Run the Numbers

In this episode of Run the Numbers, CJ sits down with Bruno Annicq, CFO of Wellhub (formerly Gympass), to unpack a practical finance playbook built around cash discipline, sustainable growth, and simplicity. Bruno explains how he rebuilt forecasting using an AI-driven, probabilistic ensemble model, moving teams beyond single-scenario planning. They also dig into his EMPOWER planning framework, usable OKRs, and why tighter alignment between finance, HR, and wellbeing is becoming a durable lever for long-term performance.—SPONSORS:RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome 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:Bruno on LinkedIn: https://www.linkedin.com/in/bannicq/Wellhub: https://wellhub.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leaderhttps://youtu.be/iNHbkcG7YEo—TIMESTAMPS:00:00:00 Preview and Intro00:02:19 Sponsors — RightRev, Rillet, Tabs00:06:43 Accidental CFO Origin Story00:07:34 Consulting to Operations Pivot00:08:12 Why Finance Clicked for Bruno00:09:28 McKinsey Prioritization in Real World00:10:02 Eisenhower Matrix and Prioritization00:11:08 Investing in Non-Urgent Work00:13:30 Lessons From AOL Reinvention00:16:10 Sponsors — Abacum, Brex, Metronome00:20:01 Career Growth Through Hard Problems00:20:52 Broadening Skills Through Change00:23:12 Five Core Finance Principles00:24:02 Cash Is King00:25:14 Driving Sustainable Growth00:26:01 No Surprises and Forecasting00:26:07 Finance as Business Enabler00:27:22 Less Is More Philosophy00:28:47 Hardest Principle: Less Is More00:29:46 Deterministic vs Probabilistic Forecasting00:31:11 Marketplace Volatility and Forecast Error00:32:10 Ensemble Models Explained00:33:37 Forecast Accuracy Gains00:34:53 Building Models In-House00:36:46 Why Explainability Matters00:37:48 Empower Framework Introduction00:47:47 Urgency, Compounding, Long-Term Thinking00:48:10 Advice to Younger Self00:50:06 Finance Stack and Expense Stories00:52:51 Credits#RunTheNumbersPodcast #CFO #FinanceLeadership #Forecasting #AIinFinance 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 Jason Kong, General Partner at Base10 Ventures, to unpack the firm’s focus on “automation for the real economy” — software built for industries most tech investors overlook, but the world depends on. Jason breaks down what makes Series B investing uniquely hard, how he evaluates back-office and vertical SaaS opportunities, and where markets tip from niche to overcrowded. They also discuss Base10’s decision to donate 50% of profits to fund scholarships, plus a lightning round spanning fantasy football, shorting SaaS in 2022, and a venture take that might spark debate.—SPONSORS: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.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics—LINKS:Jason on LinkedIn: https://www.linkedin.com/in/jasonykong/Base10 Partners: https://base10.vc/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillipshttps://youtu.be/vBY6WZBMljw—TIMESTAMPS:00:00:00 Preview and Intro00:02:20 Sponsors — Metronome, RightRev, Rillet00:06:02 Base10 Background00:06:41 Automation for the Real Economy00:09:27 Vertical vs. Horizontal Software00:10:38 Cash Flow and Durability00:11:19 Product-Market Fit and ROI00:12:56 Growth Limits Selling to Tech00:13:19 The Size of the Real Economy00:14:16 Sponsors — Tabs, Abacum, Brex00:18:50 Base10’s Giving Model00:20:30 Access, Education, and Tech00:21:53 Purpose and Founder Alignment00:22:51 Radical Transparency00:23:56 Portfolio Focus and Strategy00:24:05 Investing Ahead of Consensus00:26:29 ERP Adjacency as Alpha00:28:58 Lessons From Hedge Funds00:32:29 Public Markets Reality00:34:05 Public vs. Private Investing00:34:48 The Series B Sweet Spot00:36:49 A Bifurcated Series B Market00:38:56 Fast Series Bs and 2021 Vibes00:42:16 What Series B Looks Like Now00:44:36 Back Office Automation00:46:02 ERP-Centric Workflows00:48:33 Long-Ass Lightning Round00:49:36 Shorting SaaS in 202200:50:16 Fantasy Football and Investing00:52:57 Career Advice That Surprises00:55:03 A Contrarian Venture Take00:56:22 Credits#RunTheNumbersPodcast #SeriesB #RealEconomy #VerticalSaaS #BackOfficeAutomation 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 Dominic Phillips, CFO of Samsara, to unpack what it takes to scale a capital-intensive SaaS business from startup to public company in under a decade. Dominic reflects on his six-plus years at Samsara through hypergrowth, COVID disruption, supply chain constraints, a down-round survival raise, and an IPO at the very end of the 2021 tech window. Drawing on his earlier career at ServiceNow under Mike Scarpelli, he shares how experience across FP&A, IR, corp dev, and treasury shaped his approach to capital allocation, investor education, and analyst management. The conversation dives into asset-based pricing, selling into non-discretionary operations budgets, balancing hardware and software economics, and building credibility with a broad analyst base while scaling past $1B in ARR.—SPONSORS:Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome 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.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai—LINKS:Dominic on LinkedIn: https://www.linkedin.com/in/dominicphillips/Company: https://www.samsara.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/VRpTNDIfzPYFrom SMB to Enterprise: The CFO Scaling Playbook With Andrew Casey | Mostly Classicshttps://youtu.be/kMuJ6gAuEpgDriving revenue without selling | Greg Henry of 1Passwordhttps://youtu.be/f5FsNoG8A3E—TIMESTAMPS:00:00:00 Preview & Intro00:02:40 Sponsors — Brex | Metronome | RightRev00:06:18 Interview Begins00:06:46 Dominic’s Early Career00:08:47 From ServiceNow to CFO00:09:47 Joining Samsara00:10:54 COVID, Burn, and a Down Round00:12:40 IPO Messaging and Investor Education00:15:50 Sponsors — Rillet | Tabs | Abacum00:20:27 Hardware + Software Story00:21:29 What Samsara Does00:22:30 Data, AI, and ROI00:23:23 Horizontal Platform and Verticals00:24:27 Growth Drivers at Scale00:26:09 Selling Into Operations00:28:19 Change Management in Legacy Orgs00:29:46 Non-Discretionary Budgets00:33:02 Storytelling Lessons from Scarpelli00:36:14 Managing Analysts00:39:23 Earnings Timing Strategy00:41:06 Metrics and Investor Trust00:42:38 Investor Communication Channels00:44:22 Investor Days and Long-Term Vision00:45:37 Annual Planning Maturity00:48:24 Forecast Accuracy and Cadence00:49:28 The 1000-Day Strategy00:50:40 Top-Line and Margin Targets00:51:59 Capital Allocation by Function00:54:46 Becoming a CFO00:58:21 Lightning Round and a CFO Mistake01:02:41 End Credits#RunTheNumbersPodcast #CFO #ScalingCompanies #B2BSaaS #PublicMarkets 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 Gordon Coyle, a 40-year commercial insurance veteran, to demystify one of the most anxiety-inducing topics for founders and CFOs: business insurance. Drawing on decades of experience with startups, scaleups, and regulated industries, Gordon breaks down what leaders need to know about D&O, E&O, cyber, and general liability, why investor pressure is rising, and where “cheap and easy” online policies fail when real risk hits. Through real-world examples, they explore how claims arise, how defense costs erode limits, why cyber insurance is as much about response as reimbursement, and how to balance budget, risk tolerance, and peer benchmarks—treating insurance as a critical layer of protection, not a box-checking exercise.—SPONSORS:Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome 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.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run—LINKS:Gordon on LinkedIn: https://www.linkedin.com/in/gordoncoyle/The Coyle Group: https://thecoylegroup.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:The Coyle Group - Business Insurancehttps://www.youtube.com/@TheCoyleGroupNY—TIMESTAMPS:00:00:00 Preview and Intro00:01:53 Sponsors — Abacum | Brex | Metronome00:05:39 Interview Begins with Gordon Coyle00:06:23 Gordon Coyle & The Coyle Group00:07:21 Explaining Insurance on YouTube00:08:40 Turning Education into Inbound Leads00:09:40 Content as a Pull Strategy00:10:53 Insurance Complexity for Tech Founders00:13:28 Why Investors Require D&O Insurance00:14:09 What D&O Covers and Why It Matters00:15:50 Sponsors — RightRev | Rillet | Tabs00:20:19 Who D&O Covers and Rising Investor Pressure00:22:37 D&O Limits and Cost Tradeoffs00:23:21 Panic Calls and Late D&O Purchases00:24:39 How Defense Costs Erode Coverage00:25:31 Common D&O Claims and Employment Risk00:27:08 D&O vs E&O Explained00:29:12 Cyber Insurance and Social Engineering00:31:59 AI’s Impact on Cyber Risk00:33:50 Real-World Ransomware Stories00:34:17 Cyber Insurance as Money and Response00:35:29 Business Email Compromise Scams00:39:43 Why Tech Still Needs General Liability00:41:16 What a BOP Covers00:42:32 Convenience vs Proper Coverage00:44:29 Surprising General Liability Claims00:46:45 Insurance Costs for Startups00:47:36 Higher Costs in High-Risk Industries00:48:26 Balancing Budget, Risk, and Coverage00:50:39 PEOs, Workers’ Comp, and EPLI00:54:39 Choosing the Right Insurance Partner00:56:42 End Credits#RunTheNumbersPodcast #StartupFinance #BusinessInsurance #RiskManagement #CyberRisk 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

[Original air date: June 19, 2025]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 LinkedIn: https://www.linkedin.com/in/immermanAndreessen Horowitz: https://a16z.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:a16z’s Alex Immerman on the Evolving Role of the CFO in the Age of AIhttps://youtu.be/JIvHp-mlnzsSo You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Meanshttps://www.youtube.com/watch?v=cgHOtvG1Ces—TIMESTAMPS:00:00:00 Preview and Intro00:01:46 AI Margins Improve Dramatically00:02:29 What Separates Great CFOs00:03:29 Founder Mindset Drives Performance00:05:31 Founder Intensity and Margin Expansion00:06:57 Backing Unproven Bets Thoughtfully00:08:29 Interviewing CFOs for Backbone00:09:55 When CFOs Push Back on Strategy00:11:25 CFO Trust With Boards and Investors00:11:50 How CFOs Engage Investors When Hiring00:14:44 Building Strong CFO Investor Relationships00:16:18 Sharing Bad News Early00:17:21 CEO Vision Versus CFO Validation00:20:57 How AI Is Changing the CFO Role00:23:56 Incumbents Versus AI-Native Finance Tools00:26:24 CFOs Driving Internal AI Adoption00:28:07 AI Impact on Customer Support Efficiency00:29:26 Internal Leverage From AI Automation00:31:29 Why Investors Care About LTV to CAC00:34:00 LTV to CAC Across Business Models00:36:26 Retention Curves Matter More Than Growth00:38:16 Evaluating AI Gross Margins Long Term00:40:04 Recipe for AI Margin Expansion00:43:01 What Makes a Public-Ready CFO00:44:47 Beating Guidance Drives IPO Performance00:46:56 Growth Versus Profitability Has Rebalanced#RunTheNumbersPodcast #CFOLeadership #FintechInvesting #AISaaS #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

[Original air date: May 8, 2025]When it comes to investor relations, an organization’s communication strategy should be a key instrument to support its business strategy. While this may seem obvious, so often we get this wrong. In this episode, CJ hosts a masterclass on investor relations with Samuel Levenson of the Arbor Advisory Group and Jon Neitzell of Andruil Partners, focusing on the strategic role of IR in driving company valuation. They cover what “audience opportunity” really means and what to do when you’ve attracted the wrong investors. They talk about metrics, KPIs, and OKRs, plus why management credibility and conveying conviction can make or break your IR strategy. They also discuss what has changed in the IR profession over time and what hasn’t (but probably should) before suggesting changes you can make to drive impact immediately.—LINKS:Samuel Levenson on LinkedIn: www.linkedin.com/in/samlevenson/Jon Neitzell on LinkedIn: www.linkedin.com/in/jonathan-neitzell/Arbor Advisory Group: www.arboradvisorygroup.com/Anduril Partners: https://www.andurilpartners.ai/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Investor Relations as a Strategic Weapon: A Masterclasshttps://youtu.be/ac9xmURhAqE—TIMESTAMPS:00:00:00 Preview and Intro00:02:22 Welcome to Sam and Jon00:03:12 Linking Business Strategy and Communication00:05:01 Proactive vs. Reactive Investor Relations00:06:39 Tailoring the Message by Investor Type00:08:05 Audience Opportunity and Ideal Shareholders00:11:05 When the Investor Base No Longer Fits00:12:21 Shifting Investors as Industries Change00:13:16 Optionality Comes From Patient Shareholders00:14:40 Conveying Conviction Through Credibility00:17:03 Why Investor Days Build Trust00:18:02 Metrics Versus Storytelling in IR00:19:10 Choosing Metrics the Market Actually Rewards00:22:30 Valuation Disconnects and Investor Confusion00:23:17 Finding Metrics That Truly Drive Value00:25:33 Avoiding Bad Capital Allocation Decisions00:26:20 Disclose Versus Guide: Confidence Intervals00:27:35 Knowing What You Don’t Know00:29:33 Science Versus Art in Storytelling00:33:11 When Algorithms Become Your Audience00:33:56 Passive Investing Now Dominates Markets00:35:16 Linking OKRs to Value-Driving KPIs00:36:42 Closing the Strategy-Metrics Feedback Loop00:38:07 When Investors Sense Operational Confidence00:39:47 Why IR Becomes Strategy Consulting00:41:28 Why IR Teams Stay Undersized00:43:23 Sam’s Accidental Entry Into Investor Relations00:44:34 Mentorship Over Formal IR Training00:46:18 How Markets Outpaced IR Practices00:47:01 Investor Days Go Virtual00:49:34 Designing a High-Quality Earnings Call00:50:41 Investor Days as High-ROI Investments00:51:45 IR Websites as Investor Onramps00:53:42 World-Class Investor Day Examples00:54:20 Using AI to Prepare Investor Communications00:56:19 Building a Proactive IR 2.0 Strategy00:58:33 Why IR Requires Full Executive Buy-In01:00:51 Data Transfers Conviction to Investors01:03:31 Closing Reflections on Trust and Valuation#RunTheNumbersPodcast #InvestorRelations #CapitalMarkets #ValuationStrategy #CFOInsights 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 year-end episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman reflect on what it actually takes to build a modern media business around newsletters and podcasts. They unpack CJ’s first year going full-time, comparing creative intuition versus metric-driven operating styles, and discuss what content truly drives growth. The conversation also covers distribution dynamics, the emotional reality of unsubscribes and burnout, and closes with a candid look at monetization, team building, and the tradeoffs between simplicity and scale.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/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/https://www.growthunhinged.com/p/deep-research-for-gtmhttps://www.growthunhinged.com/p/2025-state-of-b2b-gtm-reporthttps://www.mostlymetrics.com/p/presenting-the-state-of-the-agentic-financial-stackhttps://www.mostlymetrics.com/p/the-great-ai-arr-illusionhttps://www.mostlymetrics.com/p/presenting-the-2025-tech-stack-reporthttps://www.mostlymetrics.com/p/download-the-annual-planning-biblehttps://www.growthunhinged.com/p/how-to-sell-annual-planshttps://www.growthunhinged.com/p/get-recommended-by-chatgpthttps://www.growthunhinged.com/p/gtm-vibecoding-ideashttps://www.growthunhinged.com/p/how-to-use-ai-agents-for-marketing—RELATED EPISODES:We get roasted for swag and drop some GTM goldhttps://youtu.be/uubf_8al95wDo vanity plates bring serious business?https://youtu.be/Cm1rubFb-kgPricing in the Real World: Babies, Bots, and Billinghttps://youtu.be/T1cjFSZR0k0—TIMESTAMPS:00:00:00 Preview and Intro00:01:52 Sponsors — Pulley | Metronome00:04:12 Action Figure Swag and Year-in-Review Setup00:05:47 Going Full-Time and the First-Year Reality Check00:07:24 Writing Schedules, Creative Work, and Time Optimization00:09:16 Writing Speed, Craft, and the Myth That Time Equals Quality00:10:51 Perfectionism vs. Throughput in Newsletter Writing00:13:03 Creator Burnout, Motivation, and Engagement Anxiety00:14:08 Playing the Long Game vs. Obsessing Over Metrics00:15:42 Best Work of the Year and High-Leverage Content Bets00:17:55 Big Research Reports as Career-Defining Projects00:19:19 When Memes Outperform Deep Work00:19:52 LinkedIn Algorithms vs. Content Quality00:20:51 Writing for the Feed vs. Writing to Think00:22:03 Optimizing LinkedIn Profiles for Credibility00:23:47 Subscriber Growth, Audience Quality, and Churn Reality00:27:20 Reports and Research as Growth Engines00:28:37 Tactical “How-To” Content That Actually Converts00:30:21 Tactical Value Beats Sounding Smart00:30:40 Building a Team and Scaling Beyond a Solopreneur00:32:05 Simplicity vs. Scale in Early Business Decisions00:35:37 Avoiding Boredom and Shiny Object Syndrome00:37:12 Balancing Writing, Consulting, and Energy00:37:54 Making the Leap Financially as a Creator00:39:01 Subscriptions vs. Advertising as the Real Business Model#MostlyGrowthPodcast #CreatorEconomy #IndependentCreator #NewsletterBusiness #YearInReview This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

[Original air date: June 5, 2025]How can finance leaders identify where their capital is silently going to waste and where it can be better used to drive growth? In this episode, CJ interviews Russell Lester, the CFO of Tropic, where capital allocation is both the product and the mission. Russell introduces the concept of “spoilage”, deployed capital that fails to deliver its intended value. He also talks about “levers”, positive actions that force multiply your efforts, and “leakages”, headwinds or detractors that sap momentum. Russell believes it is the job of the CFO (or “Chief Alignment Officer”) to proactively go looking for these levers and leakages. He then explains how he uses his “center of the table” framework to redeploy the freed-up capital to fuel growth. Russell also covers how to address misalignment, what helicopter skills are and why you need them, what a data safari is and why you should take one daily, and why every CFO needs a spend management tool.—SPONSORS:Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/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/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:Russell on LinkedIn: https://www.linkedin.com/in/russell-lester-aa98463/Tropic: https://www.tropicapp.io/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Wasted Capital and Where to Find It The CFOs Guide to Spoilage Levers Leakageshttps://youtu.be/xOby7CcdljI—TIMESTAMPS:00:00:00 Mostly Classics: Russell Lester on Capital and Alignment00:00:48 Sponsors — Tipalti | Aleph | Fidelity Private Shares00:04:07 Russell Lester Joins the Show00:06:45 Capital Spoilage and Wasted Spend00:08:34 Why Spoilage Goes Unnoticed Inside Companies00:10:16 Creating Accountability for ROI00:11:08 Spoilage Beyond Tools and Software00:13:04 Strategy Drift and the Sunk Cost Trap00:14:14 Sponsors — Sage Intacct | Mercury | RightRev00:17:44 Levers and Leakages: A Framework for Momentum00:19:27 Identifying Levers Across the Funnel00:21:48 Efficiency Levers Inside the P&L00:23:31 Common Spend Leakages in Practice00:24:21 The Center of the Table Framework00:26:47 Budget Ownership vs Corporate Stewardship00:28:49 The CFO as Chief Alignment Officer00:31:31 Trust, Tact, and Executive Leadership00:33:35 Helicopter Skills for Finance Leaders00:35:41 Curiosity as a CFO Superpower00:36:02 Data Safaris and Asking Better Questions00:38:16 Breaking Down Net Dollar Retention00:40:32 Navigating Data Overload00:42:16 Building a Single Source of Truth00:43:03 Intelligent Spend Management in Action00:44:44 Capital Allocation as the CFO’s Core Job00:46:04 How Spend Management Drives Growth00:49:14 Why Companies Delay Spend Tools00:50:49 A Career Mistake with Investors00:52:49 Auto-Renewals: Revenue vs Leakage00:54:07 Advice to a Younger CFO#RunTheNumbersPodcast #CFOLeadership #CapitalAllocation #FinancialStrategy #SpendManagement This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this special, table-turning episode of Run the Numbers, CJ Gustafson steps out of the host’s chair as Paul Stansik—Operating Partner at ParkerGale and author of the Hello Operator newsletter—takes over the interview. What began as a planned discussion on annual planning best practices quickly evolves into a candid deep dive on Mostly Media, CJ’s growing niche B2B media business, and the thinking behind his own operating plan for the year ahead. Fresh off exiting his CFO role in January 2025, CJ walks through the origin story of Mostly Metrics, how it scaled into a broader media platform, and what it’s like being “the boss of me” for the first time. Paul presses on the real questions—growth opportunities, monetization, and strategic tradeoffs—making this episode a transparent look at how a modern, metrics-driven media business is built and run.—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/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/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.com—LINKS:Paul on LinkedIn: https://www.linkedin.com/in/paulstansik/Hello Operator: https://hellooperator.substack.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Portfolio Operations: This Is What You Actually Have To Do To Make Sure a Company Is Successfulhttps://youtu.be/pOj4JwGUTSoGrindr’s $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantzhttps://youtu.be/ijFIMmtpLNwScaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillipshttps://youtu.be/vBY6WZBMljw—TIMESTAMPS:00:00:00 Preview and Intro00:02:10 Sponsors — RightRev | Tipalti | Aleph00:06:23 Episode Setup and Context00:07:22 Why This Episode Exists00:08:44 The Origin Story00:10:03 First Signs of Traction00:10:26 Memes, Early Growth, and “Big Ballers”00:12:01 Defining the Brand Feel00:13:28 Leaving a Job to Write00:15:07 Writing His Way to CFO00:16:26 Sponsors — Fidelity Private Shares | Sage Intacct | Mercury00:19:01 Growth Tactics That Worked00:21:31 First Monetization Moment00:22:13 Balancing CFO Life and Media00:24:06 Going All-In on the Business00:25:02 A CFO Lens on Media00:28:09 Asset Businesses vs Cash Flow00:31:35 How the Business Makes Money00:32:42 Revenue Compounding Over Time00:33:29 Scaling to $3M00:34:08 Partnerships and Buying Cycles00:36:19 Building the Core Team00:39:09 Adding Recruiting to the Mix00:41:01 Strategy for the Next Phase00:42:03 Boredom, Discipline, and Craft00:43:08 Defining the Core Audience00:46:09 Staying in the Game00:47:22 Advice for Creators00:49:15 Brand, Fun, and Value00:52:08 Following the Momentum00:53:14 Finding Your Unique Edge00:55:19 Enjoying the Build00:56:25 Closing and Outro#RunTheNumbersPodcast #creatoreconomy #mediabusiness #cfoperspective #buildinpublic This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

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, Kyle Poyar, and Ben Hillman unpack a wide-ranging set of predictions and observations about where go-to-market strategy, AI, and pricing models are headed next. They discuss why what ChatGPT says about your product may become a core marketing KPI, the resurgence of direct mail and physical touchpoints in an AI-saturated world, and why “almost as good as a human” is a dangerous positioning for AI-driven products. The conversation also explores AI monetization paths through advertising, the risk of an AI infrastructure timing mismatch leading to a broader financial pullback, and what historical parallels like railroads and the Sears catalog can teach us about today’s buildout. The episode closes with real-world pricing lessons, from energy-as-a-service solar subscriptions to the surprisingly massive standalone economics of Apple’s AirPods, tying together how distribution, perception, and monetization shape durable growth.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/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:996 Culture, Exploding AI Bills & SaaS Chaoshttps://youtu.be/qhrxDL0gsRoThe Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberghttps://youtu.be/yPxWvhPISKoOpenAI’s Impossible Math: $500B or Bust?https://youtu.be/L6PLnvjcnpkFrom Birding Apps to Billion-Dollar Bundles: The Future of SaaS Growthhttps://youtu.be/mzITrIP70OkWhere Did All the Middle Managers Go?https://youtu.be/LvN7RzmApPU—TIMESTAMPS:00:00:00 Preview and Intro00:01:40 Sponsors — Pulley, Metronome00:04:00 Welcome Back And Consumer Friction00:05:29 Insurance Middlemen Frustrations00:07:07 Explaining Newsletter Businesses00:07:58 Family Perceptions Of Work00:09:05 GTM And Growth Predictions00:10:19 Trust And Objectivity In ChatGPT00:12:01 ChatGPT As Marketing KPI00:14:14 Direct Mail Marketing Comeback00:15:56 Tech Buying Media Assets00:17:52 Fake Subscribers And Email Lore00:19:03 AI Quality Over Automation00:22:11 AI Healthcare And Ad Models00:24:40 Advertising Fuels AI Economics00:25:40 AI Boom Versus Bust Timing00:27:49 Infrastructure Before Killer Apps00:30:21 Railroad Economics And Real Estate00:30:46 Solar Subscriptions And Pricing00:32:50 AirPods As Recurring Revenue00:34:57 Show Outro And Credits#MostlyGrowthPodcast #GrowthMarketing #AITrends #GoToMarket #StartupStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

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