Running the Long Game in Growth Equity | Larry Contrella

In this episode of Run the Numbers, CJ Gustafson sits down with Larry Contrella, General Partner at JMI Equity, to unpack how JMI invests in software without financial engineering or roll-up strategies. Larry explains how the firm builds conviction through founder relationships, long-term partnership, and a product-and-brand-first view of durable growth. They discuss how JMI supports companies through scaling, why operating partners keep returning, and how underwriting looks different in mission-driven sectors like K–12 and nonprofit tech where customers are schools and communities, not Fortune 500s. Larry’s background as a competitive runner at Penn ties the conversation together with a clear ethos: patience, discipline, and playing the long game.—SPONSORS:Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHt—LINKS:Larry on LinkedIn: https://www.linkedin.com/in/larry-contrella-160a8a25/JMI Equity: https://www.jmi.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Is taking a company public even worth it? | Fullstory’s Chad Goldhttps://youtu.be/zSD8y9dr4VgSo You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Meanshttps://youtu.be/cgHOtvG1Ces—TIMESTAMPS:00:00:00 Preview and Intro00:02:49 Sponsors — Mercury | RightRev | Tipalti00:06:41 Joining the JMI Conversation00:07:13 College Running and Team Dynamics00:08:13 New York Marathon Story and Career Intersection00:11:04 Competitive Drive and Patience With Founders00:12:54 Building Long-Term Partnerships and Underwriting Credibility00:15:27 Growth Equity as a Long Sales Cycle00:15:48 Sponsors — Aleph | Fidelity Private Shares | Sage Intacct00:18:44 Fund Planning, Deal Pacing, and Board Commitments00:20:59 Sourcing Philosophy and Developing Investors Over Time00:22:09 Hustle as the Only Sustainable Edge in Sourcing00:24:14 Early Sourcing Tactics and Information Arbitrage00:26:06 Reputation, Experience, and Breaking Into Competitive Deals00:29:42 Organic Growth Over Roll-Ups and M&A Discipline00:32:51 Brand, Product Leadership, and Paying for the Best Businesses00:33:29 Bloomerang and Brand-Led Growth in Nonprofit Software00:34:46 Why JMI Operators Keep Coming Back00:36:28 Collaborative Leadership and Giving Constructive Advice00:38:20 Using Data Without Slowing Decisions00:39:20 Transparency, Alignment, and Knowing Where You Stand00:40:31 Why JMI Invests in K–12 and EdTech00:42:07 Mission-Driven Businesses and Talent Advantage00:43:24 Monetization Models in Nonprofit SaaS00:45:40 Conviction Bets and Product-Market Fit Stories00:48:49 Rethinking TAM and Expanding Markets Over Time00:50:40 Lightning Round: Sourcing Stories and Lessons00:52:58 Traits of Great Founders and Changing Beliefs00:54:20 Closing Thoughts and Outro#RunTheNumbersPodcast #GrowthEquity #B2BSoftware #FounderRelationships #PrivateEquity This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Brian Brown, Chief Financial Officer and Treasurer at Rocket Companies, to unpack how Rocket has built a differentiated, full-stack fintech business far beyond its mortgage roots. The conversation explores Rocket’s approach to long-tail monetization, the strategic importance of mortgage servicing, and how recapture rates become a durable competitive advantage in volatile rate environments. Brian shares lessons from leading complex M&A transactions, managing a business that reacts in real time to macro signals, and building a finance organization that prioritizes storytelling, strategy, and cross-functional thinking over pure accounting prowess. The result is a wide-ranging discussion on what traditional financial services companies can teach modern SaaS and fintech leaders about metrics, brand, and disciplined execution.—SPONSORS:Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.—LINKS:Brian on LinkedIn: https://www.linkedin.com/in/brian-brown-3aa37a8a/Rocket Companies: https://rocket.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:From $500M Losses to $500M Profits: The CFO Who Helped Major League Baseball Win off the Fieldhttps://youtu.be/7xw9qY2w5C4—TIMESTAMPS:00:00:00 Preview and Intro00:02:30 Sponsors — Sage Intacct | Mercury | RightRev00:05:55 CJ’s Rocket Mortgage Fanboy Moment00:07:13 How Rocket Mortgage Actually Makes Money00:12:06 Investing in Brand Trust for Infrequent but High-Stakes Decisions00:15:17 Mortgage Servicing as a Long-Term Relationship Engine00:17:17 Sponsors — Tipalti | Aleph | Fidelity Private Shares00:20:40 Why the Long Tail of Customer Relationships Is Underrated00:23:01 Recapture Rate and Why Mortgage Loyalty Is Broken00:25:23 Lower CAC Through Lifetime Value and Repeat Borrowers00:30:55 Financial Storytelling as a CFO’s Real Job00:33:03 Why CFOs Must Sell the Story, Not Just the Numbers00:40:49 Public vs. Private M&A and Why Public Deals Are Harder00:45:21 Redfin Acquisition Thesis and Top-of-Funnel Strategy00:52:18 Being Swarmed by Merger Arb Funds Like Taylor Swift00:55:18 How Rocket Forecasts in a Volatile Interest Rate Environment00:58:04 Weekly Forecasting, Scenario Planning, and Avoiding Forecast Fatigue01:00:32 Finance Teams as Business Consultants and Strategic Partners01:02:23 Why CFOs Need a Seat at the Strategy Table01:04:19 Long-Ass Lightning Round: A Leadership Mistake and Building Teams01:05:58 Leadership Lessons on Team Size and Accountability01:07:33 Advice to Younger Self and Slowing Down01:08:49 Finance Software Stack and AI Tools01:11:31 Lessons from Working with Dan Gilbert01:16:58 Craziest Expense Story01:17:55 Outro#RunTheNumbersPodcast #CFOLeadership #FinanceStrategy #MergersAndAcquisitions #FinancialStorytelling This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowthMostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar explore the hidden mechanics behind focus, competition, and value creation across both consumer culture and B2B SaaS. They unpack why point-solution companies like Untuckit and Raising Cane’s can outperform diversified rivals, examine how competition actually strengthens category demand, and break down the gray zone of mid-market venture exits where founder incentives and investor expectations diverge. The conversation ranges from private equity roll-ups to the realities of cold-calling returning as a top-performing growth channel, to pricing transparency, algorithmic price discrimination, and how everyday behaviors—from mall Santas to $12 club water—reflect deeper strategic forces. It’s a fast, practical look at how operators can stay focused, understand market pressure, and avoid chasing the wrong game.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/—RELATED EPISODES:Building AI-Native Software With No Rules | Christopher O’Donnellhttps://youtu.be/Fr1027kZyC0SaaS Founder or Pop Star? CJ Gets Schooledhttps://youtu.be/LMZq_DwVmkYThe Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberghttps://youtu.be/yPxWvhPISKoThe One Use Case for Venture Debt That Most Founders Never Think Abouthttps://youtu.be/XxH_Y9OH_i0—TIMESTAMPS:00:00:00 Preview and Intro00:01:42 Sponsors – Pulley | Metronome00:04:02 Mall Fashion & Nostalgia00:05:50 The Modern Mall Santa Reinvented00:06:52 Untuckit & the Platform vs. Point Solution Debate00:08:31 The Power of Category Focus00:09:56 Obsession, Craft, and the Raising Cane’s Lesson00:10:46 Germany’s “Hidden Champions”00:12:44 Competition: When to Care and When Not To00:14:05 OpenAI, Gemini & the “Code Red” Mindset00:15:34 Competition to Category Education00:17:00 Pricing Pages as Competitive Battlegrounds00:18:05 VC Deck Theater & Competitive Grids00:18:54 Rise of B2B Newsletter Advertising00:19:48 Awkward Exits: The Venture “Gray Zone”00:21:46 Founder Life-Changing Exits vs. VC Math00:23:04 Why Secondaries Exist (and When They Help)00:24:58 Why $100–500M Is the Most Common SaaS Exit Range00:26:14 Structural Misalignment in Venture Exits00:27:20 How Much Secondary Is Too Much?00:30:25 Business Blunders: Justin Bieber the PM00:31:54 Voice Notes, Etiquette, and Chaos00:33:23 Cold Calling Makes a Comeback00:35:50 Catherine Jhung Still Cold Calls CFOs00:37:44 Algorithm Pricing Labels & Data-Driven Pricing00:41:11 Why Clubs Charge $12 for Water00:42:40 Closing Credits#MostlyGrowthPodcast #keepitsimple #focuswins #businessstrategy #operatorsmindset This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Blake Grayson, CFO of Docusign, joins CJ Gustafson to discuss how a company that redefined e-signature and became a verb is now navigating its next chapter in intelligent agreement management. Drawing on more than a decade at Amazon—where he helped forecast AWS and worked inside some of the company’s most operationally demanding businesses—Blake explains how financial discipline, operational depth, and clear narrative-building shape his approach as CFO. The conversation explores how to evolve a beloved product without diluting the brand, why pricing is as much about positioning as revenue, how to communicate go-to-market mechanics without losing the room, and why effective capital allocation accepts that not every big bet needs to land to shape the leader you become.—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run—LINKS:Blake on LinkedIn: https://www.linkedin.com/in/blake-grayson-3197043/Docusign: https://www.docusign.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Steal Your Boss’s Job”: Calendly CFO John McCauley on Leadership, Ownership & Growthhttps://youtu.be/VRpTNDIfzPY—TIMESTAMPS:00:00:00 Preview and Intro00:02:39 Sponsors – Fidelity Private Shares | Sage Intacct | Mercury00:05:09 DocuSign as a Top CFO Tool00:07:33 From E-Signature to Intelligent Agreement Management00:09:09 Complexity Before and After a Signature00:11:02 Cost of Poor Agreement Management00:12:30 Agreement Oversight and CFO Risk00:13:28 Pricing: Usage to Seat Models00:14:12 Enterprise vs SMB Pricing00:15:00 Sponsors – RightRev | Tipalti | Aleph00:19:18 Simplicity, Tiers, and IAM Value00:20:36 Forecasting New Products in a Renewals Base00:22:13 Modeling Mix Shift and GTM Enablement00:23:56 Faster Time-to-Value With Intelligent Repositories00:25:06 Building GTM Muscle for a Platform00:26:29 Launching IAM in Commercial First00:27:31 Forecasting Growth vs Cost00:28:41 Company-Wide Alignment on Priorities00:30:02 Aligning Investor Messaging With Operations00:31:20 Staying Focused on Long-Term Outcomes00:32:27 Customer-First Decision Making00:33:41 Transparency and What Not to Disclose00:34:52 Asking Better Metric Questions00:36:28 Avoiding Data Paralysis00:38:52 Amazon’s Weekly Business Reviews00:41:07 Bezos Meetings and the Silent Read00:45:09 The “Question Mark Email” and Customer Anecdotes00:50:22 Unit Economics of a Server and Early AWS Bets00:53:42 Handling Nonpayment Risk00:55:07 Operational Chaos: Perishables and Regulation00:57:04 The “No Eggs in California” Story00:59:31 Treating Escalations as Company Problems01:00:59 Biggest Career Mistake01:02:44 Advice to His Younger Self01:06:34 Tools Finance Uses: Oracle, Bots, IAM, Salesforce, Workday01:09:21 Wildest Expense Attempts01:12:32 Closing Thanks and Credits#RunTheNumbersPodcast #Docusign #CFOInsights #SaaSLeadership #AIManagement This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Cassie Young brings hard earned lessons from a career spanning CRO roles, customer success leadership, turnarounds, and now investing as a General Partner at Primary Venture Partners. She talks about building and rebuilding go to market teams, why sometimes you should fire customers on purpose, and how churn is a lagging indicator that hides deeper retention issues. Cassie shares strong views on overrated metrics like NPS, the incentives that actually drive behavior inside a business, and the myth of finding one perfect KPI. She also brings signature Cassie isms like sunlight is the best disinfectant and the reminder that leaders often get stuck working in the business instead of on it offering practical insights for anyone trying to keep their SaaS metrics from going sideways.—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is the cloud financial management platform that replaces spreadsheets, eliminates manual work, and keeps your books audit-ready—so you can scale without slowing down. It combines accounting, ERP, and real-time reporting for retail, financial services, logistics, tech, professional services, and more. Sage Intacct delivers fast ROI, with payback in under six months and up to 250% return. Rated #1 in customer satisfaction for eight straight years. Visit Sage Intacct and take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.—LINKS:Cassie on LinkedIn: https://www.linkedin.com/in/cassyoung/Primary Venture Partners: https://www.primary.vc/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Getting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0—TIMESTAMPS:00:00:00 Preview and Intro00:02:30 Sponsors Aleph | Fidelity Private Shares | Sage Intacct00:05:21 Returning From Pavilion & GTM Summit Takeaways00:06:49 What Makes a Great Executive00:11:07 The Importance of True P&L Fluency00:12:17 First Team Leadership vs Functional Loyalty00:13:33 Reading the Macro Environment and Market Forces00:14:29 Sponsors Mercury | RightRev | Tipalti00:18:26 Applying First Team Leadership in Practice00:22:24 Churn as a Lagging Indicator00:24:23 Finding Real Leading Indicators of Renewal00:25:30 Customer Value as the Only Path to Enterprise Value00:26:52 Product Adoption Perception and Retention00:29:16 Price to Value Ratio as a Predictor of Guaranteed Churn00:30:37 The Ultimate Question What Gets Your Customer Promoted00:32:33 How NPS Is Actually Calculated00:34:56 Sailthru’s Minus 26 NPS and What It Signaled00:37:31 Rebuilding Customer Trust Through Transparency00:40:24 Why Net and Gross Retention Must Be Paired00:42:51 Aligning the Executive Team Through a Unified Bonus Plan00:45:18 Firing Customers When Misaligned Segments Drain the Org00:49:35 Carrot vs Stick How to Motivate a Modern GTM Org00:52:31 Why MBO Plans Fail CSMs01:03:51 Why Time to Value Matters More Than Ever#RunTheNumbersPodcast #CustomerSuccess #ChurnPrevention #GoToMarket #VentureCapital This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowthMostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar bounce between sharp SaaS insights and delightfully weird internet culture. They start with an unexpected dive into competitive bird-watching apps, then break down recent software mergers like Superhuman + Grammarly + Coda and what they signal about scaling, cross-sell strategy, and private equity mechanics. CJ and Kyle explore why PE portfolios are becoming powerful distribution channels for AI solutions, how niche data “signals” are outpacing generic ones in sales, and share hedge-fund-style tactics for uncovering proprietary business information. The conversation rounds out with “business blunders” — from Y-axis chart crimes to clickbait headlines — and a lively discussion on Spotify’s pricing power and how companies should (and absolutely should not) communicate price increases.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/—RELATED EPISODES:The Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberghttps://youtu.be/yPxWvhPISKo—TIMESTAMPS:00:00:00 Preview and Intro00:01:43 Sponsors – Pulley and Metronome00:04:05 Birding, Big Year & AI Bird Apps00:06:42 Software M&A Trends in SaaS00:08:57 Superhuman–Grammarly–Coda Reverse Merger00:10:34 How Larger Valuations Attract a New Investor Class00:11:55 Streaming Wars & Platform Consolidation00:13:20 Private Equity as a Distribution Channel for AI00:14:48 How PE Firms Drive Multi-Company Expansion00:15:56 AI for Efficiency: The PE CFO Playbook00:17:44 When AI ROI Really Matters in PE00:19:23 Signal-Based Selling: High-Intent Buyer Detection00:21:15 Signal Fatigue & the Hunt for Better Data00:22:50 Why Proprietary Signals Win00:24:05 Creative (and Creepy) Data Tactics00:26:09 Pinterest vs. Google: Aspirational vs. Actual Behavior00:27:17 Blurring Work & Personal Signals in AI Tools00:27:46 The Michael Jordan of Y-Axis Crimes00:30:33 Notion Agents Billboard: “Let Them Cook”00:32:31 Pricing in the Real World: Spotify00:34:60 → 00:35:00 How to Communicate a Price Increase00:35:40 Closing Credits#MostlyGrowthPodcast #PricingStrategy #AIGrowth #GoToMarket #PrivateEquity This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

CoreWeave CFO Nitin Agrawal joins Run the Numbers to unpack the finance engine behind one of the fastest-growing AI infrastructure companies on the planet. CJ and Nitin dive into what it takes to build financial discipline in an environment where business models are being invented in real time, discussing the company’s 700% growth last year and massive first-quarter performance as a newly public company. They cover capex strategy, securitizing GPUs, managing billion-dollar revenue backlogs, and structuring incentives for hyperscale deals, all while keeping investors grounded and servers running at full tilt. If you want a front-row seat to finance in the AI arms race, this episode delivers.—SPONSORS:Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is the cloud financial management platform that replaces spreadsheets, eliminates manual work, and keeps your books audit-ready—so you can scale without slowing down. It combines accounting, ERP, and real-time reporting for retail, financial services, logistics, tech, professional services, and more. Sage Intacct delivers fast ROI, with payback in under six months and up to 250% return. Rated #1 in customer satisfaction for eight straight years. Visit Sage Intacct and take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.—LINKS:Nitin on LinkedIn: https://www.linkedin.com/in/nitin-agrawal-cloudcfo/Company: https://www.coreweave.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:The Art and Science of a Day-One IPO Pop with OneStream Software CFO Bill Koefoedhttps://youtu.be/kYCn7XNkCBcFrom Facebook’s Hypergrowth to Daffy’s Disruption: A CFO’s Playbook for Saying Yeshttps://youtu.be/bRIZ6oNPGD0—TIMESTAMPS:00:00:00 Preview and Intro00:02:54 Sponsors – Tipalti | Aleph | Fidelity Private Shares00:06:12 Interview Begins: Scaling CoreWeave00:06:52 CoreWeave’s Pivot From Crypto to AI00:11:41 Why CoreWeave Is Uniquely Positioned to Lead AI Infrastructure00:13:32 Hiring for Both Scrappiness and Scale00:16:01 Post-IPO Whirlwind: Acquisitions, Debt Raises, and 10-Year Deals00:16:43 Sponsors – Sage Intacct | Mercury | RightRev00:20:13 Managing Investor Expectations With Radical Transparency00:22:39 Doubling Active Power in Six Months00:25:19 Risk-Balanced Capital Deployment: Power First, GPUs Second00:27:12 Financing GPUs With Delayed-Draw Facilities00:29:38 CoreWeave Rated Platinum for GPU Cluster Performance00:32:25 Compute as the Bottleneck for AI Growth00:33:47 Explaining Revenue Backlog Shape & Timing00:35:06 The Strength of Reserved Instance Contracts00:36:07 Giving Tight but Honest Guidance00:40:26 How Mega-Deals Require C-Suite Participation00:42:19 Tackling Revenue Concentration Through Diversification00:44:05 Building an AI-Only Cloud, Not a General-Purpose Cloud00:46:27 Capital Markets Muscle: Raising Billions at Speed00:47:47 Accounting Complexity in a Business With No Precedent00:49:33 Even the CFO Must Unlearn Old Cloud Assumptions00:51:29 Scaling Public-Company Processes in 90-Day Cycles00:54:42 The Couch Fire vs. House Fire Framework00:57:17 Balancing Risk Mitigation With Opportunity Seeking01:00:30 No Downtime for ERP Changes During Hypergrowth01:02:33 Why the Team Stays Energized Despite the Chaos#RunTheNumbersPodcast #CFOInsights #Hypergrowth #AIInfrastructure #FinanceStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Greg Henry, CFO of 1Password and one of the most commercially minded finance leaders in tech, to break down why he left the public-company grind at Couchbase for a PLG-driven security business and what he’s relearning in the private sphere. Greg explains how forecasting changes when the product does the selling, how to think about comp and pricing in a usage-led world, and the early tells that a model is quietly over- or under-performing. He shares why CFOs should meet far more customers than they do, how finance can drive revenue without stepping on sales, and what it actually takes for a company to plan with clarity instead of reacting. Greg also recounts the near-derailing of the Couchbase IPO, reflects on the “back nine” of his career, and offers grounded advice for aspiring first-time CFOs.—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com—LINKS:Greg on LinkedIn: https://www.linkedin.com/in/greghenry23/1Password: https://1password.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Behind the Earnings Calls: Couchbase CFO Greg Henry on Consumption Models & Analyst Relationshttps://youtu.be/o_pDfz5a-Hw—TIMESTAMPS:00:00:00 Preview and Intro00:02:57 Sponsors – RightRev | Tipalti | Aleph00:07:03 Back in the Private Sphere: Why Greg Joined 1Password00:07:49 Greg’s Four-Part Framework for a Great Role00:10:12 Thinking About the “Back Nine” & Legacy00:13:16 Transitioning to PLG & SLG at 1Password00:15:12 Blending PLG Efficiency with Enterprise Sales00:17:12 Sponsors – Fidelity Private Shares | Metronome | Mercury00:20:03 B2C vs. B2B ARPU Contrast00:22:41 Forecasting in PLG vs. Sales-Led Models00:24:18 Building Toward Chunky Enterprise Upside00:25:39 Comp Plans: Complexity, Pitfalls & the Alexander Group00:27:35 Keep Comp Plans Simple & Focused on ARR00:29:10 Why Mid-Year Comp Plan Changes Are Dangerous00:31:04 Governance & Guardrails for SPIFFs00:33:19 Using the CFO Network to Drive Revenue00:34:52 Why CFOs Must Meet Customers Directly00:36:19 Wallet Share & Being a Buyer AND a Seller00:38:08 Why He Avoids 3-Year+ Commitments00:40:20 How Much Discount Is a “Year” Worth?00:42:31 Greg’s Structured Annual Planning Framework00:43:50 3–5% Upside/Downside Menu00:44:57 Comp Plans Must Go Out Early00:47:23 January Compensation & System Cutover Challenges00:48:31 Why Roadmap Alignment Must Kick Off Planning00:50:21 Sustain / Differentiate / Durable Growth / World-Class Teams Framework00:52:29 Couchbase IPO Almost Going Sideways00:54:59 How to Actually Become a CFO01:00:11 Legacy Greg Wants to Leave at 1Password#RunTheNumbersPodcast #CFOInsights #SaaSLeadership #PLGvsSLG #FinanceStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this Thanksgiving-week Mostly Growth episode, CJ Gustafson and Kyle Poyar ditch the serious finance talk for a looser, drinks-in-hand conversation with Ben Hillman, bouncing between CJ’s nostalgic emo-punk concert adventure, the curse of vanity license plates, and the epidemic of “Y-axis crimes” in founder charts. They riff on Spotify Wrapped copycats, YouTube becoming living-room TV, kids’ YouTube empires, and the game theory behind The Traitors and the Monty Hall problem before shifting into real-world pricing: newsletter perk economics, the pitfalls of hourly consulting, and why value-based packaging always wins. The episode stays playful but still sneaks in sharp insights on growth, psychology, and how weird the business world can be when you actually pay attention.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Brian Balfour: brianbalfour.comBrian on LinkedIn: https://www.linkedin.com/in/bbalfour/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/https://x.com/parikpatelcfa/status/1992706757073023191?s=46https://www.wired.com/story/null-license-plate-landed-one-hacker-ticket-hell/https://x.com/im_roy_lee/status/1992692253257855261/photo/1https://www.economist.com/finance-and-economics/2025/01/16/the-traitors-a-reality-tv-show-offers-a-useful-economics-lessonhttps://www.cdccard.com/https://nyulangone.org/news/one-third-americans-are-trying-avoid-gluten-it-villain-we-think-it-ishttps://x.com/techsalesguy3/status/1991585201601016161?s=46https://www.fletchpmm.com/https://paintvine.co.nz/blogs/news/the-legend-of-picassos-napkin-sketch?srsltid=AfmBOooiyTYGfUdKJZLpblbQAcJzQLg011Os_xeyaCgSpEIXrtIuD6hHhttps://cityfeedandsupply.com/https://www.linkedin.com/posts/cj-gustafson-13140948_started-from-the-email-now-were-here-activity-7397607230600126465-iVPv/https://cooking.nytimes.com/recipes/1018731-buttermilk-brined-roast-chickenhttps://cooking.nytimes.com/recipes/1026610-porcini-ragu—RELATED EPISODES:Is a weekly martini ARR? | with Dave Kellogghttps://youtu.be/Yb1lUQLJ6qw—TIMESTAMPS:00:00:00 Special Message00:00:35 Preview and Intro00:01:41 Sponsors – Pulley & Metronome00:04:01 Mostly Drinks Episode00:05:14 Concert Stories & Pop-Punk Nostalgia00:08:05 Concert Parenting & Full-Circle Moment00:08:36 Business Blunders Begin00:10:26 License Plate Fails & Accounting Humor00:12:08 Y-Axis Crime Chart Review00:14:21 Global Podcast “Success” & Listener Jokes00:16:00 Spotify Wrapped: Retention vs. Acquisition00:17:04 YouTube as the Future of Podcasts00:17:56 Kids’ Shows, Blippi & Creator Economics00:18:55 The Traitors Show Overview00:20:30 Game Theory & Winning as a Traitor00:22:46 Monty Hall Problem Setup00:24:27 Game Show Logic & Gambler’s Fallacies00:26:09 Pricing in the Real World00:27:03 Community Discount Card Business Model00:29:09 Newsletter Perks & Subscriber Value00:30:34 Marketplace Discount Math00:32:01 Negotiating Like a CFO00:33:00 Gluten-Free Nights & Pricing Strategy00:35:24 Outbound Pizza as a Go-to-Market Play00:37:03 Outbound Pizza Tuesdays to Gluten-Free Tuesdays00:37:37 Pricing Services: Value vs. Hourly00:40:47 The Picasso Pricing Story00:42:55 Harvard Business School Case Study & Kim K Photo00:44:02 Thanksgiving Cooking: Roast Chicken & Porcini Ragu00:44:56 Wrap & Credits#MostlyGrowthPodcast #SaaSOperators #BusinessStrategyPod #CreatorEconomyTalks #FinanceNerds This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

How do you know when a company is ready to go public? And what do you do to prepare for this? Chirag Shah, CFO of Motive and former CFO of Kong and Cornerstone OnDemand, joins CJ to share insights from his experience of scaling businesses from $30 million to nearly $1 billion and tripling ARR. He talks about taking companies public and how he helped take one private again in a $5.2 billion deal. In this episode, he explains what signals indicate that a company is ready to accelerate its growth, the art and science of building sales capacity, and how to balance efficiency and growth in hypergrowth mode. He also covers how to achieve a great valuation without a strong performance, the biggest headache on the road to IPO, and whether you should IPO in the first place or remain private.—SPONSORS:Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—Chirag Shah on LinkedIn: https://www.linkedin.com/in/chirag-shah-787b1b20/Motive: https://gomotive.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:From $30M to Almost $1B: A Guide to Hypergrowth, IPO Prep, and Navigating the Public Markethttps://youtu.be/_pJfdN5p-ik—TIMESTAMPS:00:00:00 Preview and Intro00:02:57 Sponsors – Mercury | RightRev | Tipalti00:06:49 Motiv CFO Intro & Company Background00:07:01 Product Market Fit as a CFO00:09:26 Lessons From Taking Companies Public00:11:04 Preparing for Life as a Public Company00:11:26 Moving From Finance Into a GM Role00:12:50 Learning the Business Beyond Finance00:14:23 Empathy for Sales & Carrying a Quota00:15:51 Sponsors – Aleph | Fidelity Private Shares | Metronome00:19:03 Asking Better Questions After Operating Experience00:21:23 Knowing When to Accelerate Growth00:23:16 High-ROI Capacity Signals00:24:51 Scaling Requires Supporting Functions00:26:19 The Art + Science of Adding Reps00:27:53 Sales Team Buy-In Before Scaling00:29:15 Reading Product-Market Fit Through Sales00:30:08 Where Scaling Breaks First (Enablement)00:31:36 Importance of SE / SC Ratios00:33:13 Timing Supporting Hires00:34:32 Maintaining Momentum While Scaling00:36:33 Longest Pole in IPO Prep: Predictability00:38:47 Building Confidence Through Consistency00:40:45 Large Deals Swing Small Companies00:42:41 Growth Still Drives Quarterly Volatility00:44:43 Investor Education as a Core IPO Task00:46:00 Harder to Make Big Changes Publicly00:47:39 Managing Morale in Volatile Markets00:48:33 Taking Cornerstone Private00:52:32 Advice: Know Why You Want to Go Public00:56:18 Efficiency Without Sacrificing Growth01:00:58 Operating Roles Prepared Him for CFO01:06:23 Finance Software Stack Overview#RunTheNumbersPodcast #Hypergrowth #IPOreadiness #CFOInsights #MostlyClassics This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com