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In this episode of Run the Numbers, CJ sits down with Brett Queener, Managing Director at Bonfire Ventures, to trace the origins of ARR and examine how new revenue models are reshaping B2B software. Drawing on Brett’s time at Salesforce and SmartRecruiters, they explore the shift from annual contracts to outcome-based pricing, what it means for forecasting and gtm strategy, and where the next major inflection points in SaaS are likely to emerge. — 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.com Rillet 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/cj Tabs 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 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.ai 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/metrics 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 — LINKS:  Brett on LinkedIn: https://www.linkedin.com/in/brettqueener/ Brett’s Substack: https://queener.substack.com/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com The Staffing Ratios Salesforce Used, with Brett Queener of Bonfire VC https://youtu.be/lJVgstAXjJs — TIMESTAMPS: 00:02:54 Welcome Brett & episode setup 00:03:51 On-prem software to SaaS 00:05:54 Salesforce & recurring revenue 00:07:15 On-prem costs & partner bloat 00:09:58 Contracts, control & comp shifts 00:14:15 Lock-in, renewals & SaaS drift 00:16:20 Sponsors — RightRev | Rillet | Tabs 00:19:48 From buying to hiring software 00:21:59 Agents change pricing & planning 00:25:59 Forecasting without ARR 00:28:03 Talent models break 00:29:45 Sponsors — Abacum | Brex | Metronome 00:33:01 Rethinking sales & comp 00:36:47 Selling by doing the job 00:40:50 The future role of sales 00:46:10 Zombie SaaS & category collapse 00:51:07 Context as the moat 00:56:07 Where AI hits next 00:58:44 Vertical AI & hidden TAMs 01:02:12 $1B startups vs mega rounds 01:05:48 Dilution, fund math & pressure 01:08:03 Choosing your founder path

In this special CFO Explains episode of Run the Numbers, CJ Gustafson sits down with executive producer Ben Hillman to unpack the real history of EBITDA. From John Malone and cable TV to private equity, SaaS, and today’s AI boom, CJ explains how a metric invented out of desperation became the default language of valuation—and how adjusted EBITDA can both clarify and distort the truth about a business. — 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.com 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.com Rillet 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/cj Tabs 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 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.ai 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/metrics — LINKS:  CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com Slacker Stuff: https://www.slackerstuff.com/ Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/ — RELATED EPISODES: How Much Revenue Do You Need to IPO in 2025? https://youtu.be/7ajWVCNVDmI — TIMESTAMPS: 00:00:00 Intro 00:01:17 The Origins of EBITDA 00:06:48 Sponsors — Metronome | RightRev | Rillet 00:10:12 The Mechanics of EBITDA 00:13:46 Impact on Other Industries 00:15:38 The Many Faces of EBITDA 00:19:09 Sponsors  — Tabs | Abacum | Brex00:22:30 EBITDA’s AI Encore 00:24:56 Wrap Up 00:28:19 Credits #RunTheNumbersPodcast #CFOExplains #EBITDA #FinancePodcast #BusinessMetrics

In this episode of Run the Numbers, CJ sits down with Intercom CFO Dan Griggs to discuss pricing and forecasting in the AI era. Dan shares the “it’s not zero” rule, the logic behind Fin’s $0.99 pricing, and how to bet on AI without blowing up the core business. — 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/metrics 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 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.com Rillet 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/cj Tabs 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 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.ai — LINKS:  Dan on LinkedIn: https://www.linkedin.com/in/dan-griggs-0970181/ Intercom: https://www.intercom.com/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brown https://youtu.be/ttedn4AULt8 — TIMESTAMPS: 00:00:00 Cold Open 00:01:03 Dan Griggs and Intercom’s AI Pivot 00:02:45 Ice Cream to SaaS 00:04:19 Learning the Business 00:06:26 Operational Reality and Forecasts 00:08:00 “It’s Not Zero” Forecasting 00:10:09 Scenario Planning and Ambiguity 00:11:23 Sponsors — Brex | Metronome | RightRev 00:14:43 Mental Models for Metrics 00:16:15 Mental Math for Forecasts 00:17:28 Core CFO Ratios 00:19:13 Intercom’s Burn-the-Boats Moment 00:20:53 AI as an Existential Bet 00:22:21 SaaS Categories AI Can Replace 00:23:04 Why Finance Lags on AI 00:23:39 Sponsors — Rillet | Tabs | Abacum 00:27:05 Why Fin Uses Outcome Pricing 00:28:59 The $0.99 Resolution Tradeoff 00:30:46 Why Support Work Varies 00:32:01 AI Resolution Unit Economics 00:33:08 Model Choice as Costs Fall 00:35:19 Domain-Specific vs Generic LLMs 00:36:08 Selling Against the Core 00:38:50 Founder vs Professional CEOs 00:41:47 Hiring Mistakes and Instincts 00:44:28 Intercom’s Finance Stack 00:45:49 Craziest Expense Request

In this episode of Run the Numbers, CJ sits down with Maria Izurieta, CFO of Huntress, to unpack what it really means to lead finance as a connective tissue across the organization. Drawing on experience across VC-backed, PE-owned, and public companies, Maria shares how she balances impact versus perfection, builds trust through small wins, and helps teams move from transactional finance to insight-driven decision making. They dig into data transparency, centralized BI, partnering with sales and marketing on revenue, and why the best CFOs unblock friction instead of becoming the “no” department — all while bringing a deeply people-first lens to scale. — 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.ai 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/metrics 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 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.com Rillet 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/cj Tabs 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: Maria on LinkedIn: https://www.linkedin.com/in/maria-izurieta-909a3b/ Company: https://www.huntress.com/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: How the Best CFOs Lead Without Being the CEO | Ken Stillwell https://youtu.be/O4cx9NBqQso — TIMESTAMPS: 00:00:00 Preview and Intro 00:01:01 Maria’s Background 00:03:09 People-First Team Building 00:05:16 People, Process, Systems at Scale 00:07:13 Removing Friction Outside Finance 00:09:15 Data Transparency & Decision-Making 00:11:06 Sponsors — Abacum | Brex | Metronome 00:14:22 Forward-Deployed Data 00:16:21 Centralized Data vs. Silos 00:19:23 Finance as Data Steward 00:21:08 Cost-to-Price Feedback Loop 00:22:35 Curiosity Builds Credibility 00:23:43 Sponsors — RightRev | Rillet | Tabs 00:27:12 Trust First, Then Impact 00:30:27 Celebrating Small Wins 00:31:21 From Transactions to Insights 00:33:00 CFO at the Revenue Table 00:34:32 Educating the Org on Metrics 00:36:21 Customer-Level Margin Reality 00:37:13 Using Facts to Change Decisions 00:38:27 Ownership Mindset in Growth Companies 00:39:10 VC vs. PE vs. Public CFO Tradeoffs 00:41:02 Operating Inside Constraints 00:42:18 Finding Your Stage Fit 00:44:17 Building a Personal Advisor Network 00:46:43 Visibility and Women in Leadership 00:47:44 Work–Life Integration, Not Balance 00:48:45 Lightning Round: Biggest Mistake 00:50:10 Advice to Younger Self 00:51:36 Finance Tech Stack 00:52:01 Craziest Expense Story 00:52:44 Credits #RunTheNumbersPodcast #CFOLeadership #ScalingCompanies #DataDrivenDecisions #ExecutiveLeadership 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 Ken Stillwell, CFO and COO of Pegasystems, to explore the realities of leading from the second seat. Ken shares hard-earned lessons from guiding Pega through the shift from term licenses to ARR and ACV, including how to rework sales compensation without losing trust or momentum. They discuss the limits of KPI obsession, the importance of directional clarity over false precision, and why private equity often drives sharper execution than public markets—and how to apply that discipline while still playing the long game. — SPONSORS: Tabs 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 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.ai 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/metrics 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 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.com Rillet 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/cj — LINKS: Ken on LinkedIn: https://www.linkedin.com/in/ken-stillwell-83a499a/ Pegasystems: https://www.pega.com/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker https://youtu.be/T2YjdoiJtFA — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:57 Sponsors — Tabs | Abacum | Brex 00:07:26 The Strategic Value of Being Number Two 00:08:46 Earnings Calls, Messaging, and Real-Time Judgment 00:10:41 Using Feedback to Sharpen Executive Communication 00:11:38 CFOs as Storytellers & Message Repetition 00:12:31 Managing Up: Reading the Room 00:13:59 Learning the Hard Way: Misreading Dynamics 00:15:18 Confidence, Aggression, and Early CFO Mistakes 00:15:58 Sponsors — Metronome | RightRev | Rillet 00:19:45 When to Email vs Pick Up the Phone 00:22:48 Tailoring Communication to Different Functions 00:23:23 Audience-Specific Messaging: “Why Me?” 00:25:24 Values vs Behaviors in Leadership 00:28:13 Why Big Changes Need Anchoring 00:31:14 Moving Pega to the Cloud 00:32:43 Rewiring Sales Comp for ARR & ACV 00:34:56 Sales Credibility Breakdowns with Customers 00:36:20 Economics vs Trust in Sales Teams 00:37:48 Balancing Field Feedback with Company Goals 00:39:17 De-Emphasizing New Logos to Fix the Sales Model 00:41:12 The Danger of Over-Obsessing on KPIs 00:42:51 Public vs Private: Incentives and Operating Discipline 00:45:57 Why Companies Go Private: Motivation Over Patience 00:47:29 The Shrinking Public Markets 00:47:57 Private vs Public CFO Mindsets 00:49:39 Meeting Investors Where They Are 00:50:16 A Risky Decision That Paid Off: Going All-In on the Cloud 00:51:29 Long-Ass Lightning Round 00:53:24 Ken’s Finance Tech Stack & Craziest Expense 00:54:39 Credits #RunTheNumbersPodcast #CFOLeadership #ExecutiveCommunication #SalesStrategy #PublicVsPrivate 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 Chris Brubaker, SVP of Finance at Postscript, who’s helped build the finance function from the ground up. Chris shares how he partners with sales through deal desks, sets pricing guardrails, and makes sure finance helps close deals instead of slowing them down. They dig into his hands-on approach to automation using AI with limited engineering resources, how Postscript’s metrics evolved as the company scaled, when to trust internal data over benchmarks, and where teams get tripped up. Plus, a private jet accounting story—because of course. — SPONSORS: Rillet 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/cj Tabs 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 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.ai 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/metrics 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 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.com — LINKS: Chris on LinkedIn: https://www.linkedin.com/in/wchrisbrubaker/ Postscript: https://postscript.io/ CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — RELATED EPISODES: So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means https://youtu.be/cgHOtvG1Ces The IPO Playbook: Expert Advice from Lee Kirkpatrick, Twilio’s Former CFO https://youtu.be/PTKAUD7PSWU The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq https://youtu.be/Dl8nDZPJMpE — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:22 Sponsors — Rillet | Tabs | Abacum 00:06:55 Interview Begins 00:07:36 First Finance Hire and Early Scale at Postscript 00:09:02 Usage-Based Margins, COGS, and the Twilio Parallel 00:10:31 Partnering With Sales and Building Deal Desk 00:13:16 Pricing Guardrails, Payback, and Deal Economics 00:15:35 How Deal Desk Evolves Over Time 00:16:01 Sponsors — Brex | Metronome | RightRev 00:19:44 Making Finance a Deal-Closing Partner 00:20:44 Automating Deal Desk With a Slack Bot 00:23:48 How Technical Finance Leaders Need to Be 00:25:17 Automating Without Engineering Help 00:27:12 Why Human Touch Still Matters in SaaS 00:27:53 Postscript’s Finance Tech Stack 00:28:30 ERP Migration and Month-End Efficiency 00:29:42 The Reality of Continuous Close 00:30:34 First Real AI Wins in Accounting 00:31:18 Experimenting With AI Forecasting 00:33:32 Metrics That Matter: Usage as a Leading Indicator 00:35:49 How Metrics Evolve as the Company Scales 00:37:41 Understanding the Product in a Usage-Based Model 00:39:27 Micro-Seasonality and Forecasting Volatility 00:42:21 How to Use Benchmarks Without Misusing Them 00:43:50 Long-Ass Lightning Round: A Costly Modeling Mistake 00:45:45 Advice to a Younger Finance Leader 00:47:05 The Private Jet Accounting Story 00:49:11 Credits #RunTheNumbersPodcast #FinanceLeadership #DealDesk #UsageBasedSaaS #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 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.com Rillet 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/cj Tabs 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 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.ai 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/metrics 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 — 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 Leader https://youtu.be/iNHbkcG7YEo — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:19 Sponsors — RightRev, Rillet, Tabs 00:06:43 Accidental CFO Origin Story 00:07:34 Consulting to Operations Pivot 00:08:12 Why Finance Clicked for Bruno 00:09:28 McKinsey Prioritization in Real World 00:10:02 Eisenhower Matrix and Prioritization 00:11:08 Investing in Non-Urgent Work 00:13:30 Lessons From AOL Reinvention 00:16:10 Sponsors — Abacum, Brex, Metronome 00:20:01 Career Growth Through Hard Problems 00:20:52 Broadening Skills Through Change 00:23:12 Five Core Finance Principles 00:24:02 Cash Is King 00:25:14 Driving Sustainable Growth 00:26:01 No Surprises and Forecasting 00:26:07 Finance as Business Enabler 00:27:22 Less Is More Philosophy 00:28:47 Hardest Principle: Less Is More 00:29:46 Deterministic vs Probabilistic Forecasting 00:31:11 Marketplace Volatility and Forecast Error 00:32:10 Ensemble Models Explained 00:33:37 Forecast Accuracy Gains 00:34:53 Building Models In-House 00:36:46 Why Explainability Matters 00:37:48 Empower Framework Introduction 00:47:47 Urgency, Compounding, Long-Term Thinking 00:48:10 Advice to Younger Self 00:50:06 Finance Stack and Expense Stories 00:52:51 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.com 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.com Rillet 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/cj Tabs 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 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.ai 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/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 Phillips https://youtu.be/vBY6WZBMljw — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:20 Sponsors — Metronome, RightRev, Rillet 00:06:02 Base10 Background 00:06:41 Automation for the Real Economy 00:09:27 Vertical vs. Horizontal Software 00:10:38 Cash Flow and Durability 00:11:19 Product-Market Fit and ROI 00:12:56 Growth Limits Selling to Tech 00:13:19 The Size of the Real Economy 00:14:16 Sponsors — Tabs, Abacum, Brex 00:18:50 Base10’s Giving Model 00:20:30 Access, Education, and Tech 00:21:53 Purpose and Founder Alignment 00:22:51 Radical Transparency 00:23:56 Portfolio Focus and Strategy 00:24:05 Investing Ahead of Consensus 00:26:29 ERP Adjacency as Alpha 00:28:58 Lessons From Hedge Funds 00:32:29 Public Markets Reality 00:34:05 Public vs. Private Investing 00:34:48 The Series B Sweet Spot 00:36:49 A Bifurcated Series B Market 00:38:56 Fast Series Bs and 2021 Vibes 00:42:16 What Series B Looks Like Now 00:44:36 Back Office Automation 00:46:02 ERP-Centric Workflows 00:48:33 Long-Ass Lightning Round 00:49:36 Shorting SaaS in 2022 00:50:16 Fantasy Football and Investing 00:52:57 Career Advice That Surprises 00:55:03 A Contrarian Venture Take 00:56:22 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/metrics 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 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.com Rillet 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/cj Tabs 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 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.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 & Growth https://youtu.be/VRpTNDIfzPY From SMB to Enterprise: The CFO Scaling Playbook With Andrew Casey | Mostly Classics https://youtu.be/kMuJ6gAuEpg Driving revenue without selling | Greg Henry of 1Password https://youtu.be/f5FsNoG8A3E — TIMESTAMPS: 00:00:00 Preview & Intro 00:02:40 Sponsors — Brex | Metronome | RightRev 00:06:18 Interview Begins 00:06:46 Dominic’s Early Career 00:08:47 From ServiceNow to CFO 00:09:47 Joining Samsara 00:10:54 COVID, Burn, and a Down Round 00:12:40 IPO Messaging and Investor Education 00:15:50 Sponsors — Rillet | Tabs | Abacum 00:20:27 Hardware + Software Story 00:21:29 What Samsara Does 00:22:30 Data, AI, and ROI 00:23:23 Horizontal Platform and Verticals 00:24:27 Growth Drivers at Scale 00:26:09 Selling Into Operations 00:28:19 Change Management in Legacy Orgs 00:29:46 Non-Discretionary Budgets 00:33:02 Storytelling Lessons from Scarpelli 00:36:14 Managing Analysts 00:39:23 Earnings Timing Strategy 00:41:06 Metrics and Investor Trust 00:42:38 Investor Communication Channels 00:44:22 Investor Days and Long-Term Vision 00:45:37 Annual Planning Maturity 00:48:24 Forecast Accuracy and Cadence 00:49:28 The 1000-Day Strategy 00:50:40 Top-Line and Margin Targets 00:51:59 Capital Allocation by Function 00:54:46 Becoming a CFO 00:58:21 Lightning Round and a CFO Mistake 01:02:41 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.ai 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/metrics 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 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.com Rillet 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/cj Tabs 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 Insurance https://www.youtube.com/@TheCoyleGroupNY — TIMESTAMPS: 00:00:00 Preview and Intro 00:01:53 Sponsors — Abacum | Brex | Metronome 00:05:39 Interview Begins with Gordon Coyle 00:06:23 Gordon Coyle & The Coyle Group 00:07:21 Explaining Insurance on YouTube 00:08:40 Turning Education into Inbound Leads 00:09:40 Content as a Pull Strategy 00:10:53 Insurance Complexity for Tech Founders 00:13:28 Why Investors Require D&O Insurance 00:14:09 What D&O Covers and Why It Matters 00:15:50 Sponsors — RightRev | Rillet | Tabs 00:20:19 Who D&O Covers and Rising Investor Pressure 00:22:37 D&O Limits and Cost Tradeoffs 00:23:21 Panic Calls and Late D&O Purchases 00:24:39 How Defense Costs Erode Coverage 00:25:31 Common D&O Claims and Employment Risk 00:27:08 D&O vs E&O Explained 00:29:12 Cyber Insurance and Social Engineering 00:31:59 AI’s Impact on Cyber Risk 00:33:50 Real-World Ransomware Stories 00:34:17 Cyber Insurance as Money and Response 00:35:29 Business Email Compromise Scams 00:39:43 Why Tech Still Needs General Liability 00:41:16 What a BOP Covers 00:42:32 Convenience vs Proper Coverage 00:44:29 Surprising General Liability Claims 00:46:45 Insurance Costs for Startups 00:47:36 Higher Costs in High-Risk Industries 00:48:26 Balancing Budget, Risk, and Coverage 00:50:39 PEOs, Workers’ Comp, and EPLI 00:54:39 Choosing the Right Insurance Partner 00:56:42 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/immerman Andreessen Horowitz: https://a16z.com CJ 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 AI https://youtu.be/JIvHp-mlnzs So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means https://www.youtube.com/watch?v=cgHOtvG1Ces — TIMESTAMPS: 00:00:00 Preview and Intro 00:01:46 AI Margins Improve Dramatically 00:02:29 What Separates Great CFOs 00:03:29 Founder Mindset Drives Performance 00:05:31 Founder Intensity and Margin Expansion 00:06:57 Backing Unproven Bets Thoughtfully 00:08:29 Interviewing CFOs for Backbone 00:09:55 When CFOs Push Back on Strategy 00:11:25 CFO Trust With Boards and Investors 00:11:50 How CFOs Engage Investors When Hiring 00:14:44 Building Strong CFO Investor Relationships 00:16:18 Sharing Bad News Early 00:17:21 CEO Vision Versus CFO Validation 00:20:57 How AI Is Changing the CFO Role 00:23:56 Incumbents Versus AI-Native Finance Tools 00:26:24 CFOs Driving Internal AI Adoption 00:28:07 AI Impact on Customer Support Efficiency 00:29:26 Internal Leverage From AI Automation 00:31:29 Why Investors Care About LTV to CAC 00:34:00 LTV to CAC Across Business Models 00:36:26 Retention Curves Matter More Than Growth 00:38:16 Evaluating AI Gross Margins Long Term 00:40:04 Recipe for AI Margin Expansion 00:43:01 What Makes a Public-Ready CFO 00:44:47 Beating Guidance Drives IPO Performance 00:46:56 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 Masterclass https://youtu.be/ac9xmURhAqE — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:22 Welcome to Sam and Jon 00:03:12 Linking Business Strategy and Communication 00:05:01 Proactive vs. Reactive Investor Relations 00:06:39 Tailoring the Message by Investor Type 00:08:05 Audience Opportunity and Ideal Shareholders 00:11:05 When the Investor Base No Longer Fits 00:12:21 Shifting Investors as Industries Change 00:13:16 Optionality Comes From Patient Shareholders 00:14:40 Conveying Conviction Through Credibility 00:17:03 Why Investor Days Build Trust 00:18:02 Metrics Versus Storytelling in IR 00:19:10 Choosing Metrics the Market Actually Rewards 00:22:30 Valuation Disconnects and Investor Confusion 00:23:17 Finding Metrics That Truly Drive Value 00:25:33 Avoiding Bad Capital Allocation Decisions 00:26:20 Disclose Versus Guide: Confidence Intervals 00:27:35 Knowing What You Don’t Know 00:29:33 Science Versus Art in Storytelling 00:33:11 When Algorithms Become Your Audience 00:33:56 Passive Investing Now Dominates Markets 00:35:16 Linking OKRs to Value-Driving KPIs 00:36:42 Closing the Strategy-Metrics Feedback Loop 00:38:07 When Investors Sense Operational Confidence 00:39:47 Why IR Becomes Strategy Consulting 00:41:28 Why IR Teams Stay Undersized 00:43:23 Sam’s Accidental Entry Into Investor Relations 00:44:34 Mentorship Over Formal IR Training 00:46:18 How Markets Outpaced IR Practices 00:47:01 Investor Days Go Virtual 00:49:34 Designing a High-Quality Earnings Call 00:50:41 Investor Days as High-ROI Investments 00:51:45 IR Websites as Investor Onramps 00:53:42 World-Class Investor Day Examples 00:54:20 Using AI to Prepare Investor Communications 00:56:19 Building a Proactive IR 2.0 Strategy 00:58:33 Why IR Requires Full Executive Buy-In 01:00:51 Data Transfers Conviction to Investors 01:03:31 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/@MostlyGrowth Mostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102 Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3 In 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/mostlymetrics 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 — LINKS: Mostly Metrics: https://www.mostlymetrics.com CJ 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-gtm https://www.growthunhinged.com/p/2025-state-of-b2b-gtm-report https://www.mostlymetrics.com/p/presenting-the-state-of-the-agentic-financial-stack https://www.mostlymetrics.com/p/the-great-ai-arr-illusion https://www.mostlymetrics.com/p/presenting-the-2025-tech-stack-report https://www.mostlymetrics.com/p/download-the-annual-planning-bible https://www.growthunhinged.com/p/how-to-sell-annual-plans https://www.growthunhinged.com/p/get-recommended-by-chatgpt https://www.growthunhinged.com/p/gtm-vibecoding-ideas https://www.growthunhinged.com/p/how-to-use-ai-agents-for-marketing — RELATED EPISODES: We get roasted for swag and drop some GTM gold https://youtu.be/uubf_8al95w Do vanity plates bring serious business? https://youtu.be/Cm1rubFb-kg Pricing in the Real World: Babies, Bots, and Billing https://youtu.be/T1cjFSZR0k0 — TIMESTAMPS: 00:00:00 Preview and Intro 00:01:52 Sponsors — Pulley | Metronome 00:04:12 Action Figure Swag and Year-in-Review Setup 00:05:47 Going Full-Time and the First-Year Reality Check 00:07:24 Writing Schedules, Creative Work, and Time Optimization 00:09:16 Writing Speed, Craft, and the Myth That Time Equals Quality 00:10:51 Perfectionism vs. Throughput in Newsletter Writing 00:13:03 Creator Burnout, Motivation, and Engagement Anxiety 00:14:08 Playing the Long Game vs. Obsessing Over Metrics 00:15:42 Best Work of the Year and High-Leverage Content Bets 00:17:55 Big Research Reports as Career-Defining Projects 00:19:19 When Memes Outperform Deep Work 00:19:52 LinkedIn Algorithms vs. Content Quality 00:20:51 Writing for the Feed vs. Writing to Think 00:22:03 Optimizing LinkedIn Profiles for Credibility 00:23:47 Subscriber Growth, Audience Quality, and Churn Reality 00:27:20 Reports and Research as Growth Engines 00:28:37 Tactical “How-To” Content That Actually Converts 00:30:21 Tactical Value Beats Sounding Smart 00:30:40 Building a Team and Scaling Beyond a Solopreneur 00:32:05 Simplicity vs. Scale in Early Business Decisions 00:35:37 Avoiding Boredom and Shiny Object Syndrome 00:37:12 Balancing Writing, Consulting, and Energy 00:37:54 Making the Leap Financially as a Creator 00:39:01 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/run 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/3Kn4YHt 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.com 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. — 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 Leakages https://youtu.be/xOby7CcdljI — TIMESTAMPS: 00:00:00 Mostly Classics: Russell Lester on Capital and Alignment 00:00:48 Sponsors — Tipalti | Aleph | Fidelity Private Shares 00:04:07 Russell Lester Joins the Show 00:06:45 Capital Spoilage and Wasted Spend 00:08:34 Why Spoilage Goes Unnoticed Inside Companies 00:10:16 Creating Accountability for ROI 00:11:08 Spoilage Beyond Tools and Software 00:13:04 Strategy Drift and the Sunk Cost Trap 00:14:14 Sponsors — Sage Intacct | Mercury | RightRev 00:17:44 Levers and Leakages: A Framework for Momentum 00:19:27 Identifying Levers Across the Funnel 00:21:48 Efficiency Levers Inside the P&L 00:23:31 Common Spend Leakages in Practice 00:24:21 The Center of the Table Framework 00:26:47 Budget Ownership vs Corporate Stewardship 00:28:49 The CFO as Chief Alignment Officer 00:31:31 Trust, Tact, and Executive Leadership 00:33:35 Helicopter Skills for Finance Leaders 00:35:41 Curiosity as a CFO Superpower 00:36:02 Data Safaris and Asking Better Questions 00:38:16 Breaking Down Net Dollar Retention 00:40:32 Navigating Data Overload 00:42:16 Building a Single Source of Truth 00:43:03 Intelligent Spend Management in Action 00:44:44 Capital Allocation as the CFO’s Core Job 00:46:04 How Spend Management Drives Growth 00:49:14 Why Companies Delay Spend Tools 00:50:49 A Career Mistake with Investors 00:52:49 Auto-Renewals: Revenue vs Leakage 00:54:07 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/run 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/3Kn4YHt 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.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 Successful https://youtu.be/pOj4JwGUTSo Grindr’s $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantz https://youtu.be/ijFIMmtpLNw Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillips https://youtu.be/vBY6WZBMljw — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:10 Sponsors — RightRev | Tipalti | Aleph 00:06:23 Episode Setup and Context 00:07:22 Why This Episode Exists 00:08:44 The Origin Story 00:10:03 First Signs of Traction 00:10:26 Memes, Early Growth, and “Big Ballers” 00:12:01 Defining the Brand Feel 00:13:28 Leaving a Job to Write 00:15:07 Writing His Way to CFO 00:16:26 Sponsors — Fidelity Private Shares | Sage Intacct | Mercury 00:19:01 Growth Tactics That Worked 00:21:31 First Monetization Moment 00:22:13 Balancing CFO Life and Media 00:24:06 Going All-In on the Business 00:25:02 A CFO Lens on Media 00:28:09 Asset Businesses vs Cash Flow 00:31:35 How the Business Makes Money 00:32:42 Revenue Compounding Over Time 00:33:29 Scaling to $3M 00:34:08 Partnerships and Buying Cycles 00:36:19 Building the Core Team 00:39:09 Adding Recruiting to the Mix 00:41:01 Strategy for the Next Phase 00:42:03 Boredom, Discipline, and Craft 00:43:08 Defining the Core Audience 00:46:09 Staying in the Game 00:47:22 Advice for Creators 00:49:15 Brand, Fun, and Value 00:52:08 Following the Momentum 00:53:14 Finding Your Unique Edge 00:55:19 Enjoying the Build 00:56:25 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