career Mistake (55:48) Advice to Younger Self (57:14) Finance Software Stack (58:26) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Uncovering Blind Spots and Other Lessons from High-Growth Companies with Five-Time CFO David Lapter | 10 Mar 2025 | 01:11:12 | |
In this episode, Dashlane’s David Lapter, a five-time CFO, joins CJ to discuss the challenges of steering high-growth companies. He breaks down the common blind spots that CFOs face, why many double down on their strengths and avoid their weaknesses, and how the Eisenhower Matrix helped him tackle his own gaps. David also gives his take on competitors and his philosophy of differentiating your org from theirs without demonizing them, as well as how they can be used for motivation. David shares insights on building high-functioning teams, when teams should move from overlapping responsibilities to more defined roles, how to simplify your OKRs to be more effective, and the nature of the ideal HR-CFO relationship. This episode is packed with valuable takeaways for finance leaders navigating the complexities of high-growth environments. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS:(00:00) Preview and Intro (01:52) Sponsor – Vanta | Tropic | Netsuite (06:18) Identifying Blind Spots (10:44) Hiring to Fill Your Blind Spots (14:21) The Eisenhower Matrix and Prioritising Your Blind Spots (17:15) Sponsor – RightRev | Planful | Brex (20:58) The Traps of Execution Mode Syndrome (26:37) David’s Philosophy on Speaking About Competitors (31:09) Tips for Communicating How You’re Differentiated (33:02) How Competitors Can Motivate Teams (39:46) When to Move from Overlapping Responsibilities to More Defined Roles (46:50) Simplifying OKRs (52:16) The Urge to Copy the Goal Setting of Other Companies (54:56) Should HR Report to the CFO? (57:57) Long-Ass Lightning Round: A VAT Mistake (01:00:21) Advice to Younger Self (01:03:32) Finance Software Stack (01:06:14) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Capital Spoilage and Leakage: A CFO’s Guide to Finding What’s Lost | Mostly Classics | 25 Dec 2025 | 00:57:17 | |
[Original air date: June 5, 2025] How can finance leaders identify where their capital is silently going to waste and where it can be better used to drive growth? In this episode, CJ interviews Russell Lester, the CFO of Tropic, where capital allocation is both the product and the mission. Russell introduces the concept of “spoilage”, deployed capital that fails to deliver its intended value. He also talks about “levers”, positive actions that force multiply your efforts, and “leakages”, headwinds or detractors that sap momentum. Russell believes it is the job of the CFO (or “Chief Alignment Officer”) to proactively go looking for these levers and leakages. He then explains how he uses his “center of the table” framework to redeploy the freed-up capital to fuel growth. Russell also covers how to address misalignment, what helicopter skills are and why you need them, what a data safari is and why you should take one daily, and why every CFO needs a spend management tool. — SPONSORS: Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more. Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off. Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHt Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo. — LINKS: Russell on LinkedIn: https://www.linkedin.com/in/russell-lester-aa98463/ Tropic: https://www.tropicapp.io/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: Wasted Capital and Where to Find It The CFOs Guide to Spoilage Levers Leakages — TIMESTAMPS: 00:00:00 Mostly Classics: Russell Lester on Capital and Alignment 00:00:48 Sponsors — Tipalti | Aleph | Fidelity Private Shares 00:04:07 Russell Lester Joins the Show 00:06:45 Capital Spoilage and Wasted Spend 00:08:34 Why Spoilage Goes Unnoticed Inside Companies 00:10:16 Creating Accountability for ROI 00:11:08 Spoilage Beyond Tools and Software 00:13:04 Strategy Drift and the Sunk Cost Trap 00:14:14 Sponsors — Sage Intacct | Mercury | RightRev 00:17:44 Levers and Leakages: A Framework for Momentum 00:19:27 Identifying Levers Across the Funnel 00:21:48 Efficiency Levers Inside the P&L 00:23:31 Common Spend Leakages in Practice 00:24:21 The Center of the Table Framework 00:26:47 Budget Ownership vs Corporate Stewardship 00:28:49 The CFO as Chief Alignment Officer 00:31:31 Trust, Tact, and Executive Leadership 00:33:35 Helicopter Skills for Finance Leaders 00:35:41 Curiosity as a CFO Superpower 00:36:02 Data Safaris and Asking Better Questions 00:38:16 Breaking Down Net Dollar Retention 00:40:32 Navigating Data Overload 00:42:16 Building a Single Source of Truth 00:43:03 Intelligent Spend Management in Action 00:44:44 Capital Allocation as the CFO’s Core Job 00:46:04 How Spend Management Drives Growth 00:49:14 Why Companies Delay Spend Tools 00:50:49 A Career Mistake with Investors 00:52:49 Auto-Renewals: Revenue vs Leakage 00:54:07 Advice to a Younger CFO #RunTheNumbersPodcast #CFOLeadership #CapitalAllocation #FinancialStrategy #SpendManagement This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| CoreWeave IPO: A Future Giant or Just WeWork with GPUs? | 08 Mar 2025 | 00:24:49 | |
This is the CoreWeave IPO breakdown. I studied their S1 filing so you don’t have to. What we’ll cover: * What CoreWeave does * Their business model * Their financials * Key themes heading into IPO * Investors * Bull, Bear and Base cases for the stock This is not investment advice. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Eliminating Operational Inefficiencies with Hanan Aharoni of Operative | 06 Mar 2025 | 01:00:13 | |
In this episode, CJ interviews Hanan Aharoni, CFO of Operative, who is an expert in operational excellence, particularly in private equity. Hanan shares insights on managing acquisitions and overcoming silos, inefficiencies, and decision paralysis in the process. He highlights the importance of having a clear org chart and a unified leadership team before discussing the critical role of culture in successful integrations. He breaks down how to spot inefficiencies, consolidate systems, and optimize costs without stifling innovation. He also sheds light on how the private equity model differs from the venture capital model in terms of allocating resources, managing debt, and being prepared for an exit or sale. This is a masterclass in private equity operations. — SPONSORS: Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: 00:00 Preview and Intro 01:50 Sponsor – Tropic | Netsuite | RightRev 05:55 Hanan’s Impressive Career Rise to CFO 08:20 Overcoming Silos and Inefficiency When Scaling 10:46 Overcoming Inefficiency and Paralysis in M&A 15:50 Sponsor – Planful | Brex | Vanta 19:18 The Importance of Having a Clear Org Chart 22:07 “Vision Without Execution Is Just Hallucination” 25:33 Operational Excellence: Identifying Inefficiencies and Optimizing Costs 28:40 Acknowledging Biases 29:40 Using Industry Benchmarks 32:20 Balancing Optimizing Expenses and Preserving Innovation 35:16 Forming a Mitigation Plan 41:09 Areas Notorious for Inefficient Costs 42:56 Allocating Resources in a PE Model Versus a VC Model 45:57 How Debt Impacts How You Operate in PE 49:12 Tips for Finance Professionals Moving from VC to PE Models 50:48 Being Prepared for an Exit or Sale in a PE Environment 53:00 Long-Ass Lightning Round: A Massive Excel Spreadsheet Error 54:53 Advice to Younger Self: Fast Decisions 55:17 Finance Software Stack 55:55 Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| From Massive Corporate to Tiny Startup: Foodics CFO Abdullah Tahboub on Making the Leap | 03 Mar 2025 | 00:52:09 | |
Today’s guest went from being the CFO of a very large telecom company where he was meeting with ministers in Jordan to joining a team of just four people at a startup in Saudi Arabia. Abdullah Tahboub, CFO of Foodics, a cloud-based POS and restaurant management solution, joins CJ to talk about this leap and explain why he wishes he had joined the startup world sooner. The conversation delves into the differences between corporate and startup CFO roles. Abdullah also explores the rapid digital transformation in the food and beverage industry in the Middle East. He outlines Foodic's business model and evolution from cashier systems to payments, becoming a comprehensive fintech and SaaS company. He provides insights into the crawl-walk-run process of this business and how he balances growth in both the SaaS and payments aspects of the org. — SPONSORS: NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: 00:00 Preview and Intro 02:27 Sponsor – RightRev | Planful | Brex 06:10 Abdullah’s Bold Career Move & Why CFOs Avoid Risks 09:56 Being a Corporate World CFO Versus a Startup CFO 16:03 Digital Transformation in the Food and Beverage Industry 17:54 Sponsor – Vanta | Tropic 21:38 Food & Beverage and Tech in the Middle East and North Africa 24:24 The Evolution of Foodics’ Business Model 31:35 How Lending Works in This Industry 34:55 Balancing Growth in SaaS and Payment Revenue Streams 37:21 Forecasting for Payments 40:30 Staffing for Both SaaS and Payments 42:27 The Most Difficult Part of Adding Payments 45:34 Long-Ass Lightning Round: Dealing with Underperformers 47:39 Advice to Younger Self 48:22 Finance Software Stack 49:03 Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| State of the Private Tech Markets (February) | 28 Feb 2025 | 00:13:26 | |
State of the Private Markets delivers an insider’s look at the forces reshaping the pre-IPO landscape. In this episode, we break down the latest valuation surges and hiring trends, spotlight key moves from tech giants in security, HR tech, and legal automation, and dive into company updates from Wiz, Harvey, and Deel. We also cover major fundraising rounds and notable executive shifts that signal where the market is headed. Tune in for an in-depth analysis of the trends and shifts driving today’s private markets. Thanks to our sponsor Netsuite. Visit netsuite.com/metrics for the CFO’s guide to machine learning. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| The Era of “I Need a COO and a CFO” Is Over: Jim Cook on the Next Evolution of the CFO | 27 Feb 2025 | 01:02:18 | |
Jim Cook, Netflix co-founder, former CFO of Mozilla, early employee at Inuit, executive coach, and author of Substack Cook’s Playbooks, returns to the podcast for the third time. In this episode, he breaks down the evolution of the role of CFOs from traditional scorekeepers to more strategic and operator roles, before looking ahead at what’s to come. This episode is packed full of helpful advice about transparency, building trust, authenticity in your executive role, and why “fake it till you make it” is actually bad advice. Looking at the future of the CFO role, Jim explains why he believes there will be no need for both COO and CFO roles in an organization, the biggest mistake a CFO can make at this time, and how CFOs should be adapting in order to succeed in this next era. — SPONSORS: Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. — FOLLOW US ON X: @cjgustafson222 (CJ) LINKS: — TIMESTAMPS: (00:00) Preview and Intro (01:37) Sponsor – Planful | Brex | Vanta (05:49) CJ’s Career Growth Since First Interviewing Jim (08:35) Making Finance Transparent (14:40) Sponsor – Tropic | RightRev (17:07) The Influence of Bill Campbell (18:57) How to Get to Trust Faster (20:32) Letting Your Freak Flag Fly in Your Executive Role (23:06) Is “Fake It Till You Make It” Bad Advice? (25:25) Why CFO Tenures Are Getting Longer (28:16) The Evolution of the CFO Role and Technological Capability (32:45) Scorekeeping and Actuals Don’t Matter Anymore (34:38) The Era of the Strategic CFO (36:48) SaaS and the Operator CFO Era (41:09) Jim’s Prediction on the Next Era: The CFO Architect (49:47) The Biggest Mistake We Could Make in This Era (51:48) The Era of, “I Need a COO and a CFO,” Is Over (55:41) Where a CFO Will Spend Most of Their Time in This Next Era This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Investors vs Operators: Aidoc’s Arvind Kadaba on the “Grass Is Greener” Trap and How to Escape It | 24 Feb 2025 | 01:02:53 | |
Today’s guest, Arvind Kadaba, the CFO of Aidoc, started his career as a high-profile investor before transitioning into the role of a CFO. He joins CJ to share his career journey and discuss the challenges he faced in transitioning into an operational role. The conversation explores the “grass is always greener” mentality that drives career shifts, and how to find the right career fit. Arvind describes the evolving landscape of healthcare technology and AI. He emphasizes the need for innovation and how to choose whether to build, buy, or partner to achieve this, giving listeners a masterclass in portfolio theory for operators. He also gives helpful tips for balancing short-term and long-term investments and explaining long-term shareholder value to employees. The episode concludes with Arvind defending his contrarian views that not all businesses should be venture-backed and not all great businesses are tech businesses. — SPONSORS: Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:21) Sponsor – Brex | Vanta | Tropic (06:59) Transitioning from Investor to Operator (11:13) The Problem-Specific Nature of Being an Operator (14:29) Sponsor – RightRev | Planful (16:39) Personal Product Market Fit (23:18) “All You Need Is One” (25:46) How Arvind Decided to Switch Careers (33:07) The State of Healthcare Technology in AI (36:05) Innovation: Build Versus Buy Versus Partner (37:36) Portfolio Theory for Operators (44:36) Explaining Long-Term Shareholder Value to Employees (47:50) Not All Businesses Should Be Venture-Backed (53:38) Not All Great Businesses Are Tech Businesses (57:03) Long-Ass Lightning Round: Cross-Functional Trust (58:04) Finance Software Stack (58:54) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Stripe, Klarna, & the Fintech Resurgence—What’s Driving Valuations? | 22 Feb 2025 | 00:11:00 | |
Fintech Is Back: What’s Driving Valuations & Back-Office Convergence Fintech is making a comeback, and the private markets are shifting fast. In this episode, we break down the biggest fintech moves—from Stripe’s $85B valuation jump to Klarna and Chime’s rumored IPOs—and explain why investors are paying up for some business models while discounting others. Plus, we dive into a major shift in back-office software: HiBob’s acquisition of Mosaic signals a growing convergence between HR and finance, with implications for the future of ERP. Is the back-office stack consolidating into a new source of truth? Topics we cover:✅ Why Stripe commands a 20x revenue multiple, and Mercury’s latest fundraise✅ Klarna vs. Chime: Who will get the better IPO valuation?✅ Affirm’s comeback—does it validate BNPL’s future?✅ The next evolution of back-office SaaS: HR meets FP&A If you're a founder, operator, or investor in fintech or SaaS, this episode is packed with insights on positioning for the highest valuation. 🎧 Listen now and don’t forget to rate & review—first round’s on me if we ever meet in person. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Inside Grab: How a Super App Transformed Southeast Asia — with CFO Peter Oey | 20 Feb 2025 | 00:48:00 | |
This episode takes a deep dive into the business model of super app Grab as CJ interviews CFO Peter Oey. Peter introduces listeners to Grab and how it operates in Southeast Asia, highlighting the company’s journey from a ride-hailing service to acquiring Uber's operations in the region, expanding into food delivery, and even branching into banking services, all in one single super app. Peter explains why this model thrives in Southeast Asia and speculates on its potential in Western markets. He sheds light on the flywheel effect of branching into banking services, how they get customers to use Grab’s different products, and the advertising opportunities that exist for the platform. He also discusses how Grab has positively affected economic activity in the region and shares one customer’s incredible success story. The podcast concludes with insights into Grab's proprietary technology, including its unique mapping system, and advice for Western companies looking to enter the Southeast Asian market. — SPONSORS: Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:15) Sponsor – Vanta | Tropic | RightRev (05:54) Super Apps and Grab’s Business Model (11:16) Why the Super App Model Thrives in Southeast Asia (15:33) The Super App Model and Western Markets (17:03) Sponsor – Planful | Brex (19:16) The Role of Banking Services in Grab’s Business Model (23:05) The First Step to Becoming a Fintech (25:05) Getting Users to Use Multiple Grab Products (30:31) The Advertising Opportunity for Grab (32:14) Why Southeast Asia Is Overlooked as a Tech Hub (35:30) Advice to Western Tech Companies Operating in Southeast Asia (37:15) How Grab Increases Economic Activity (40:51) A Grab Success Story (41:45) Grab’s Proprietary Tech and Mapping System (45:43) Long-Ass Lightning Round: A Forecast Accuracy Error This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Scoring Big: The Playbook for Nonprofit Financial Success with USA Hockey CFO Kelly Mahncke | 17 Feb 2025 | 00:43:47 | |
In this episode, CJ is joined by Kelly Mahncke, the CFO of USA Hockey, and the first CFO of a nonprofit to come on the show. They discuss the organization's business model and its revenue streams. Kelly emphasizes the importance of having a successful business whether it’s a nonprofit or not, and what she means when she says that there's no mission without margin. The conversation also covers USA Hockey's efforts to balance grassroots development with elite programs, the role of data and technology in enhancing operations, and the challenges of making hockey accessible to underprivileged communities. Kelly shares insights into the financial management of USA Hockey, including the for-profit and nonprofit aspects of the business, and how the four-year cadence of the Winter Olympics affects annual planning. — SPONSORS: Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:00) Sponsor – Tropic | RightRev | Planful (06:23) The Companies Under the USA Hockey Umbrella (07:50) Balancing Investing in Grassroots Development and Elite Teams (10:01) USA Hockey’s Revenue Streams (11:14) USA Hockey’s Data and IT (13:07) Learnings from USA Hockey’s Data and Analytics (16:38) Sponsor – Brex | Vanta (19:10) Why Kids Should Try Different Sports (20:03) Anecdotes About Hockey Players (21:56) No Mission Without Margin (23:40) The Most Surprising Line Items in USA Hockey’s Budget (24:32) How the Winter Olympics Affects Annual Planning (26:12) For-Profit Money in the Space (29:14) The Business of Rink Ownership (32:54) Making Hockey Accessible to Underprivileged Communities (35:30) The For-Profit and Nonprofit Aspects of USA Hockey (36:56) How Being a Nonprofit Impacts Hiring and Volunteers (39:31) Lightning Round: Advice to Younger Self (40:04) Technology at USA Hockey (41:30) Finance Software Stack (42:20) The Legacy Kelly Hopes to Leave This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| How much revenue do you need to IPO in 2025? | 15 Feb 2025 | 00:09:36 | |
How Much Revenue Do You Need to IPO in 2024? The IPO bar has risen—big time. In the 2010s, companies like RingCentral and Etsy went public with $100M-$250M in revenue. But today? You likely need $500M+ just to get a shot. We’ll break down how IPOs evolved from the SaaS boom to the 2021 mega-deals (think Coinbase, Snowflake, and Airbnb), the 2022-23 freeze, and why 2024’s IPO class—Reddit, Klaviyo, Instacart—looks different. Plus, we’ll preview 2025’s biggest potential IPOs, including Stripe, Databricks, and Deel. What’s the new rule? If you want to IPO, bring half a billion in revenue—or a damn good reason why you deserve to be public. Visit mostlymetrics.com for more analysis like this This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| From CFO to Founder: Inside the Making of Mostly Media | Paul Stansik Interviews CJ | 22 Dec 2025 | 00:56:55 | |
In this special, table-turning episode of Run the Numbers, CJ Gustafson steps out of the host’s chair as Paul Stansik—Operating Partner at ParkerGale and author of the Hello Operator newsletter—takes over the interview. What began as a planned discussion on annual planning best practices quickly evolves into a candid deep dive on Mostly Media, CJ’s growing niche B2B media business, and the thinking behind his own operating plan for the year ahead. Fresh off exiting his CFO role in January 2025, CJ walks through the origin story of Mostly Metrics, how it scaled into a broader media platform, and what it’s like being “the boss of me” for the first time. Paul presses on the real questions—growth opportunities, monetization, and strategic tradeoffs—making this episode a transparent look at how a modern, metrics-driven media business is built and run. — SPONSORS: RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo. Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more. Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off. Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHt Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com — LINKS: Paul on LinkedIn: https://www.linkedin.com/in/paulstansik/ Hello Operator: https://hellooperator.substack.com/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: Portfolio Operations: This Is What You Actually Have To Do To Make Sure a Company Is Successful Grindr’s $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantz Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillips — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:10 Sponsors — RightRev | Tipalti | Aleph 00:06:23 Episode Setup and Context 00:07:22 Why This Episode Exists 00:08:44 The Origin Story 00:10:03 First Signs of Traction 00:10:26 Memes, Early Growth, and “Big Ballers” 00:12:01 Defining the Brand Feel 00:13:28 Leaving a Job to Write 00:15:07 Writing His Way to CFO 00:16:26 Sponsors — Fidelity Private Shares | Sage Intacct | Mercury 00:19:01 Growth Tactics That Worked 00:21:31 First Monetization Moment 00:22:13 Balancing CFO Life and Media 00:24:06 Going All-In on the Business 00:25:02 A CFO Lens on Media 00:28:09 Asset Businesses vs Cash Flow 00:31:35 How the Business Makes Money 00:32:42 Revenue Compounding Over Time 00:33:29 Scaling to $3M 00:34:08 Partnerships and Buying Cycles 00:36:19 Building the Core Team 00:39:09 Adding Recruiting to the Mix 00:41:01 Strategy for the Next Phase 00:42:03 Boredom, Discipline, and Craft 00:43:08 Defining the Core Audience 00:46:09 Staying in the Game 00:47:22 Advice for Creators 00:49:15 Brand, Fun, and Value 00:52:08 Following the Momentum 00:53:14 Finding Your Unique Edge 00:55:19 Enjoying the Build 00:56:25 Closing and Outro #RunTheNumbersPodcast #creatoreconomy #mediabusiness #cfoperspective #buildinpublic This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| From CF-No to CF-Go: Serial CFO Michael Bayer’s Guide to Hypergrowth | 13 Feb 2025 | 00:53:36 | |
Serial CFO Michael Bayer, who is currently the CFO of Wasabi, joins CJ to share wisdom from his long career. He talks about his journey from being a “CF-no" to becoming a “CF-go” while emphasizing the importance of strategic investment to fuel hypergrowth companies. He breaks down the epochs of growth that a company goes through as it scales from driving revenue to focusing on cash flow. He highlights the significance of order of magnitude thinking and hiring for future needs. Michael also introduces his “rock-turning” exercise for identifying and addressing issues when joining a company, and shares his three guiding principles: speed is God, best ideas win, and if you’re not making mistakes, you’re not trying hard enough. The episode concludes with an insightful story about Van Halen's "brown M&M" clause, and what finance leaders can learn from it. — SPONSORS: RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:16) Sponsor – RightRev | Planful | Brex (06:02) The Reason for a Sloth Background (08:31) A Company’s Epochs of Growth (12:52) Staffing for the Different Epochs of Growth (17:08) Sponsor – Vanta | Tropic (21:29) The CF-No Versus CF-Go Mentalities (23:42) The “Rule Of” Metric: EBITDA or Cash Flow (27:05) The Rock-Turning Exercise (29:12) The First Rock Michael Turns Over (30:26) Forming Relationships Before Solving Problems (32:08) The Time Factor in Becoming a Good CFO (36:01) Michael’s Three Simple Rules for Being a Great CFO (38:45) Creating Space for the Best Ideas (41:18) What It Means to “Rent Capital” (47:25) The Brown M&M Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| How Upwork CFO Erica Gessert Drove 20 Points of EBITDA Growth in Just 3 Quarters | 10 Feb 2025 | 00:56:27 | |
Erica Gessert, CFO of Upwork, and former Senior Vice President of Finance & Analytics at PayPal, joins CJ for this episode. They discuss Erica's experience with forecasting models at PayPal, emphasizing the need for adaptable models that change with economic conditions. Delving into her role at Upwork, Erica explains the company’s approach to customer acquisition costs, the significance of network effects in marketplace businesses, and Upwork’s take rate strategies. The conversation covers Upwork’s investment in R&D, how the company maintains platform trust in the face of bad actors, and the impact of AI. Apart from explaining how Upwork gained 20 points of EBITDA in just three quarters, Erica also sheds light on their North Star metrics, how they balance growth and profitability, their approach to M&A, and her experience reporting to Masayoshi Son during her time at Sprint. — SPONSORS: Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. MUFG is the largest bank in Japan and a global banking powerhouse with a focus on empowering Growth and Middle Market stage companies in North America and Europe. MUFG provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. The bank combines its global capabilities with deep operational understanding to help companies accelerate their growth trajectory. Contact group head Bob Blee at bblee@us.mufg.jp to find out more. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:30) Sponsor – Planful | MUFG | Brex (06:17) Budgeting at PayPal (10:23) Forecasting Methodologies at PayPal (13:15) The Impact of the Calendar on Forecasting (15:01) Forecasting and Macroeconomic Indicators (16:29) Planning Will Take as Long as the Time You Allot for It (17:56) Surprising Insights About Freelancers (19:26) Sponsor – Vanta | Tropic | RightRev (24:55) Upwork’s Customer Acquisition Cost (27:59) Freelancers and AI Adoption (29:07) Network Effects in Upwork’s Model (31:14) Upwork’s Take Rate Strategies (34:49) R&D Investing at Upwork (38:36) Selling Trusted Transactions (41:12) Upwork’s North Star Metrics (42:59) Recognising the Potential of AI (44:05) How Upwork Gained 20 Points of EBITDA in Three Quarters (45:29) Balancing Growth and Profitability (46:41) Upwork’s M&A Strategy (48:35) Long-Ass Lightning Round: A Big Career Mistake (50:55) Reporting to Masa from SoftBank (52:49) Advice to Younger Self (54:18) Finance Software Stack (54:55) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Profits vs. Growth: What X, Deel & Clay Are Teaching Us | 08 Feb 2025 | 00:09:29 | |
Hey everyone, welcome back to the show! Last week, our report and podcast on the state of private markets went absolutely bonkers. So, we’re building on that momentum today and giving you even more private tech company headlines. The goal? By the end of this episode, you’ll feel like you have a backstage pass to the best companies before they hit the public markets—and you’ll sound like the smartest person in the room next time you’re talking to colleagues (hopefully not over Microsoft Teams, because let’s be real, that thing sucks). Honestly, the U.S. government should ban Teams before they ban TikTok. But I digress. A lot happened in the tech market this week when it comes to valuations, efficiency metrics, and overall financial performance, so let’s get into it. * X (Formerly Twitter) Profits Surge, But Revenue Tells a Different Story * Deel’s Breakneck Growth and Market Positioning * Clay’s Valuation Jump Raises Eyebrows in the Data Space Hit subscribe, share this with your favorite estranged family member, and give us five stars (it would mean a lot to me). This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| A CFO’s Guide to Raising Take Rates and Increasing Gross Margins, with Kapil Agrawal | 06 Feb 2025 | 01:00:56 | |
In this episode, CJ is joined by Kapil Agrawal, CFO at Outschool, former CFO of Poshmark, and former Global Head of Pricing and Finance Business Partner at Uber. Kapil shares insights on Uber's pricing strategies and the use of promotions to drive customer growth. He discusses the multiple North Star metrics used at Uber before explaining his role in changing the company’s take rate. He also talks about his role at Poshmark and how he raised the company’s gross margin. The conversation explores the advantages and challenges of marketplace models versus subscription models and highlights the potential of combining both. Also covered is the significance of high-quality decision-making as a leader and the role of hard work in achieving this. — SPONSORS: MUFG is the largest bank in Japan and a global banking powerhouse with a focus on empowering Growth and Middle Market stage companies in North America and Europe. MUFG provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. The bank combines its global capabilities with deep operational understanding to help companies accelerate their growth trajectory. Contact group head Bob Blee at bblee@us.mufg.jp to find out more. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (0:00) Preview and Intro (02:50) Sponsor – MUFG | Brex | Vanta (07:15) Discounting and Promotions at Uber (09:26) Pros and Cons of Acquiring Customers with Promotions (13:48) How Uber Determined the Promotion Term of Nine Months (14:33) Promotional Launch Strategies Across Different Uber Platforms (17:49) Sponsor – Tropic | RightRev | Planful (21:10) The Multiple North Star Metrics at Uber (24:31) Retention for Drivers Versus Passengers (25:25) Tackling the Competition for Drivers (27:20) Changing Uber’s Take Rate (31:55) Raising the Gross Margins at Poshmark (37:53) Moving from Buyer and Seller Cohorts to User Cohorts (39:20) Poshmark’s Take Rate (42:46) Intro to Outschool (43:20) Transaction-Based Models Versus Subscription-Based Models (45:04) The Role of Capital Allocation (47:22) Combining Transaction-Based and Subscription-Based Models (49:45) Being Judged on the Quality of Your Decisions (54:00) Hiring: Generalists Versus Specialists (56:06) Long-Ass Lightning Round: A Price Cut Regret (57:34) Advice to Younger Self (58:44) Finance Software Stack (59:28) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| You Can Securitize Anything! — Art as an Asset Class with Nigel Glenday of Masterworks | 03 Feb 2025 | 01:00:33 | |
In this episode, CJ interviews Nigel Glenday, CFO, COO, and board member at Masterworks, a company that allows investors to buy shares in high-value artworks. He sheds light on the art market and Masterworks’s business model. They discuss the intricacies of art as an asset class, its historical significance, and its potential as an investment. Nigel explains the process of securitizing art, comparing it to other unique asset classes like racehorses and athlete contracts. He highlights the importance of data in valuing art and the company's approach to managing a large portfolio of art investments, before discussing the evolution of Masterworks' business model. The episode provides insights into the unique aspects of this asset class and the innovative ways Masterworks is scaling its business. — SPONSORS: Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:23) Sponsor – Vanta | Tropic (04:53) Overcoming the Thomas Crown Affair (06:22) Finance Within the Art World (07:34) The Most Expensive Piece of Art Ever Purchased (09:15) The History of Art as an Asset Class (10:51) The Data-Rich Nature of Trading Art (12:46) The Performance of the Art Market Compared to Other Markets (15:37) Emotional Dividends in Art Investing (17:13) Sponsor – RightRev | Planful | Brex (20:55) Securitizing Anything with a Cash Flow (24:45) Securitizing Art (27:28) Determining When to Sell (30:03) Museums: Owned Versus Loaned (30:55) Masterworks’ Revenue Streams (34:21) How Masterworks Services Their Investors (36:06) Data and How It Informs What Masterworks Buys and Sells (41:55) Evaluating the Value of the Art (43:04) The Trading Market (44:59) The Scaling and Evolution of Masterworks (49:24) Long-Ass Lightning Round: Auto-Renewal Contract Mistakes (50:43) Advice to Younger Self: No Style Points (53:52) Finance Software Stack (57:31) Craziest Expense Story: Defend Your Spend This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| State of the Private Markets: January 2025 | 02 Feb 2025 | 00:15:36 | |
This is our inaugural State of the Private Markets, a monthly series where we’ll deliver the most compelling valuation, hiring, and revenue insights on pre-IPO candidates. Think of this as your backstage pass to the companies shaping the future before they hit the public markets. Today we will cover: * Valuation: The most valuable private tech companies * Hiring: The fastest hiring companies * Layoffs: The companies shedding headcount * Sector specific highlights: This month we check in on Foundational Models, Fintech, and Autonomous Driving * Company spotlights: This month we check in on DataBricks, Anduril, and Canva * Fundraising: Recent rounds you should know about * Execs: Pre IPO CFO hires This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| “What’s in It for Me?” The Art of Storytelling in an IPO - with Monday.com CFO Eliran Glazer | 27 Jan 2025 | 00:57:32 | |
Eliran Glazer is the CFO of Monday.com. He joined the company just four months before its IPO. As a big believer in the art of storytelling, in this episode, Eliran explains how to be a great storyteller while weaving it into the story of Monday.com’s IPO. The conversation also delves into the unique aspects of the Israeli tech scene, the impact of military service on entrepreneurship, and the importance of resilience and adaptability in leadership. Eliran highlights the evolution of Monday.com's narrative, the strategic use of benchmarks, the importance of authenticity, tips for talking about your competition, and the pillars of a good story to help CFO’s supercharge their skillsets. — SPONSORS: Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. It doesn’t just show you where the problems are—it helps you solve them. From spotting hidden optimization opportunities, like duplicative spend, to automating those painful procurement workflows, to giving you the best market data that turns every vendor negotiation in your favor. Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:53) Sponsor – Tropic | Vanta (04:22) The Story Behind Monday.com’s Name (09:25) What Makes Israel’s Tech Scene So Unique (14:30) How Being an Expat in the USA Shaped Eliran as a CFO (16:56) Sponsor – RightRev | Brex | Planful (20:36) Managing the IPO Four Months After Joining Monday.com (25:02) Differentiating Your Company Through Storytelling (27:14) The Importance of Authenticity (31:03) Avoiding “Robot Mode” When You Repeat Your Company’s Story (32:43) The Pillars of a Good Story (35:42) How the Story Changed Throughout the Process (38:25) Being Bold in Your Storytelling (40:39) Using Benchmarks to Support Your Valuation (44:38) Tips for Talking About Competition (46:34) How Monday.com’s Story Is Evolving Post-IPO (51:04) Long-Ass Lightning Round: A Mistake Eliran Made (52:27) Advice to Younger Self (53:39) Finance Software Stack (55:03) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| The Analytics Escalator: Unlocking Value in Finance with Mambu CFO Jesper Sorensen | 23 Jan 2025 | 00:51:48 | |
CJ delves deep into the world of analytics in this interview with Jesper Sorensen, the CFO of Mambu, a leading fintech and banking platform in Europe valued at over $5 billion. Jesper, who has authored three books on analytics, introduces the Analytics Escalator—a framework for unlocking real value through descriptive, diagnostic, predictive, and prescriptive analytics. In the discussion, Jesper covers everything from getting started with analytics and deciding where it should sit within an organization to identifying key opportunities, building a solid BI tech stack, and understanding the role of analytics tools and data lakes. He outlines the journey to creating a high-impact analytics function within a company, emphasizing the critical interplay between people, processes, and systems in fostering a thriving analytics culture—and shares practical advice on how to achieve it. — SPONSORS: RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:01) Sponsor – RightRev | Brex (04:53) Jesper’s Pre-CFO Career (06:50) The Huge Success of Mambu (10:40) Understanding What Analytics Is (13:56) Sponsor – Planful | Vanta (16:02) Where Analytics Should Sit in the Org (20:12) Model for Serving a Team’s BI Needs Internally (22:03) Creating Value with the Analytics Escalator (29:51) Prescriptive Analytics and How to Achieve Them (31:08) The Steps on the Analytics Escalator (33:36) Establishing People, Processes, and Systems (34:54) Self-Service Versus Customer Service BI (37:57) The Components of a Good BI Tech Stack (38:50) Data Visualization Tools Versus Analytics Tools (41:59) The Value of a Data Lake (44:26) Build-Versus-Buy for Analytics Tools (46:50) The Need for a Proof-of-Concept for Analytics Tools (48:10) Managing the Trade-Off Between Performance and Cost (50:19) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| "Be Interesting" and Other Unconventional Finance Career Advice from CFO Jeff Cassidy | 20 Jan 2025 | 00:51:39 | |
In this episode, CJ interviews Jeff Cassidy, CFO of Prodigy Education about navigating a diverse career across multiple industries and building strong teams based on ambition and skills rather than credentials. Having worked in financial services, biotech, restaurants, travel, edtech, and even crypto, Jeff shares the story of his own varied career, giving advice on finding the “right” career path, achieving personal product market fit, and what he looks for in a new role. He talks about how he goes about building a strong team and the qualities he looks for in applicants, while sharing stories of some of the hiring choices he’s made. The conversation touches on the evolving landscape of higher education, the failures of American four-year colleges, and the need for more practical skills and diverse experiences. Jeff also discusses the challenges of leading a travel company through the COVID-19 pandemic, highlighting the importance of transparency, customer empathy, and supplier management. — SPONSORS: Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (03:28) Sponsor – Brex | Planful (06:48) Finding Personal Product Market Fit (12:13) Qualities to Look for in a New Role (14:01) The Misconception About Finding the “Right” Career Path (16:04) Sponsor – Vanta | RightRev (18:32) Linear and Non-Linear Career Moves (20:16) Hiring Based on Ambition and Skills (22:38) How American Four-Year Colleges Are Failing (29:20) Transitioning into Finance (32:05) The Story of a Surprising Finance Hire (35:20) Lessons from an Applicant’s Interview Fail (38:16) Running a Travel Company in the Pandemic (41:45) Supplier Management in a Crisis (43:59) Lessons on Communicating Internally (45:43) Long-Ass Lightning Round: An Early Career Mistake (48:25) Advice to Younger Self: Pursue Interests (49:28) Finance Software Stack (49:59) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| “Your budget is counter-productive” — Michiel Boere, CFO of Remote | 16 Jan 2025 | 00:59:22 | |
Michiel Boere, the CFO of Remote, joins CJ to talk about building multinational companies and the benefits of ditching traditional budgets for better business outcomes. Michiel introduces listeners to Remote's business model and discusses how it levels the global job market by enabling companies to hire talent from anywhere while absorbing complications regarding payroll, taxes, and legal entity status. The conversation also covers the complexities of managing a multinational company and the challenges of scaling finance operations globally. As a risk-on CFO, he breaks down how he looks at unit economics in order to underwrite certain risks necessary for in growth. He also shares insights from his experience at Uber before explaining how budgets can lead to suboptimal decisions, such as unnecessary spending or missing out on valuable investments. — SPONSORS: Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:32) Sponsor – Planful | Vanta (04:43) How Remote Levels the Playing Field (08:02) The Marketplace-Like Element of Remote (09:52) Increasing Optionality Versus Decreasing Costs (13:11) How Remote Built a Multinational Company in Five Years (14:58) Sponsor – RightRev | Brex (17:48) The Complexity of Building a Multinational Company (20:53) Scaling Finance Globally with a Distributed Team (21:51) Remote’s Revenue Lines (23:06) Managing FX in Multiple Countries (26:06) Embracing Investment and Risks (29:37) The Biggest Challenge Michiel Tackled at Uber (32:50) Lessons Michiel Learned About Complexity from Uber (37:42) Why Your Budget May Be Counterproductive (40:56) How to Get Your Board to Change Their Thinking About Budgeting (44:04) Setting Ambitious Goals for Revenue Generators Without a Budget (45:06) Changing Your North Star Metric as Your Company Grows (46:21) Non-Standard Metrics That Michiel Looks At (47:31) Long-Ass Lightning Round: HR Mistakes (49:55) Michiel’s Biggest Career Risk (56:21) Finance Software Stack (57:40) The Wall Street Journal Test and the Blush Test for Expenses This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| AirPods as Recurring Revenue, Direct Mail’s Revival, and Other Growth Predictions | Mostly Growth | 20 Dec 2025 | 00:35:22 | |
Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowth Mostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102 Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3 In this episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman unpack a wide-ranging set of predictions and observations about where go-to-market strategy, AI, and pricing models are headed next. They discuss why what ChatGPT says about your product may become a core marketing KPI, the resurgence of direct mail and physical touchpoints in an AI-saturated world, and why “almost as good as a human” is a dangerous positioning for AI-driven products. The conversation also explores AI monetization paths through advertising, the risk of an AI infrastructure timing mismatch leading to a broader financial pullback, and what historical parallels like railroads and the Sears catalog can teach us about today’s buildout. The episode closes with real-world pricing lessons, from energy-as-a-service solar subscriptions to the surprisingly massive standalone economics of Apple’s AirPods, tying together how distribution, perception, and monetization shape durable growth. — SPONSORS: Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics 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 — LINKS: Mostly Metrics: https://www.mostlymetrics.com CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Growth Unhinged: https://www.growthunhinged.com/ Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/ Slacker Stuff: https://www.slackerstuff.com/ Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/ — RELATED EPISODES: 996 Culture, Exploding AI Bills & SaaS Chaos The Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberg OpenAI’s Impossible Math: $500B or Bust? From Birding Apps to Billion-Dollar Bundles: The Future of SaaS Growth Where Did All the Middle Managers Go? — TIMESTAMPS: 00:00:00 Preview and Intro 00:01:40 Sponsors — Pulley, Metronome 00:04:00 Welcome Back And Consumer Friction 00:05:29 Insurance Middlemen Frustrations 00:07:07 Explaining Newsletter Businesses 00:07:58 Family Perceptions Of Work 00:09:05 GTM And Growth Predictions 00:10:19 Trust And Objectivity In ChatGPT 00:12:01 ChatGPT As Marketing KPI 00:14:14 Direct Mail Marketing Comeback 00:15:56 Tech Buying Media Assets 00:17:52 Fake Subscribers And Email Lore 00:19:03 AI Quality Over Automation 00:22:11 AI Healthcare And Ad Models 00:24:40 Advertising Fuels AI Economics 00:25:40 AI Boom Versus Bust Timing 00:27:49 Infrastructure Before Killer Apps 00:30:21 Railroad Economics And Real Estate 00:30:46 Solar Subscriptions And Pricing 00:32:50 AirPods As Recurring Revenue 00:34:57 Show Outro And Credits #MostlyGrowthPodcast #GrowthMarketing #AITrends #GoToMarket #StartupStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| A Masterclass with the Michael Jordan of B2C Subscription, Reid DeRamus | 13 Jan 2025 | 01:11:22 | |
Reid DeRamus, formerly of Hulu, Crunchyroll, HBO Max, and Substack, joins CJ in this episode to discuss B2C business models and growth strategies. Reid sheds light on some of the profound evolutions he’s experienced in his career at the intersection of tech and media. The discussion dives into the nuances of price increases in B2C subscriptions—how they affect revenue growth, customer acquisition, and retention—and explores strategies for effectively communicating these changes. They examine the pitfalls of discounting, the pros and cons of annual plans, and the art of segmenting consumers who may be willing to pay more. Reid introduces the concept of “elevating the cohort floor” and emphasizes the importance of the initial subscription period for retention and conversion. The episode also tackles the paradox of "too healthy" metrics and why you should consider pairing your KPIs up. The podcast is not over until they touch on balancing advertising and subscription models, and discuss unique monetization lessons from platforms like OnlyFans, among others. — SPONSORS: Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) LINKS: Growth Croissant - https://www.reidtandy.com — TIMESTAMPS: (00:00) Preview and Intro (02:00) Sponsor – Vanta | RightRev (04:40) Reid’s Career Path Through Evolutions in the Media World (11:40) Price Increases for Revenue Growth (15:14) Why Price Increases Impact Subscriber Acquisition More than Retention in B2C (18:00) Sponsor – Brex | Planful (20:25) Strategies for Price Increases Without Dropping Subscriptions (24:32) Pricing B2C to Allow for Room to Discount (25:52) Can Discounting Cheapen Your Brand (29:26) The Pros and Cons of Pushing People Towards Annual Plans in B2C (34:50) The Hierarchy of What Monetizes Best in Paid Subscriptions (39:59) Targeting Consumers Who Are Willing to Pay More (45:00) The Importance of the Initial Subscription Period for Retention and Conversion (50:01) Why Your Health Metrics Can Be Too Good (51:49) Paired Metrics: Growing Two KPIs at the Same Time (54:08) Balancing Advertising and Subscription (01:00:49) The B2C Business Application of OnlyFans (01:04:35) Substack and the Value in Focus (01:07:07) Interesting Emerging B2C Apps (01:07:59) B2C Apps Becoming B2B Apps This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| “Most Decisions Are Reversible” – A Masterclass in Decision Making with Zapier’s Ryan Roccon | 09 Jan 2025 | 00:56:40 | |
In this episode, CJ sits down with Ryan Roccon, CFO of Zapier, to explore the power of storytelling in finance, decision-making frameworks, and the company's commitment to extreme transparency. Ryan highlights the significance of storytelling in finance to connect complex data with company strategy. He explains how he adapts a story for a specific audience and how he avoids “robot mode” when repeating it. The discussion delves into Zapier's unique approach to transparency, how this plays out, the benefits of it, the challenges of it, and how it has become an integral part of the company’s culture. Ryan unpacks the unique dynamics of being a remote-first, bootstrapped company with a cash flow break-even or better requirement. The conversation also covers the importance of effective decision-making, where Ryan suggests that most decisions are reversible and breaks down different frameworks for effective decision-making and fostering organizational buy-in. — SPONSORS: RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:34) Sponsor – RightRev | Brex (06:31) What Storytelling Is in Finance (09:01) Adapting Your Story for the Audience (12:19) Avoiding “Robot Mode” When Repeating a Story (17:30) Sponsor – Planful | Vanta (19:37) Frequently Used Analogies (21:33) The Cohort of Companies Zapier Compares Itself To (23:33) Storytelling to Potential New Employees (24:38) Zapier’s Extreme Transparency (26:08) The Challenges of Extreme Transparency (29:36) Avoiding Creating Anxiety by Oversharing (31:11) Zapier’s Cash Flow Break-Even or Better Requirement (34:18) Other Rules and Ambitions at Zapier (34:55) Burdening the P&L by Product Line (37:24) Getting People to Use the DACI Framework (40:51) The “Fist to Five” Framework (44:51) Making It Safe to Fail While Expecting Excellent Performance (48:35) What Ryan Would Most Like to Automate (49:46) The US Steel and Stanley Cup Story (52:21) Long-Ass Lightning Round: A Mistake Made Early in Ryan’s Career (53:31) What Ryan Wishes He Had Known Earlier in His Career (54:27) Finance Software Stack (55:25) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| The Best Ever Answer to Build Versus Buy, and Other Wisdom from Matt Hudson of Coda | 06 Jan 2025 | 01:05:05 | |
In this episode, CJ interviews Matt Hudson, CFO of Coda, who shares insights from his unique career path that spans roles as a product manager at Google, YouTube, and Coda before becoming a CFO. He breaks down a number of frameworks he’s used in his career from the Blue and Black Loop framework for understanding the growth of a shareable product like Coda’s, Eigenquestions for getting to the one question at the center of all questions, and the Vacation Rule for determining whether to build or buy software tools. Matt also discusses the evolution of Coda's pricing model and offers perspectives on community-driven growth instead of typical product-led growth. He sheds light on how to better understand and work with product managers, how to minimize SaaS sprawl, and the role of luck and failure in one’s success, before sharing nuggets of wisdom from working with notable investors like Mamoon Hamid and Reid Hoffman. — SPONSORS: Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:13) Sponsor – Brex | Planful (04:30) Matt’s Journey from Product Manager to CFO (08:59) The Blue and Black Loop Framework (12:42) Modeling for Growth Loops (16:32) Why Looking at User Cohorts Can Be Misleading (17:59) Sponsor – RightRev (21:08) How Coda’s Pricing Model Has Evolved over Time (27:37) The Downside to PLG (31:35) Community-Driven Growth Versus Product-Led Growth (32:29) The Billing Mechanism for PLG (34:16) The Biggest Misconceptions About Product Managers (38:09) Build Versus Buy: The Vacation Rule (42:43) SaaS Sprawl (45:45) Eigenquestions (50:15) Nuggets of Wisdom from Investors (53:32) Reconciling Hard Work and Luck (57:05) Long-Ass Lightning Round: Clarity over Comprehensiveness (1:01:09) Something Matt Wishes He Had Known Earlier (1:03:19) Finance Software Stack (1:03:36) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means | 02 Jan 2025 | 00:53:54 | |
Steve Isom, the CFO of Bloomerang, joins CJ to talk about what it really means to be a “strategic” CFO. Steve shares profound insights on the people element of the job and how finance leaders can avoid making the business a math problem. He discusses the CFO’s job in playing offense not just defense, and what that looks like. He sheds light on how as a CFO, you can prove yourself as a valuable contributor and earn an invitation to various conversations instead of being seen as an umpire or “CF-no”. He also explains how to deal with friction when you do have to play that role. The conversation covers transaction readiness as part of the CFO’s job and how this helped Steve when a previous company, Flywheel, was acquired in a process that took just 31 days even though it wasn’t even for sale. He closes with advice on how to build a kick-ass finance team. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics. RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:40) Sponsor – Planful | RightRev (07:48) What It Means to Be a Strategic Finance Leader (12:44) Having Empathy for Sales and Other Roles (15:29) Sponsor – Brex (16:48) Playing Offense Versus Playing Defense (21:02) Balancing the Metrics with the People Element (29:05) Earning a Seat at the Table as a CFO (31:58) Dealing with Friction When You Have to Play Umpire (38:36) Transaction Readiness as Part of the CFO’s Job (41:14) Flywheel’s 31-Day Acquisition (47:47) Building a Kick-Ass Finance Team This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| “Annual Planning Is So Last Year” – Ross Grainger, CFO of Paradox, on What He Does Instead | 26 Dec 2024 | 00:49:35 | |
In this episode, CJ interviews Ross Grainger, the CFO of Paradox, to discuss work-life integration (instead of balance), why the corporate ladder is less like a ladder and more like a jungle gym, and the hallmarks of a great CFO/FP&A/controller relationship. He starts by sharing his own unconventional career journey and talks about the importance of the hustle, giving examples from his own life of periods when things were weighted towards life or work and how this benefited him. He also describes why the career ladder is more like a jungle gym and gives examples of times when he had to step backwards or sideways to get ahead. He sheds light on the value of investing in work relationships outside of finance, such as product marketing and sales, before discussing the hallmarks of a good CFO/controller/FP&A relationship. With a team in Vietnam, he gives advice on how to expand internationally. The episode includes an explanation of why Ross doesn’t believe in annual planning, what he does instead, and how he justifies this to the board. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. RemoFirst is a full-service Employer of Record solution that handles all your global employment needs. RemoFirst can help you navigate the maze of regulations and logistical challenges to onboard employees and contractors from anywhere in the world and streamline payroll, taxes, and compliances. Get two months free on EOR fees for your first hire in any country by visiting RemoFirst.com/metrics. Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:08) Sponsor – Operators Guild | Maxio (06:00) Work-Life Integration Versus Work-Life Balance (09:15) The Importance of the Hustle (10:53) Periods of Ross’s Life That Were Weighted Towards Life or Work (12:54) Why It’s Not a Career Ladder but a Jungle Gym (16:38) Sponsor – RemoFirst | Mercury | NetSuite (20:27) Examples of Downward Career Moves That Got Ross Ahead (25:17) The Value of Work Relationships Outside of Finance (29:30) The Hallmarks of a Good CFO/Controller/FP&A Relationship (32:38) Paradox’s Team in Vietnam and How to Expand Internationally (37:11) Ross’s Views on R&D Spend and Advice on Payback Periods (39:27) Why Ross Doesn’t Believe in Annual Planning (42:18) Justifying This Flexibility to the Board (43:51) Communicating Bad News (45:20) Long-Ass Lightning Round: Career Regrets (46:41) Advice to Younger Self on the Hustle (47:12) Finance Software Stack (47:46) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Mitigating Churn: A Masterclass in Customer Retention with Will Cureton, CFO of Nitrogen Wealth | 23 Dec 2024 | 00:44:44 | |
In this episode, CJ has an exceptionally candid conversation with Will Cureton, the CFO of Nitrogen Wealth. Will sheds light on what Nitrogen Wealth does and how it incorporates a tolerance functionality built on the prospect theory into its software platform to better serve wealth management firms. After taking on some private equity backing in 2021, Nitrogen Wealth made a big price increase mistake. Will talks about how the company went about revisiting its growth assumptions. He explains how they assessed the company’s TAM, exited unsustainable business lines, and unbundled some of their products in order to maintain or regain their customers. Will then does a deep dive on mitigating churn, covering which metrics Nitrogen tracks to predict churn, how they formulate a churn score, and other steps they take to support customer retention. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. RemoFirst is a full-service Employer of Record solution that handles all your global employment needs. RemoFirst can help you navigate the maze of regulations and logistical challenges to onboard employees and contractors from anywhere in the world and streamline payroll, taxes, and compliances. Get two months free on EOR fees for your first hire in any country by visiting RemoFirst.com/metrics. Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:32) Sponsor – Maxio | RemoFirst (04:03) An Intro to Nitrogen Wealth and Prospect Theory (07:34) Nitrogen’s Private Equity Backing and Price Increase Mistake (11:27) Revisiting Growth Assumptions: Assessing TAM (14:30) Time to Land the Customer Versus the Number of Customers (16:34) Sponsor – Mercury | NetSuite | Operators Guild (19:58) Building Test Plans for TAM Expansion (22:28) Exiting Unsustainable Business Lines (25:36) Bundling or Unbundling Products (27:43) Nitrogen’s Price-of-Value Mismatch and Drivers to Mitigate Churn (28:30) Formulating a Churn Score (31:47) Why Nitrogen’s RevOps Team Reports to the CFO, Not Sales (33:31) Learnings on Mitigating Churn (34:40) Metrics to Track to Predict Churn (35:40) The Severity of Nitrogen’s Price Increase (36:58) Long-Ass Lightning Round: A Business Trip to Manitoba (39:25) A Brown-Nosing Mistake Will Made (40:52) Advice to Younger Self (41:51) Finance Software Stack (43:01) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| The ROI of OKRs (and Advice on Building Analytics Teams) with Sisense CFO Alyssa Shadinger | 19 Dec 2024 | 00:46:22 | |
Alyssa Shadinger, CFO of Sisense, sits down with CJ in this episode for a masterful deep dive on building and scaling analytics teams and perfecting the art of the OKR (Objectives and Key Results). They discuss the optimal structure for data and analytics teams and where they should sit within the org. Alyssa explains how Sisense clarified their data models for more accurate self-service reporting, how the company maps their analysts to different teams, and where the costs of this should sit in the P&L. Then CJ and Alyssa delve into OKRs, the biggest challenge to their success, the role of finance in helping the rest of the company define them, and the necessity of linking them to measurable financial outcomes. They also talk about the optimal number of OKRs that an org should have, and other tips for achieving them. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: RemoFirst is a full-service Employer of Record solution that handles all your global employment needs. RemoFirst can help you navigate the maze of regulations and logistical challenges to onboard employees and contractors from anywhere in the world and streamline payroll, taxes, and compliances. Get two months free on EOR fees for your first hire in any country by visiting RemoFirst.com/metrics. Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:38) Sponsor – RemoFirst | Mercury (04:06) Where Data and Analytics Should Sit Within an Org (09:52) If BI Should Start as an Engineering Function at an Early-Stage Company (11:53) Delineating Between Systems Management Versus Actual Data Work (14:11) How to Go About Building Out the Analytics Team (16:31) Sponsor – NetSuite | Operators Guild | Maxio (20:15) Business Partnering Versus Self-Service (23:46) The Role of the BI Team in Clarifying Definitions (24:28) How Sisense Maps Analysts to Different Teams (26:27) Where the Cost of These Analysts Should Sit in the P&L (27:09) The Biggest Challenge to OKRs (29:50) The Role of Finance in Helping Groups Come Up with OKRs (30:52) The ROI of OKRs (31:49) Why OKRs Should Be Visible to the Entire Org (32:24) The Right Number of OKRs (33:53) Why Some OKRs Just Disappear Mid-Year (35:49) Who Should Be Responsible for Reporting on OKRs (36:36) Baking OKRs into Your Weekly Cadence (37:15) Long-Ass Lightning Round: Hiring Mistakes (42:26) Advice to Younger Self (43:10) Finance Software Stack (44:23) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| 16 P&Ls: The CFO’s Guide to M&A Operational Complexity with Dotmatics’ Rebeca Sanchez Sarmiento | 16 Dec 2024 | 00:54:18 | |
In this episode, CJ interviews Rebeca Sanchez Sarmiento, the CFO of Dotmatics and the queen of managing operational complexity. With over seven acquisitions under her belt in just a few years, Rebeca shares insights on managing the complex realities of inorganic growth. She breaks down how Dotmatics balances autonomy and integration across multiple entities while finding synergies and implementing system consolidations. The conversation delves into the intricacies of managing 16 P&Ls, creating consistent forecasting frameworks, and determining whether to lean into an 80/20 approach or aim for all-around excellence. Beyond M&A, Rebeca’s extensive experience in investor relations and as a sell-side equity analyst adds depth to the discussion. The conversation also touches on her personal journey, including a bold move to Los Angeles, how it helped her career, and her approach to work-life balance and remote work. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. RemoFirst is a full-service Employer of Record solution that handles all your global employment needs. RemoFirst can help you navigate the maze of regulations and logistical challenges to onboard employees and contractors from anywhere in the world and streamline payroll, taxes, and compliances. Get two months free on EOR fees for your first hire in any country by visiting RemoFirst.com/metrics. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:30) Sponsor – Mercury | NetSuite (04:51) Managing Acquisitions from an Operational Angle (08:19) Why Finance Staff Aren’t the First to Go After an Acquisition (09:10) Approaching a Company’s Financials After Diligence (10:07) Why Dotmatics Manages These Companies Separately (12:14) Prioritizing System Consolidation and Process Changes (13:45) Forecasting for the Acquisition Company (15:12) How Rebeca Forecasts for 16 P&Ls (16:16) Why Dotmatics Distribute Instead of Having a Sales Team (17:21) Sponsor – Operators Guild | Maxio | RemoFirst (21:03) How Rebeca Structures the FP&A Team (23:05) The 80/20 Approach to Forecasting (25:44) Why They Don’t Budget for M&A Itself (27:54) How Rebeca’s IR and Research Background Informs Her Current Role (34:38) Rebeca’s Research on the Latin American Market (37:09) How Rebeca Moved to LA on a Whim (41:28) The Benefits of a Remote Workforce (44:09) Rebeca’s Approach to Work-Life Balance (47:59) Why Employees Will Leave a Job (48:46) Long-Ass Lightning Round: Why People Stay in Bad Work Environments (51:22) Advice on Patience (51:53) Finance Software Stack This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Building a Billion-Dollar Pipeline: A Deep Dive into Rubrik’s Sales Strategy with Samarth Mital | 12 Dec 2024 | 00:54:16 | |
Samarth Mital, Senior Director of Global Sales Strategy, Planning & Analytics, Renewals & Sales Development at Rubrik joins CJ for this episode to talk all things pipeline, territory creation, commission plans, and renewals. Samarth joined the company when it was doing 70 million in ARR. Rubrik is now doing $1 billion and recently went public. He sheds light on his role at Rubrik in fostering this growth, the teams under his purview, and the cadence of the recurring meetings they have for forecasting. He discusses the value of an “accountability forum”, the best practices for inspecting pipeline, how to set up sales reps for success, and the art and science of territory design. He explains why territories get smaller as you add more products. He also delves into the characteristics of a good comp plan and how he deals with reps who feel their quota’s too high, before breaking down what a healthy renewals function looks like. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. RemoFirst is a full-service Employer of Record solution that handles all your global employment needs. RemoFirst can help you navigate the maze of regulations and logistical challenges to onboard employees and contractors from anywhere in the world and streamline payroll, taxes, and compliances. Get two months free on EOR fees for your first hire in any country by visiting RemoFirst.com/metrics. Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:33) Sponsor – NetSuite | Operators Guild (04:48) Samarth’s Role at Rubrik (06:26) The Cadence of Recurring Meetings (08:59) Getting Down to the Tactical Level of Which Deals Matter (13:39) The Value of an “Accountability Forum” (16:52) Sponsor – Maxio | RemoFirst | Mercury (20:14) The Roles of Tension and Friction in Samarth’s Work (22:02) Best Practices for Inspecting Pipeline (27:22) Setting Sales Reps Up for Success (33:51) The Art and Science of Territory Design (36:23) Preventing Reps from Horse-Trading Accounts (37:54) Not Leaving Opportunities Untapped When a Rep Leaves a Territory (38:41) Why Territories Get Smaller as You Add More Products (44:03) The Characteristics of a Good Comp Plan (46:32) Dealing with Reps Who Feel Their Quotas Are Too High (49:30) What a Healthy Renewals Function Looks Like This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Is Stock-Based Compensation Real? A Masterclass with Clio CFO Curt Sigfstead | 09 Dec 2024 | 00:57:12 | |
This episode does a deep dive into stock-based compensation (SBC) and employee equity. Joining CJ for this conversation is Curt Sigfstead, the CFO of Clio, a leading vertical software provider for legal firms. CJ and Curt unpack the complexities of SBC, examining its importance, evolution, and how to effectively communicate its value to potential hires and the organization as a whole. They cover the evolution of share types as a company scales and how finance leaders should budget for equity compensation. Then Curt provides a detailed walkthrough of Clio's recent fundraising process, highlighting the importance of meeting and beating financial targets to maintain investor confidence. You’ll also hear about building trust with everyone you work with and strategies for CFOs to empower founders to do their best work. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. RemoFirst is a full-service Employer of Record solution that handles all your global employment needs. RemoFirst can help you navigate the maze of regulations and logistical challenges to onboard employees and contractors from anywhere in the world and streamline payroll, taxes, and compliances. Get two months free on EOR fees for your first hire in any country by visiting RemoFirst.com/metrics. Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:56) Sponsor – Operators Guild | Maxio (04:47) Is Stock-Based Compensation Real? (06:36) Why SBC Has Been Ignored for So Long (11:39) SBC for Private Versus Public Companies (13:05) The Mechanism by Which Employees Are Rewarded with Equity (16:28) Sponsor – RemoFirst | Mercury | NetSuite (19:52) Explaining the Potential Value of Equity to Prospective Hires (23:18) Talking to the Organization About the Value of Equity (26:09) Budgeting for Equity Compensation (30:41) The Round That Clio Just Raised (35:58) Strategies for Empowering Founders (42:22) Filling the Trust Battery (44:03) Meeting and Beating Your Numbers During a Fundraise (49:31) Long-Ass Lightning Round: The Biggest Mistakes Curt Made (53:06) Advice to Younger Self (54:40) Finance Software Stack (55:38) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Running the Long Game in Growth Equity | Larry Contrella | 18 Dec 2025 | 00:54:56 | |
In this episode of Run the Numbers, CJ Gustafson sits down with Larry Contrella, General Partner at JMI Equity, to unpack how JMI invests in software without financial engineering or roll-up strategies. Larry explains how the firm builds conviction through founder relationships, long-term partnership, and a product-and-brand-first view of durable growth. They discuss how JMI supports companies through scaling, why operating partners keep returning, and how underwriting looks different in mission-driven sectors like K–12 and nonprofit tech where customers are schools and communities, not Fortune 500s. Larry’s background as a competitive runner at Penn ties the conversation together with a clear ethos: patience, discipline, and playing the long game. — SPONSORS: Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo. Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more. Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off. Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHt — LINKS: Larry on LinkedIn: https://www.linkedin.com/in/larry-contrella-160a8a25/ JMI Equity: https://www.jmi.com/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: Is taking a company public even worth it? | Fullstory’s Chad Gold So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:49 Sponsors — Mercury | RightRev | Tipalti 00:06:41 Joining the JMI Conversation 00:07:13 College Running and Team Dynamics 00:08:13 New York Marathon Story and Career Intersection 00:11:04 Competitive Drive and Patience With Founders 00:12:54 Building Long-Term Partnerships and Underwriting Credibility 00:15:27 Growth Equity as a Long Sales Cycle 00:15:48 Sponsors — Aleph | Fidelity Private Shares | Sage Intacct 00:18:44 Fund Planning, Deal Pacing, and Board Commitments 00:20:59 Sourcing Philosophy and Developing Investors Over Time 00:22:09 Hustle as the Only Sustainable Edge in Sourcing 00:24:14 Early Sourcing Tactics and Information Arbitrage 00:26:06 Reputation, Experience, and Breaking Into Competitive Deals 00:29:42 Organic Growth Over Roll-Ups and M&A Discipline 00:32:51 Brand, Product Leadership, and Paying for the Best Businesses 00:33:29 Bloomerang and Brand-Led Growth in Nonprofit Software 00:34:46 Why JMI Operators Keep Coming Back 00:36:28 Collaborative Leadership and Giving Constructive Advice 00:38:20 Using Data Without Slowing Decisions 00:39:20 Transparency, Alignment, and Knowing Where You Stand 00:40:31 Why JMI Invests in K–12 and EdTech 00:42:07 Mission-Driven Businesses and Talent Advantage 00:43:24 Monetization Models in Nonprofit SaaS 00:45:40 Conviction Bets and Product-Market Fit Stories 00:48:49 Rethinking TAM and Expanding Markets Over Time 00:50:40 Lightning Round: Sourcing Stories and Lessons 00:52:58 Traits of Great Founders and Changing Beliefs 00:54:20 Closing Thoughts and Outro #RunTheNumbersPodcast #GrowthEquity #B2BSoftware #FounderRelationships #PrivateEquity This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Guiding Stakeholders Through Business Model Transitions with Varonis CFO & COO Guy Melamed | 05 Dec 2024 | 00:53:46 | |
Guy Melamed, CFO & COO of Varonis, joins CJ to discuss the company’s two major transitions. In 2019, Varonis shifted from a perpetual model to an on-prem subscription model, completing the transformation in record time. They are currently in the process of transitioning from an on-prem subscription company to a SaaS company. Guy and CJ delve into the challenges of these transitions, the pressure of doing them in the public eye, and how to communicate these processes to your customers, investors, and sales reps. He highlights the key KPIs that Varonis tracks, the ones that are overrated, and the importance of clearly defined metrics. Guy also touches on the challenge of keeping your eye on short, medium, and long-term strategy, before reflecting on his career, the risks he has taken, and lessons learned from his time in sports and business. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. RemoFirst is a full-service Employer of Record solution that handles all your global employment needs. RemoFirst can help you navigate the maze of regulations and logistical challenges to onboard employees and contractors from anywhere in the world and streamline payroll, taxes, and compliances. Get two months free on EOR fees for your first hire in any country by visiting RemoFirst.com/metrics. Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (02:11) Sponsor – Maxio | RemoFirst (04:57) Varonis’s Two Major Company Transformations (08:02) The Pressure of Undergoing a Transition in the Public Eye (09:54) Communicating to Key Stakeholders in a Transition (13:59) The Biggest Challenge to Varonis’s Transition (15:36) Sponsor – Mercury | NetSuite | Operators Guild (19:00) The Grading System That Varonis Introduced (23:50) Advice to Finance Leaders Facing Business Model Transitions (26:15) Varonis’s Three North Star Metrics (30:00) A Common KPI or Metric That Is Overrated (31:32) EBITDA Versus Free Cashflow When Communicating to Investors (32:47) The Importance of Well-Defined KPIs (40:21) How Guy Decides Where His Attention Is Most Needed (41:36) Keeping Your Eye on Short, Medium, and Long-Term Strategy (43:40) The Influence of Sports on How Guy Faces Business Challenges (44:51) Long-Ass Lightning Round: What Gets CFOs in Trouble (49:30) Guy’s Biggest Career Risk (50:11) Unconventional Financial Advice (52:12) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Less but Better: Miro’s Justin Coulombe on the Power of Strategic Divestment in SaaS | 02 Dec 2024 | 01:03:57 | |
In this episode, CJ interviews Justin Coulombe, the CFO of Miro. Apart from his “less but better” philosophy where he encourages listeners to strategically divest from less important things to focus on what’s most impactful, he also shares a wealth of profound advice on being an effective CFO in SaaS. He explains Miro’s approach to blending data from usage patterns, predictive modeling, and AI to identify upsell opportunities, prevent churn, and enhance customer retention. The discussion dives into the company’s unique combination of product-led growth (PLG) and human-touch sales motions, exploring how to harness both while avoiding internal channel conflict. Justin also offers his perspective on the per-seat pricing model, why it still works for Miro, and whether outcome-based pricing is the future. Drawing on his experiences leading major transformations at Autodesk, Box, SurveyMonkey, and now Miro, he provides a framework for CFOs navigating business model transitions and explains why they fail. He also shares bold takes on SaaS business practices that need rethinking and his thoughts on how to balance growth and profitability in SaaS. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: RemoFirst is a full-service Employer of Record solution that handles all your global employment needs. RemoFirst can help you navigate the maze of regulations and logistical challenges to onboard employees and contractors from anywhere in the world and streamline payroll, taxes, and compliances. Get two months free on EOR fees for your first hire in any country by visiting RemoFirst.com/metrics. Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:58) Sponsor – RemoFirst | Mercury (04:13) An Intro to Miro (05:47) Justin’s Framework for Using Data to Drive Outcomes (12:09) The “Less but Better” Philosophy (14:34) Examples of Divesting from Things (16:54) Sponsor – NetSuite | Operators Guild | Maxio (21:49) Slowing Down to Speed Up (22:51) How to Say No Gracefully (25:43) Maintaining Standards While Encouraging People to Take Risks (28:16) Using Usage Patterns to Drive Monetization (30:07) “Sticky Installation” – Meeting the Customer Where They Are (32:41) Blending Self-Serve PLG and Field Sales Motions (37:16) Per Seat-Based Pricing Versus Outcome-Based Pricing (42:08) Why Seat-Based Pricing Model Works Miro (44:08) Advice for CFOs Navigating Major Transitions in Their Business Models (47:41) The Reasons Business Transformations Fail (49:25) SaaS Business Practices from the Last Decade That Need Rethinking (53:02) The Trade-Off Between Growth and Profitability in SaaS (56:00) Long-Ass Lightning Round: A Poor Hiring Decision (59:34) Finance Software Stack (01:00:51) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||
| Private to Public to Private: Navigating Major Transitions with Dialogue Health CFO, Navaid Mansuri | 28 Nov 2024 | 00:47:51 | |
While companies often go public, not many CFOs have taken a company private. In this episode, CJ interviews Navaid Mansuri, the CFO of Dialogue Health, a Canadian health tech company, that went from private to public to private again in less than five years. The discussion covers Navaid's career journey, including his experience negotiating broadcast rights at Rogers, his involvement in a joint venture with VICE Media, and his role in Dialogue's significant business transitions including being acquired by Sun Life. Navaid shares insights into the challenges and strategies of managing a company's financial health and P&L through these stages and breaks down the differences between the roles of public and private CFOs. He also highlights the importance of adaptability and credibility for CFOs and the unique aspects of operating a healthcare business in Canada. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — SPONSORS: Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning. Operators Guild is where the best CEOs, CFOs, VPs of finance, and BizOps leaders in the business connect, network, and grow together. Built by operators for operators, this members-only community is home to more than 1000 of the most elite high-growth operators in the world. Experience connection and knowledge share with professionals who understand you like no one else does. Learn more and apply at operators-guild.com. Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. — FOLLOW US ON X: @cjgustafson222 (CJ) — TIMESTAMPS: (00:00) Preview and Intro (01:59) Sponsor – Mercury | NetSuite (04:14) Navaid’s Career Negotiating Broadcast Rights (09:26) Navaid’s Joint Venture with VICE Media (11:15) Going from Private to Public to Private at Dialogue (14:37) Sponsor – Operators Guild | Maxio | Leapfin (18:09) Joining a Company at an Inflexion Point (19:56) The Differences Between the US & Canadian IPO Markets (21:38) The Differences Between Public and Private CFOs (26:05) How a Company Goes Private (29:18) Managing Dialogue’s P&L During These Transitions (31:47) Accountability and Credibility on the Journey to Profitability (33:17) The Shift from Growth at All Costs to Profitable Growth (35:47) The Nuances of Being a Canadian Healthcare Company and Profitability (39:08) The Value of Being Adaptable as a CFO (40:33) Long-Ass Lightning Round: The Value of Networking (44:51) Finance Software Stack (46:01) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com | |||