In this bucket list interview, CJ speaks with Larry Roseman, the CFO of Thumbtack, who shares his deep understanding of running marketplace businesses at scale. They explore Thumbtack's business model and monetization strategy, discussing the customer acquisition cost for both service providers and homeowners. Larry explains why going broad rather than niche can be fundamental for marketplace success, offering a counterintuitive view to that of many marketplace experts. He also talks about the flywheels Thumbtack has developed over time and the company’s shift towards becoming a proactive operating system for homes instead of a reactive marketplace. Additionally, Larry offers valuable insights on value creation from a CFO's perspective, emphasizing the importance of making NPV-positive decisions and the strategic role of the CFO in guiding big business decisions. Hear about the crises that Larry has seen in his career and his advice to “never waste a good crisis”.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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. 

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.

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro(02:31) Sponsor – NetSuite | Maxio(06:13) How Thumbtack Makes Money(09:30) Being Broad as the Key to Marketplace Success(12:31) Charging for the LTV(13:45) The Evolution of the Marketplace Industry(16:21) Sponsor – Leapfin | Planful | Mercury(19:40) Thumbtack’s Two North Stars(21:31) CAC and LTV: Supplier versus Household(23:59) Flywheels versus Network Effects(25:52) Thumbtack’s Evolution: Reactive to Proactive(29:09) Thumbtack’s North Star Metric(32:34) Making the Right NPV Positive Decision(36:43) Helping the C-suite Size Up Big Bets(39:20) Learnings from Crises(40:44) Share-Based Compensation(45:37) Long-Ass Lightning Round: CAC Framework Regrets(50:33) Finance Software Stack(51:53) Craziest Expense Story

In this episode, CJ sits down with Eric Newcomer, who runs “Newcomer," or newcomer.co, the largest independent media outlet focused on venture capital. They delve into the art of crafting fundraising announcements, particularly from the CFO’s angle when pitching a company’s raise to the media. The conversation explores the unique appeal of venture capitalists as a subject matter and some of the big stories and personalities that Eric has featured. The discussion also covers the fascinating trend of media companies morphing into VCs, VCs morphing into media companies, and the reasons behind this. Eric sheds light on how a good fundraising announcement should work, how this relates to a company's efforts to attract talent, and how and why to build relationships with the media when not fundraising. Drawing from Eric’s vast industry experience, hear his perspectives on what makes a story compelling and shareable, lessons from his own media business, and his insights on all things venture capital. 

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.

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. 

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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FOLLOW US ON X:

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@EricNewcomer (Eric Newcomer) 

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TIMESTAMPS:

(00:00) Preview and Intro(02:03) Sponsor – Maxio | Leapfin(05:37) What Makes Venture Capitalists So Intriguing to Cover(08:06) Big Stories and Personalities Covered on Newcomer(11:21) a16z’s Moves into the Media Space(12:37) Conflicts of Interest in the Media Space(14:45) The Convergence of Media and Investing(16:56) Sponsor – Planful | Mercury | NetSuite(21:35) How Eric Gets Tips and Scoops(23:07) How a Good Fundraising Announcement Should Work(26:17) Fundraising Announcements and Attracting Talent(29:33) “Off the Record” Relationships with the Media(36:05) Eric’s Database of Investor Profiles and the Value of Lists(42:12) Differentiated Competitive Moats for Companies versus VCs(43:31) Eric’s Decision to Monetize via Subscriptions(49:42) Regrets from the First Year of Eric’s Business(51:30) Building Newcomer’s Subscriber Base(52:25) The Next Big Thing versus Evergreen Content(56:15) Whether VC Is Bigger or Smaller Than Eric Expected(58:50) Wrap

In this episode, Evan Fein, CFO of TextNow and Global Chairman of The F Suite, a professional group for CFOs, joins CJ for a deep dive into the complexities of being acquired. Evan introduces listeners to his company TextNow, and how it remains free while making money. He also covers important metrics for CFOs in telecom such as Average Revenue Per User and the importance of considering the time value of money. While we often hear from people on the buying side of M&A, Evan then sheds light on what it’s like being the CFO of a business that is being acquired, discussing the different types of acquisitions and how the due diligence process differs. He shares insights on continuing to run a company while managing due diligence and key lessons learned. Evan also offers advice on managing board expectations, sharing customer data, handling bad news, communicating with CEOs and investment bankers, when to include optimism, and generally mastering the art of being acquired while simultaneously also often working yourself out of a job.

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.

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.

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:16) Sponsor - Maxio | Planful

(06:38) How TextNow is Free and Makes Money

(09:21) Evan’s Start in Finance and Telecom

(11:15) Important Metrics for CFOs in Telecom

(15:49) Considering the Time Value of Money

(16:15) Sponsor - Leapfin | Mercury | NetSuite

(19:31) The Metric of Average Revenue Per User

(21:01) Definition of a Customer Versus a User

(24:39) Managing Churn & Churn Metrics

(26:16) Different Flavors of Acquisitions at a Company Getting Acquired 

(27:57) How the Due Diligence Process Differs Based on Type

(30:37) Running the Company While Doing Due Diligence as a CFO

(32:13) Key Learnings From the Due Diligence Process

(33:52) When to Include Optimism in Your Model

(36:06) Conversations With the CEO in the Acquisition Process

(38:23) Insight and Advice for Working With Investment Bankers 

(45:27) Managing Board Expectations

(47:11) CFO Job Security in an Acquisition

(48:50) Long-ass Lightning Round: Controlling Outcomes and Scarcity Complexes 

(51:49) Finance Software Stack

(53:02) Craziest Expense Story

Jim Caci, CFO of AvePoint, a global leader in robust data management and data governance, joins CJ for this episode. He talks about the harrowing experience of transforming a company from perpetual licenses to SaaS, how the key metrics he tracked changed throughout this process (and what his top three key metrics are), what he needed to convey to members of the company about the basics of SaaS, and how paying sales reps changed with this shift. He also emphasizes the importance of understanding the difference between bookings, ARR, revenue, and sales. Jim unpacks why he believes that AI is a worthy investment for CFOs to champion, describing tactical examples of how he incorporates AI into his work, and explaining how he goes about avoiding buyer's remorse considering the fast-evolving nature of this technology.

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.

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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

(02:05) Sponsor - Planful | Leapfin

(04:23) Transitioning From Perpetual Licenses to SaaS

(10:34) The Shift in Metrics With the Change to SaaS

(14:35) AvePoint’s SaaS Learning Curve

(17:08) Sponsor - Mercury | Netsuite | Maxio

(20:30) How Paying Sales Reps Changed With the Shift to SaaS

(24:31) Why AI is a Worthy Investment for CFOs to Champion

(26:28) Avoiding Buyer's Remorse With AI Tooling

(29:00) Tactical Examples of Incorporating AI

(30:24) Building a Diversified Career as a CFO

(33:31) Sales as a Skill in Jim’s Career

(36:09) Wisdom From Jerry Seinfeld & Roger Federer

(39:41) Long-ass Lightning Round: Hiring Advice

(44:07) Finance Software Stack

In this episode, CJ interviews Dustin Pederson of Locus Robotics, as part of his series of interviews with CFOs from pre-IPO companies recorded live on the floor of the New York Stock Exchange. Dustin explains the Robot-as-a-Service (RaaS) model, a subscription-based service, how it works, and how it makes money. He and CJ do a deep dive into business models that rely on supply chains, the unique challenges of managing inventory, and tactical tips for CFOs looking to optimize their cash conversion cycles. They also examine the unique metrics tracked by Locus Robotics as both a hardware and software company compared to that of pure SaaS models. Dustin provides helpful information and tactical advice on how to build an ROI model and present it to buyers. He also shares insights on Locus Robotics’ market positioning, specialized ERPs for warehouses, and how the interactions between humans and robots play out in the companies Locus Robotics serves.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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.

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

(02:05) Sponsor - Leapfin | Mercury

(04:19) The Robot-as-a-Service Model

(07:42) Supply Chain Challenges for Hardware Companies

(08:50) Working Capital in a Hardware Company

(11:12) Tips for CFOs Managing Inventory

(12:44) Metrics Tracked by Locus Robotics

(14:39) Explaining Locus Robotics’ ROI to a CFO

(16:27) Sponsor - Netsuite | Maxio | Planful

(19:46) Building and Presenting an ROI Model

(22:41) Managing Assets in Unique Business Models

(23:51) How Locus Robotics Positions Itself in the Investor Market

(25:21) Locus Robotics’ Go-To-Market Motion

(27:18) ERPs for Warehouses

(28:46) The Interaction Between Humans and Robots

(30:14) The Industries Served by Locus Robotics

(31:26) Long-ass Lightning Round: A Lesson Learned About Presentations

(32:29) Dustin’s Top Three Tips

(34:50) Negotiating Tips

(37:37) Finance Software Stack

Continuing in the series of interviews with CFOs from pre-IPO companies recorded live from the New York Stock Exchange, in this episode, CJ is joined by Marcos Torres, CFO of Huntress. Marcos talks about his unusual career path and how he believes there are outsized prizes for people who take the path less traveled. He discusses the qualities of a good CFO such as critical thinking and adaptability, and how this relates to the survival of the fittest versus the survival of the strongest in Darwin's theory. He explains the significance of having a clear vision, making strategic decisions in the face of ambiguity, and the role of the CFO as a business leader, not just a finance leader. Listen out for an exciting fundraising announcement.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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.

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.

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

(02:19) Sponsor - Mercury | Netsuite

(04:32) Marcos’s First Job and Early Tech Nostalgia

(10:14) Outsized Prizes for People Who Take the Path Less Traveled

(12:44) The Importance of Critical Thinking for CFOs

(14:29) Underwriting Uncertainty

(15:56) The CFO as a Business Leader, Not a Finance Leader

(18:11) Sponsor - Maxio | Planful | Leapfin

(21:15) Survival of the Fittest Versus Survival of the Strongest

(22:42) Adaptability and Failure

(25:22) The Importance of Clarity of Vision

(26:58) The Art of Saying No

(31:53) Advice From Abe Lincoln and Its Application

(34:03) Dealing With Ambiguity

(37:05) Long-ass Lightning Round: Hiring Mistakes and Other Advice 

(41:22) Finance Software Stack and the Value of Data

(44:05) Craziest Expense Story

(44:50) An Exciting Announcement From Huntress

In this special edition, live from the New York Stock Exchange, CJ interviews Paul Mulé, CFO of Arcadia, as the first in a series of episodes featuring CFOs from pre-IPO companies. Paul explains what inspired his leap from investment banker to operator after 14 years at JP Morgan Chase and emphasizes the importance of betting on oneself. He also provides a unique perspective on the scarcity of CFOs capable of guiding tech companies through an IPO. Paul delves into the evolution of Arcadia's business model and how they built their M&A playbook. He and CJ discuss how to get M&A right as a private company and the role of current employees in this process. Paul highlights why a CFO needs to be able to tell the company's whole story, not just the financial aspect. He also underscores the importance of transparency and not being afraid to share too much information with employees. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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.

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.

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. 

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

(02:08) Sponsor - Netsuite | Maxio 

(04:53) Making the Leap From Banker to Operator 

(05:40) The Scarcity of CFOs Who Can Take a Tech Company Public

(06:50) Betting on Yourself in Any Role

(10:07) What Led Paul to Arcadia

(12:55) Building a Playbook for M&A

(16:28) Sponsor - Planful | Leapfin | Mercury

(19:18) Getting M&A Right as a Private Company

(21:11) The Value of Cross-selling in M&A

(22:13) Guardrails in M&A

(23:21) The Role of Current Employees in M&A at Private Companies

(26:05) CFO Frameworks: Telling the Whole Story, Not Just the Finance Story

(27:03) The Importance of Transparency

(32:56) Staying Nimble

(35:15) Paul’s Mantra

(37:50) Long-ass Lightning Round

In this episode, CJ interviews Alex Song, the VP of Finance and Capital Markets at Ramp who has also had a fascinating career in the world of investment. He explains how Ramp’s business model impacts liquidity, the unique balance sheet considerations of a payments company, and how credit card issuers approach risk management. He talks about the finance function as a trade-off between risk and return, and its job in brokering risk. He discusses how being in the payments flow lends itself to value creation and the value of owning the customer relationship. From seismic shipping vessels to rough diamonds, rail cars, and Colombian litigation finance claims, Alex also shares a number of fascinating stories about investments he has been involved in.  

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.

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.

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro

(02:04) Sponsor - Maxio | Planful 

(04:09) How Ramp’s Business Model Impacts Liquidity

(07:17) Risk Management as a Credit Card Issuer

(09:47) What Duration Mismatch is

(14:00) The Finance Function as a Trade-off Between Risk and Return 

(18:18) The Value of Owning the Customer Relationship

(22:16) Sponsor - Leapfin | Mercury | Netsuite

(25:28) The Role of a Finance Person to Be Risk-off

(26:32) Trading Mortgage-backed Securities After the 2009 Banking Collapse

(31:26) Storytime With Alex: Seismic Shipping

(33:17) The Story of Securitizing Rough Diamonds

(36:26) Colombian Litigation Finance Claims

(38:33) Alex’s Biggest Investment: Land Lots

(40:13) Investing in Rail Cars

(41:49) A Spicy Take on the Securitizations of Artists’ Back Catalogs

(45:05) Long-ass Lightning Round: Fat Fingering a Trade

(48:35) How Alex Has Changed as a Negotiator

(51:18) Craziest Expense Story

Nick Chammas, CFO of Eight Sleep, joins CJ to discuss his career journey from working as a first-year analyst on Google's IPO to his current role as CFO of Eight Sleep. He shares anecdotes from the Google IPO process (including a memorable story about Eric Schmidt) and a wealth of knowledge that he gained throughout the years. He talks about what it was like being a banker versus an operator and offers a word of caution for startup operators working with investment bankers for the first time. He emphasizes the necessity for sales skills irrespective of your role and gives tips on how to convey a balanced story to your board. He also provides insight into decision-making, explaining the difference between one-way and two-way doors, how to approach each, and how to navigate numbers versus gut feelings.

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.

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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.

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FOLLOW US ON X:

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TIMESTAMPS:(00:00) Preview and Intro

(02:57) Sponsor - Planful | Leapfin 

(05:25) Introduction to Eight Sleep

(07:05) Working on the Google IPO 

(11:50) A Story From the Google IPO Roadshow

(13:40) Banking Versus Investing Versus Operating 

(15:21) Date the Banker, Marry the Analyst 

(17:06) Sponsor - Mercury | Netsuite | Maxio

(20:29) Advice for Startup Operators Working With Investment Bankers

(22:34) Deal Fatigue Versus Deal Momentum

(23:53) Knowing How to Sell

(27:29) Decision Making: One-way Versus Two-way Doors

(30:32) Numbers Versus Gut Feel or Anecdotes

(36:17) Tips on Conveying a Story to Your Board

(39:22) Long-ass Lightning Round: Choosing a Job Versus Choosing a Boss

(40:49) Finance Software Stack

(41:37) Craziest Expense Story

In this episode, CJ interviews Anna King, CFO of Mesh, a spend and travel management platform. They explore changes in the CFO tech stack in recent years and how automation and storytelling can greatly complement each other. Anna explains how she got to revenue recognition on a daily basis, the importance of connecting production data with financial data for better insights, and the advantages of automation for driving value. They discuss the future of physical credit cards, the enduring role of cash, why some countries are more forward thinking in terms of payments than others, and how Anna would like to see the current finance ecosystem disrupted. Anna also shares her experience at Freddie Mac during the mortgage crisis and the lessons learned about economic change. This episode tackles imposter syndrome, fostering inclusion for women in finance, and finding your voice as a leader.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:19) Sponsor - Mercury | NetSuite

(04:57) Balancing Storytelling and Automation as a CFO

(07:11) How Anna Got to Revenue on a Daily Basis

(08:05) The Important Role of Production Data

(10:27) Automation for Driving Value

(11:46) Changes in the CFO Tech Stack in Recent Years

(14:49) Disruption in the Finance Ecosystem

(17:42) Sponsor - Maxio | Leapfin

(21:12) The Evolution of Fraud

(22:28) Why Some Countries Are More Forward-thinking About Payments

(23:32) The Future of Physical Credit Cards and Cash

(25:51) Working at Freddie Mac During the Mortgage Crisis

(28:20) The Importance of Regulation and the Pitfalls of Comparison 

(33:20) Fostering a Culture of Inclusion for Women in Finance

(37:42) Overcoming Imposter Syndrome

(40:57) Finding Your Own Voice in a New Role

(43:02) An Inspirational Story That Impacted Anna’s Journey

(45:05) Long-ass Lightning Round: Two of Anna’s Biggest Mistakes

(46:38) The Importance of Networking and Other Advice

(48:16) Anna’s Finance Software Stack

(48:51) Craziest Expense Story

In this episode, CJ interviews Rob Goldenberg, the CFO of 6sense, a B2B predictive intelligence engine that uses AI, machine learning, and big data to help sales and marketing teams find the best accounts to target. Rob has experience in both high and low macro environments and talks about the tools and strategies he uses to handle these situations. He emphasizes the need for alignment in a company and in finance and accounting teams and shares his framework for achieving this. Rob also highlights the dual role of finance teams as internal and external service providers and their function as an external concierge service. They discuss the potential pitfalls of tool consolidation, how to ask for funding for important initiatives or tools, managing spend in tough times, advice for taking advice, his decision-making framework, and the genius of Charlie Munger, including why sometimes the best thing to do is to do nothing. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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. 

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)

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TIMESTAMPS:(00:00) Preview and Intro

(02:06) Sponsor - Netsuite | Maxio

(04:38) Disdain for Google Sheets

(06:11) Driving Alignment in Finance and Accounting

(09:09) Finance and Accounting as an External Concierge Service

(12:12) Why Tool Consolidation is Overrated

(18:29) Sponsor - Leapfin | Mercury

(20:27) Advice for Asking for Funding

(24:37) Managing Spend During Tough Times

(30:30) Wisdom From Charlie Munger on Doing Nothing

(33:05) Advice on Taking Advice

(35:35) Frameworks for Making Difficult Decisions 

(40:36) A Decision Based on a Gut Feel Not Data

(43:31) Long-ass Lightning Round: Learnings From a Big Mistake and Other Advice

(46:38) Most Recent Software Tool

(47:37) Craziest Expense Story and the Fraud Triangle

Adam Ante is the CFO of Paycor, a publicly traded payroll provider. Not only did he scale the ranks of leadership quickly, but he took Paycor public in the first two years of his first role as a CFO. Today he joins CJ to discuss his career journey and share the wisdom he’s gained along the way. Inspired by the book Extreme Ownership by Jocko Willink and Leif Babin, Adam explains how aggressively stepping into your fear can help you succeed in the world of finance. He talks about overcoming imposter syndrome, training your capacity for stress, and why the small things are really the big things. He gives advice on not pigeonholing oneself but pressing into other parts of the company and earning your seat at the table. He also sheds light on how Paycor makes money, its North Star metric, its competitive moat, how its IPO share price was determined, the evolution of the Human Capital Management (HCM) market, and how payroll companies have unique insights into the economy's health. 

—

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.

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:13) Sponsor - Maxio | Leapfin

(04:58) Scaling the Ranks of Leadership Quickly 

(10:02) Overcoming Imposter Syndrome as a New CFO

(12:25) Pricing Paycor's IPO Share Price

(14:58) How Paycor Makes Money

(17:16) Sponsor - Mercury | Netsuite

(19:25) Paycor’s Atomic Unit and North Star Metric

(20:36) The Evolution of the HCM Market

(22:47) Navigating Finance and HR in Payroll 

(24:07) Paycor’s Competitive Moat

(25:10) The Unique Insights of Payroll Companies Into the Economy 

(27:30) Advice for Asking for Advice

(28:52) Valuable Advice Adam’s Received

(35:34) Not Pigeonholing Oneself in Finance

(38:55) Extreme Ownership in Finance 

(42:01) Strategy Vs Execution

(44:35) Training Your Capacity for Stress

(46:48) The Return of the Culture of Grinding

(48:57) Long-ass Lightning Round: One of Adam’s Biggest Failures

(50:39) Finance Software Stack

(51:06) Craziest Expense Story

In this episode, CJ interviews Bryan Morris, CFO of Demandbase, for an in-depth discussion on the complexities of OKRs (Objectives and Key Results). As the planning season for 2025 kicks into gear, Bryan shares his insights on setting the right OKRs, aligning them across departments, and explaining why they often lose momentum. He discusses his approach to tracking OKRs, the tools he uses, and his thoughts on making midyear adjustments. Bryan also talks about the value of weekly written executive team updates and formats for efficient meetings. Bryan, a strong advocate of personality tests, unpacks how they enhance talent management, before shedding light on the tough side of leadership and how to approach moving people out of the company when it’s not working. The episode wraps up with Bryan’s insights on a CFO’s decision-making power over an organization’s software stack, including the risks of tool consolidation and the hidden costs of poor tech choices.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

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. 

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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)

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TIMESTAMPS:(00:00) Preview and Intro(02:34) Sponsor - Leapfin | Planful(05:04) OKRs in Planning Season(07:55) Department OKRs Versus Company OKRs(10:04) The Pros and Cons Stretch Goals(12:19) When and Where Do OKRs Fail(16:28) Sponsor - Mercury | NetSuite | Maxio(19:52) Adjusting OKRs During the Year(21:50) Tools to Track OKRs(22:41) How Weekly Written Team Updates Work(24:53) Formats for Executive Team Meetings(28:20) Talent Management and the Benefits of Personality Tests(32:49) Soft Skills to Screen for When Hiring(33:45) Advice for Off-boarding People(37:25) CFOs and Company-wide Software Decisions(41:59) The Pros and Cons of Tool Consolidation(44:21) Hidden Costs of Choosing the Wrong Technology(45:40) Tips for Negotiating Software Deals(47:30) Long-ass Lightning Round: Wire Fraud Regrets(49:15) Advice to Bryan’s Younger Self(51:58) Finance Software Stack(52:36) Craziest Expense Story

Today CJ is joined by Thomas Ream, the CFO of Workato, an intelligent automation platform that is heavily involved in AI. Thomas opens up about what it was like working in AI in the early days of the 90s. They discuss AI as a component of workflow and what it means to train AI models. He talks about the differences between working in hardware and software, the growing trend of hardware and software combinations, and the vast potential of quantum computing. Having worked for a social network prior to the existence of Facebook and other tech companies doing interesting things too soon, Thomas explains the importance of timing in tech and challenges the assumption that there is a first mover’s advantage in this field. He shares wisdom from his experience as a CFO, what makes a great one, why he doesn’t necessarily hire based on experience, and the importance of quick decision-making as well as his “lead, follow, or get out of the way” framework. 

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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

(01:42) Sponsor - Leapfin | Mercury

(03:45) The Need for Humans in Training AI Models

(05:54) Thomas’s Early Work in AI in the 90s

(07:50) What It Means to Train an AI Model

(08:38) AI as a Component of Workflow

(13:04 ) Working in Hardware Vs Software

(16:02) Sponsor - Netsuite | Maxio

(18:30) Hardware-software Combinations and Quantum Computing

(22:28) The Importance of Timing in Tech

(26:33) Frameworks for Quick Decision-making

(34:28) Qualities Thomas Looks for When Hiring

(37:52) The Qualities of a Great CFO

(39:12) Balancing Time Between Internal and External Stakeholders 

(43:01) Long-ass Lightning Round: Advice on When to Move on

(47:36) Workato’s Finance Software Stack

(50:35) Craziest Expense Story

In this episode, CJ interviews Chuck Fisher, CFO of Turo, the world’s largest peer-to-peer car rental marketplace, doing more than $800 million in revenue per year. Chuck breaks down the company’s business model, what separates it from traditional car rental companies, and how it differs from marketplaces like Airbnb and Uber. He explains how Turo helps people build micro businesses and sheds light on the company’s total addressable market and why it shouldn’t be compared to its offline analog. He also talks about the company’s take rate, what substantiates it, and the benefits you may reap from keeping the take rate as low as possible, including the story about Turo’s own success in 2021. Chuck describes Turo’s Risk Score system, the data used in this, and how they use this information to market back to the best prospective customer. He also shares his firsthand account of the fall of Lehman Brothers and what he took away from it.

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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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.

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

(03:14) Sponsor - Maxio | NetSuite

(05:59) The Business Model of Turo

(10:59) The Sign of a Healthy Marketplace 

(13:31) Turo Vs Airbnb Vs Uber

(16:58) Sponsor - Mercury | Leapfin

(18:54) Turo’s Total Addressable Market

(25:16) Why Marketplaces Shouldn’t Be Compared to Offline Analogs

(26:25) Customers Turned Hosts and What This Means for the Business 

(28:50) The Take Rate and What Substantiates It

(32:53) Turo’s Risk Score System

(38:27) Whether or Not Marketplaces Can Survive at Scale Without Cheap Money

(41:22) The Benefits of Keeping the Take Rate Low

(45:58) Marketplaces and M&A 

(49:10) Chuck’s First-hand Account of What Happened at Lehman Brothers

(55:52) Long-ass Lightning Round: Advice on Prioritization 

(58:29) Chuck’s Finance Software Stack

(01:01:20) Craziest Expense Story

Rich Gotham, the president of the Boston Celtics, joins CJ to discuss the business side of one of the world’s best basketball teams and most recognizable sports brands. He explains the evolution of the Celtics' business model over the last decade, how the team diversifies its revenue streams to mitigate its dependence on in-game income, how they grow the team’s revenue given the finite number of seats at each game, and the role that digital technology and sponsorships play in this. He talks about how the team's performance affects the revenue they generate and he sheds light on how the use of ticket sale data, dynamic pricing, and building a membership model contribute to the team’s financial success. He also clears up, once and for all, what really happened with Paul Pearson in the 2008 NBA finals!

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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. 

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)

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TIMESTAMPS:

(00:00) Preview and Intro

(01:45) Sponsor - NetSuite | Maxio

(04:37) The Evolution of the Boston Celtics’ Business Model

(06:31) Diversifying Revenue Streams 

(10:08) Growing Revenue With a Finite Product

(12:31) The Impact of the Team's Performance on Revenue 

(14:52) Adding a Jersey Logo and the Role of Sponsorship 

(17:50) Sponsor - Leapfin | Mercury

(19:49) How Making the Playoffs Effects the Revenue Model

(23:03) Dynamic Pricing and How Ticket Prices Are Set

(25:14) The Role of Data in Ticket Sales

(28:57) Rich’s Epiphany About the Fans’ Values

(30:32) How This Functions as a Membership Model

(33:02) The Estimated Lifetime Value of a Fan

(36:24) Sports Teams That Rich Tries to Emulate

(40:39) Long-ass Lightning Round: Career Advice and Insights

(48:54) The Truth About Paul Pierce and the 2008 Final

Kevin Kraus, the CFO of publicly traded technology company 8x8 is CJ’s guest for this episode. Having done over 14 M&A transactions in his career, he has a wealth of knowledge on the subject to share. Kevin explains the best practices for M&A in tech companies, touching on the customer diligence aspect of the process and giving valuable advice on how to approach the post-M&A integration process. He also talks about standing up deal desks to speed up sales, not slow them down, and what to consider in terms of pricing and payment terms. He shares learnings from the book The Outsiders and what it taught him about resource allocation. Other profound insights that Kevin offers in this episode include his “one throat to choke” philosophy for FP&A teams, the qualities of a great CFO, and the importance of creating a succession plan. 

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.

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:00) Sponsor - Maxio | Leapfin

(04:21) Strategy for M&A in Tech

(07:06) Customer Diligence in M&A

(08:58) The Post M&A Integration Process

(13:34) Structuring a Deal Desk to Speed Up Sales

(17:54) Sponsor - Mercury | Netsuite 

(21:09) Deal Desks: Pricing and Payment Terms 

(24:32) The Significance of Ramp Deals

(29:08) Resource Allocation Decisions

(33:07) Repurchasing Shares Versus Buying Back Debt

(35:44) The “One Throat to Choke” Philosophy for FP&A Teams

(40:20) The Qualities of a Great CFO

(43:07) Why You Should Hire Someone Who Wants Your Job

(45:49) How to Create a Succession Plan 

(47:13) Long-ass Lightning Round: a Comp Structure Mistake

(49:52) Advice to Kevin’s Younger Self

(52:35) 8x8’s Finance Software Stack

(54:37) Craziest Expense Story

In this episode, CJ is joined by Bill Zerella, the CFO of the publicly traded auto marketplace ACV Auctions and former CFO of Fitbit, Inc. to discuss hypergrowth and taking companies from the private to public markets at scale. Bill sheds light on his days at Fitbit and the friction he faced in managing a business in hypergrowth mode, as well as its impacts on company culture and managing employees. He explains the CFO’s role in understanding tech debt and his approach to forecasting R&D spend. He also talks about Fitbit’s unprecedented growth, the company’s cash conversion cycle, and how it achieved negative working capital, before he tells the story of what it was like going up against the Apple Watch. Overall, he shares what he learned from his varied career in data-driven businesses. Tune in to hear about navigating hypergrowth and other insights from a CFO with an impressive career in later-stage tech firms. 

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

SPONSORS:

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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:

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TIMESTAMPS:

(00:00) Preview and Intro

(02:10) Sponsor - Leapfin | Mercury

(04:14) Managing a Business in Hypergrowth Mode

(07:15) Hypergrowth and Company Culture

(09:54) Managing Employees and Over-hiring

(14:05) Board Dynamics and Investment in Hypergrowth

(14:59) Understanding Tech Debt as a CFO

(17:59) Sponsor - Netsuite | Maxio

(20:26) Forecasting R&D Spend 

(21:41) How Fitbit Was Still Running on Quickbooks at $300 Million in Revenue

(23:10) Fitbit’s Unprecedented Growth 

(27:10) The Company’s Cash Conversion Cycle

(28:22) How to Achieve Negative Working Capital

(30:09) Going Up Against the Apple Watch

(39:01) The Impact of Stock Price and Valuation on Mindset

(42:14) The Through-line of Data-driven Businesses in Bill’s Career

(46:05) The Benefits of a Broad Focus in a CFO Career

(49:07) Long-ass Lightning Round: Bill’s Early Stage Startup Mistake

(51:55) Bill’s Advice to His Younger Self

(53:05) Finance Software Stack

(54:35) Craziest Expense Story

Andy Ivanovich, the CFO of The Knot Worldwide, joins CJ to dissect the company’s business model. He sheds light on how The Knot, which functions like an operating system for weddings, has grown to expand its product suite and reach, and now touches two-thirds of adult Americans each year. Andy explains the five dimensions of the company’s transactions that make it so unique. He also breaks down The Knot Worldwide’s ICP (Ideal Customer Profile) and customer LTV (Lifetime Value), and how they optimize for a supplier's lifetime value through their subscription model. He shares some M&A wisdom, explaining the Build, Buy, or Buddy framework for a roadmap expansion, and why “burning the lifeboats” is necessary for fully committing to change. Tuning in, you’ll hear about the CFO’s job of “truth-seeking”, why your team should be encouraged to challenge conventional wisdom, and how to manage a healthy level of friction amongst your peers.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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:

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—

TIMESTAMPS:

(00:00) Preview and Intro

(02:26) Sponsor - Mercury | NetSuite

(05:17) The Knot Worldwide’s Business Model

(14:06) The Five Dimensions of the Knot’s Transactions

(19:11) Sponsor - Maxio | Leapfin 

(21:25) High-Risk Transactions and Trust

(23:40) The Knot Worldwide’s Customer LTV (Lifetime Value)

(27:54) The ICP (Ideal Customer Profile) of The Knot Worldwide

(31:38) The Reach of the Company 

(34:01) The Impact of the Pandemic

(38:53) When Revenue is Recognised From a GAAP Perspective

(40:17) The Number One Customer Request

(43:02) The Role of “Truth Seeking” in Being a CFO

(44:48) The Build, Buy, or Buddy Framework 

(48:30) Encouraging Dissenting Opinions and Critical Reasoning

(52:01) Long-ass Lightning Round: The Biggest M&A Mistake

(55:49) The Knot Worldwide’s Finance Software Stack

(56:31) Andy’s Craziest Expense Story

In this episode, CJ interviews Guido Torrini, CFO of OneTrust and former CFO of Celonis, who has played a crucial role in shaping finance strategy and operations at two successful pre-IPO companies. Guido shares profound insights into managing his finance team more like an agile tech organization than a traditional planning function. He explains why he doesn’t believe in budgets, breaks down the V2MOM framework essential to his team’s success, and sheds light on how he ties company priorities back to the budgeting process. Additionally, Guido and CJ discuss the qualities that differentiate wartime and peacetime leaders. Guido also explains what he means when he says he wants his finance teams to make the news, not just report it, and shares wisdom on riding waves both professionally and as a company. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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. 

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

(02:38) Sponsor - NetSuite | Maxio

(05:10) Peacetime Versus Wartime Leaders

(13:11) Influencing Inputs Versus Reporting Outputs

(17:47) Leapfin | Mercury

(20:42) Guido’s Revenue Equation

(23:00) The V2MOM Framework for Capital Allocation

(27:34) Why Guido Doesn’t Believe in Budgets 

(30:08) How This Agile Planning Plays Out

(35:38) Sizing Up Controllable Versus Non-controllable Spends

(36:56) Forecasting Growth and Challenging Mindsets

(40:43) Riding Waves Professionally and as a Company

(43:36) The Impact of Geographical Location on Guido’s Career

(48:01) Long-ass Lightning Round: Mistakes Guido Has Learned From

(49:58) Guido’s Advice to His Younger Self

(51:05) OneTrust’s Finance Software Stack

(53:21) Craziest Expense Story

In this, the first solo episode of Run the Numbers, our host CJ Gustafson gives a crash course in sales compensation. He explains how to go about designing sales rep comp plans, covering who’s involved in this process, getting the base to variable split right, on-target earnings ratios, how to baseline core achievement, the role of accelerators, what actually counts as a booking, and comp plan flaws, referencing Salesforce's early comp plans as a case study. He also delves into the art and science of SPIFs (Sales Performance Incentive Funds), explaining why SPIFs succeed or fail, the best times to run one, and how you should structure them. He finishes the episode talking about paying sales reps, commission rates and benchmarks for account executives, and what the total commission stack should look like after you factor in everybody.

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.

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

(00:00) Preview and Intro

(01:44) Sponsor - Maxio | Leapfin

(03:58) Designing Sales Rep Comp Plans

(06:09) Getting the Split Right

(10:41) Baselining Core Achievement

(13:29) Sponsor - Mercury | NetSuite

(15:24) Accelerators

(18:05) Paying Sales Managers

(19:21) Case Study: Salesforce - Cash, Years, and ACV

(22:15) What Counts as a Booking

(23:15) Comp Plan Flaws

(25:31) An Introduction to SPIFs

(26:42) Why SPIFs Fail

(29:25) Where SPIFs Succeed

(30:23) Good Times to Do a SPIF

(33:37) SPIF Structures That You Can Copy

(35:28) Strategy Recap

(37:48) Paying Sales Reps

(40:44) The Total Commission Stack

(43:40) Factors That Can Push the Stack Higher

(45:15) Wrap

Aneal Vallurupalli, CFO of Airbase, an AP automation, spend management, and procure-to-pay solution, joins CJ to discuss all things risk management. He explains the different categories of spend outside of payroll and the biggest pain points within them. Aneal does a deep dive into fraud and how to prevent it, explaining how Airbase's number one product is really trust. He covers the non-payment risks to your company, the need for stage and growth-appropriate risk, and the benefits of a risk roadmap for your company. Aneal also delves into value metrics and what makes a good one. As someone with experience in the people function, he provides a unique perspective on why every finance person should get some recruitment experience, before explaining the qualities that separate good CFOs from great ones, and the role of the CFO as a "chief alignment officer".

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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

(01:52) Sponsor - Leapfin | Mercury

(03:57) Managing the People Function as a CFO

(05:28) Parallels Between Sales Pipelines and Candidate Pipelines

(07:49) The Evolving Nuances of Hiring Globally 

(11:54) Different Categories of Spend Outside of Payroll

(13:20) The Biggest Pain Points in These Spend Categories

(17:22) Sponsor - NetSuite | Maxio

(19:50) Fraud Prevention at Airbase

(24:43) Risk Management and Standing Up a Risk Function

(28:00) Non-payment Risks

(30:20) The Need for Some Risk and a Risk Roadmap

(32:25) Value Metrics  

(35:32) Airbase's North Star Metric of “Spend Under Management” 

(38:53) Examples of Value Metrics for Other Companies

(44:03) Metrics Aneal Looks at Each Morning 

(45:59) The Qualities of a Great CFO

(48:54) The Long-ass Lightning Round: Aneal’s Mindset Shift

(50:55) Aneal's Finance Software Stack

(52:41) Craziest Expense Story

In this episode, Ruslan Sergeyev, Managing Director of Hercules Capital gives CJ a masterclass in venture debt. He explains what venture debt is, its various types, and the potential benefits it can bring to your business. Ruslan sheds light on the current landscape and big players in venture dept. He provides insight on covenants, rates, warrants, and success fees in debt structure, and the difference between banks and funds. The discussion covers how much debt is appropriate for a capital stack and when you should refrain from raising venture debt altogether. Discover strategies for leveraging each banking activity as a chip to get the best deals with banks and learn what red flags to look out for in the process. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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

(02:36) Sponsor - Mercury | NetSuite

(05:13) Venture Debt: A Definition and Its Flavors

(08:07) Valuations Versus Distressed Sale Value for Venture Debt

(10:10) The Truth About Excess Cash Balances Held as Collateral Post-SVB Collapse

(14:28) The Percentage of Debt Deals Done in Conjunction With Equity Raises

(15:22) Typical Covenants Imposed on Startups

(16:38) Advice for CFOs Trying to Get the Best Terms or Covenants

(17:41) Covenants, Rates, and Warrants in Debt Structure

(20:00) Sponsor - Maxio | Leapfin

(23:19) When Not to Raise Venture Debt

(24:22) How Much Debt is Appropriate for a Capital Stack

(27:20) Ratios for Presenting the Business Case for Venture Debt 

(28:28) The Current Landscape and Big Players in Venture Debt

(33:01) Banks Versus Funds

(35:24) The Skews That Make the Most Money for the Bank

(36:25) Why Venture Debt is at the Top of Funnel for Banking Services 

(39:33) Whether or Not You Want to Be One of the Smallest Clients in the Bank's Portfolio

(41:31) Debt Versus Equity

(43:08) The Nature of the Relationship Between VCs and Venture Debt Players

(48:00) Using Each Banking Activity as a Chip to Get the Best Deals 

(50:05) Red Flags in the Venture Debt Process

(52:34) The Types of Deals Hercules Capital is Interested in

In this mailbag edition, CJ introduces listeners to Run the Numbers’ first intern. Intern Charlie fills us in on what his internship entails and the nature of the early recruitment process for college internships these days. Then CJ answers questions submitted by listeners. He shares his thoughts on when to join a startup to maximize your equity outcome, where to pull cash from when you need to free up budget, what experience he believes is required to run a $100 million+ SaaS company, whether or not you have to sell to the enterprise to become a public SaaS company, and what he means when he says that the gross profit is where the race starts. CJ talks about his own career path, why he switched from consulting and private equity to operator and CFO, and what he wishes he had known about his skills and potential job paths when he was in college. This episode is full of advice and insights for college students and finance professionals alike.

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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(02:32) Sponsor - Planful | Mercury(04:17) Intern Charlie’s Role at Run the Numbers(07:42) When to Join a Startup to Maximize Your Equity Outcome(12:13) Equity at Different Stages of a Company(13:57) Where to Pull Cash From When You Need to Free Up Budget(15:22) Sponsor - NetSuite | Maxio | Leapfin(18:57) Path to Become CFO of a $100 million+ SaaS Company(21:36) Finding “Personal Product Market Fit”(26:53) Selling to the Enterprise to Become a Public SaaS Company(28:15) The Gross Profit is Where the Race Starts(29:47) The Cost of Goods Sold for SaaS Versus Physical Products(31:02) CJ’s Favorite Writers(32:40) What CJ Would Ask a Candidate in an Interview Process but Can’t(36:10) Common Threads in the “Advice to Younger Self” Question(38:04) CJ’s Advice to College Graduates and Junior Year Students

Boris Wertz, the founding partner at Version One Ventures, a VC firm that invests in marketplaces and other startups, joins CJ to discuss the evolution and dynamics of marketplace models. Boris sheds light on his early years as a founder and operator at AbeBooks, and what he learned from selling the platform to Amazon during the dot-com boom. He explains the benefits of focusing on a niche instead of going too broad, how he solved the chicken and egg problem, and what it means to be a long-tail model operator. He and CJ discuss where we are today in the development life cycle of marketplaces and why having the mindshare of the buyer is more important than owning the underlying supply. Hear how the financial profiles of marketplace models differ from typical SaaS models, the importance of understanding where demand and supply match in what Boris refers to as a “hotspot”, and what metric is more important than the take rate and the average selling price. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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. 

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)

@bwertz (Boris)

Version One Ventures’ Guide to Marketplaces https://versionone.vc/marketplaces-guide-ed3/ 

—

TIMESTAMPS:(00:00) Preview and Intro

(02:33) Sponsor - NetSuite | Maxio

(06:55) Winning in a Niche and Not Going Too Broad

(09:32) AbeBooks and the Chicken and Egg Problem

(11:22) Data Standardization and Abebooks’ Competitive Moat

(12:37) Buying Your Own Inventory and Doing Things That Don't Scale

(15:01) What It Means to Operate a Long-tail Model 

(17:28) Sponsor - Leapfin | Mercury

(19:27) Having the Mindshare of the Buyer Versus Owning the Supply

(23:35) The Shift From Products to Services in Marketplaces

(29:30) Where We Are Today in the Development Life Cycle of Marketplaces

(31:59) The Main Catalyst Driving the New Wave of Marketplaces

(33:25) Understanding Product Market Fit and Liquidity Ratios

(37:33) Financial Profiles of Marketplace Models Versus Typical SaaS Models

(43:46) The Importance of the Take Rate Metric in Marketplaces

(46:30) Why Frequency of Transactions Trumps Take Rate and Average Selling Price

(49:51) Boris’s Hit Rate in Returns on Early-stage Venture Investing

(50:56) The Most Important Question Boris Asks Pitching Founders

(51:22) Cracking the Chicken and Egg Problem

(53:09) Wrap

In this episode, CJ is joined by Angela Winegar, Head of Growth Strategy at Carta and recovering venture capitalist. Having had an unconventional career path, Angela’s experience in the worlds of both marketing and investing gives her a unique perspective on growth. She and CJ discuss the parallels between marketing and investing and Angela explains how marketing is really a form of capital allocation. She sheds light on what the return on investment should be for media budgets and why CFOs should seek to better understand the differences in outcomes and timelines behind individual campaigns. She covers the differences between brand, demand gen, and growth, and the value of each. She also provides insight into marketing metrics and attribution models before sharing entertaining anecdotes from her unusual career.

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.

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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@anggwin (Angela)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:28) Sponsor - Maxio | Leapfin

(04:58) Angela’s Unconventional Career Path 

(10:29) Marketing as a Form of Capital Allocation

(14:59) Expected Returns From Marketers Versus Investors

(15:44) Sponsor - Mercury | NetSuite

(17:56) What the Return on Investment Should Be on Your Media Budget

(19:50) Brand Versus Demand Gen Versus Growth

(27:35) When to Do Marketing Internally Versus Outsource 

(30:56) Marketing Metrics and Attribution Models

(35:55) Where Marketing Ops Should Sit Within an Org

(39:55) Working for Obama and Working in Government Versus Startups

(42:29) Angela on Meeting Michael Dell

(43:43) The Efficient Market Hypothesis: Right or Wrong?

(46:12) Insight Into Churn at Carta 

(49:05) Carta’s ICP of Lawyers

Scott Haralson, CFO of Spirit Airlines, joins CJ in this episode to discuss the complexities of operating an airline business. He explains what it means to run an ultra-low-cost carrier model and what goes into calculating the operating costs per available seat mile, Spirit’s most important metric. He talks about the difficulty of forecasting for an airline, explaining the costs you may not think about, what goes into network planning, the challenges of hedging fuel prices, navigating capital intensive decisions such as buying airplanes, and doing all of the above through unpredictable economic cycles and volatility. He also sheds light on why Spirit’s ICP (Ideal Customer Profile) is leisure travelers over business travelers and the important role of dynamic pricing in the airline industry. 

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

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. 

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:40) Sponsor - Leapfin | Mercury

(04:46) Unit Cost Production in an Ultra-low-cost Carrier Model

(08:02) The North Star Metric of Cost Per Available Seat Mile

(13:24) Spirit’s ICP of Leisure Travelers Over Business Travelers

(16:10) The Impact of Flight Utilization on Spirit’s Business Model

(19:42) Sponsor - NetSuite | Maxio 

(22:11) The Difficulty of Forecasting for an Airline 

(29:52) Flight Profitability and Network Planning

(31:21) The Operating Costs of Running an Airline

(37:06) Navigating Economic Cycles and Volatility in the Airline Industry 

(39:52) The Challenges of Hedging the Fuel Price

(44:33) Understanding Major Capital Allocation Decisions

(48:24) Navigating Dynamic Pricing  

(54:16) Scott’s Advice on Understanding What Really Matters

(55:33) Spirit Airlines’ Finance Software Stack

(57:54) Craziest Expense

Silicon Valley veteran and early employee at Google, Facebook, and Quip, Molly Graham, joins CJ to discuss all things related to scaling startups, growing as a leader, and progressing in your career. Molly talks about her famous “Give Away Your Legos” talk and how this came about before she and CJ discuss the concept of “work grief” and how to get through it when you have to give up something that your identity is tied to. Having had a very non-linear career path and “stumbling sideways into things”, Molly explains the J-Curve versus staircase analogy for career progression and encourages especially those in finance roles to take big risks. From handling the grief of laying someone off to learning the skill of saying no, mastering the art of destruction as an important part of building a company, and knowing how to fire people not just hire them, Molly shares profound insights from her impressive career. 

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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FOLLOW US ON X:

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@molly_g (Molly)

MOLLY’S SUBSTACK: “Lessons”

“‘Give Away Your Legos’ and Other Commandments for Scaling Startups” - Molly Graham:

https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/ 

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TIMESTAMPS:

(00:00) Preview and Intro

(01:54) Sponsor - Maxio | Mercury

(04:15) What It Means to “Give Away Your Legos”

(07:59) The Concept of “Work Grief” and How to Get Through It

(12:30) Using the Worst-case Scenario as a Motivator

(15:41) Handling the Grief of Laying Someone Off

(17:28) Sponsor - Netsuite

(18:44) The J-curve Versus Staircase Analogy for Career Progression

(27:31) The Powerful Combo of Risky Paths and Network Building

(30:45) Why You Should Take a Risk if You’re in FP&A or Finance

(33:22) What It Was Like Working Directly for Chamath at Facebook

(34:19) Learning the Skill of Saying No 

(40:18) Why It’s Okay Not to Have a Career Path Mapped Out

(42:41) Destruction as an Important Part of Building a Company

(46:04) The Skill of Time Compression for Leaders

(49:23) The Importance of Knowing How to Fire People, Not Just Hire Them

(53:58) Glue Club and Who Can Benefit From It

(55:21) Finding Your Product Market Fit at Companies of Different Sizes

(59:38) Wrap

In this episode, CJ is joined by Lanny Baker, the CFO of Eventbrite, and former CFO of Yelp, Monster.com, and ZipRealty. Lanny has been a part of some incredible business transformations or pivots at each of these companies and has some profound insights to share on the topic. First, he explains some of the differences between consumer-facing internet businesses versus SaaS or B2B. He sheds light on Eventbrite’s unique creator and consumer model, the virtuous cycle of network effects it benefits from, and how the company’s take rate is determined. Lanny also talks about the ways that internet platforms expand their TAM over time. This leads to a conversation on business transformations or pivots, the role of a CFO in them, whether to retain or replace people in such a situation, and how to handle investors. Tune in for all this and the hilarious story about a marketing stunt gone wrong.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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.

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.

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FOLLOW US ON X:

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TIMESTAMPS:

(00:00) Preview and Intro

(02:25) Sponsor - NetSuite | Maxio 

(05:16) How to “Show Up for Life” in Business

(06:54) Consumer-facing Internet Businesses Versus SaaS or B2B

(11:03) First Principles in Building Your Operating Plan as a Finance Team

(13:13) The Benefits of Eventbrite’s Unique Creator and a Consumer Model

(17:28) The Most Important Metric for Eventbrite

(19:04) Sponsor - Mercury 

(21:34) The Factors That Determine Eventbrite’s Take Rate

(25:57) How Internet Companies Expand Their TAMs Over Time

(29:46) The Role of a CFO in a Business Transformation

(40:38) Replacing Versus Retaining People in a Business Transformation

(48:08) Handling Investors in a Business Transformation

(52:33) Long Ass-lightning Round: a Profound Lesson From Lanny’s Time at Monster

(55:26) The Hilarious Story About a Marketing Stunt Gone Wrong

(57:07) Lanny’s Parking-related Life Hack

(58:37) Eventbrite’s Finance Team’s Tech Tooling

(01:00:35) The Craziest Thing Someone Tried to Expense

In this episode, CJ sits down with John McCauley, the CFO of Calendly. From his learnings under the leadership of Frank Slootman and Mike Scarpelli at ServiceNow to his first CFO role at Seismic, and his current position, John shares valuable insights from his career. He gives advice on hiring and getting promoted, why you should consider your value prop to your company, the benefits of seeking healthy confrontation, and why the CFO should take responsibility for overall company performance. From tracking product-led growth in your metrics to debunking the myths of benchmarking, John offers profound insights into what it takes to excel as a CFO in today's evolving software climate. He also explains the role of loyalty in software organizations and why businesses are teams, not families.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:02) Sponsor - Mercury | NetSuite

(04:49) What John Learned Under Frank Slootman and Mike Scarpelli

(10:30) A Big Mistake That John Made at ServiceNow

(15:54) John’s Mindset Going Into His First CFO Role

(18:23) Sponsor - Maxio

(21:22) A Lesson on Hiring and Getting Promoted

(24:48) Brand Equity and Calendly’s Viral Coefficient

(28:22) Tracking Product-led Growth in Your Metrics

(32:36) The Changing Climate of Software

(36:16) Creating Value as a Privately Held Tech Company in M&A

(39:12) The Truth About Benchmarking

(42:17) What Makes a Great CFO

(44:41) John on “Moving Slow to Move Fast” 

(47:01) The Role of Loyalty in Business: Team Versus Family

(50:49) The Long-ass Lightning Round: John’s Advice to His Younger Self

(52:20) John’s Finance Software Stack

(53:35) The Craziest Thing Someone Tried to Expense

In this episode, CJ is joined by Jeff Cooper, the CFO of Guidewire, a publicly traded vertical software company serving the insurance industry. Jeff explains the strategic advantage Guidewire has in owning the control point within a customer's tech infrastructure and how they achieved this. He sheds light on the challenges and benefits of Guidewire's industry-specific business model, including long sales cycles, non-standard fiscal years, and the risks of burning through their market. He also discusses ARR as the most important metric, how he decides on the metrics he reports on, and how to think about the value of professional services within your valuation and value proposition. 

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.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro

(01:57) Sponsor - Maxio | Mercury

(04:20) How Guidewire Monetizes Its Business

(08:48) Guidewire’s Strategic High Ground and How They Earned It

(13:53) The Benefits of Owning the Control Point in a Customer's Tech Stack

(16:09) Guidewire’s Long Deal Cycles and Sales Capacity Model

(18:47) Sponsor - NetSuite

(20:09) Navigating Big Deals, Long Sales Cycles, and Seasonality

(22:33) Guiding to ARR

(24:38) The Pros and Cons of Having Fiscal Year End in July

(28:27) Concerns Over Burning Through Your Market

(31:39) Professional Services: In-house Versus Outsourcing

(36:11) The Nature of a Good Partner Ecosystem

(38:44) Communicating the Most Important Metrics

(42:03) Long-ass Lightning Round: One of Jeff’s Biggest Metric Mistakes 

(44:33) The Advice Jeff Would Give His Younger Self

(45:53) Jeff’s Finance Software Stack

Today, CJ hosts Taylor Holiday, a legend in the e-commerce and D2C (Direct-to-Consumer) world. He is also the CEO and founder of Common Thread Collective, one of the leading marketing agencies for e-commerce brands. Taylor takes us on a deep dive into marketing best practices and shares profound insights from his years of experience in D2C and e-commerce businesses. He talks about bridging the gap between marketing and finance and what marketers often miss about monetization. He explains when to do marketing in-house and when to hire experts, how unit economics and expectations differ in B2C versus B2B, and why it’s so challenging to forecast inventory in e-commerce. Taylor also gives his top tip for anyone starting an e-commerce or D2C business today.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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.

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

@TaylorHoliday (Taylor)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:45) Sponsor - NetSuite | Maxio

(05:28) Bridging the Gap Between Marketing and Finance

09:03) What All Marketers Need to Know

(15:48) In-house Marketing Versus Hiring Experts

(18:35) Sponsor - Mercury 

(21:05) Unit Economics and Expectations in B2C Versus B2B

(25:56) Working With Social Networks in B2C Versus B2B

(28:55) The Four Quarter Accounting Framework for Your Social Media Budget

(31:31) The Challenge of Forecasting Inventory in E-commerce

(35:52) How Gymshark Mastered the Cash Conversion Cycle

(39:16) E-commerce and D2C Companies That Hit It Big

(42:40) How Taylor Made a Fortune Selling Rubber Wedding Rings

(44:43) Takeaways From Taylor’s Years in E-commerce

(49:39) Podcasting as a Marketing Medium

(52:26) Wrap

Jim Kelliher, the former CFO of PTC, LogMeIn, and Drift, and general CFO legend in Boston, joins CJ to discuss the secrets behind the success of these companies and the lessons he’s learned in his 35-year career. From the importance of product investment to how to navigate IPOs during economic downturns, Jim shares profound insights into how CFOs can drive growth rather than just manage budgets. He explains the importance of investing in product, how to vet budget requests, and how to build a winning team spirit. He also talks about venture capital versus later-stage private equity buyouts and how the growing trend towards the latter is doing what Jim believes to be a disservice to the startup communities they operate within. 

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.

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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:27) Sponsor - Mercury | Maxio

(05:11) The Six Things That Made PTC Software, LogMeIn, and Drift Succeed

(12:38) The Importance of Investing in Product

(17:28) Sponsor - NetSuite

(18:59) Questions to Ask to Vet Budget Requests

(20:31) Inspiring People to Spend Company Money Like It Was Their Own

(21:51) The Difference Between Being Frugal and Being Cheap

(25:26) How to Learn Negotiation

(27:10) The Importance of Adding High-Caliber People to Your Team

(28:56) Advice for CFOs Mentoring Future CFOs

(30:47) Jim’s Proudest Career Achievement

(32:08) Building a Winning Team Spirit

(38:19) VC Versus PE Buyouts

(45:19) Advice to CEOs or CFOs Vetting Private Equity Sponsors

(51:16) Tips for Timing Your IPO

(55:12) Two of Jim’s Biggest Career Mistakes

(56:38) The Craziest Thing Jim Saw Someone Try to Expense

(58:01) Wrap

This episode dives into the world of short-selling and activist investing with guest Edwin Dorsey, the writer behind The Bear Cave Substack. Edwin tells CJ the story of how he made a name for himself by exposing wrongdoing at Care.com and how this inspired his current writing career. He goes on to explain how short selling works and what differentiates it from long-only investing, before talking about how he researches corporate misconduct, the clues he looks for in consumer industry reports, and other red flags apparent in the actions of management, auditing firms, and board members. He also discusses what it means for employees when an activist investor takes a stake in your company.

Subscribe to Edwin’s newsletter, The Bear Cave

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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.

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)

@StockJabber (Edwin Dorsey)

@turpentinemedia

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:35) Sponsor - NetSuite | Mercury

(05:16) The Care.com Story That Put Edwin on the Map

(09:43) The Genesis of The Bear Cave

(13:09) An Introduction to Short Selling

(16:29) Sponsor - Maxio

(17:39) Betting on Binary Outcomes

(20:38) What Edwin Looks for in a Short Sell

(24:16) Management Turnover as a Short Sell Signal

(26:31) Red Flags Relating to Auditors

(31:35) Corporate Fraud and Financial Misconduct Red Flags

(41:13) Financial Statement Mishaps

(44:36) Why Edwin Watches Board Members Over CEOs or CFOs

(48:07) Activist Investing: What It Means for Employees

(53:33) A Parting Story on Exposing Corporate Wrongdoing

(55:27) Wrap

Having listened to a number of Couchbase’s earning calls, the company’s CFO Greg Henry sits down with CJ to answer some in-depth questions, starting with the rationale behind Couchbase's non-standard fiscal year and the advantages of it. He then delves into his experience of transforming a traditional enterprise subscription model into a managed service consumption business. The conversation covers Couchbase's focus on Annual Recurring Revenue (ARR) as their North Star metric and the art and science of multi-year deals. They discuss how best to interact with sell-side analysts, how callbacks after earnings calls work, and how to manage relationships on the buy side. Greg also reflects on his time at General Electric during its heyday, offering insights into the culture and frameworks that shaped his approach to business today before talking about Matt Cain's framework for Couchbase and how it enables function. Tune in to hear all this and the story of how Greg lost $1 million of operating profit.

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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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. 

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(03:16) Sponsor - Mercury | NetSuite(05:40) Non-standard Fiscal Years(09:00) Transitioning From Subscription to Consumption(14:53) Couchbase’s North Star Metric of ARR(16:55) ARR versus RPO and CRPO(18:38) Sponsor - Maxio | Leapfin | Planful(22:14) The Art and Science of Multi-year Deals(24:33) Interacting With Sell-side Analysts(27:28) The “Open Window” After an Earnings Call(31:22) The Benefits of Having Analyst Coverage(32:16) Relationships on the Buy Side(35:44) Working at General Electric During Its Heyday(38:32) Frameworks From Jack Welch(40:52f) Matt Cain’s Framework for Couchbase(42:19) Learnings From GE’s Consent Decree(45:35) Long-ass Lightning Round: How Greg Lost a $1 Million Operating Profit(48:56) Finance Software Stack(50:13) Craziest Expense Story

In this episode, CJ is joined by Jason Kap, the founder and CEO of Blue Rocket, a world-renowned pricing consultancy for top enterprise tech companies like Salesforce, Cisco, PagerDuty, Brex, and GitLab. Jason discusses the invaluable experience he gained working at Microsoft under Bill Gates in the early 2000s, including his role in the canonical antitrust case. Then he takes a deep dive into all things pricing, covering where in the organization pricing should sit, how often companies should update their pricing models, his philosophy on discounting, how CFOs can better work with sales teams to determine pricing ranges, the role of framing and psychology in how a deal is presented in price to the end consumer, and how this all relates to corporate strategy.

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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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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.

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FOLLOW US ON X:

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TIMESTAMPS:

(00:00) Preview and Intro

(02:21) Sponsor - Maxio | NetSuite

(05:27) Microsoft Culture in the Early 2000s

(08:06) Pricing and Packaging the Microsoft Office Suite

(10:30) The Antitrust Law and Consent Decree

(12:34) The Project That Jason Shot Down

(14:58) Online Services and the Origin of SaaS

(17:54) Managing Big Projects: the “No Delegation Rule”

(19:18) Sponsor - Mercury

(20:39) Decisions in Pricing: Company Strategy, Segmentation, Financial Strength

(22:43) Ideal Location for Pricing Within an Organization

(25:02) Repackaging Products and Considering Competition

(26:53) An Introduction to Value-based Pricing

(32:15) Challenges in Competitor Comparison and Pricing

(35:58) An Explanation of Non-price Terms

(41:55) Jason’s Philosophy of Discounting

(48:52) Evolving Your Discounting Strategy Over Time

(50:53) Frameworks for Discounting: The Pricing Maturity Model

(51:49) Discounting for Different Macro Environments

(55:04) Anecdotes from Jason’s Career

(1:00:51) Wrap

In this episode, CJ discusses the business of global payments and B2B fintech with Camilla Matias Morais, COO of Brex. Camilla came up in the FP&A world and is a stellar guide to Brex’s strategic bets and moats. Also covered is how she balances the COO role of risk management and company strategy while also being in the weeds with customer feedback. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024.

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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ Now through April 15th NetSuite is offering a one-of-a-kind flexible financing program https://netsuite.com/metrics 

Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

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FOLLOW US ON X:

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TIMESTAMPS:

(00:00) Preview

(01:06) Intro

(02:21) Sponsor: Maxio | NetSuite

(05:39) Exploring Fintech Monetization and Business Models

(09:36) How the Founder of the Fyre Festival Possibly Started a Credit Card Company

(11:11) Making Money Out of Free Fintech Services

(14:26) Competitive Moats in Fintech

(16:11) Global Expansion: Brex's Strategy for Success

(21:01) Sponsor: Attio | Thoropass

(23:01) B2C FinTech versus B2B FinTech

(29:57) Lifetime Value of a Brex User

(32:44) Brex’s Northstar Metric

(34:45) Revenue Per Rep: A Deep Dive into Sales Metrics

(38:04) Balancing Strategy and Execution: Insights from a COO

(39:07) Credit Limit and Managing Risks

(44:06) Frameworks for Success: Metrics, Talent, and Internal Mobility

(50:24) Avoiding Burnout

(54:42) Camila’s Career Screw-Up

(58:43) Brex’s Software Stack - Sponsored by Tropic

(1:00:10) Wrap

In this episode, CJ talks with the original duo of the Salem Witch Trials the HR Heretics podcast, Kelli Dragovich and Nolan Church about tech layoffs in 2024. Kelli and Nolan hold no punches and give straight answers to tough questions on layoffs, the job market, and employment best practices. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024.

RECOMMENDED PODCAST: HR Heretics

Join Nolan Church and Kelli Dragovich for  unfiltered conversations with people leaders, investors, and CEOS. Dive deep into the kind of leadership-level strategy that often happens behind closed doors. 

Substack:

Spotify:

Apple:

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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ Now through April 15th NetSuite is offering a one-of-a-kind flexible financing program https://netsuite.com/metrics Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

@kellidragovich (Kelli)

@NolanChurch (Nolan)

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TIMESTAMPS:

(00:00) Preview

(00:25) Round 2 with HR Heretics 

(01:57) Sponsor: Maxio | NetSuite 

(04:27) Why Heretics?

(05:05) Millennials, Social Media, and Recorded Layoffs

(11:26) Navigating Layoffs and Role Eliminations

(15:31) Human-Centered is Good Business

(17:52) Role Eliminations or Layoff? 

(19:00) Sponsor: Thoropass | Tropic

(21:27) Managing Out Bottom Performers

(26:37) Severance Packages: From Crappy to Great

(28:11) Supporting Low Performers

(31:55) The Illusion of Safety in Big Companies 

(34:33 ) When Big Company Experience is Sending a Negative Signal

(43:20) Working at Smaller Startups

(45:31) On Attrition Rates

(50:19) Quiet Quitting and Beyond

(53:55) Wrap

In this episode CJ is joined by Fred Havemeyer, a leading sell-side equity analyst from Macquarie specializing in AI and software research within the US. They delve deep into AI’s impact on the near term role of a CFO. Fred offers an unparalleled analysis of how to quantify productivity gains with AI, the difference between the metrics the sell side uses versus operators and their day to day models. They also cover why company valuations are both an art and a science, and the difference in metrics that operators vs bankers use to make decisions.

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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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ Now through April 15th NetSuite is offering a one-of-a-kind flexible financing program https://netsuite.com/metrics 

Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTNThoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

@Montaukmagic (Fred)

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TIMESTAMPS:

(00:00) Preview

(01:03) Episode Summary and Intro on Fred

(03:10) Sponsor - Maxio | Netsuite 

(05:46) 2021: High-Profile Breaches

(08:19) CFO Metrics and Managing Expectations

(11:05)  The Beauty Of The Software Space

(12:16) Carefully Playing the Game of Metrics

(15:40) Does Everything End Up in a DCF Model?

(18:06) The AI Revolution: Adoption, Impact, and Future Prospects

(22:42) AI's Productivity Paradox: Boosting the Bottom Line

(27:10) Sponsor - Attio | Thoropass

(29:25) CFOs on AI Pricing Models

(32:56) Cost Management and Avoiding Misconfiguration Mistakes

(37:39) Margin Profile of Generative AI

(42:50) Sponsor - Tropic

(44:00) Optimizing Hardware Usage and Mapping the Right Hardware to the Right Problem

(46:09) On Snowflake and Optimization, Infrastructure, and Negotiation

(50:36) Exploring AI's Capabilities and Limitations on Working with Numbers

(58:02) The Future of AI in Business and Risk Management

(1:00:09) Wrap

Todd Rakow, CFO of Gladly joins CJ for this deep dive into usage-based revenue models, strategic finance leadership, and the complexities of managing growth at scale. Todd shares tons of tactical insights, including building out the usage-based model, forecasting customer usage patterns, commissioning sales reps, and teaching your teams to distinguish between reoccurring and recurring revenue. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024.

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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ Now through April 15th NetSuite is offering a one-of-a-kind flexible financing program https://netsuite.com/metrics 

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@turpentinemedia

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TIMESTAMPS

(00:00) Preview

(01:11) Intro

(02:31) Sponsor: Maxio | Netsuite

(06:09) Usage Based Benchmarks: Here to Stay?

(08:01) Understand ARR and its Components

(10:30) Recurring or Reoccurring?

(12:33) Computing Gladly's ARR 

(18:13) Seasonality and Alternative Methods to Better Track Revenue

(22:25) Sponsor: Thoropass

(23:45) Commission Structures And Incentivizing Sales Reps

(27:28) Avoiding Foot Faults in Usage-Based Models

(28:57) Frameworks for the Day-to-Day

(31:36) Strategic Leadership, Customer Support and Success 

(32:50) Being a CFO: A Series of Long Uncomfortable Conversations

(36:12) Removing the Stigma Around CFOs

(37:45) Todd's Insights on the Difference Between a Good and a Great CFO

(40:07) Forging a Good Relationship with Your CEO

(43:29) Long Ass Lightning Round: What Did Todd Mess Up in His Career?

(45:37) What Would Todd Tell His Younger Self?

(50:35) Todd’s Software Stack - Sponsored by Tropic

(52:41) Craziest Expense Request

(53:30) Wrap

Today CJ is joined by Cameron Hyzer, the CFO of ZoomInfo, one of the world's most successful publicly traded data businesses. Cameron is a master capital allocator and this conversation touches on why you should focus on quality versus reducing costs as a CFO, share repurchase programs 101, and frameworks for making resource allocation bets. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@turpentinemedia

—TIMESTAMPS:(00:00) Intro

(02:11) Sponsor: Maxio | NetSuite

(04:44) ZoomInfo's Secret Sauce

(15:13) ZoomInfo's Success

(21:50) Translating Macro Trends into Business Strategy

(25:14) Strategies for Maintaining Margins and Cash Flow

(26:14) Sponsor : Attio | Thoropass

(28:27) Managing Customer Relationships and Retention

(30:11) Qualities of a Great CFO

(33:47) Effective Financial and Operational Data Management

(37:26) CFO-CEO Relationship

(39:51) Balancing Risk and Opportunity

(41:24) CFO as Chief Investment Officer

(43:53) Cameron’s Tech Stack Brought to You By Tropic

(45:52) Wrap

Today CJ welcomes Dave Kline, a leadership coach and owner of the MGMT Accelerator to the pod. The discussion covers tactical advice for managers and leaders to develop high performance cultures among their current teams, including setting clear expectations, running productive 1:1s, and encouraging a compounding ownership mentality from direct reports. They also touch on Dave’s lessons from working at Bridgewater under Ray Dalio, whether a company can have a Dennis Rodman, and strategies to better delegate. 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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

—

FOLLOW US ON X:

@DKlineii (Dave)

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LINKS:Dave’s Newsletter: https://mgmt.beehiiv.com/Dave’s Accelerator Program: https://maven.com/dave-kline/mgmt-accelerator 

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TIMESTAMPS: 

(00:00) Intro

(02:55) Sponsors: Maxio | NetSuite 

(05:32) Bridgewater’s Unusual Feedback cycle

(08:05) People Capital: the Importance of Understanding Individual Strengths

(18:24) Sponsors: Thoropass | Tropic

(20:46) Defining Ownership Mentality in Business

(26:40) Implementing Ownership Mentality in Teams

(28:00) Aligning Incentives for Retention

(33:36) The Impact of Job Hopping

(35:00) What to Do About Dennis Rodmans 

(36:28) The Problem with Exceptions

(41:27) The Danger of 'That's Okay, I'll Do It'

(45:58) Better 1:1 Meetings

(49:26) Wrap

Today, the tables are turned as guest Alex Peterson, an expert in Financial Planning & Analysis (FP&A) – and CJ’s first hire – puts CJ in the hot seat. Tune in for two old friends sharing war stories and talking about performance reviews, net dollar retention rates, and Frank Slootman’s retirement. 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.

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@turpentinemedia

—

TIMESTAMPS:

(00:00) Preview and Intro

(01:57) Sponsor - Maxio |NetSuite

(04:47) On Swimming, Endurance and Working in FP&A

(07:45) Understanding the Headcount Model

(13:12) Reflections on Working Relationships and Working Against the Norm

(22:27) Sponsor - Attio | Thoropass

(24:42) Alex’s CJisms and Navigating the Job Market Post-COVID

(32:14) FP&A Is a Customer Service Role

(41:15) Sponsor - Tropic

(42:28) A Really Cool Performance Review

(44:21) The Legacy of a Leader

(47:47) On Frank Slootman’s Retirement

(53:28) Understanding the Product You're Selling

(56:36) 30-Minute Standing Water Cooler Friday Mornings

(59:30) Wrap

On this episode, CJ interviews Adam Swiecicki, CFO at Rippling and former CFO at Brex. They cover valuable strategies that have fueled Rippling's growth as a “Compound Startup” in the competitive HR, Finance, and IT space. Adam also shares lessons from being a short seller that he applies to being a company CFO, the ROI on R&D investment, capital allocation decision making frameworks and how to avoid CFO burnout. 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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@turpentinemedia

—

TIMESTAMPS:

(00:00) Preview

(02:27) Sponsor - NetSuite | Thoropass

(05:23) Understanding Rippling's Business Model

(09:42) Resource Allocation in a Compound Startup

(15:54) Sponsor - Maxio

(17:02) Competitive Moats in the SaaS Industry

(23:01) Launching Rippling’s Finance Cloud

(26:43) Understanding Customer Lifetime Value at Rippling

(28:36) The Signal of a Strong PMF

(30:34) Rippling's Northstars

(32:45) The Concept of Revenue Growth Endurance

(33:40) The Role of a CFO

(36:12) Balancing Strategy and Execution

(40:25) Adam’s Frameworks, Methods, or Processes for Prioritizing Work

(44:10) From Short Selling to Running a Company

(48:10) Avoiding CFO Burnout: Enjoying the Journey

(51:23) Adam’s Craziest Work Experience and Expense

(53:27) Rep Yo Stack Sponsored by Tropic: Adam’s Finance Software Stack

(57:57) Wrap

In this episode, CJ interviews Jack Greco, the co-founder of ACV Auctions, a publicly traded B2B marketplace for automobiles. Greco is now a prolific Angel investor. In this conversation they cover the human element necessary in any marketplace business, setting up make-good budget for mistakes, business seasonality, and how the auction model affects supply and demand liquidity. This is truly a masterclass in all things marketplaces and valuable for anyone who is interested in businesses which depend on a high degree of trust. 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 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN

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.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@turpentinemedia

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TIMESTAMPS:

(00:00) Preview

(02:20) Sponsors: NetSuite by Oracle | Attio

(05:12) Understanding the Human Aspect of Business

(09:07) Using a 'Make Good Budget' in Business

(13:18) Marketplace is the Cart, Not the Horse (Understanding the Nature of Marketplaces)

(14:59) Sponsor: Maxio | Thoropass

(17:27) Creating Liquidity From Marketplaces

(22:55) Auction in Marketplaces: Where Kinetic Energy Dances On

(26:12) Seasonality in Business

(30:45) The Role of Timing in Business Success

(32:25) How ACV Evolved and Developed its Competitive Edge

(35:52) Human Interaction - A Necessary Spice

(39:04) Sponsor: Tropic

(39:48) The Single Decision that Unlocked the Most Value

(42:49) Jack's General Philosophy Around Setting a Take Rate

(47:11) Payment Responsibility and Demand Generation

(48:18) The Colorful People in the Used Car Business (and other wacky operational things)

(50:44) The Importance and Frequency of Investor Updates

(52:51) Wrap

In this episode, CJ talks to Jessica Lanier, CFO of Restaurant365 and the first CFO guest on the podcast who has firsthand experience as a founder. On top of this, every company she has worked for has been acquired, so she has a wealth of knowledge on all things M&A. She talks about what makes a great CEO-CFO relationship and why a good relationship with the CRO is also so important. She also explores the benefits of operating a company at scale and whether private and public companies require different skills. Jessica shares her most extreme experience of M&A, what finance leaders should expect after their companies are acquired, and the role of trust and credibility in this process. She also discusses her framework for evaluating a company you may want to work for, before offering profound advice on recognizing when you’re ready for your next role. 

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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SPONSORS:

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

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. 

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.

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(03:00) Sponsor - NetSuite | Maxio 

(05:44) How Being a Founder Makes You a Better CFO

(10:37) The CFO’s Role in Supporting the CEO

(13:07) The Hallmarks of a Good CFO-CRO Relationship

(17:00) Skills for Private Companies Versus Public Companies 

(20:34) The Benefits of Operating a Company at Scale

(22:52) Sponsor - Leapfin | Planful | Mercury 

(26:28) Important Qualities for Operating at Scale

(27:57) Re-interviewing for a Job After Being Acquired

(31:22) Jessica’s Most Extreme Experience of M&A

(34:45) Fairness, Trust, and Credibility in M&A

(39:07) What a CFO Should Expect After Their Company is Acquired

(43:22) Jessica’s Framework for Evaluating a Company

(50:08) How You Know You’re Ready for Your Next Role

(52:59) Long-ass Lightning Round: Hiring Mistakes and Other Advice

(57:02) Finance Software Stack

(58:16) Craziest Expense Story 

In this episode, CJ is joined by Matt Gallatin, CFO of Stack Overflow, the largest online community for developers and one of the most popular websites in the world. They cover the impact of doing SaaS 101 learning sessions with departments across the org, how CFOs can get involved in customer lifecycle reviews, CFO career stories that demonstrate high stress decision-making in action, and more.  If you’re looking for an ERP platform, check out our sponsor, NetSuite: https://netsuite.com/metrics

—

SPONSORS:

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@turpentinemedia

—

TIMESTAMPS:

(00:00) Preview

(02:25) Sponsors: NetSuite by Oracle | Thoropass

(05:05) Tying Together the SaaS Model for the Whole Company

(06:54) SaaS 101 Sessions

(09:36) Understanding SaaS Metrics

(13:51) Customer Life Cycle Review

(17:16) Sponsor: Maxio

(18:29) Matt’s Bold Decision at Drawbridge

(25:57) The Aftermath and Lessons Learned from that Decision

(27:33) Not All Revenue is Created Equal

(28:14) Understanding Business Growth and Trajectory

(29:55) Using Public Companies As Aspirational Benchmarks

(37:59) Digging Into S1s

(40:30) Matt’s Favorite Benchmark Reports

(43:50) CFOs are like NFL Coaching Trees

(48:20) Matt’s Finance Software Stack Brought to you by Tropic

(50:51) Wrap

Today CJ welcomes back Jim Cook, a renowned coach to chief financial officers throughout Silicon Valley via his company BenchBoard Advisory -- and a co-founder of Netflix. Jim takes us through a number of frameworks for decision making and communication, including the three eras of CFO requirements, the concept of disagreeing, but still committing as a management team, challenging the problem, not the person, how the most valuable skill CFOs can learn is communication, the leadership SECS talk, and much more. If you’re looking for an ERP platform, check out our sponsor, NetSuite: https://netsuite.com/metrics

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PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode

Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140

Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV?si=7fa9ea2d53ae404a

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SPONSORS:

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN

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.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

-

FOLLOW US ON X:

@cjgustafson222 (CJ)

@cookflix (Jim)

@turpentinemedia

-

TIMESTAMPS:

(00:00) Introduction: The Power of Data-Driven Decisions

(02:32) Sponsor - Netsuite | Attio

(04:46) The Return of Jim Cook: A Masterclass in CFO Communication

(07:06) The Four C's of Teams: A Framework for Decision Making

(16:40) Sponsor - Maxio | Thoropass

(23:29) The Three Eras of a CFO: From Ownership to Leadership

(26:10) The Five Steps to Ownership

(31:20) Sponsor - Tropic

(32:33) Communication> Who is in the room?

(37:16) SECS Talk 

(40:10) Being Comfortable in Silence

(40:40) 3 Things Humans Remember 

(48:00) Captain of Three Ships: Relationships, Partnerships, and Leadership

(49:06) Wrap

Seven Frameworks Timestamps:

(23:29) The Three Eras of CFO Requirements 

(07:03) The Four Cs 

(26:10) The Five Ownership Steps 

(32:33) Communication> Who is in the room 

(37:16) SECS Talk 

(40:40) 3 Things Humans Remember 

(48:00) Captain of Three Ships

On Today’s episode, CJ welcomes Chad Gold, the CFO of G2 and the former CFO of Salesloft. Gold shares valuable insights on the role of finance in startups and the qualities that set you on the path for a successful CFO career in venture-backed ecosystems.

Chad has raised money from some of the best investors in the business, including Vista Equity, Permira, Accel, IVP, and Insight. And he’s built world class finance teams for hypergrowth.

On this episode we cover 

* The concept of building lines, not dots, with investors

* How to decide how much time to dedicate to investor meetings vs running the business

* How majority recaps work, and the equity implications for execs and employees

* How finance teams can make the news, in a good way

* And we go way back to get some early lessons he learned on the finance team at Home Depot when he was just starting his career

Not only does Chad have the best name for a CFO, he’s extremely thoughtful about how FP&A and finance can plug into the business to be drivers, not passengers, during periods of hypergrowth. He’s also one of the people who comes to mind when I think about building a durable, successful career as a reputable venture backed chief financial officer. 

If you’re looking for an ERP platform, check out our sponsor, NetSuite: https://netsuite.com/metrics

—

SPONSORS:

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@chadjgold (Chad)

@turpentinemedia

—

TIMESTAMPS:

(00:00) Intro

(02:32) Sponsors: NetSuite | Thoropass  

(05:04) Building Relationships with Investors

(11:28) Understanding Majority Recapitalization

(18:16) Sponsor: Maxio 

(22:07) Building Great Finance Teams

(25:06) Ownership Mentality

(25:42) How Finance Teams Can Empower Their Company

(29:39) Making The News and proactivity

(33:15) Feedback Cycle

(37:20) The Importance of Relationships

(40:16) The Role of Finance in Business Operations

(42:03) Chad’s Past Mistakes 

(45:55) Chad’s software stack brought to you by Tropic 

In this episode, CJ welcomes Andre Retterath, investing partner at Earlybird Venture Capital. This is a masterclass on AI where they cover the different levels of the AI tech stack and how to implement AI across tech organizations in the months and years ahead. They also cover how AI is changing back office functions for finance and operations folks, why large language models aren't necessarily built to deal with numbers, and Andre’s favorite decision-making frameworks. If you’re looking for an ERP platform, check out our sponsor, NetSuite: https://netsuite.com/metrics

Andre has a PhD in AI and machine learning. He writes the popular Data-driven VC Substack and he is one of the foremost thought leaders of the intersection of machine learning and data to make investment decisions within the private markets.

—

SPONSORS:

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN

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.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@andreretterath (Andre)

@EarlybirdVC (Earlybird)

@turpentinemedia

–

Timestamps:

(00:00) Intro

(01:02) Welcome to Run the Numbers Podcast

(02:36) Sponsor Break: NetSuite by Oracle

(03:55) Sponsor Break: Attio CRM

(04:50) Interview with Dr. Andre Retterath

(05:40) Understanding the AI Tech Stack

(09:53) The Role of AI in Finance and Operations

(17:44) The Impact of AI on Sales and Marketing

(27:35) AI in Contract Management and Reporting

(30:38) Sponsor Break: Maxio and Thoropass

(33:00) The Role of AI in Contract Management

(33:43) The Limitations of AI Models

(34:59) The Challenges of AI in Financial Analysis

(35:30) Understanding the Mechanism of AI Models

(36:58) The Downside of AI Models

(40:22) AI in Finance: Fraud Detection and Dynamic Pricing

(42:48) The Human Element in Venture Capital

(50:54) The Future of Venture Capital with AI

(54:48) The VC Software Stack: A Data-Driven Approach

(1:00:16) Closing Remarks and Contact Information