Run the Numbers – Details, episodes & analysis

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. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@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.

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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:

@cjgustafson222 (CJ)

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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.

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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

(02:19) 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