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