Inside the “PayPal Mafia”: One of the Most Influential “Seed Funds” in Tech History with Jimmy Soni

Elon Musk, Peter Thiel, Reid Hoffman, Max Levchin, David O. Sacks, Roelof Botha, Chad Hurley, Russel Simmons, and Jeremy Stoppelman are among those considered the “PayPal Mafia”. These are cofounders or early team members of PayPal who went on to found or invest in major tech companies like Yelp, Palantir, YouTube, Facebook, SpaceX, X, LinkedIn, Affirm, Airbnb, and others. In this episode, CJ is joined by Jimmy Soni, bestselling author of The Founders, which chronicles the early years of PayPal. He delves into some of the lesser-known aspects of PayPal's history. He sheds light on Peter Thiel's prediction of the dot-com collapse, why he advocated for the employment of Roelof Botha as CFO at the age of just 26, and his second-chance philosophy for hiring failures. The conversation covers PayPal’s “frenemy relationship” with eBay, how they convinced their users to advocate for them, and pivotal moments that influenced their IPO and sale. Tune in for unique insights into one of the most important "seed funds" in tech history.—LINKS:Jimmy Soni on X (@jimmyasoni): https://x.com/jimmyasoniJimmy Soni on LinkedIn: https://www.linkedin.com/in/jimmysoniThe Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley: https://www.amazon.co.za/Founders-Paypal-Entrepreneurs-Shaped-Silicon/dp/1501197266CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:How Upwork CFO Erica Gessert Drove 20 Points of EBITDA Growth in Just 3 Quarters: —TIMESTAMPS:(00:00) Preview and Intro(02:12) Sponsor – Pulley | Brex | Aleph(07:40) Jimmy’s Approach to Writing the Book(08:56) An Intro to the “PayPal Mafia”(10:57) The 1998 to 2002 Time Period(12:36) Present-Day Successes of “PayPal Mafia” Members(14:06) Challenges of Interviewing High-Profile Figures(16:06) Sponsor – RightRev | Navan | NetSuite(19:46) Comparisons to Other Influential Tech Groups(21:05) PayPal, YouTube, and the Embed Strategy(23:21) The Company’s $20 Referral Program(27:10) Peter Thiel’s Prediction of the Dot-Com Collapse(30:48) The Fallout From the Merger That Resulted in PayPal(33:00) The Evolution of PayPal’s Business Model(36:58) The Unique Skillset That Roelof Botha Brought to the CFO Role(41:04)) Fraud-Fighting Techniques(43:26) PayPal’s “Frenemy Relationship” With eBay(47:10) Challenges Faced by PayPal That Modern Fintechs Still Grapple With(49:13) How PayPal Made Its Users Advocates for the Business(53:44) PayPal’s Talent Acquisition and “Misfits” Culture(56:54) Peter Thiel’s Talent-Spotting Abilities and Second-Chance Philosophy(1:00:12) The Outcome of the eBay Sale(1:05:03) One of the Most Important “Seed Funds” in Tech History(1:08:07) Advice for Moving From Fast Work To Slow Work(1:11:18) Favorite Behind-the-Scenes Anecdote(1:13:04) The Most Underrated Member of the “Mafia”(1:14:04) One of the Most Pivotal Decisions Made(1:15:03) Wrap—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.#PayPalMafia #JimmySoni #CAPTCHA #PayPal #fintech Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

Figma Figma just raised the bar for IPOs in 2025.Today we break down their revenue, margins, retention, and potential valuation in the public markets.You can find the full analysis in written form at:https://www.mostlymetrics.com/p/figma-ipo-s1-breakdownThis week’s podcast is brought to you by Campfire (www.campfire.ai)We’ve all used legacy ERPs. Painful migrations, endless consulting fees, and even after you’re live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It’s the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I’m excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai. Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

In many companies, the CFO is more important than the CEO. And the majority of private equity-backed CFOs are actually not up to par. In this episode, CJ is joined by Scott Engler, of LinkedIn fame, to explain why he believes these bold statements to be true. Scott is the CEO and co-founder of Sync Executive Partners and the co-founder of PE-Xcelerate. He has decades of experience studying, recruiting, and coaching CFOs. He shares insights on the evolving role of the CFO, the many hats they wear, and which they should prioritise. He gives advice on how to navigate your relationship with your CEO, your PE sponsor, and other stakeholders, and provides some social profiling hacks that can help. The conversation covers the benefits of upside-down reviews and why not having a recommendation can be the smartest move, before examining the best way to get a CFO job at a PE-backed company, and how to negotiate equity packages.—LINKS:Scott Engler on LinkedIn: https://www.linkedin.com/in/scottengler/Sync Executive Partners: https://www.syncexecutivepartners.com/PE-Xcelerate: https://www.pexcelerate.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comLooking for Leverage: RELATED EPISODES:So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means - CFO of FloQast on Why Finance Teams are Data Curators: “What’s in It for Me?” The Art of Storytelling in an IPO - with Monday.com CFO Eliran Glazer: Inside the "Triangle of Doom”: How Great CFOs Navigate CEO and Board Dynamics: —TIMESTAMPS:(00:00) Preview and Intro(02:20 ) Sponsor – Brex | Aleph | RightRev(07:12) How the CFO Role Has Changed Over the Last Decade(12:08) Why the CFO Needs To Drive the Pace(14:49) Why Most Private Equity-Backed CFOs Aren’t up to Par(16:36) Sponsor – Navan | NetSuite | Pulley(20:07) The PE-Backed CFO Versus Hypergrowth VC CFO(21:54) How Senior Leaders Are Incented To Play It Safe(26:04) The Operational CFO: The CFO Becoming More of a COO(28:41) Why the CFO Is More Important Than the CEO(32:16) How a CFO Should Prioritize Their Many Roles(34:46) The Importance of Being a Good Storyteller(38:49) What an Upside-Down Review Is(43:46) Why Not Having a Recommendation Can Be the Smartest Move(49:50) The Hardest CFOs Are the Easiest To Influence(55:37) The Art and Science of Managing Your CEO(57:48) Social Styles Hack(1:00:47) Working With Your CEO and PE Sponsor(1:04:08) The Best Way To Get a CFO Job at a PE-Backed Company(1:11:54) The State of Comp for PE-Backed CFOs in This Market(1:13:16) Negotiating Equity Packages(1:15:39) The Biggest Challenge for PE-Backed CFOs Today—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.#CFO #CEOversusCFO #ChiefFinancialOfficer #PrivateEquity #ScottEngler Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

The number one thing listeners of the pod ask me for is to flip the script and let someone interview me. I’ve historically been reluctant to do it because it feels little self aggrandizing or whatever the term is. But you gotta give the people what they want.On this episode my friend Mike Wu, founder of Hire Frame, interviews me on my transition to full time content creation. We talk about* How I sold a company as CFO, and then fired myself immediately* Why having supportive partners in any entrepreneurial endeavor is the real key to success* How I came up with the idea for my second newsletter Looking for Leverage.Mike’s a gracious host and shout out to him for letting me share this with my audience. Mike’s Podcast: What Worked on Spotify | Apple | YouTubeMike’s Company: Hire FrameRun the Numbers is brought to you by Zenskar.Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.Step into the future of finance today. Visit zenskar.com/rtn and book a demo! Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

The CFO software ecosystem is highly fragmented and ripe for disruption. Sean Jacobsohn, partner at Norwest, has a front-row seat to the action: He’s backed 10 companies selling to CFOs, while Norwest has invested in 20. Having identified 300 companies in 15 different categories operating in the space, he joins CJ to share takeaways from his market map of the evolving CFO software stack. They dig into what’s driving disruption, how new players are challenging legacy systems, and what it takes for founders to stand out. The conversation spans everything from the staying power of spreadsheets to the debate between building for verticals versus horizontals, the future of FP&A, and how AI agents might reshape the stack. Sean delves into the dynamics of partnerships, outlining five key rules for successful collaborations. Additionally, he talks about his Failure Museum which showcases a collection of items representing failed products and companies, and breaks down what he has identified as the six forces of failure.—LINKS:Sean Jacobsohn on LinkedIn: https://www.linkedin.com/in/seanjacobsohnNorwest: https://www.nvp.comMarket Map: Reimagining the CFO Software Stack: https://www.nvp.com/blog/market-map-reimagining-cfo-software-stackFailure Museum: https://failure.museum/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:CFO of FloQast on Why Finance Teams are Data Curators: The $7 Million Wake-Up Call: Mastering Rebates for Profitability with Enable’s Nick Rose: G2 CFO Chad Gold on Building A Durable Career as a Venture Backed Exec: —TIMESTAMPS:(00:00) Preview and Intro(02:04) Sponsor – Rippling Spend | Pulley | Navan(06:08) The Fragmentation of the CFO Tool Ecosystem(07:24) Advice for Founders on Deep Domain Expertise(10:39) Enable: Disrupting an Existing Solution Versus Creating a New Category(12:32) The Prevalence of Spreadsheets in the Current Ecosystem(13:39) Solutions Built for Verticals Versus Horizontals(16:24) Sponsor – NetSuite | Planful | Tabs(20:22) Vertical Software and the Move to the Cloud(22:17) The Likelihood of Consolidation by Incumbents in the Space(24:53) Developments in the FP&A Space(26:55) The Future of AI Agents in Finance(28:05) The Five Key Rules of Partnerships: Partner Fit(29:17) Entering New Markets(30:16) Enablement: The Importance of Training(32:28) Reciprocation(33:49) How Often the Little Guy Approaches the Big Guy in Partnerships(34:51) M&A in Partnerships(37:01) The Best Way To Form a Partnership(37:45) The Inspiration Behind the Failure Museum(39:14) The Six Forces of Failure(40:38) Falling out of Product-Market Fit(41:25 Examples of Failures From the Failure Museum(44:58) How the Failure Museum Informs Sean’s Work at Norwest(46:12) The Magic of Pivoting—SPONSORS:Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.Planful’s financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you’ll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.#CFOsoftware #marketmap #verticalSaaS #FPandA #FailureMuseum Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

When the COVID-19 pandemic hit in March 2020, Zoom went from steady growth to hyperscale almost overnight, even generating a backlog of a million tickets. Sarah Riley was a finance leader in the company at the time. She joins CJ to talk about what she learned from the experience and how it impacted her in her current role as CFO of dbt Labs. She also explains the influence of Helmer’s Seven Powers framework on her strategic decisions. The discussion covers how Sarah’s evolved pricing models, and helped bring product-led and sales-led growth together into a single go-to-market strategy at dbt Labs. She breaks down how she uses big systems thinking to build out a finance org, how to create healthy off-ramps for pilots, and what’s actually okay to break when “moving fast and breaking stuff”. She also touches on the current use cases for AI in finance and for turning your team from “doers to reviewers”.—LINKS:Sarah Riley on LinkedIn: https://www.linkedin.com/in/sarahjriley/dbt Labs: https://www.getdbt.com7 Powers: The Foundations of Business Strategy: https://7powers.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Wasted Capital and Where to Find It: The CFO’s Guide to Spoilage Levers Leakages: —TIMESTAMPS:(00:00) Preview and Intro(02:18) Sponsor – Pulley | Navan | NetSuite(05:53) Being at Zoom at the Start of the Pandemic(10:14) Challenges Caused by the Influx of Customers(14:06) Takeaways From Sarah’s Time at Zoom: M&A and Build Versus Buy(15:49) Sponsor – Planful | Tabs | Rippling Spend(19:38) Taking Advantage of Your High Share Price for M&A(20:56) What dbt Labs Does(24:27) Pricing Evolutions at dbt Labs: Freemium and Open-Source(27:51) Seat-Based, Usage-Based, Hybrid, or Outcome-Based Pricing(30:27) Pros and Cons of a Free Component(32:17) Finance and Sales in dbt’s Evolving Go-to-Market Strategy(34:09) The Evolution of dbt Labs’ ICP(35:09) The Helmer 7 Powers Framework(40:39) Being a Big Systems Thinker While Building a Finance Org(44:16) Moving and Iterating Quickly: Creating Healthy Off-Ramps for Pilots(46:19) What You Can and Can’t Break When “Moving Fast and Breaking Stuff”(47:32) The Current State of AI and Use Cases in Finance(51:20) Long-Ass Lightning Round: Boundary Definition(52:08) Advice to Younger Self(52:56) Finance Software Stack(55:20) Craziest Expense Story—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.Planful’s financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you’ll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.#hypergrowth #7Powers #FinanceStrategy #bigsystemsthinking #GoToMarketStrategy Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

We’re heading towards a world where Google not only stops sending us traffic, but uses our own content against us.In today’s podcast we discuss how Google’s incorporation of AI summaries into search is changing the shape of the search funnel. For those responsible for making resource allocation bets across their companies to drive new users, this is a fundamental shift.How are you preparing for it? And what are we seeing? Tune in.Run the Numbers is brought to you by Zenskar.Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.Step into the future of finance today. Visit zenskar.com/rtn and book a demo!Referenced:* Link to The Rebooting newsletter* Link to The Rebooting Podcast “Google Zero” episodeWant a Run the Numbers or Mostly Metrics custom Yeti Mug? They’re dope. Share mostlymetrics.com in a Slack of Teams channel with +25 members, screenshot it, and email it to me at [email protected]’ll hook you up. Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

In this episode, Alex Immerman, partner at Andreessen Horowitz, joins CJ to discuss the CFO role and how it's changing in the era of AI. He explains what the components of a company’s AI agenda the CFO should own, how and where it should be leveraged in an organization, and why, if you’re preparing to go public, AI needs to be mentioned in your S-1. He breaks down how the financial landscape differs greatly between AI-native SaaS companies and traditional B2B SaaS companies in terms of retention curves and gross margins, and how this relates to the ever-important LTV to CAC metric. As someone who has worked with prominent CFOs and interviewed many for a16z’s portfolio companies, Alex also describes the qualities of a great CFO, and shares his favorite interview question, before discussing CFOs, CEO, and board dynamics.—LINKS:Alex Immerman on X (@aleximm): https://x.com/aleximmAlex Immerman on a16z: https://a16z.com/author/alex-immermanAlex Immerman on LinkedIn: https://www.linkedin.com/in/immermanAndreessen Horowitz: https://a16z.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means: —TIMESTAMPS:(00:00) Preview and Intro(02:19) Sponsor – Navan | NetSuite | Planful(05:52) What Separates Good CFOs From Great Ones(11:56) Questions Alex Asks When Interviewing CFOs for Portfolio Companies(15:17) How CFOs Should Engage With Investors During the Hiring Process(17:22) Sponsor – Tabs | Rippling Spend | Pulley(22:22) What a Great CFO-Investor Relationship Looks Like(24:46) The CFO-CEO-Board Dynamic(28:27) How the Role of a CFO Is Changing in the Era of AI(31:41) AI-Native Company Versus Incumbent for Finance Category Leader(33:49) Components of a Company’s AI Agenda That the CFO Should Own(38:39) Why the LTV to CAC Metric Is So Important to Investors(41:13) LTV to CAC by Sector(42:41) The Importance of Gross Margin Adjusting Your CAC Payback(43:21 Retention and Churn Patterns in AI-Native Companies(45:23) Gross Margin in AI-Native Companies Versus Traditional B2B SaaS(50:11) What It Takes To Be a Public Company-Ready CFO Today(53:58) How IPO Expectations for the CFO Have Shifted in the Past Few Years(55:05) Wrap—SPONSORS:Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.Planful’s financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you’ll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.#AINativeSaaS #a16z #CFO #LTVtoCAC #AIinSaaS Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

If you work for a software company, odds are that people make up 80-90% of your business’s costs. Today’s guest argues that in order to effectively manage a company’s greatest asset, the CFO should be heavily involved in shaping the company culture. Bill Tole is the CFO of TrustRadius, a trusted platform where tech buyers find real reviews. He is skilled in creating structures around ambition and breaks down how TrustRadius creates and implements Objectives and Key Results (OKRs). He explains how they differ from KPIs, why they fail, and how to set aggressive but achievable goals. He discusses the Rule of 40 and why it’s essential for the rest of the company to understand it. Bill also shares how CFOs can influence culture from a finance perspective and why a lack of failure is a cause for concern.—LINKS:Bill Tole on LinkedIn: https://www.linkedin.com/in/bill-tole-0a99789/TrustRadius: https://www.trustradius.com/15Five: https://www.15five.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Less but Better: Miro’s Justin Coulombe on the Power of Strategic Divestment in SaaS: —TIMESTAMPS:(00:00) Preview and Intro(02:15) Sponsor – NetSuite | Planful | Tabs(06:00) TrustRadius’s Business Model(09:20) OKRs at TrustRadius and Finance’s Role in Them(14:07) Finance’s Role in Asking the Stupid Questions(15:58) Sponsor – Rippling Spend | Pulley | Navan(20:10) How To Set Aggressive but Achievable Goals(23:19) The Ideal Number of OKRs(24:21) Leaving Room for Failing or Innovating(25:57) OKR Derivatives at Department Level(27:36) Why OKRs Fail(28:55) Rewriting or Killing Off an OKR Mid-Way(29:51) Where To Track Your OKRs(32:03) Applying the Rule of 40(34:39) Educating the Org on the Rule of 40(37:34) EBITDA Versus Free Cash Flow for Calculating Rule of 40(39:24) The CFO As the Culture Leader(43:21) Using Money To Change the Culture in a Positive Way(45:42) Mistakes CFO’s Make When It Comes to Culture(47:06) Long-Ass Lightning Round: Why Failure Is Okay(51:41) Advice to Younger Self(53:44) Finance Software Stack(55:12) The State of SaaS Fragmentation or SaaS Sprawl(57:28) Craziest Expense Story—SPONSORS:NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.Planful’s financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you’ll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.#failure #companyculture #OKR #KPI #Ruleof40 Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

This one’s for anyone who’s ever mistaken SaaS metrics for gospel. I sit down (ok, dine out) with two CFOs—one from a dating app, the other from an HVAC parts company—and come away questioning the whole tech-is-king narrative.Turns out, the guy replacing dirty rugs in Georgia public schools pulled in $22 million last year. And no, he doesn’t have a Substack.In this episode:* A billion-dollar business that makes… bolts* SaaS dreams vs. rug-cleaning realities* The myth of “build it once, sell it forever”* Why R&D is just COGS in a costume* A gentle roast of hustle culture and spreadsheet empiresThis is a reminder that while tech has its perks, the world is full of quiet, profitable businesses that don’t require churn curves or pitch decks. Sometimes, the best margins come with dirt under the fingernails.Run the Numbers is brought to you by Zenskar.Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.Step into the future of finance today. Visit zenskar.com/rtn and book a demo! Get full access to Mostly metrics at www.mostlymetrics.com/subscribe