Run The Numbers

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Run the Numbers is a weekly podcast about financial metrics and business models, designed for ambitious people operating tech startups. It's a collection of things host CJ Gustafson (CFO at Partstech and writer of Mostly Metrics) has learned and thought about in the trenches as a tech CFO. This show is meant to serve as a playbook of sorts for the stuff CJ wishes he knew earlier in his career, both from experience and from copying people smarter than himself. Topics frequently touch upon Startup SaaS Metrics, Annual Budgeting, Financial Forecasting, Headcount, Equity, Dilution, and Fundraising – and how all of these drive business performance and growth.

CJ Gustafson


    • Nov 22, 2025 LATEST EPISODE
    • weekdays NEW EPISODES
    • 50m AVG DURATION
    • 253 EPISODES


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    Latest episodes from Run The Numbers

    Running the Product-Market Fit Treadmill with Brian Balfour | Mostly Growth

    Play Episode Listen Later Nov 22, 2025 52:58


    Brian Balfour, Founder & CEO of Reforge and former VP of Growth at HubSpot, joins Mostly Growth to explore why product-market fit is a moving target. He introduces the concept of the Product-Market Fit Treadmill, a state where rising customer expectations and competitive pressure make it harder than ever to stay ahead. Brian breaks down how AI has accelerated PMF collapse, explains the hidden costs of product adoption, and shares how Reforge shipped five AI-native products with a team of just 20 people. Packed with frameworks, strategic insight, and startup realism, this episode is essential listening for product leaders, operators, and founders navigating the next wave of GTM.—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://brianbalfour.com/four-fits-growth-frameworkhttps://x.com/amasad/status/1981201454032703662?s=46https://getlatka.com/companies/firefliesaihttps://x.com/rowancheung/status/1988218743952916537?https://gamma.app/insights/how-we-built-a-usd100m-business-differently—RELATED EPISODES:When the marketing math doesn't math | with Emily Kramerhttps://youtu.be/sSuoV_YSrlwWhy Founders Are Posting Sad Dinnershttps://youtu.be/Zl6NSIHF2Gk—TIMESTAMPS:00:00:00 Preview and Intro00:01:51 Sponsors – Pulley, Metronome00:04:11 Introducing Brian Balfour & Reforge background00:07:22 Evergreen frameworks & Four Fits resurgence00:11:01 PMF treadmill and rising expectations00:14:26 AI shocks and PMF collapse (Chegg)00:16:43 CRM expectations & AI-native workflows00:20:44 R&D as ongoing cost to serve00:22:26 Customers buying based on future product velocity00:24:32 Communicating rapid releases & driving adoption00:25:17 Reforge's expanding AI product suite00:27:52 Product delivery vs. product adoption bottlenecks00:29:32 Platform distribution shifts introduction00:30:51 Evaluating emerging platforms00:32:04 The open → close platform cycle00:33:31 Moats, escape velocity & platform dominance00:36:32 Choosing major vs. emerging platforms00:40:22 ChatGPT dominance in AI discovery00:42:16 Hiring, resumes & filtering AI-generated applications00:43:30 AI note-taking market & “Flintstoning”00:47:03 Trying Gamma & AI-generated presentation tools00:50:08 AI onboarding innovations (WhatsApp agent)#MostlyGrowthPodcast #ProductMarketFit #BrianBalfour #StartupStrategy #Reforge 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

    Mercury, Snowflake, and Boulder Care Finance Pros Weigh In | Campfire Roundup

    Play Episode Listen Later Nov 20, 2025 76:06


    In this special episode of Run the Numbers, CJ Gustafson records live from Campfire's AI Finance Forward conference in San Francisco, serving up a trio of rapid-fire interviews with top-tier finance leaders. First, Daniel Kang, CFO of Mercury, breaks down the quality of fintech revenue streams, the mechanics of float in a falling rate environment, and what investors really value. Then, Brad Floering, SVP of Finance at Snowflake, shares war stories on usage-based pricing, forecasting consumption, and the role of AI in modern FP&A. Finally, Mitzi Yue of Boulder Care brings a mission-driven perspective, reflecting on dual roles in finance and culture, career product-market fit, and the ethical frontier of AI in healthcare. It's a fast, thoughtful taste of where modern finance is headed.—LINKS:Daniel Kang on LinkedIn: https://www.linkedin.com/in/dmkang/Mercury: https://mercury.com/Brad Floering on LinkedIn: https://www.linkedin.com/in/brad-floering/Snowflake: https://www.snowflake.com/Mitzi Yue on LinkedIn: https://www.linkedin.com/in/mitziyue/Boulder Care: https://www.boulder.care/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Grindr's $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantzhttps://youtu.be/ijFIMmtpLNw—TIMESTAMPS:00:00:00 Preview and Intro00:04:03 Sponsors – Fidelity Private Shares, Metronome, Mercury00:06:49 Guest – Daniel Kang (Mercury) joins00:07:55 Lessons from being first finance hire00:10:49 Finance collaborating on product decisions00:13:12 Comparing customer segments and revenue models00:16:58 Sponsors – Right Rev, Tipalti, Aleph00:21:11 Market shift for consumer fintech models00:23:14 Balancing gross profit with product growth00:24:41 Misconceptions about fintech revenue00:26:57 Guest – Brad Floering (Snowflake) joins00:30:22 Aligning pricing with cloud resource consumption00:33:17 Forecasting challenges with usage-based revenue00:35:06 Complexity of sales commissions under consumption model00:38:23 Lessons from AWS: committing for discounts00:41:16 Cold start forecasting challenges and the role of employee size00:44:01 Customer behavior and rollover credit challenges00:47:08 Using professional services to recover unused credits00:49:05 Seasonality and forecasting challenges in Q400:54:16 Guest – Mitzi Yue (Boulder Care) joins00:57:05 The pandemic's impact on telemedicine adoption01:00:33 Finance decisions with human consequences in healthcare01:02:26 Finding personal product-market fit in Series B/C stage01:03:33 Finance as the central nervous system of the company01:07:10 Nonprofits inspired by personal values and experience01:10:52 Exploring AI's potential in healthcare and finance—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.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.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—#RunTheNumbersPodcast #FintechStrategy #UsageBasedPricing #HealthcareFinance #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

    Grindr's $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantz

    Play Episode Listen Later Nov 17, 2025 51:43


    In this episode of Run the Numbers, CJ Gustafson sits down with Vanna Krantz, former CFO of Disney+ and Grindr, to explore what it takes to lead finance through massive inflection points. Vanna reflects on building Disney+'s subscription model from scratch under Bob Iger's leadership and the pressure of launching a global product with no precedent. She discusses forecasting as both science and art, and the importance of appreciating high-stakes moments amid chaos. Shifting to Grindr, Vanna breaks down how the company went public with remarkable efficiency—boasting 40% EBITDA margins and under 200 employees—and how she modeled for a user base that consistently churns and returns. She also opens up about career longevity, work-life balance, and helping women find sustainability and acceleration in leadership.—LINKS:Vanna on LinkedIn: https://www.linkedin.com/in/vannakrantz/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Monetizing Community Engagement: The Business of Fitness with Strava CFO Lily Yanghttps://youtu.be/zlLb5yZDKQE“Let's Just See What Breaks” — Intuit's CFO on Being a Disruptor When You're Already the Incumbenthttps://youtu.be/Le1D9HXHvGI—TIMESTAMPS:00:00:00 Preview and Intro00:03:02 Sponsors – Aleph, Fidelity Private Shares, and Metronome00:06:09 Meeting at A16z and Disney Plus Discussion00:07:13 Interviewing with Bob Iger and Joining Bamtech Media00:10:43 Forecasting the Unknown at Disney Plus00:13:01 Launch Strategy – Mandalorian and Retention00:15:15 Sponsors – Mercury, RightRev, and Tipalti00:19:23 Forecasting, Retention Curves, and the Art vs. Science Balance00:22:20 Lessons in Art and Science of Finance at Disney00:25:08 Launch Day Chaos and the Disney Plus CDN Outage00:26:24 Celebrating the 10 Million Subscriber Milestone00:27:21 Grindr IPO and Financial Discovery00:32:42 Active User Metrics and Reactivation Trends00:34:29 Seasonality and Human Behavior in App Usage00:36:02 Free vs. Paid Users and Revenue Optimization00:38:21 Pricing Strategy and Global Monetization00:40:23 Women in Leadership and Staying in the Game00:43:30 Work–Life Balance and Career Seasons00:46:12 Wisdom, Experience, and Staying in the Game00:50:08 Finance Stack, Craziest Expense, and Closing Remarks—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.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.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.—#RunTheNumbersPodcast #CFOInsights #DisneyPlus #GrindrIPO #Leadership 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

    Too Big to Fail: The OpenAI Edition | Mostly Growth

    Play Episode Listen Later Nov 15, 2025 47:14


    In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar dig into what it means to be useful rather than just right at work, exploring how communication, empathy, and impact matter more than technical precision as careers mature. They share candid lessons from their own paths—CJ's focus on making others look good to earn promotions and Kyle's evolution into a domain expert through public writing—before unpacking what separates good from great VPs of Sales with insights from Pavilion founder Sam Jacobs. The conversation then shifts to OpenAI's “too big to fail” claims, the economic ripple effects of AI infrastructure spending, and how finance leaders can stay grounded in reality. Rounding out the episode, the hosts preview their latest research—CJ's “Agentic Finance” report on AI in the finance stack and Kyle's 2025 SaaS Benchmarks—and close with lighthearted banter about founder age stats, home maintenance mishaps, and the price of professional Christmas lights—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://sarahcharlton.substack.com/p/from-being-right-to-being-usefulhttps://www.highalpha.com/saas-benchmarkshttps://www.mostlymetrics.com/p/presenting-the-state-of-the-agentic-financial-stackhttps://www.mostlymetrics.com/p/finance-in-2030https://worksinprogress.co/issue/the-algorithm-will-see-you-now/https://www.theinformation.com/briefings/openai-ceo-sam-altman-forecasts-20-billion-annualized-revenue-yearhttps://www.growthunhinged.com/p/your-pricing-is-broken—RELATED EPISODES:When the marketing math doesn't math | with Emily Kramerhttps://youtu.be/sSuoV_YSrlwGetting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0How To Win at Early Stage Sales With the Guy Who Helped Take Snyk From $0 to $100M+https://youtu.be/VKrZCte8fyM996 Culture, Exploding AI Bills & SaaS Chaoshttps://youtu.be/qhrxDL0gsRo—TIMESTAMPS:00:00:00 Preview and Intro00:02:18 Sponsors – Pulley and Metronome00:05:09 Flight Cancellation and Airport Chaos00:07:58 Being Right vs. Being Useful00:11:17 Getting Promoted Early by Making Others Look Good00:15:25 What Separates a Good VP of Sales from a Great One00:18:24 Sales Leaders as Capital Allocators00:21:14 The Organizational Tax of Sales Support00:22:33 Is OpenAI Too Big to Fail?00:25:31 AI Investments, Alternatives, and Market Impact00:27:50 Bailouts and Economic Reality00:28:20 Agentic Finance and the AI-Driven Finance Stack00:31:43 SaaS Benchmarks Report 2025 Overview00:33:59 Growth Rates by ARR Tier and Scale00:35:40 AI's Impact on Engineering Teams00:37:45 Age and Startup Success00:39:42 Building Durable Businesses Over Time00:41:25 Something You Tried This Week – HVAC Cleaning00:43:19 Outsourcing Holiday Cheer – Professional Light Installation00:47:08 Credits – Mostly Growth Closing Remarks—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—#MostlyGrowthPodcast #StartupFinance #AIPodcast #SaaSLeadership #GoToMarket 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

    SPACs Are Back (Maybe) | Jeff Bernstein of Riveron

    Play Episode Listen Later Nov 13, 2025 62:42


    In this episode of Run the Numbers, CJ sits down with Jeff Bernstein, managing partner at Riveron, to unpack what really happens when a company decides it might be time to go public. Jeff draws on his experience across banking, hedge funds, operating roles, and advisory work to break down IPOs, dual-track processes, and the surprising realities behind price discovery—including why a 20x-oversubscribed book isn't what it seems. He also dives into the re-emergence of SPACs, what's different this time, and the key considerations CFOs should weigh before choosing that route. From IPO-readiness must-haves to building the muscle memory needed for public-company life to the sketchiest EBITDA adjustment he's ever seen, Jeff brings stories, frameworks, and hard-won lessons for any finance leader thinking about the road to the public markets.—LINKS:Jeff Bernstein on LinkedIn: https://www.linkedin.com/in/jeff-bernstein-498a23158/Company: https://riveron.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:00:00:00 Preview and Intro00:02:59 Sponsors – Tipalti, Aleph, Fidelity Private Shares00:06:20 The Mechanics of Going Public at Riveron00:09:59 The State of Tech Capital Markets00:11:19 Comparing the Internet, Mobile, and AI Waves00:14:11 Understanding Dual Track Processes00:15:34 Sponsors – Metronome, Mercury, RightRev00:19:35 Why Companies Choose to Go Public or Sell00:23:02 Why Price Discovery Is Harder in Today's Market00:26:05 The Pros and Cons of Direct Listings00:29:16 Balancing Fairness Between Employees and Investors00:30:47 Inside the IPO Pricing Process00:34:26 How Banks and Investors Game Allocations00:41:22 The Return of SPACs and Why They're Back00:43:46 Key Considerations for CFOs Evaluating SPAC Mergers00:47:53 The Most Successful SPACs to Date00:49:00 Building Public Company Readiness00:52:03 Developing Muscle Memory for Quarterly Reporting00:55:31 The CFO's Role as Chief Communicator00:57:47 Long-Ass Lightning Round – Overhyped Metrics and Sketchy EBITDA—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.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.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.—#RunTheNumbersPodcast #IPOmistakes #CFOinsights #SPACs #FinanceLeadership 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

    The Marketplace Plus Model Explained | Colin Gardiner of Yonder VC

    Play Episode Listen Later Nov 10, 2025 56:13


    In this episode of Run the Numbers, CJ Gustafson sits down with Colin Gardiner, General Partner at Yonder VC and former Chief Revenue and Product Officer at Outdoorsy, to unpack what really drives successful marketplace businesses. Colin shares lessons from scaling a peer-to-peer RV platform, where the biggest unlock came not from casual users but from power hosts optimizing utilization and yield through the SaaS tools they built. He introduces his “Marketplace Plus” investing framework—showing how layering SaaS and professional tools can transform a platform into an operating system—and where founders risk overreaching by taking on inventory or managing supply too tightly. The conversation dives deep into monetization, pricing psychology, take rates, and the fine balance between product-market fit and margin obsession, before zooming out to explore how AI and the decline of SEO are reshaping marketplace discovery.—LINKS:Colin on LinkedIn: https://www.linkedin.com/in/colingardiner/Company: https://www.yonder.vc/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:996 Culture, Exploding AI Bills & SaaS Chaoshttps://youtu.be/qhrxDL0gsRo“Keep the Take Rate Low” - Turo's Chuck Fisher on Scaling a Successful Peer-to-peerhttps://youtu.be/LKH8o1MjnZoThe Art of Stacking S-Curves: Olo's Winning Vertical SaaS Strategy with CFO Peter Benevideshttps://youtu.be/1X2VoYogj44—TIMESTAMPS:00:00:00 Intro and Guest Overview00:02:57 Sponsors – RightRev, Tipalti, and Aleph00:07:13 Outdoorsy and the RV Market00:10:33 Balancing Supply and Demand00:13:05 Marketplace Plus Model00:16:59 Sponsors – Fidelity Private Shares, Metronome, and Mercury00:21:45 Professionalizing Marketplaces00:24:10 Building Software, Insurance, and Financing Layers00:28:07 Avoiding Fully Managed Models00:32:34 Take Rates and Pricing Strategy00:35:00 Monetizing Both Sides00:37:06 Advertising and Marketplace Scale00:39:48 Marketplaces Meet Social Platforms00:42:36 AI and Marketplace Distribution00:45:54 AI Agents and Matchmaking00:47:03 When AI Becomes the Supply00:49:09 Negative Gross Margins and Scale00:53:04 Picking a Side – Supply or Demand00:54:35 Branding, Utilization, and Growth00:55:42 Closing and Credits—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—#RunTheNumbersPodcast #MarketplaceStrategy #AIPoweredBusiness #SaaSModel #StartupFinance 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

    Guess That Name: Pop Star or SaaS Bro? | Mostly Growth

    Play Episode Listen Later Nov 8, 2025 36:31


    In this high-energy episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman dive into the hidden levers of SaaS growth and what truly separates startups that scale to $20M+ ARR from those that stall out. They explore eye-opening data from 6,500 companies, revealing how the best improve net retention, raise pricing, and re-engineer their revenue models over time. Alongside the metrics, there's plenty of playful chaos—like a naming debate over “Yoshinobu Yamamoto Gustafson,” a rapid-fire game of “Founder or Pop Star,” and CJ's accidental IPO embargo break. It's part insight, part inside joke, and 100% for SaaS operators and C-suite climbers.—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/the-compounding-startuphttps://www.growthunhinged.com/p/the-odds-of-making-ithttps://www.superme.ai/kylepoyar?conversationId=VgDXTOl2Z89mW7UYXstU0bhttps://a16z.com/anatomy-of-an-enterprise-platform-company/https://www.investopedia.com/terms/h/hhi.asphttps://navan.com/https://www.mostlymetrics.com/p/navan-ipo-s1-breakdownhttps://x.com/amendandpretend/status/1983588137453416763?s=46https://x.com/ryan_c_walsh/status/1983705182371475630?s=46https://www.reddit.com/r/TwinCities/comments/z6hxp8/how_much_are_people_paying_for_residential_snow/—RELATED EPISODES:Getting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0Why Founders Are Posting Sad Dinnershttps://youtu.be/Zl6NSIHF2Gk—TIMESTAMPS:00:00:00 Preview and Intro00:01:55 Sponsors – Pulley & Metronome00:04:25 Dodgers Banter & Baby Naming00:05:38 Founder or Pop Star Game00:07:50 ChartMogul Data & Growth Levers00:08:30 Expansion, Upsell & Retention Discussion00:15:53 Testing Kyle's AI Avatar00:17:07 CJ's AI Self-Query & Beta Discussion00:18:04 AI Use Cases & Knowledge Retention00:22:03 Platform Debate & A16z Analysis00:24:29 Herfindahl-Hirschman Index Explained00:25:34 Platform Metrics & Valuation Upside00:26:48 CrowdStrike, Datadog & Multi-Product Expansion00:28:13 Core Systems of Record & AI's Impact00:29:49 Business Blunders – Navan IPO & Snowflake CRO00:34:07 Snow Removal Pricing & Insurance Logic00:35:56 Closing Remarks & Credits—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.comPulley 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—#MostlyGrowthPodcast #SaaSGrowth #StartupStrategy #B2BTech #RevenueRetention 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

    Getting fired 4 times made me a founder | Sam Jacobs of Pavilion

    Play Episode Listen Later Nov 6, 2025 62:23


    In this episode of Run the Numbers, CJ Gustafson sits down with Sam Jacobs, Founder and CEO of Pavilion, the global community for GTM leaders. Sam shares how getting fired multiple times as a CRO led him to build a business rooted in belonging — one that monetized members first, prioritized intimacy over growth, and turned a Slack group into a multimillion-dollar company. He and CJ unpack the mechanics of community: the tradeoffs between exclusivity and expansion, why venture capital doesn't always fit human-centered businesses, and how Pavilion balances pricing, curation, and access. They also explore the evolution of the GTM function — from the myth of the plug-and-play VP of Sales to how AI is reshaping RevOps, forecasting, and leadership. Finally, Sam reflects on building durable value beyond personal brand and what it really takes to scale trust as a product.—LINKS:Sam Jacobs on LinkedIn: https://www.linkedin.com/in/samfjacobs/Company: https://www.joinpavilion.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:E120: What does the future of tech look like when it costs $0 to switch software?https://www.youtube.com/live/Cpw2pkq-FXI?si=-0y0tcLTIlIbkmyOCFOs: Want to Outmaneuver Your Competitors? Here's the Jedi Mind Trickhttps://youtu.be/Yte_fe1xF90?si=hVfgdd0Fg0PQuuoSThe Gross Margin Episode with Sarah Wang of a16zhttps://youtu.be/72aP5ohBxvE—TIMESTAMPS:00:00:00 Preview and Intro00:03:05 Sponsors – Mercury, RightRev, and Tipalti00:06:50 Pavilion, Community, and Go-to-Market Leadership00:10:28 Career Tenure and Executive Turnover00:12:55 Compensation Structure and Equity Negotiation00:14:31 Building Wealth Through Equity00:16:30 Sponsors – Aleph, Fidelity Private Shares, and Metronome00:19:36 Managing Wealth, Lifestyle, and Longevity in Leadership00:22:58 Founding Pavilion to Empower Operators00:25:13 Taking Roles for Learning, Titles, and Leverage00:28:47 Contrarian Executives, Team Dynamics, and Leadership Lessons00:30:36 What Makes a Great VP of Sales00:33:23 Revenue, Profitability, and Misaligned Incentives00:35:08 Quota Setting, Forecasting, and Spreadsheet Pitfalls00:39:07 AI in Sales and the Myth of the AI SDR00:40:32 The Future of Playbooks in the Age of AI00:43:38 The Dangers of AI and the Need for Humans in the Loop00:45:27 Monetizing Pavilion – Memberships, Sponsors, and Pricing Strategy00:49:30 Building Higher-Margin Community Businesses00:57:46 Building a Personal Brand with Long-Term Value01:01:52 Closing Credits and Outro—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#RunTheNumbersPodcast #Finance #CommunityBuilding #Leadership #GoToMarket 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

    Do the things spreadsheets can't do | SeatGeek's Teddy Collins

    Play Episode Listen Later Nov 3, 2025 64:09


    In this episode of Run the Numbers, CJ Gustafson sits down with Teddy Collins, EVP of Finance at SeatGeek, who helped scale the company from its first in-house finance hire to a tech-forward finance team powering one of the most dynamic businesses in live events. Teddy shares what it was like leading finance through the pandemic when live events went dark overnight, how that period reshaped his approach to forecasting and uncertainty, and how SeatGeek is now using AI and machine learning to enhance planning accuracy and decision-making. He and CJ also dive into how finance can evolve from a cost center to a strategic partner, the toughest manual processes he's eliminated, and where he sees the next big leap in the CFO tech stack. Finally, Teddy opens up about his rapid rise—four promotions in ten years—and offers practical advice on career growth, feedback, and building trust in a world where AI is redefining what “junior” really means.—LINKS:On LinkedIn: https://www.linkedin.com/in/teddycollins/Company: https://seatgeek.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:CFO of FloQast on Why Finance Teams are Data Curators—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:49) Sponsor – Metronome | Mercury | RightRev(00:06:36) Joining SeatGeek and the Early Finance Journey(00:08:05) Managing Finance When Live Events Went Dark(00:10:23) Forecasting Through Uncertainty(00:13:12) Building Systems and Processes from Scratch(00:15:34) Sponsor – Tipalti | Aleph | Fidelity Private Shares(00:18:06) Using AI and Machine Learning in Forecasting(00:22:44) Build vs. Buy: SeatGeek's Tech Philosophy(00:26:31) Turning Finance into a Strategic Partner(00:30:42) Killing Manual Processes and Automating Insights(00:34:55) The Next Big Leap in the CFO Stack(00:38:46) Leading Teams Through Change and Growth(00:42:11) Talent, Tools, and the Future of Finance Roles(00:46:07) Climbing the Ladder: Four Promotions in Ten Years(00:49:50) Career Advice and Earning Trust in Fast-Growing Teams(00:53:16) How AI Is Reshaping the Definition of “Junior”(00:56:22) Lightning Round and Closing Thoughts—SPONSORS:Today's podcast is brought to you by Metronome. You just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books. With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time. Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing. That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome. Visit metronome.com to learn more.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.#RunTheNumbersPodcast #FinanceLeadership #CFOStack #AIForecasting #SeatGeek 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

    The Gross Margin Episode with Sarah Wang of a16z

    Play Episode Listen Later Oct 27, 2025 56:04


    Gross margins, GPUs, and the future of finance — this one's for the metrics nerds. CJ sits down with Sarah Wang, General Partner at Andreessen Horowitz, to talk about what happens when the traditional SaaS playbook collides with AI. Sarah shares how legacy benchmarks like payback period and burn multiple start to break down in a world where compute, not headcount, drives costs. She explains why sky-high gross margins can actually be an orange flag, how finance leaders can think about resource allocation between engineers and GPUs, and why the most valuable finance teams today are deeply operational. They also unpack what it's like partnering with AI-native founders, the evolution of pricing models as LLM costs drop, and whether we'll see a private trillion-dollar company anytime soon.—LINKS:on LinkedIn: https://www.linkedin.com/in/sarah-wang-59b96a7/Company: https://a16z.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:996 Culture, Exploding AI Bills & SaaS ChaosFrom Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage5,762 Job Applications. Zero Offers.Thinking About Adding Payments to Your Software Product? Listen to This First!—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:40) Sponsors – Fidelity Private Shares, Mercury, RightRev(00:05:50) Sarah Joins the Show(00:06:06) The Future of Excel in the Age of AI(00:08:24) Why Gross Margins Don't Tell the Whole Story(00:10:42) When Sky-High Margins Are an Orange Flag(00:12:57) Finance as a Strategic Lever in AI Companies(00:15:04) Sponsors – Tipalti, Aleph, Rillet(00:17:22) Partnering with AI-Native Founders(00:20:35) When Traditional SaaS Benchmarks Break Down(00:23:58) Forecasting and Financial Planning for Compute Costs(00:27:16) The Engineers-Versus-GPUs Trade-Off(00:30:29) Resource Allocation and Infrastructure Efficiency(00:33:47) How Pricing Models Evolve as LLM Costs Drop(00:37:15) Circular Finance: When Big Tech Funds Its Own Vendors(00:40:39) Metrics That Still Matter in AI-Driven Businesses(00:44:12) The Evolving Role of Finance Leaders(00:47:26) What “Operational Finance” Really Means(00:50:58) Building Sustainable Efficiency in AI Companies(00:54:03) Will We See a Private Trillion-Dollar Company?(00:55:33) Outro—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.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/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#RunTheNumbersPodcast #FinanceLeadership #AIinBusiness #VentureCapital #SaaSMetrics 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

    Sloponomics: Surviving the AI Content Flood with Rudeness | Mostly Growth

    Play Episode Listen Later Oct 25, 2025 38:15


    Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleIn this episode, CJ Gustafson, Kyle Poyar, and Ben Hillman dive into the concept of “sloponomics”—a tongue-in-cheek look at the overwhelming flood of mediocre AI-generated content and what it means for creators, startups, and investors. They discuss how unique voices and genuine creativity will stand out in an AI-saturated landscape, the economic parallels between modern content creation and startup growth, and the tricky dynamics of building sustainable momentum in a world of noise. The trio also unpack the “$10K MRR” meme, pricing psychology, and the difference between chasing vanity metrics and building lasting value. With humor and real-world insight, they explore how AI, distribution, and early-stage investment are reshaping what success looks like in tech and media.Timestamps:00:00 Preview and Intro00:35 Being Mean to AI and Early Banter02:05 When You're Rude to AI: The Penn State Study04:57 Sponsor – Metronome06:02 The Rise of AI-Generated “Slop” Content07:15 The Creator “Haves and Have-Nots”09:00 Losing Credit to AI Models11:20 Feeding the Beast: 400 Posts Later13:13 “Slop Talk” and Human-Made Slop14:27 The $10K MRR Meme and Startup Momentum15:49 Pricing Psychology and Product Traction17:42 Hunting Mice, Buffalo, and Elephants20:19 Venture Funds, Bubbles, and Ecosystem Investing23:39 When Startups Invest in Startups26:25 Slack, Lattice, and the Platform Play30:39 Wrapping Up and Late-Night Insights33:12 The Hemingway Story and CJ's No-Instagram Lifestyle36:10 Electric Boats, Group Discounts, and Sign-OffEpisodes Referenced:Slop Talk (coming soon)⁠https://www.youtube.com/slackerstuff⁠Why Only 2% of Startups Make ItWhen startups burn cash faster than they learn | Ivan Makarov:⁠996 Culture, Exploding AI Bills & SaaS Chaos⁠Links:⁠https://www.dexerto.com/entertainment/study-proves-being-rude-to-ai-chatbots-gets-better-results-than-being-nice-3269895/⁠⁠https://www.usg.edu/galileo/skills/unit07/internet07_02.phtml⁠⁠https://futurism.com/altman-please-thanks-chatgpt⁠⁠https://futurism.com/artificial-intelligence/over-50-percent-internet-ai-slop⁠⁠https://www.axios.com/2025/10/14/ai-generated-writing-humans⁠⁠https://www.economist.com/business/2025/10/16/sloponomics-who-wins-and-loses-in-the-ai-content-flood⁠⁠https://x.com/madhuraaa_/status/1978390720881819884⁠⁠https://www.mostlymetrics.com/p/eat-what-you-kill⁠⁠https://christophjanz.blogspot.com/2014/10/five-ways-to-build-100-million-business.html⁠⁠https://www.growthunhinged.com/p/how-to-build-your-early-gtm-strategy⁠⁠https://www.mostlymetrics.com/p/startups-investing-in-startups-peak-bubble-behavior⁠⁠https://www.economist.com/science-and-technology/2025/10/10/are-barefoot-shoes-good-for-runners⁠⁠https://x.com/ivanomaksf/status/1978852000298320068?s=46⁠⁠https://www.linkedin.com/news/story/uber-offers-drivers-extra-pay-to-perform-tasks-that-train-ai-7116401/⁠⁠https://www.mostlymetrics.com/p/is-ltv-to-cac-the-nickelback-of-metrics⁠⁠https://www.hollywoodreporter.com/tv/tv-news/final-2024-25-network-tv-ratings-tracker-high-potential-1236312223/⁠⁠https://christophjanz.blogspot.com/2014/10/five-ways-to-build-100-million-business.html⁠⁠https://www.theinformation.com/articles/ben-horowitz-hires-jensen-vercel-starts-venture-fund⁠⁠https://www.instagram.com/chasemytail/Today's podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. 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

    Decoding the Psychology of Price in the Age of AI | Michael Stanisz

    Play Episode Listen Later Oct 23, 2025 64:00


    In this episode of Run the Numbers, CJ sits down with Michael Stanisz, Partner at Revenue Management Labs, the person companies call when their pricing model stops making sense. For decades, software pricing was predictable: sell more seats, add more margin. But with AI, every usage prompt has a real cost, and the old economics no longer hold. CJ and Michael dive into what happens when your product looks like software but behaves like infrastructure, how pricing power erodes as features become free, and why value-based pricing might not be as customer-friendly as it sounds. They also explore the chaos of real-world pricing: from Microsoft cloning your startup to measuring ROI when your product's impact is undeniable but hard to prove; all wrapped in sharp insights and a few “we still run this on DOS” war stories.—LINKS:Michael on LinkedIn: https://www.linkedin.com/in/michael-stanisz-27418a28Revenue Management Labs: https://revenueml.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Anything new needs to have AI core to its offering”: Amy Butte, How Navan Is Redefining Finance OpsFrom Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:23) Sponsor – Rillet, Fidelity Private Shares, and Mercury(00:05:27) The new economics of AI pricing(00:07:51) When variable costs replace software margins(00:10:30) The fall of 80% SaaS margins(00:13:23) From premium feature to table stakes(00:15:07) Sponsor – RightRev, Tipalti, and Aleph(00:19:12) Spotting a feature before it becomes a commodity(00:23:31) The real cost of switching and why stickiness matters(00:27:46) The rise of AI white labeling(00:30:03) Outcome-based pricing — altruism or strategy?(00:34:22) Rewarding throughput and avoiding “tollbooth” pricing(00:36:29) Measuring usage and why telemetry matters(00:40:49) What makes a value exchange credible(00:44:14) Cost avoidance vs. revenue gain(00:46:02) The stages of pricing maturity(00:49:49) Why startups see what big companies can't(00:52:09) When hype meets hard costs in AI(00:55:17) When customers refuse to leave on-prem(01:03:29) Credits and Sign-Off—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity 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.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/run#RunTheNumbersPodcast #PricingStrategy #SaaSModels #AIPricing #B2BRevenue 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

    Finance vs. Marketing: Who's Really Right About ROI? | Brandon Sullivan

    Play Episode Listen Later Oct 20, 2025 60:29


    In this episode, CJ sits down with Brandon Sullivan, CFO at 2X, to unpack one of the most enduring tensions in business — the uneasy relationship between finance and marketing. From the myth of clean ROI to the chaos of martech spend, Brandon explains why measuring marketing impact is far harder than most CFOs think, and how spreadsheet logic can lead to bad decisions. He shares what it's like to run finance inside a 1,200-person marketing org, why cutting too deep in downturns can backfire, and what it takes to actually bridge the gap between teams that speak different languages. Along the way, he reveals lessons from scaling 2X across time zones, building global reporting rhythms, and redefining how finance and marketing can finally pull in the same direction.—LINKS:Brandon Sullivan on LinkedIn: https://www.linkedin.com/in/brandonsullivan2x/2X: https://2x.marketing/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:From Facebook's Hypergrowth to Daffy's Disruption: A CFO's Playbook for Saying Yes—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:28) Sponsor – Aleph | Rillet | Fidelity Private Shares(00:05:55) Behind Enemy Lines: Finance Meets Marketing(00:07:00) Why CFOs and CMOs Clash(00:08:12) The Myth of Marketing ROI(00:10:19) Why Marketing Is So Hard to Measure(00:11:23) The Single Source of Truth Problem(00:15:29) Sponsor – Mercury | RightRev | Tipalti(00:19:35) The Three Buckets of Marketing Spend(00:21:26) The Long-Term Cost of Cutting Program Spend(00:23:27) How AI and ChatGPT Are Changing Marketing Attribution(00:25:43) Building a Modern Finance Team(00:27:55) The First-Time CFO Learning Curve(00:31:05) From Solo Operator to Scaled Finance Org(00:32:41) Why Weekly Reporting Beats Monthly Reviews(00:40:10) Working with Private Equity Partners(00:43:43) The Founding Story of 2X(00:48:12) Running a Global Team Across Time Zones(00:54:00) Long-Ass Lightning Round(00:57:00) Advice to Younger Self(00:58:58) Finance Stack and Craziest Expense Story(00:59:58) Credits and Sign-Off—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/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity 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.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.#RunTheNumbersPodcast #FinanceVsMarketing #CFOInsights #MarketingROI #BusinessStrategy 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

    Inside the AI Feedback Loop: Nvidia, OpenAI, and the Bubble Building Itself

    Play Episode Listen Later Oct 18, 2025 46:56


    Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleIn this episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman dive into the question on everyone's mind: are we in an AI bubble? What starts as a lighthearted riff on the U.S. Postal Service launching a podcast quickly spirals into a sharp, funny breakdown of today's AI hype cycle — from Nvidia, OpenAI, and AMD trading money and GPUs in a trillion-dollar feedback loop, to startups burning cash chasing “AI-powered” everything. The trio share real examples of when AI helps and when it backfires (including one newsletter that totally tanked), debate whether companies are over-optimizing for automation, and laugh through the absurdity of the hype while grounding it in practical insights on product, finance, and growth.Timestamps:00:00 Preview and Intro00:14 Are We in an AI Bubble?00:44 The AI Feedback Loop: Nvidia, OpenAI, and AMD01:00 Perplexity, We Caught You (Again)02:18 The USPS Podcast and the End of Original Ideas04:24 How the Team Actually Uses AI at Work06:07 CJ's DIY Dunning Saga08:38 When Automation Goes Too Far10:49 The Perplexity Gaslight Moment13:27 AI vs. AI: Outsmarting Resume Screeners16:09 What Recruiters Really Think of AI Resumes17:17 The Chief of Staff Hiring Story19:15 Is AI Adoption Already Slowing Down?22:42 The “Crossing the Chasm” Moment for AI Tools26:22 Bundling AI Like Streaming Services28:49 Everyone's Paying Everyone: The Circular AI Economy31:15 Betting Big on AGI and Data Centers34:09 The Margin: AI Erotica and Peak Absurdity35:23 OpenAI's Token Leaderboard and Other Blunders41:43 What Kyle Tried This Week: Building an AI Agent44:52 Wrap-Up and OutroEpisodes Referenced:5,762 Job Applications. Zero Offers.Episodes Referenced:5,762 Job Applications. Zero Offers.Why Only 2% of Startups Make ItThe War for Talent is just getting started | Joe FloydLinks:https://usps-mailin-it.simplecast.com/https://i.imgflip.com/a92oy5.jpghttps://tabs.inc/webinar/tabs-agenthttps://www.nytimes.com/2025/10/07/business/ai-chatbot-prompts-resumes.html?_bhlid=1b5906cdc6781a738a150d9c32f846ebf11fc318https://substack.com/home/post/p-175615945https://ramp.com/data/ai-index?utm_source=econlab.substack.comhttps://medium.com/@samuelvandeth/crossing-the-chasm-162802d1cf27https://x.com/TrungTPhan/status/1922669292929024017/photo/1https://x.com/zerohedge/status/1977902195472322620?s=42https://topline.beehiiv.com/p/the-era-of-haves-and-have-notshttps://www.bbc.com/news/articles/cpd2qv58yl5ohttps://www.linkedin.com/posts/cj-gustafson-13140948_imagine-getting-called-into-your-cfos-office-activity-7381681514532458496-NOqa/https://fortune.com/2025/10/01/red-lobster-ceo-damola-adamolekun-comeback-plan-bankruptcy/https://fortune.com/2024/11/13/red-lobster-ceo-damola-adamolekun-says-endless-shrimp-is-never-coming-back/#https://www.relay.app/Today's podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. 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

    Cash Flow, Control, and Company-Building with Ivan Makarov of Andreessen Horowitz

    Play Episode Listen Later Oct 16, 2025 63:15


    In this episode of Run the Numbers, CJ Gustafson sits down with Ivan Makarov, Operating Partner at Andreessen Horowitz and former VP of Finance at Webflow, to explore what it takes to build a finance function from scratch inside a fast-growing startup. Ivan shares lessons from the trenches—how to decide between outsourcing and hiring in-house, what makes a great first finance hire, and why early-stage companies often run out of cash before they run out of ideas. He also dives into fundraising pitfalls, audit readiness, and the tools that make up a modern finance stack. Beyond the spreadsheets, Ivan opens up about the shift from operator to venture partner, the value of helping founders avoid his past mistakes, and what makes an offsite actually work.—LINKS:Ivan Makarov on LinkedIn: https://www.linkedin.com/in/ivansmakarov/Andreessen Horowitz: https://a16z.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Webflow's VP Finance Ivan Makarov on Understanding Startup Equity:Portfolio Operations: This Is What You Actually Have To Do To Make Sure a Company Is Successful:Brex COO/CFO Michael Tannenbaum on Taking Risks996 Culture, Exploding AI Bills & SaaS Chaos—TIMESTAMPS:(00:00:00) Preview, Intro(00:01:18) Meet Ivan Makarov of Andreessen Horowitz & Episode Setup(00:02:39) Sponsor – Tipalti | Aleph | Rillet(00:06:51) From Webflow to Andreessen: Becoming an Operating Partner(00:09:19) When and Why Founders Hire Their First Finance Leader(00:12:52) Hiring Early in Complex or Regulated Industries(00:13:58) The First Finance Hire in 2025 vs. 2015(00:15:46) Sponsor – Fidelity Private Shares | Mercury | RightRev(00:19:02) The Many Hats of Finance Leaders & The Rise of RevOps(00:24:55) What Founders Look For: Startup DNA and Work Ethic(00:26:05) Grind Culture, Return to Office, and New Expectations(00:28:20) From BizOps to RevOps: How Finance Roles Are Evolving(00:31:57) The First 12 Months of a Finance Leader's Playbook(00:35:05) Choosing Audit Partners and Avoiding Hidden Costs(00:36:32) Why Startups Really Fail — Running Out of Cash(00:39:16) Cash Controls, Banking Diversification, and Fraud Prevention(00:43:48) Fundraising Red Flags: Metrics, Definitions, and Diligence(00:47:50) 409A Valuations, Equity Clarity & Candidate Questions(00:50:09) The Modern Finance Tech Stack & Gen 3 Tools(00:55:05) AI's Impact: Replacing Labor, Not People(01:00:00) Offsites, Team Building & The Future of Finance Leadership(01:02:28) Wrapping Up: Reflections, Gratitude & Closing Credits—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/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity 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.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.#RunTheNumbersPodcast #StartupFinance #VentureCapital #CFOInsights #Leadership 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

    Circular Finance, $1T Dreams, and the AI War for Talent with Joe Floyd of Emergence Capital

    Play Episode Listen Later Oct 13, 2025 51:20


    In this episode, CJ sits down with Joe Floyd, General Partner at Emergence Capital, for a candid conversation about the venture landscape reshaped by AI. They unpack how acqui-hires are rewriting the social contract between founders and investors, why AI engineers are commanding “boy band money,” and how SaaS playbooks are being torn up and rebuilt in real time. Joe explains the economics of AI-native startups — from circular capital flows to model-provider costs — and explores whether the next trillion-dollar private company could come from this new wave. Along the way, they discuss valuation frenzy, headcount discipline, and why curiosity might be the most valuable skill in tech today.—LINKS:Joe Floyd on LinkedIn: https://www.linkedin.com/in/joefloyd/HarbourVest Partners: https://www.emcap.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Why Fundraising Has Slowed Down: Insights from Emergence Capital's Benchmarking Report: From Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage:—TIMESTAMPS:(00:00:00) Preview and Intro(00:00:54) Opening and Episode Overview(00:02:53) Sponsor – RightRev | Tipalti | Aleph(00:07:07) Back to the Office and Startup Pace in San Francisco(00:08:40) AI Tooling Experiments and the Risk of Short-Term Hype(00:10:19) Building Stickier AI Products and Competing in Crowded Markets(00:12:27) SaaS Moats, Product-Market Fit, and the AI Shift(00:14:00) How Productivity Platforms Use AI To Stay Sticky(00:15:58) Continuous Authentication and the Next Wave of Security Tech(00:16:36) Sponsor – Rillet | Fidelity Private Shares | Mercury(00:19:54) Acqui-Hires, the Social Contract, and the War for AI Talent(00:22:42) Stock-Based Comp and the Economics of Attracting Engineers(00:24:39) The New Go-to-Market Playbook and Curiosity as a Superpower(00:27:59) AI's Impact on Sales, Forecasting, and Buyer Behavior(00:29:11) Coding Agents, Headcount Reduction, and the Future of Engineering(00:32:21) Building Defensible IP and Competing in the LLM Ecosystem(00:34:34) AI ROI, Payback Periods, and the Search for Efficiency(00:37:17) Valuations, Fund Cycles, and the Venture Market Reset(00:40:20) The Circular Flow of AI Capital and Infrastructure Overbuild(00:45:37) AI Pricing Models, Platform Wars, and Open Source Futures(00:50:02) The Race to the First $1 Trillion Private Company(00:51:09) Credits and Outro—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.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/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#RunTheNumbersPodcast #VentureCapital #ArtificialIntelligence #StartupStrategy #FutureOfWork 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 to Crush Your Keynote (Even If You're Dying Inside)

    Play Episode Listen Later Oct 11, 2025 47:29


    Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleConference season is back, and CJ and Kyle are swapping stories from the stage—how to nail a keynote, whether conferences are worth the money, and why your walkout song matters more than you think. From there, they dig into a new a16z report revealing where AI startups are actually spending their dollars, and CJ shares results from his summer survey showing that CFOs talk a big game about measuring AI ROI—but nobody knows how to do it. The crew also unpacks how SaaS companies like Slack are bundling AI into their products and hiking prices, before spiraling into a late-night “potentially reliable” rabbit hole featuring a Soviet pole vaulter, beat-and-raise forecasting, and J. Edgar Hoover. They close with lessons on pricing in the real world (yes, Amsterdam's architecture is involved) and one experiment CJ tried this week.Timestamps:00:00 Preview and Intro02:03 Walkout Songs & Kicking Off Conference Season04:12 Sponsored Segment — Metronome05:16 How To Give a Great Keynote and Not Bore the Room11:16 Are Conferences Worth the Money16:02 What AI Companies Are Actually Paying For — The a16z Report21:56 Summer Survey Results: The Elusive ROI of AI23:56 Why No One Knows How To Measure ROI on AI29:38 SaaS Companies Forcing AI — Bundling, Pricing, and Pushback35:32 A Potentially Reliable Thing I Read at 2 AM36:02 Soviet Pole Vaulter, Beat-and-Raise Forecasting & Hoover's Borders41:02 Pricing in the Real World — Lessons from Amsterdam's Skinny Houses44:37 Something I Tried This Week — FixyerEpisodes Referenced: ⁠Are You Bad at LinkedIn… or Is the Algorithm Lying?⁠⁠Why Founders Are Posting Sad Dinners⁠Links:⁠⁠⁠https://www.getmobly.com/⁠⁠https://a16z.com/the-ai-application-spending-report-where-startup-dollars-really-go/⁠⁠https://www.growthunhinged.com/p/how-to-nail-your-next-big-talk⁠⁠https://www.leahtharin.com/p/113-vincent-pierri-how-to-deal-with⁠⁠https://www.freepik.com/⁠⁠https://cluely.com/⁠⁠https://www.mostlymetrics.com/p/it-was-the-summer-of-25⁠⁠https://www.crescendo.ai/⁠⁠https://www.linkedin.com/posts/justintropic_slack-just-raised-prices-125-by-forcing-activity-7379132597009870848-XI6N/⁠⁠https://www.mostlymetrics.com/p/what-a-soviet-era-pole-vaulter-can-teach-us-about-beating-and-raising⁠⁠https://www.nytimes.com/1972/05/03/archives/j-edgar-hoover-made-the-fbi-formidable-with-politics-publicity-and.html⁠⁠https://www.reddit.com/r/todayilearned/comments/73vh2j/til_that_the_dutch_government_once_enforced_a_tax/⁠⁠https://www.clearspaceliving.com/blog/why-dutch-stairs-are-so-steep/⁠⁠https://mjwrightnz.wordpress.com/2012/10/28/amsterdams-taxing-narrow-houses/⁠⁠https://www.fyxer.com/Today's podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. 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

    From Take-Privates to AI: Mapping the New Market Cycle with Scott Voss

    Play Episode Listen Later Oct 9, 2025 62:58


    Private markets are swelling, public markets are shrinking, and the line between the two has never been blurrier. In this episode, CJ sits down with Scott Voss, Managing Partner at HarbourVest, to make sense of what's happening across venture, private equity, credit, and secondaries. Scott explains why companies like SpaceX and OpenAI are now valued alongside public giants, how the surge in take-privates is reshaping corporate strategy, and what happens when the quarterly earnings pressure disappears. They dive into the rise of GP-led deals, the evolving role of private credit as the “third voice in the room,” and why liquidity—not scarcity—will define this cycle. Scott also breaks down the growing appeal of evergreen and permanent capital structures, plus what AI mega-deals signal about the next phase of private investing.—LINKS:Scott Voss on LinkedIn: https://www.linkedin.com/in/scott-voss-b91b94/HarbourVest Partners: https://www.harbourvest.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Secondaries, Continuation Vehicles, and Sidecar Funds: Private Equity with HarbourVest's Scott Voss -—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:49) Sponsor – Mercury | RightRev | Tipalti(00:06:43) Opening Conversation(00:07:23) The Blurring Line Between Public and Private(00:09:36) The Rise of Mega Venture(00:11:20) The First $10 Trillion Company(00:12:28) The Shrinking Public Markets(00:13:09) Take-Private Playbook(00:14:04) Why Companies Go Private(00:16:00) Sponsor – Aleph | Rillet | Fidelity Private Shares(00:19:21) Efficiency and Exits(00:23:15) Liquidity in Private Markets(00:24:01) Secondaries and GP-Led Deals(00:27:14) Yale and the Secondary Market(00:29:09) Innovation and the Rise of GP-to-GP Trades(00:30:16) Liquidity Cycles and Interest Rates(00:33:18) The Third Voice in the Room – Private Credit(00:34:44) Private Credit and GP-Led Deals(00:36:02) Interest Rates and Deal Spreads(00:37:15) The Major Players in Private Credit(00:38:09) Regulation and Risk(00:39:25) Private Credit vs. Traditional Lending(00:40:33) Evergreen and Permanent Capital(00:45:57) Expanding Access to Private Markets(00:47:03) Understanding the Cap Table(00:47:44) AI Deals and Consolidation(00:50:00) The Evolution of AI and Blockchain(00:53:20) Funding Innovation and Risk(00:55:28) Lessons From Investing(00:55:39) Nostalgia and Life Phases(00:57:06) Nostalgia and the 1990s(00:59:21) Learn, Earn, and Return(01:00:45) Talking Nostalgia at Dinners(01:01:27) Summer Surfing(01:02:25) Wrap-Up and Closing—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.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/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#RunTheNumbersPodcast #PrivateMarkets #VentureCapital #TakePrivate #FinanceLeadership 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

    From Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage

    Play Episode Listen Later Oct 6, 2025 58:13


    Rama Katkar has helped steer some of the most iconic companies in tech through moments of scale and transformation. Now CFO at Notion and formerly a finance leader at Instacart and Credit Karma, she joins CJ to unpack what it means to build a modern finance function inside a product-led growth company. They discuss how to design finance for velocity without losing discipline, the art of forecasting when virality drives your business, and why Notion's path to profitability looks different from its peers. Rama also shares lessons from scaling Credit Karma through its $8.1B acquisition by Intuit, what she learned about IPO readiness at Instacart, and how finance leaders can balance ambition with realism in uncertain markets.—LINKS:Rama Katkar on LinkedIn: https://www.linkedin.com/in/ramakatkar/Notion: https://www.notion.so/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:“Let's Just See What Breaks” — Intuit's CFO on Being a Disruptor When You're Already the Incumbent— —TIMESTAMPS:(00:00) Preview – Credit Karma, Instacart, and the Road to Notion(00:01:14) Welcome & Episode Overview – Rama Katkar, CFO of Notion(00:02:22) Sponsor – Fidelity Private Shares | Mercury | RightRev(00:06:10) Interview Begins – From Dinner Conversations to Notion's Pricing Evolution(00:09:20) Early Launch of Notion AI and Add-On Pricing(00:12:40) Community-Led Growth and Notion's Viral Flywheel(00:14:38) Sponsor – Tipalti | Aleph | Rillet(00:18:39) Who Adopts Notion First? Product, Design, and Engineering(00:20:32) Turning Free Users Into Paid Teams(00:22:09) Why Notion Added an Enterprise Sales Motion(00:26:29) The CFO's Long Game: Balancing Free Users and Cost(00:30:44) How Notion Experiments With AI Pricing(00:32:42) Rama's Three-Part Framework for Forecasting(00:36:38) Why Notion Plans on a Six-Month Cadence(00:40:56) Transition – From Forecasting to M&A: Credit Karma's Wild Ride(00:41:31) Selling Credit Karma During the Pandemic and DOJ Review(00:44:04) Closing the Deal With Intuit(00:49:47) Why the Org Chart Is the Most Important M&A Slide(00:52:08) The Long-Ass Lightning Round(00:56:45) Career Advice to Her Younger Self – Context Over Calculation—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.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/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#CFOInsights #StartupFinance #NotionHQ #ProductLedGrowth #RunTheNumbersPodcast 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

    SEO's Collapse, Job Hunt Grind & Cone King Bob

    Play Episode Listen Later Oct 4, 2025 57:16


    Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleAI may be rewriting the playbook for growth, but it's also leaving behind some of the old startup gospel. CJ and Kyle (with Ben jumping in) dig into what happens when the “rules” no longer fit — from dead frameworks and disappearing SEO traffic to board members quietly checking out.Is T2D3 Dead? Did AI Kill It? The “triple-triple-double-double-double” path to $100M ARR worked in the old SaaS world. But what happens when AI companies blow past $100M in less than a year — often with questionable margins and pass-through revenue?SEO Down 20–40%: Is AEO the Savior? Google traffic is tanking. ChatGPT is rewriting recommendations. Is “AI Engine Optimization” the new growth channel, or just SEO with a different wrapper?The Brutal Tech Job Market CS grads face unemployment rates double those of art history majors. With 5,000+ applications going nowhere, does anyone get hired without networking or Loom videos anymore?Is Your Board Quiet Quitting? When growth slows and AI isn't your story, some VCs go ghost. From missing intros to pushing for M&A, boards are quietly exiting stage left.Business Blunders* Hospital Bed LinkedIn Photos: Hustle so hard you end up in the ER (and still post about it).* The @Company Non-Tag: Execs copy-paste updates but forget to actually tag anyone. Peak passive-aggressive LinkedIn.* Ramp's Y-Axis Crime: A 0.4% bump in weekend meals turned into a chart that looked like the apocalypse. Two burritos never looked so big.Pricing in the Real World: Bob's Barricades It's not Bob, it's Happy — and he's quietly running a barricade rental empire. Fifty cents per cone, thousands per site, tens of millions a year. The most Florida business model you've ever heard.Something We Tried This Week Kyle runs a test with Typeform — what worked, what didn't, and what it says about the state of survey tools today.Today's podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. 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

    Running a Company Like It Could Go Public Tomorrow with CFO Chad Gold

    Play Episode Listen Later Oct 2, 2025 56:37


    The IPO market may be slowing down, but the discipline of operating like a public company has never been more important. In this episode, CJ is joined by Chad Gold, CFO of FullStory and veteran operator with previous stints at G2, SalesLoft, and Rubicon, to discuss how capital markets and financing strategies are shifting in real time. Chad explains why more companies are staying private longer, how the rise of private credit is changing the CFO toolkit, and why building IPO-ready discipline matters even if you never go public. The conversation also dives into one of his specialties—pricing models and sales incentives—covering how seat-based, usage, and blended structures influence rep behavior, comp plans, and long-term revenue quality, as well as how the wrong incentives can quietly derail a business. Finally, Chad reflects on lessons from his early career at Home Depot and how fundamentals from retail operations still inform his instincts in SaaS today.—LINKS: Chad Gold on LinkedIn: https://www.linkedin.com/in/chadgold/Fullstory: https://www.fullstory.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222 Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:G2 CFO Chad Gold on Building A Durable Career as a Venture Backed Exec:Big Systems Thinking for Building a Finance Org: Advice From a Zoom Hypergrowth Survivor:—TIMESTAMPS:(02:14) Sponsors – Mercury | RightRev | Tipalti(06:10) What's New at FullStory(09:22) Hypotheses, Data, and Unlocking Use Cases(10:13) Early CFO Career and the Evolution of Data(11:09) From Deterministic Models to Analytics-Driven Forecasting(12:17) Cohorts, Segmentation, and Revenue Quality(13:17) Why Companies Stay Private Longer(15:28) Sponsors – Aleph | Rillet | Fidelity P.S.(19:01) Capital Flows Into Hot Sectors Like AI and Cybersecurity(20:20) More Companies Going Private Than Public(21:41) Costs and Tradeoffs of Being Public(22:46) Secondary Markets and Access to Top Companies(24:14) Staying Private Longer and CFO Planning(25:29) Keeping the Org Exit-Ready(26:10) The Rise of Private Credit(27:37) Banks vs. Venture Debt After SVB(30:47) Pricing Models Across Chad's CFO Roles(35:47) How to Incentivize Sales Reps Across Pricing Models(43:26) Lessons From Home Depot + Lightning Round—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/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity 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.#CFOInsights #SaaSFinance #CapitalMarkets #IPOReady #RevenueStrategy #GrowthStageCFO 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

    Prompt Anxiety, Sad Dinners, & the $8B Question

    Play Episode Listen Later Sep 27, 2025 56:18


    Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleAI may be changing how we work, but it's also changing how we interact with software — and not always for the better. CJ and Kyle Poyar dig into the growing pains of product design, IPOs in weird markets, and the unexpectedly depressing world of startup networking.* Navan IPO: Why a $613M company burning $80M is still pushing for an $8B valuation — and what it says about the state of software IPOs.* Prompt Bars Are Everywhere: The rise of “blank box” UX, why every app suddenly looks like ChatGPT, and how that's giving users prompt anxiety.* Referral Programs: Ponzi Scheme?: Incentives are up, CAC is down — but is this growth channel actually sustainable or just marketing MLMs in disguise?* When to Disclose AI-Generated: If your calendar link feels cold, wait until your AI avatar shows up in an ad. We debate where the ethical (and strategic) line is for AI transparency.* Business Blunders:• Sad Dinners (CJ): Why every LinkedIn dinner photo looks depressing — and what it says about startup culture.• ChatGPT Bad Chart (Kyle): An incredible dataset ruined by a rainbow mess of tiny fonts and meaningless categories.* Potentially Reliable Thing at 2AM:• Arnold Twins Revenue (CJ): The wild deal behind Arnold Schwarzenegger's comedy debut — and how it made more money than Terminator.• Reese Witherspoon Book Club (Kyle): Viral influence, middle-of-the-night decisions, and what media we trust half-asleep.* Pricing in the Real World:• CJ: Iced Coffee Variable Pricing: Starbucks, cold brew, and the surprising economics of how product pricing actually works day to day.* Something We Tried This Week:• Kyle: Fyxer Virtual Assistant: A hands-on experiment with offloading operational drag — what worked, what didn't, and what Kyle's still skeptical about.Today's podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you're curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don't miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You'll hear directly from industry leaders on how they're using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. 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

    Cowboy Forecasting: The Power of Fast Informed Estimates on the Back of an Envelope

    Play Episode Listen Later Sep 25, 2025 78:51


    In the early days of a startup, forecasting isn't about nailing the numbers, it's about setting the course. In this episode, the world's most interesting CFO describes the art of “Cowboy forecasting” and how this back-of-the-envelope model can be far more valuable than a complex simulation. Kevin Drost started his career as a musician and talent scout for Sony before becoming the chief strategy officer of the music gear marketplace Reverb. Now, as the CFO of New Era ADR, he explains how the company is disrupting the notoriously expensive legal industry by replacing the billable hour with flat fees, and making dispute resolution faster and more predictable for businesses. The conversation also covers why simplicity often beats complexity in financial modeling, how a hands-on understanding of the product and customer builds real financial confidence, and how finance teams can empower every employee to understand and drive the business.—LINKS:Kevin Drost on LinkedIn: https://www.linkedin.com/in/kevindrostNew Era ADR: https://www.neweraadr.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Secrets to Scaling a Marketplace Business with Jack Greco, VC and Co-founder of ACV Auctions — —TIMESTAMPS:(00:00) Preview and Intro(02:40) Sponsor – Aleph | RightRev | Navan(07:18) Kevin's Music Background & A&R at Sony(12:09) Record Labels Versus Venture Capital(17:01) Sponsor – Rillet | Pulley | Brex(20:53) Finding Motivation After Success(21:34) Building Reverb & the Etsy Acquisition(25:33) Stacking Skillsets & Interests(27:11) Cowboy Forecasting at Reverb(32:01) The Importance of Simplicity in Forecasting in the Early Stages(35:46) The Art and Science of Making Estimated Guesses(41:42) Building Firsthand Customer & Product Knowledge(45:36) Teaching Finance Across the Company(50:44) New Era ADR & Legal Industry Disruption(57:35) Legal Strategy Versus Financial Strategy(1:01:30) How New Era Gets Parties To Use the Platform(1:05:27) Other White Hot Use Cases for New Era ADR(1:09:25) The Long Ass Lightning Round: Kevin's Biggest Mistake(1:12:41) Advice to a Younger Self(1:14:01) Finance Software Stack(1:15:21) Life as an A&R Rep—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 personalized demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#CowboyForecasting #FinanceLeader #StartupFinance #LegalTech #StartupForecasting 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

    The Hidden ROI of Generosity: Meghan McKenna on How Human Connection Closes Deals

    Play Episode Listen Later Sep 22, 2025 50:58


    In a world increasingly dominated by software and automation, how vital are human relationships in banking and finance? In this episode, CJ sits down with Meghan McKenna, founder of Females in Finance (FIF) and a seasoned banker with experience at JPMorgan, HSBC, and Stifel, to explore how trusted connections continue to drive success. As a community builder and banker, Meghan has a unique perspective on the intersection of human connection and capital markets. She explains the philosophy behind her community, which is based on generosity and genuine connection rather than a transactional mindset, and how this has become her competitive advantage. The conversation also covers sales as an essential leadership skill, the rise of the modular banking stack, changes in private credit, the evolving ERP landscape, how a personal touch proved invaluable during the SVB crisis, and career lessons Meghan learned along the way.—LINKS:Meghan McKenna on LinkedIn: https://www.linkedin.com/in/meghan-curtin-mckenna-%F0%9F%94%A5-66a5022b/FIF Collective: https://www.fifcollective.comMeghan McKenna email: meghan@fifcollective.coCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Venture Debt for Growth With Ruslan Sergeyev of Hercules Capital — The One Use Case for Venture Debt That Most Founders Never Think About — —TIMESTAMPS:(00:00) Preview and Intro(02:30) Sponsor – RightRev | Navan | Rillet(06:41) Connecting People as a Skill(08:03) Sales as an Essential Leadership Skill(12:07) The Power of In-Person Community & Events(14:39) FIF's Ideal Customer Profile(15:42) Sponsor – Pulley | Brex | Aleph(20:05) The Evolution of the Banking Ecosystem(22:00) Modular Banking Stacks and Fintech Challengers(24:37) The Rise of Private Credit(27:32) Banks Adapting to Companies That Stay Private Longer(30:06) Fintechs vs. Traditional Banks(31:54) Current Trends in AI and ERP in Finance(35:07) Importance of Human Relationships When Software Fails(36:09) Reflecting on the SVB Bank Run & Facing New Risks in Tech(37:59) Building a Personal Brand in Finance(39:42) Community Spirit, Giving Back, & Sharing Your Network(43:25) Meghan's Early Career and Mentors(46:15) Long-Ass Lightning Round: Staying Too Long in a Role(47:49) Advice to Younger Self(48:24) A Memorable Deal & Client Story(50:07) Wrap—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.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#FemalesInFinance #FinanceLeadership #BankingInnovation #Networking #FinanceCommunity 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

    996 Workweeks, Exploding AI Bills & The SaaS Payback Problem

    Play Episode Listen Later Sep 20, 2025 57:50


    AI was supposed to make software cheaper and companies more efficient. Instead, costs are exploding, CFOs are getting squeezed, and founders are pushing their teams harder than ever. CJ and Kyle Poyar dig into the economics behind AI, usage-based pricing, and what all of this means for SaaS growth.* Usage-Based Credits: Why they're supposed to save SaaS margins but often trap customers in bad deals.* 996 Hustle Culture: The rise of 9 a.m.–9 p.m., 6-days-a-week work schedules — and why it's both romanticized and unsustainable.* SaaS Payback Periods: Public companies now take 3+ years to recoup CAC, with growth slowing and margins tightening.* Go-to-Market Engineers: Hype vs. reality of the “unicorn hire” role meant to automate GTM motions.* Consumer Businesses: Are we sleeping on DTC plays like Blue Apron and ButcherBox while chasing AI trends?* The “Cracked Engineer” Archetype: Why the most impactful hires might be the failed founders who love solving cross-functional problems.* Subscription Carwashes: What they teach us about predictable revenue and retention psychology.* More RVs Than EVs: What this surprising stat says about adoption curves and how we misread “the future.”* This Week's Growth Experiments: The tools, tactics, interview questions, and hacks we tried — what worked, what didn't, and why Kyle is disillusioned by some of them.Today's podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you're curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don't miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You'll hear directly from industry leaders on how they're using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. 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

    “90% of VCs Are Neutral to Negative Value”: Kyle Harrison on the Evolving Game of Venture Capital

    Play Episode Listen Later Sep 18, 2025 72:52


    The venture capital landscape is evolving, and a founder's choice of fund size and partner could make or break their business. In this episode, CJ sits down with Kyle Harrison, General Partner at Contrary and writer of the Substack Investing 101, to make sense of the changing incentives and power dynamics in the field of venture capital. He explains how capital agglomerators and cottage keepers are playing dramatically different games, how the ethics of backing competitors have changed since the advent of AI, why a fund's size is its strategy, and what the potential pitfalls of dilution could be for founders. The conversation also covers why the line between hype and tangible business value in AI is so blurry, the role of narrative as an economic driver, and why the most valuable thing a VC can offer might just be "borrowed credibility.”—LINKS:Kyle Harrison on LinkedIn: https://www.linkedin.com/in/kyle-harrison-9274b278/Contrary: https://www.contrary.comInvesting 101: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comLINKS MENTIONED:* “The Unholy Trinity of Venture Capital”: * “The Horse, The Jockey, or The Whole Race?” * Endowment Eddie on X (@endowment_eddie): https://x.com/endowment_eddie* “Institutionalized Belief In The Greater Fool”: * “The Unbundling of Venture Capital”: * “The Productization of Venture Capital”: https://kwharrison13.com/essays/the-productization-of-venture-capital—TIMESTAMPS:(00:00) Preview and Intro(02:23) Sponsor – Navan | Rillet | Pulley(07:13) VC Models: Cottage Keepers Versus Capital Agglomerators(11:16) Balancing Taking On Money and Finding Great Investments(16:35) Sponsor – Brex | Aleph | RightRev(20:54) Founder-Friendliness: The Ethics of Backing Competitors(26:33) When Fund Size Sabotages Outcomes(32:32) The Sins of Omission Versus Commission(36:02) The Dilution Trap for Operators in Venture-Backed Companies(38:17) Underestimating the Magnitude of the Outcomes(40:35) AI Hype, Valuation, and Real Business Impact(45:37) Market Psychology: Narrative and Story As Economic Drivers(48:21) Valuation: Cursor and Windsurf(52:50) The Unbundling of Venture Capital: What Founders Really Hire VCs For(1:01:47) Things To Consider When Choosing a VC(1:04:35) FTX Lessons & Compounding Growth(1:10:02) Kyle's Predictions for the Future of VC—SPONSORS:Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.##VentureCapital #VC #Startups #Founder #FundSize 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

    TikTok Will Beat Amazon, Google Is Going to Zero, and Other Wild Predictions With VC Turner Novak

    Play Episode Listen Later Sep 15, 2025 81:04


    Facebook is undermonetized, TikTok poses an existential threat to Amazon, and ChatGPT has probably already captured most of Google's high-value users. These are the opinions of today's guest, a venture capitalist deeply embedded in consumer networks and social product investing. In this episode, CJ chats with Turner Novak, the Founder and Managing Partner of Banana Capital, host of The Peel podcast, and a man who is known for his Twitter threads and podcast interviews as much as he is for his impressive portfolio. Turner breaks down the monetization models of some of the world's biggest platforms. Together, they discuss undervalued and overvalued business models, the long-term viability of subscription models, how platforms can identify and serve their highest-value users, and how to adapt acquisition strategies as AI reshapes the customer journey. Turner also reveals what excites him for future investments and the underestimated power of memes as a marketing tool.—LINKS:Turner Novak on LinkedIn: https://www.linkedin.com/in/turnernovakTurner Novak on X (@TurnerNovak): https://x.com/TurnerNovakBanana Capital: https://www.bananacapital.vcThe Peel: https://www.youtube.com/@ThePeelPodthespl.it: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:09) Sponsor – Rillet | Pulley | Brex(06:15) Turner's Embarrassing Accounting Story(08:10) How Turner Became an Accidental Influencer(09:02) Monetizing Content(12:22) How Turner Built His Media Platform(16:02) Sponsor – Aleph | RightRev | Navan(20:26) From Fantasy VC Portfolios to Podcasting(24:30) Turner's Main Business: Media Versus VC(25:42) Monetizing Premium Experiences on Social Products(30:27) Finding and Targeting High-Value Customers(32:27) Memes as a Tool for Marketing(36:10) Identifying High-Value Users and Opportunities(41:00) Why Pinterest Is Undermonetized(42:57) TikTok Versus Amazon for E-Commerce(46:30) Is ChatGPT Coming for Facebook and Google's Cash Flow(48:36) Facebook as an Undermonetized Business(54:24) The Long-Term Viability of Subscriptions(1:00:31) Customer Acquisition in a Platform-Dominated World(1:04:09) Paid Acquisition in the Era of AI(1:06:23) The Increasing Cost of CAC(1:08:59) What Turner Is Investing in Now(1:15:25) Doing Hard Things as a Moat(1:19:12) Wrap—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.#VentureCapital #BusinessModels #GoogleVsChatGPT #ConsumerNetworks #SocialCommerce This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    How Much Revenue Do You Need to IPO in 2025?

    Play Episode Listen Later Sep 13, 2025 22:21


    It used to be that if you built a good company, showed solid growth, and had decent unit economics, you could go public. But today? The bar has been raised—big time.Let's take a trip through the last ~15 years of tech IPOs to put today's market into context and zoom in on the most recent companies to go public.* 2010's: $100M is the Bar* 2021: The Year of the Mega IPOs* 2022-2023: The IPO Freeze* 2024: The Rebound – But With a Higher Bar* The New IPO PlaybookToday's podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you're curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don't miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You'll hear directly from industry leaders on how they're using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Humans, Robots, and Agents: UiPath on Agentifying Your Business in the Age of AI

    Play Episode Listen Later Sep 11, 2025 71:34


    Is it too soon to leverage agentic automation to drive AI transformation, streamline workflows, and boost productivity in finance? And how do you calculate the ROI of AI? Today's guest runs a high-functioning finance team at a company that's at the forefront of AI, where bonuses are tied to AI adoption. In this episode, CJ interviews Hitesh Ramani, Deputy CFO and Chief Accounting Officer at UiPath. After sharing wisdom from his years at Deloitte on the “muscle memory” that a company needs pre-IPO and mistakes to avoid after going public, he explains how his company is using its own technology to transform the finance function. He breaks down the difference between agents, robots, and workflows, describing what each does and how they interact. The conversation covers what it's like to manage org charts that include humans and AI agents, how to hire for the future of tech-savvy finance teams, and UiPath's vision for near-autonomous finance operations. Hitesh also reveals real-world AI use cases inside UiPath and offers lessons learned on embracing AI as a powerful productivity partner while maintaining trust and governance.—LINKS:LINKS:Hitesh Ramani on LinkedIn: https://www.linkedin.com/in/hitesh-ramani-a4a78118/UiPath: https://www.uipath.comMeghan Curtin McKenna: https://www.linkedin.com/in/meghan-curtin-mckenna-%F0%9F%94%A5-66a5022b/ FIF Collective: https://www.fifcollective.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(02:04) Sponsor – Pulley | Brex | Aleph(06:19) Going Public Versus Being Public(09:50) The Need for a Company-Wide Operating Rhythm Pre-IPO(12:30) Top Mistakes To Avoid Before Going Public(16:01) Sponsor – RightRev | Navan | Rillet(20:06) Common Foot Faults After Going Public(23:57) Robots Versus Agents(30:17) RPA Versus AI(31:09) Agents & Workflows(34:05) Accountability: Outsourcing Your Agency(39:46) How To Measure ROI on AI(45:06) Scaling With Robots & Agents(48:15) Budgeting for People and Automation(50:41) High-Impact Versus Low-Impact Ideas in AI Implementation(53:36) Hiring & Developing Tech-Savvy Finance Talent(57:36) Build Versus Buy & Building an Autonomous Workflow(1:00:15) The Future of Autonomous Finance(1:01:14) Use Cases for AI at UiPath(1:03:18) Long-Ass Lightning Round: A Career Mistake(1:04:25) Advice to Younger Self(1:05:58) Finance Software Stack and the Future of In-House Systems(1:10:14) Craziest Expense Story—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.#AutonomousFinance #IPOJourney #AIinFinance #FutureOfFinance #AIAdoption This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Selling Your Company? A Silicon Valley Lawyer's Guide to Not Getting Screwed Over

    Play Episode Listen Later Sep 8, 2025 62:27


    How do founders and finance leaders prepare for the sale of their company when the other side of the negotiating table does this every day? In this episode, CJ interviews David Siegel, Partner at Grellas Shah LLP, a Silicon Valley law firm that guides some of the biggest names in tech through their most significant raises and exits. David shares insights from countless deals, revealing what it really takes to prepare for a sale, negotiate with buyers, and manage conflicting advice from bankers and lawyers. He unpacks investor dynamics, deal timelines, and why the $150 million to $350 million valuation range is the “awkward middle.” The conversation also covers how companies can de-risk themselves before going to market, how to spot a bad banker, what critical pitfalls to avoid in Letters of Intent (LOIs), the emotional realities founders face when selling their “baby,” and the shifting power dynamics in today's M&A landscape.—LINKS:David Siegel: https://www.linkedin.com/in/david-siegel-a271265Grellas Shah: https://grellas.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:06) Sponsor – Brex | Aleph | RightRev(06:41) The Average Time To Close M&A Deals Today(10:55) How To Start the Process of Selling a Company(13:09) Being Realistic About Your Valuation(15:13) Sponsor – Navan | Rillet | Pulley(19:08) VCs Versus Acquirers(20:12) The $150 Million to $350 Million Valuation Awkward Middle(23:17) Investor Behavior and Founder Incentives in Deals(24:59) The Banker Versus Relationship Route in Selling(27:46) What Makes a Bad Banker(28:43) PSA: Investment Banker Engagement Letters Are Negotiable(34:43) LOIs: What Sellers Should Push To Include Before Signing(39:43) What To Prioritise as a CFO in an LOI(43:21) The Worst Case Scenario for Vague Networking Capital Targets(46:22) De-Risking Your Company in the Eyes of an Acquirer(49:17) How Acquirer Risk Aversion Derails Deals(52:07) The Emotional Impact of Selling a Company(55:32) The Rules of Negotiation(57:19) Current State of M&A in Tech(1:01:30) Wrap—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.#TechAcquisitions #AcquisitionLaw #StartupExit #MergersAndAcquisitions #ExitStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Do PE Companies Trade Innovation for Margins?

    Play Episode Listen Later Sep 6, 2025 8:51


    Do PE Companies Trade Innovation for Margins?Private equity firms love to talk about operational excellence… but when “efficiency” comes at the cost of innovation, are they mortgaging tomorrow for today's margins?In this episode I break down why 25% operating margins became the magic number in software, how PE-backed businesses chase the Rule of 50, and what happens when cutting R&D tips companies into the “Innovation Death Spiral.”Today's podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you're curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don't miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You'll hear directly from industry leaders on how they're using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    From Facebook's Hypergrowth to Daffy's Disruption: A CFO's Playbook for Saying Yes

    Play Episode Listen Later Sep 4, 2025 71:19


    How do finance leaders enable growth while fostering a culture of partnership, positivity, and saying yes? In this episode, CJ interviews Ed Park, Head of FP&A at Facebook during its explosive hypergrowth years, Head of Finance and Internal Operations at Asana, the current CFO of Daffy, and a “glass-half-full” finance leader. Ed shares stories about working at Facebook in the early days, how he brought finance into the company's engineering and product-first culture, and how he built trust while navigating rapid user and infrastructure expansion. He talks about his role at Asana, why the company plans in episodes, not quarters, how they discovered their unique “three user” metric, and how they transitioned from bottoms-up to sales-led growth. Ed also gives an introduction to donor-advised funds and how Daffy, his current company, is disrupting this field. The conversation covers how a company's business model shapes its destiny, finding the balance between what's urgent and what's important, and Ed's glass-half-full approach to being a finance leader who enables teams by saying yes.—LINKS:Edward Park on LinkedIn: https://www.linkedin.com/in/edwardyparkDaffy: https://www.daffy.orgCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:Big Systems Thinking for Building a Finance Org: Advice From a Zoom Hypergrowth Survivor — —TIMESTAMPS:(00:00) Preview and Intro(02:16) Sponsor – Aleph | RightRev | Navan(06:43) Ed's First Job at a Startup: Head of FP&a at Facebook(11:35) Bringing Finance Into an Engineering and Product-Led Culture(16:42) Sponsor – Rillet | Pulley | Brex(20:34) Balancing What Was Urgent Versus Important(25:02) Monetizing Facebook(26:48) Becoming a Glass-Half-Full Finance Leader(33:27) Managing Four Chefs at Asana(35:38) How Asana Plans in Episodes, Not Quarters(42:48) Monetization Model Intuition and the “Three User” Metric(48:13) Transitioning From Bottoms-Up to Proactive Sales at Asana(53:24) Daffy's Monetization Model and Donor-Advised Fund Innovation(57:34) How a Business Model Shapes Destiny(1:00:02) Ed's “How Might We” Approach to Being a CFO(1:01:56) Long-Ass Lightning Round: A Big Mistake(1:04:38) Advice to Younger Self(1:05:44) Finance Software Stack(1:07:57) Craziest Expense Story—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/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#FacebookBusinessModel #FPandA #StartupFinance #MonetizationStrategy #DonorAdvisedFunds This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    The Anti-Exit Strategy: Premji Invest's Approach to Evergreen Capital (& the Future of CFO Tech)

    Play Episode Listen Later Sep 1, 2025 53:59


    Premji Invest is an investment firm that backs some of the biggest names in the CFO and enterprise tech stack, including Anaplan, Zuora, Coupa, and Looker. In this episode, CJ is joined by Sandesh Patnam, the firm's Managing Partner, to discuss their approach to investing and the future of CFO tech. Sandesh talks about the evergreen nature of Premji's investment model and explains how this permanent pool of capital enables the company to focus on deep partnerships and durable growth, rather than chasing fund cycles or portfolio diversification. He breaks down why he views total addressable market (TAM) as a floor rather than a ceiling, how investing across both public and private markets creates a strategic advantage, and how startups should approach capital construction and optionality in today's market. The conversation also touches on the evolution of the CFO toolkit, how AI is shifting the finance role, what persistent finance problems are still waiting for innovation, how org design is changing inside finance teams, and why he believes AI is a bigger shift than both the dot-com and mobile eras.—LINKS:Sandesh Patnam on LinkedIn: https://www.linkedin.com/in/sandeshpatnamPremji Invest: https://in.premjiinvest.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:BlackRock Managing Director on the Secrets of Durable Companies - —TIMESTAMPS:(00:00) Preview and Intro(02:08) Sponsor – RightRev | Navan | Rillet(06:59) Evergreen Capital and Premji's Approach to Investing(09:25) Portfolio Construction(12:58) TAM Versus SAM Versus Product(15:28) Sponsor – Pulley | Brex | Aleph(19:51) Seats Versus Outcome-Based Pricing(23:30) Defining Durability(26:31) Public Versus Private Investing(28:44) Why One Team Manages Both Public and Private Investing(30:47) Capital Construction for CFOs With Evergreen Investors(32:13) How and When Evergreen Funds Seek Liquidity(35:32) Building Optionality in Capital Strategy Amid Market Changes(38:01) Secondary Markets in the Private World(41:39) The Evolution of the CFO Tech Stack(43:41) AI and Systems of Action(45:43) How CFOs Are Starting To Interact With AI Tech(49:09) A Finance Problem That's Open for Innovation(50:25) The Evolution of the CFO's Role Beyond Finance(51:33) The AI Era vs. Prior Tech Eras—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.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#EvergreenCapital #PremjiInvest #CFOTechStack #InvestmentStrategy #PortfolioDurability This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Netskope IPO: S1 Breakdown

    Play Episode Listen Later Aug 30, 2025 24:48


    Cybersecurity company Netskope has filed to go public on the NASDAQ.Today we're breaking down their S1 filing, including their financials, valuation outcomes, and potential red flags.Today's podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you're curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don't miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You'll hear directly from industry leaders on how they're using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    From Karaoke With Benioff to the Death of SEO: Alex Konrad on the Business of Media

    Play Episode Listen Later Aug 28, 2025 72:13


    The media landscape is noisier than ever. How can founders and business leaders get their stories heard? And in an age of AI-driven content, how can creators distinguish themselves and build a direct relationship with their audience? In this episode, CJ sits down with Alex Konrad, a longtime tech journalist, former Forbes editor (responsible for curating the renowned Forbes 30 Under 30, Cloud 100, and Midas lists), and founder of Upstarts, a newsletter covering startups, venture capital, and the people shaping the innovation economy. Alex shares insider stories from his decade at Forbes, including how lists like the “30 Under 30” were created and what it was like profiling (and sometimes singing karaoke with) the likes of Marc Benioff, Satya Nadella, and Sam Altman. The conversation explores the evolving landscape of media, the business fund-raising announcements, how startups can actually work with journalists to shape perception, the rise of VC firms as media powerhouses, the shifting role of platforms like Substack and LinkedIn, why relationship-driven content will outlast the race to break news, and the death of traditional SEO.—LINKS:Alex Konrad on LinkedIn: https://www.linkedin.com/in/alexrkonradAlex Konrad on X (@alexrkonrad): https://x.com/alexrkonradUpstarts Media: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: LINKS MENTIONED:No Priors: AI, Machine Learning, Tech, & Startups: https://www.youtube.com/@NoPriorsPodcastLatent Space: https://www.youtube.com/@LatentSpacePodThe Daily: https://www.nytimes.com/column/the-daily52 Sourcery with Molly O'Shea https://www.youtube.com/@SourceryVCThe Information: https://www.nytimes.com/column/the-dailyRELATED EPISODES:“Let's Just See What Breaks” — Intuit's CFO on Being a Disruptor When You're Already the Incumbent - —TIMESTAMPS:(00:00) Preview and Intro(02:32) Sponsor – Navan | Rillet | Pulley(07:13) Building the Forbes 30 Under 30, Cloud 100, and Midas List(11:49) The Meme of SEC Trouble on Forbes List and a Media Tip(14:08) Why Lists Work So Well(17:17) Sponsor – Brex | Aleph | RightRev(21:57) What Might Convince Alex To Start a List(23:13) Karaoke With Benioff & Interacting With Billionaires(29:14) Entrepreneurship & Work-Life Integration(33:25) Sales Skills Alex Learned as a Founder(37:56) The Dance Behind Fundraising Announcements(42:30) How To Capitalize on the Media Outside of Funding Rounds(45:24) Examples of Founder “Oh S**t!” Moments(47:58) VC Firms As Media Companies(51:16) Non-Journalists Interviewing in Tech(55:02) Audience Relationship & Guarding Against AI(57:41) The Death of SEO(1:00:45) The Value of Time Sensitivity and News in the Era of AI(1:02:40) Platform Relationships & Substack(1:04:55) Bootstrapping Media & VC Pressure(1:10:55) Wrap—SPONSORS:Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, 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/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.#TechJournalism #MediaStrategy #AIinMedia #StartupPR #FutureOfMedia This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    “Stop Trying To Quantify Risk”: Risk Management Wisdom (& Star Wars Analogies) From CISO Andy Ellis

    Play Episode Listen Later Aug 25, 2025 66:13


    Cybersecurity risks have become more complex and unpredictable than ever, yet many companies struggle to quantify these threats in terms that truly matter. How can CFOs and CISOs effectively communicate about risk, make smart security investments, and navigate the emerging challenges posed by AI? In this episode, CJ interviews Andy Ellis, a renowned cybersecurity leader, former CISO of Akamai, investor, director, advisor, leadership coach, and author of the book 1% Leadership. Andy unpacks why most companies measure risk the wrong way and breaks down his "Pyramid of Pain” framework for categorizing it. He discusses the dynamics between CFOs and CISOs in purchasing security tools, demystifies security budgeting and vendor negotiations, dives into the evolving role of AI in security operations, and explains why the CISO and CIO roles are on a collision course. Andy also reveals insider stories from the frontlines of major breaches, shares a compelling risk analogy inspired by vampires and zombies, and clears up once and for all why the demise of the Death Star was not a failure of risk management.—LINKS:Andy Ellis on LinkedIn: https://www.linkedin.com/in/csoandyAndy Ellis on X: (@CSOAndy) https://x.com/csoandyWebsite: https://www.csoandy.com1% Leadership: https://www.amazon.com/1-Leadership-Master-Improvements-Leaders/dp/0306830817How to CISO: https://www.howtociso.comDuha One: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:49) Sponsor – Rillet | Pulley | Brex(07:23) Defining Risk: Technical & Human-Friendly Perspectives(09:20) Actuarial Risk Versus Human-Driven Risk(15:33) Why the Demise of the Death Star Wasn't a Failure of Risk Management(16:58) Sponsor – Aleph | RightRev | Navan(21:22) How the Death Star Metaphor Relates to Real-World Security Breaches(23:20) Why Risk Should Not Be Quantified in Dollar Terms(25:15) The Pyramid of Pain: Risk Severity and Surprise Levels(30:21) How CFOs and CISOs Should Partner on Security Purchases(34:03) Are Security Budgets Over or Under-Spent?(36:22) Balancing Budget for Security Tools and People(39:48) Tips for FP&As on Brokering the Security Budget With Your CISO(44:10) Factoring AI Uncertainty in a Three-Year Security Roadmap(46:38) AI Washing in Security Products and Realistic Impact(48:55) The Limitations of Security Operations(50:53) The Future of CIO and CISO Roles and Organizational Reporting(54:55) Why IT Shouldn't Report to the CFO(57:18) Israeli Unit 8200 and Cybersecurity Innovation(59:50) Startups Versus Public Companies: Differing Risk Models(1:02:52) Wrap—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.#Cybersecurity #RiskManagement #CISO #SecurityOperations #SecurityFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Are Fractional CFOs a Grift?

    Play Episode Listen Later Aug 23, 2025 9:17


    On average, I get asked 2x a week for fractional CFO recommendations.And on average, I get complaints 3x a week about someone's current setup.Today we investigate the booming fractional CFO market, and my checklist to making sure you get a good one.This week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    From $500M Losses to $500M Profits: The CFO Who Helped Major League Baseball Win off the Field

    Play Episode Listen Later Aug 21, 2025 80:56


    In 1997, the Florida Marlins won the World Series, but they also lost $30 million in the process. In 2002, only three Major League Baseball teams had positive EBITDA. Due to a dramatic collective bargaining agreement, five years later, only three clubs had negative EBITDA, and the MLB had gone from $500 million in losses to a $500 million in profit. Today's guest had a front row seat to the action. Jonathan Mariner is the former CFO of the Florida Marlins, the Florida Panthers, and Major League Baseball. He is also he founder of TaxDay and a seasoned board member on different boards, including Tyson Foods, OneStream, and Delaware North, among others. In this episode, he takes us inside the complex economics of pro sports. The conversation covers the surprising way sports franchises are actually valued, the massive shift from cable TV to streaming, the complex world of player merchandising, the challenges of expanding sports internationally, and how Jonathan helped implement a controversial EBITDA rule to rein in league-wide debt.—LINKS:Jonathan Mariner on TaxDay: https://www.taxday.com/team/Tax Day: https://www.taxday.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:The Boston Celtics' Other Playbook: Business Insights from President Rich Gotham — —TIMESTAMPS:(00:00) Preview and Intro(02:35) Sponsor – Pulley | Brex | Aleph(07:11) How Jonathan Became CFO of the Florida Marlins and Panthers(13:17) The Marlins: Winning the World Series and Losing $30 Million(16:03) Sponsor – RightRev | Navan | Rillet(20:08) How Not Having a Salary Cap Affects the MLB(21:27) The Collective Bargaining Agreement That Changed the Economics of the MLB(30:00) The Science of How Sports Franchises Are Valued: Revenue(31:53) The Art of How Sports Franchises Are Valued: Perception(36:20) How Local Broadcast Rights and Revenue Sharing Work(37:44) Contractually Obligated Income and Its Ramifications(41:57) How Player Jersey Sales Really Work(46:34) The Shift From Cable to Streaming and the Economic Effects(53:48) The Challenges and Opportunities of Global Expansion(59:57) Expansion Teams & Franchise Fees(1:01:58) Being on the Tyson Foods Board During COVID(1:05:39) Jonathan's Other High-Stakes Moments as a Board Member(1:08:03) Founding TaxDay(1:11:41) Long-Ass Lightning Round: Career Mistakes(1:14:00) Advice to Younger Self(1:15:11) The Best Sporting Events Jonathan's Ever Attended—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.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.#SportsFinance #MLB #MajorLeagueBaseball #TeamValuation #BusinessOfSports This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Inside the $5B Plaid Deal That Never Happened and the Massive Business Model Transition That Did

    Play Episode Listen Later Aug 18, 2025 66:10


    If you're curious about what it's really like to navigate a multibillion-dollar acquisition deal during a global pandemic, while under intense scrutiny of the Department of Justice, this episode is for you. Jason Pate, Chief Strategy Officer at Plaid, takes us behind the scenes of Visa's $5 billion bid to acquire Plaid and why it ultimately didn't happen. Jason also explains the massive evolution of Plaid from a linking infrastructure company to a thriving network business powering some of the biggest names in fintech. The conversation delves into the company's pivotal moments, including its recent $575 million fundraising round to solve for employee RSU liquidity. Beyond that, Jason shares lessons from his experience, unpacking the importance of understanding a customer's P&L, breaking down how to build durable fintech revenue streams through diversification, and offering candid insights on negotiation, the future of payments, and making big bets to fix something that isn't broken.—LINKS:Jason Pate on LinkedIn: https://www.linkedin.com/in/jason-pate-50735310/Plaid: https://plaid.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(01:43) Sponsor – Brex | Aleph | RightRev(06:08) Duke and “I Hate Christian Laettner”(07:45) Jason's Product Development Experience and Career Journey(10:38) The Importance of Understanding Your Customer's P&L(12:41) Plaid's Transition From Linking Infrastructure to Network Business(15:23) Sponsor – Navan | Rillet | Pulley(18:55) Building the Plaid Data Network and Ecosystem(25:41) Friction in Payments: Feature Versus Bug(27:46) The Future of Payments: Check-In Versus Checkout(31:21) Negotiations: Less Like Chess, More Like Marco Polo(35:21) Identifying Gives That Aren't Actually Gives(37:10) Plaid's Unsuccessful Acquisition by Visa(40:45) Being Interviewed by the DOJ During the Pandemic(43:49) Plaid's Recent Raise and the Unconventional Reason for It(47:00) Valuations: Fundraises Versus Sales(48:19) Building an Equity Program When Companies Stay Private Longer(50:48) Multi-Product Diversification: The Key to Durable FinTech Revenue(53:07) When & How To Transition From an Infrastructure to a Network Business(59:03) Jason's Philosophy on Ramping Team Members(1:01:04) Lessons From Roger Federer(1:02:52) Long-Ass Lightning Round: A Career Mistake(1:04:03) Advice to Younger Self(1:04:48) A Helpful Tactic for Negotiations—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.#Plaid #Fintech #acquisition #fundraise #employeeRSU #BusinessTransition This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Emergency Capital Markets Update: Stubhub IPO (Take 2)

    Play Episode Listen Later Aug 16, 2025 6:32


    What matters more: Your company performance, or market conditions?Stubhub is preparing to go public (again) after initially pulling the plug back in March of 2025. A lot has changed since then. The market is up. And their performance is down. We analyze what's going on in the capital markets, and how to think about what matters most when you're preparing to go public.(Read: Stubhub's original S1 breakdown on Mostlymetrics.com)This week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Thinking About Adding Payments to Your Software Product? Listen to This First!

    Play Episode Listen Later Aug 14, 2025 54:38


    If you're thinking about adding payments to your software company's tech stack, listen to this first. Today's guest knows that turning payments into a prolific growth engine isn't as simple as plugging in a processor; it's about knowing when you have the “right to win” and building the infrastructure, team, and go-to-market strategy to make it work. In this episode, Andrew Mosawi of JMI Equity and a self-named “dinosaur in the world of embedded payments”, joins CJ to unpack how embedded payments are reshaping industries, why certain platforms are perfectly positioned to own the payment flow, and when you're better off staying out of the game. They share the frameworks for sizing the TAM, deciding which vertical plays make sense, and forecasting revenue in a world where payments don't behave like SaaS, while also referencing real-world use cases. The conversation covers the common mistakes companies make when entering payments, standout examples of companies that have done this well, and the right and wrong questions you should be asking before starting out.—LINKS:Andrew Mosawi on LinkedIn: https://www.linkedin.com/in/andrewmosawi/JMI Equity: https://www.jmi.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: Companies mentioned:Mindbody: https://www.mindbodyonline.comBlackbaud: https://www.blackbaud.comToast: https://pos.toasttab.comShopify: https://www.shopify.comFlagship Advisory Partners: https://insights.flagshipadvisorypartners.comBCG “Fortune Favors the Bold: Global Payments Report 2024”: https://www.bcg.com/publications/2024/fortune-favors-bold-global-payments-reportRELATED EPISODES:The Art of Stacking S-Curves: Olo's Winning Vertical SaaS Strategy with CFO Peter Benevides - Efficiency Metrics, Management, and Consolidation - Tony Boor's CFO Playbook for Scaling Blackbaud - —TIMESTAMPS:(00:00) Preview and Intro(02:17) Sponsor – Aleph | RightRev | Navan(06:50) How the Payments Ecosystem Has Changed in the Last Two Decades(09:02) The Inflection Point That Brought Payments Into the Mainstream(10:23) The Size of the Payments Pie in 2025(11:49) Why Not Every Company Should Do Payments(14:23) What Makes a Company Well-Positioned To Offer Payments(15:50) Sponsor – Rillet | Pulley | Brex(19:42) Having a Strategic High Ground To Offer Payments(21:35) The Stickiness of Embedded Payments(24:14) What “Embedded Payments” Means(27:12) Different Models Used for Embedded Payments(32:14) A Typical Take Rate for Embedded Payments(36:45) The Accretive Nature of Embedded Payments and Other Benefits(40:14) The Next Phase of Payments: Other Finance Solutions(44:56) CJ's Mental Model for Assessing Payments at PartsTech(47:45) Running a Payments Function Versus a Traditional Software Function(50:46) Sales Dynamics: Traditional SaaS Versus Payments(52:01) Companies That Have Done Embedded Payments Well(53:05) The Right and Wrong First Questions To Ask Before Starting in Payments—SPONSORS:Aleph automates 90% of manual, error-prone busywork, 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/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#EmbeddedPayments #payments #PaymentsInfrastructure #PayFac #PaymentsStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Having Gone Through Sh*t Is an Asset: Yext CFO's Playbook for the Tough Times

    Play Episode Listen Later Aug 11, 2025 59:13


    With a decade of experience at Yext, a company now approaching half a billion in ARR, Darryl Bond has seen it through negative EBITDA margins, executive turnover, and company-wide resets. In this episode, he sits down with CJ to talk about his approach to the finance function, which involves prioritizing growth over compensation, tackling the messy problems head-on, making the hard P&L calls in the “grey zones,” knowing when to ask for help, and staying focused through the tough times. Darryl shares how he scaled from controller to CFO, and how, in the process, he made sense of the chaos, led with transparency, and built a high-impact finance function that doesn't just report the numbers, but also drives the business. He explains the role of systems and processes in scaling operations, the mistakes he made early in his management journey, and why relationship-building has been the real unlock in his career. They dive into building deal desks, what operational excellence really means, and capital allocation decisions that actually start with listening to the customer.—LINKS:Darryl Bond on LinkedIn: https://www.linkedin.com/in/darryl-bond-788b962a/Yext: https://www.yext.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leader — —TIMESTAMPS:(00:00) Preview and Intro(02:49) Sponsor – RightRev | Navan | Rillet(06:54) The Reasons for Darryl's Career Loyalty(08:58) Prioritizing Learning Over Comp(11:09) What Yext and Its Finance Function Looked Like in 2015(15:40) Sponsor – Pulley | Brex | Aleph(20:03) Choosing Which Messy Problems To Take On(22:00) The Right Time To Create a Deal Desk(23:39) When To Bring General Counsel In-House(24:36) Asking for Help and Building a CFO Network(28:25) What Operational Excellence Looks Like in the Finance Team(31:11) Staying Focused Through Tough Times(35:39) Making the Hard P&L Calls In the “Gray Zone”(37:05) The Importance of Talking to Customers(38:30) A Guide to Communicating the Bad News(40:25) The Role of Systems and Automation in Gaining Control of the P&L(43:07) Capital Allocation Decisions: Yext's Two Recent Purchases(45:06) Build, Buy, or Partner(47:57) The Pros and Cons of Being a Sub-$1B Public Tech Company(49:38) How To Get (and Lose) Sell-Side Analyst Coverage(51:04) What Excites Darryl Most About Yext's Current Stage(53:13) Long-Ass Lightning Round: A Career Mistake(54:36) Advice to Younger Self(56:17) Finance Software Stack(57:42) Craziest Expense Story—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.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#CFOLeadership #FinanceLeadership #FinanceStrategy #OperationalExcellence#BusinessTurnaround #CapitalAllocation This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    An Unholy Alliance

    Play Episode Listen Later Aug 9, 2025 7:46


    What do Whitey Bulger, FBI Agent John Connolly, AI and Venture Capitalists have in common? In today's episode we explore an unholy alliance between two forces that need each other—massive capital piles and foundational model companies that can actually absorb that capital.This week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    How To Win at Early-Stage Sales (With the Guy Who Helped Take Snyk From $0 to $100M+)

    Play Episode Listen Later Aug 7, 2025 64:41


    Are you building a sales org from scratch? Or rebuilding one in the middle of an AI boom? If so, this episode is your field guide. CJ sits down with Ethan Schechter, SVP of Global Sales and Customer Success at Qodo (and the guy who helped take Snyk from $0 to $100M+ in revenue), to talk about the wild days of early-stage sales leadership. Ethan shares how he navigates “basecamp” moments and the “smile” and “cry” days of year one. He explains his approach to hiring for a new org, building internal trust while over-communicating, designing incentive structures for the early days, trading dollars for speed through discounting, and staying competitive in the fast-changing era of AI. The episode ends with an entertaining roast of LinkedIn's cringe posts, from fake ARR math to self-given nicknames and beyond.—LINKS:Ethan Schechter on LinkedIn: https://www.linkedin.com/in/ethanschechterQodo: https://www.qodo.aiCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:A CFO's Guide to Understanding Sales Teams, featuring Snyk's Ethan Schechter — —TIMESTAMPS:(00:00) Preview and Intro(02:07) Sponsor – Navan | Rillet | Pulley(06:10) Ethan's Career as an Early-Stage Sales Leader and Understanding Equity(10:04) The “Basecamp” Mindset and Restarting Strong(12:33) Building Out Your Rules of Engagement(14:25) Sponsor – Brex | Aleph | RightRev(18:45) Navigating the “Smile and Cry” Days of Year One(24:03) Ethan's Approach to Hiring for a New Org(27:38) Building Trust With Founders as a New Sales Leader(30:19) Incentives: Creating a Commission Plan for the Early Days(34:10) Why You “Can't Divide Zero”: Handling Deal Splits(35:52) Other Early-Stage-Isms or Philosophies(38:52) Discounting at an Early-Stage Company(41:17) Selling in Today's Environment: Competitive Trap-Setting(44:47) Budgets for AI Products: Experimental ARR(45:50) Monthly Deals and Decision Cycles in the Current Environment(47:33) Remaining Competitive in the Era of AI(51:08) The Lighter (and Cringier) Side of LinkedIn(1:03:01) Wrap—SPONSORS:Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.#SalesLeadership #StartupSales #SalesStrategy #SalesCompensation #discounting This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Your Company Is a Utility Function: Here's How to Pull the Right Levers

    Play Episode Listen Later Aug 4, 2025 66:03


    Have you ever tried running a business like it's a utility function? Today's guest has. CJ is joined by Michaela Lehr, a seasoned FP&A leader and former CFO of ActionIQ, who breaks down how CFOs can pull levers like growth, retention, margin, and cash runway to maximize value without blowing something up. Michaela explains how not all growth is created equal and why how you grow matters as much as how much you grow. She talks about gross margin as the most sensitive area of the P&L and how to communicate with engineers about their impacts on it. The conversation also covers the rise of “experimental recurring revenue” in AI-first products, why investors are obsessed with net dollar retention, the risks of over-servicing customers, looking out for your own finance team, and what it means to budget in the real world when everything changes after board approval.—LINKS:Michaela Lehr on LinkedIn: https://www.linkedin.com/in/michaela-lehr-2908996/ActionIQ: https://www.uniphore.com/actioniqCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: Loveable: https://lovable.devCanva: https://www.canva.comConcourse: https://www.concourse.co—TIMESTAMPS:(00:00) Preview and Intro(02:20) Sponsor – Rillet | Pulley | Brex(07:33) What It Means To Run a Company Like a Utility Function(10:45) An Example of Optimising for This Utility Function Regarding AI Spend(15:36) Sponsor – Aleph | RightRev | Navan(19:35) Less Visible but High-Impact Levers That Drive Revenue(22:15) Gating Headcount Based on Performance Milestones(25:09) Cloud Costs as a Hidden Lever(27:30) Why How You Grow Matters As Much as How Much You Grow(30:08) Professional Services as a Necessary Investment(32:43) What ERR (Experimental Recurring Revenue) Is(36:39) Margin As the Most Sensitive Area of the P&L(38:13) Communicating With Engineers About Gross Margin(41:56) Why Investors Care So Much About Net Dollar Attention(43:53) Making Sure Your Upsells Don't Mask a Churn Problem(44:40) What Over-Servicing Your Customer Looks Like(46:58) Why the “Just Give Me My Budget” Mindset Doesn't Work(49:23) Brokering the Budget With Execs in Real Time(51:38) Looking Out for Your Own Team as a CFO(56:26) The First Sign of an Erosion of Trust(59:50) Finance's Role in Upholding Capital-T Truth(1:01:31) Long-Ass Lightning Round: A COVID-Era Multitasking Mistake(1:02:06 ) Advice to Younger Self(1:04:07) Michaela's Favorite Finance Tool(1:04:17) Craziest Expense Story—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.#UtilityFunction #FPandA #BusinessStrategy #GrossMargin #NetDollarRetention This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    NEW DATA: Q2 Private Company Benchmarks

    Play Episode Listen Later Aug 2, 2025 11:51


    Today we're reviewing the state of the private markets using the NEW benchmarks released by Mostly Metrics. We surveyed our readers to see how their company's are doing… And it's tough to be a company between $5M and $25M in revenue right now.Three other things that stood out from the benchmarks this quarter:1️⃣ CAC Payback is up across the board. It's taking longer to earn back customer acquisition costs. AI is disrupting traditional search channels, and companies are building internal tooling instead of buying when it makes sense.2️⃣ Revenue is coming from existing bases. Net Dollar Retention is doing the heavy lifting — especially beyond $25M ARR. Expansion efficiency is becoming the key growth lever.3️⃣ Burn multiples keep falling. In reaction to expensive growth, capital efficiency is trending up. Even companies under $25M ARR are showing discipline.Get the whole 33 page report hereThis week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    “Let's Just See What Breaks” — Intuit's CFO on Being a Disruptor When You're Already the Incumbent

    Play Episode Listen Later Jul 28, 2025 67:44


    How do you keep innovating and disrupting when you're already the incumbent? And how do you prevent a $200B+ company from becoming slow and complacent? In this episode, CJ is joined by Sandeep Aujla, CFO of Intuit, who shares how one of the world's largest software companies continues to operate with the agility of a startup. With QuickBooks, TurboTax, Credit Karma, and MailChimp all falling in the Intuit family tree, serving both consumers and businesses, Sandeep breaks down the company's platform strategy, explains how he tells a unified story across these product lines, and describes how he prioritizes capital allocation. He also talks about Intuit's efforts to leverage AI to improve internal efficiencies, insights into the ideal CFO-CTO relationship, tactics for saying no, the benefits of letting stuff break, and how finance helped uncover a major growth opportunity for Intuit in the mid-market. The conversation touches on the company's 25 golden metrics, why leap years and the Super Bowl affect revenue, and the lesson Sandeep learned from a $2 coffee.—LINKS:Sandeep Aujla: https://www.linkedin.com/in/aujla/Intuit: https://www.intuit.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:30) Sponsor – Pulley | Brex | Aleph(07:11) Sandeep's Career Journey at Intuit(09:41) The Stigma Around CFOs and Seriousness(11:01) Being the Disruptor When You're Already the Incumbent(14:04) Intuit: Software, Payments, or Services Company?(15:21) Sponsor – RightRev | Navan | NetSuite |(19:00) The Intuit Family Tree(20:14) Cross-Platform Network Effects(21:54) Telling a Unified Story Across Multiple Product Lines(25:24) How Finance Discovered a Mid-Market Growth Opportunity(28:56) Reducing Churn by Keeping Customers on Platform(31:04) How Small Businesses Are Evolving To Leverage Tech and AI(34:11) How Sandeep Prioritises Capital Allocation(37:17) Tactics for Saying No Gracefully as a CFO(39:39) The Benefits of Letting Stuff Break(43:10) Reinvesting Across the Business: Consumer Versus Business(45:36) The CFO-CTO Relationship in the Age of AI(49:45) Tracking Intuit's Target for Internal AI Efficiency(52:06) Surprising Usage Patterns: Leap Years, Game of Thrones, etc(53:15) The Different Use Cases for AI Internally(55:48) The 25 Golden Metrics That Matter(58:45) Leap Years and Other Surprising Things That Impact the Business(1:00:04) Long-Ass Lightning Round: A Deadline Mistake(1:02:04) Advice to Younger Self(1:03:48) Finance Software Stack(1:04:36) A Bonus Question: Printed Notes(1:05:17) Craziest Expense Story—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.#platformbusiness #innovation #disruption #CapitalAllocation, #FinancialSoftware Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    The Evolution of Software Pricing (A History Lesson)

    Play Episode Listen Later Jul 26, 2025 15:33


    Pricing and packaging has undergone a radical transformation since the early 1950s. And the clear through line is a changing unit of value and how it's tracked.Historically, the tech industry has undergone six waves of change.* Hardware + Software sold together* Software Sold for Hardware* Application Service Providers* Outsourced Infrastructure + SaaS* Usage Based Pricing* HybridWe'll walk through each evolution, and leave you with some tips for overcoming common pricing challenges in the age of AI.This week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai.Referenced on podcast:* Jason Kap's expert pricing consultancy: https://bluerocket.io/ Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    “Most Sales Reps Are Coin-Operated”: A Guide To Building Better Comp Plans

    Play Episode Listen Later Jul 24, 2025 72:48


    How do you build a sales culture where top performers are empowered and poor performers are not protected? In this episode, CJ is joined by Daniel Lentz, whose career has spanned sales, taking an e-commerce platform public during a global pandemic, and, interestingly, seminary. Daniel Lentz is the CFO of BigCommerce and an expert in designing comp plans that work. In this episode, he breaks down his approach to this and how to avoid the pitfalls that can easily discourage your salespeople. He explains how to align sales and marketing efforts, touching on multi-touch attribution models, before discussing why he focuses on input metrics over output metrics. The conversation covers the importance of having an operator-first mindset, the skill of having a BS detector, the challenges of navigating macroeconomic factors, the role of mentorship, and why teaching your team how the company actually makes money is the ultimate unlock.—LINKS:Daniel Lentz on LinkedIn: https://www.linkedin.com/in/daniel-lentz-5ba8134/BigCommerce: https://www.bigcommerce.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:Customer-First Finance: PagerDuty's Secret to “Small” Public Company Success — —TIMESTAMPS:(00:00) Preview and Intro(02:28) Sponsor – Brex | Aleph | RightRev(07:04) Daniel's Unconventional Career Arc(11:40) Being an Operator-First CFO(14:05) The Skill of Having a Good BS Detector(15:45) Sponsor – Navan | NetSuite | Pulley(19:16) Why People Make Things Sound More Complicated Than They Are(21:33) Transitioning From a Top Sales Rep to a Top Sales Leader(24:46) Daniel's Philosophy When Designing Comp Plans(28:53) A Hot Take on Capping Big Deals(35:01) Onboarding Great Sales Leaders(38:17) Multi-Touch Attribution Models(42:36) How Finance Can Reduce Sales Versus Marketing Turf Wars(44:52) The Metrics That Matter: Input Versus Output(47:30) Misdiagnosing Problems in SaaS Go-to-Market Models(49:00) Why Benchmarking Can Be Misleading(51:06) How Small Companies Can Compete With Big Companies(52:22) The Power of Explaining to Employees How the Company Makes Money(55:56) Why Daniel Doesn't Want Employees To Be Distracted by the Macro(57:19) Explaining Rational Interest Rates to Employees Under 30(59:24) How Mentorship Has Influenced Daniel's Career(1:01:12) Advice for Taking Investor Advice(1:03:04) Long-Ass Lightning Round: A Big Career Mistake(1:04:51) Advice to Younger Self: Careerism Is a Trap(1:06:49) Finance Software Stack(1:10:32) Craziest Expense Story—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.#SalesComp #SalesCompPlan #InputMetrics #SalesCulture #SalesLeaders Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Beat, Raise, Repeat: Former IBM CFO on Developing Watson, AI Automation & Financial Stewardship

    Play Episode Listen Later Jul 21, 2025 66:53


    In this episode, CJ is joined by Chris Greiner, CFO of Zeta Global and former CFO of IBM's analytics division, where he worked on AI during the development of Watson. He's had a front-row seat to the evolution of AI across industries. He's also on a 15-quarter streak of beat-and-raise performance in his current role. Chris breaks down how strong financial stewardship can be a launch pad for innovation, not a constraint, and unpacks his “Closest to code, closest to customer” philosophy. The conversation covers how to determine whether a company's data advantage is real or just storytelling, what Chris learned from cataloging every task in the finance org, and why some things are better left unautomated. He explains what's on his personal IPO pre-flight checklist, how and why Zeta Global tracks daily revenue, and the “hustle metric” as a predictor of good salespeople. He also shares many lessons and anecdotes from his time at IBM, including one where he played tennis with the Emperor of Japan.—LINKS:Chris Greiner: https://www.linkedin.com/in/chrisgreiner1Zeta Global: https://zetaglobal.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:Monetizing Community Engagement: The Business of Fitness with Strava CFO Lily Yang - Everything You Need to Know About Sales Rep Comp + Commissions Planning w Ryan Walsh, CEO of RepVue - —TIMESTAMPS:(00:00) Preview and Intro(02:22) Sponsor – Aleph | RightRev | Navan(06:28) Chris's Tenure at IBM During the Development of Watson(08:24) The Evolution of Chris's Relationship With Data and AI(11:40) Why “Showing Not Telling” Is Key in Finance and Investor Relations(12:56) A Company's Data Advantage: Real Versus Storytelling(15:07) Cataloging Tasks in the Finance Org To Identify Automation Opportunities(17:02) Sponsor – NetSuite | Pulley | Brex(20:53) Enabling Internal Data Exploration Without Conflicting Results(23:13) The One Thing Chris Refuses To Automate and Why(26:46) Forecasting: The Tension Between Trusting AI and Your Own Calculations(28:58) Zeta Global's 15-Quarter Beat-and-Raise Streak(31:40) Daily Pacing and Confident Forecasting(33:58) Sizing Up Zeta Global by Daily Active Users and Usage-Based Activity(36:50) Unexpected Predictors of Customer Behaviour(38:47) The “Hustle Metric”: The Best Predictors of Good Salespeople(43:05) Chris's IPO Preflight Checklist(45:49) Strong Financial Stewardship as a Catalyst, Not a Constraint(48:10) The Top Controls That a CFO Should Have Their Eye On(49:55) The Fallacy of Having To Choose Between Growth and Margin Expansion(53:26) Finance Teams: Closer To Code Versus Closer to Customer(55:47) Value-Based Pricing(57:42) Long-Ass Lightning Round: A Career Mistake(58:20) Making Friends With the Emperor of Japan(1:02:32) Advice to Younger Self(1:03:57) Finance Software Stack—SPONSORS:Aleph automates 90% of manual, error-prone busywork, 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/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. Visit https://navan.com/runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. Head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#BeatAndRaise #CFOInsights #AIinFinance #AutomationInFinance #FinancialStewardship Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    The CEO's #1 Job: Capital Allocation

    Play Episode Listen Later Jul 19, 2025 14:23


    Today we're talking about capital allocation, and how it's one of the most powerful, yet least discussed, skills a CEO needs to learn.Every CEO has three core jobs:* Run a good company (Operations)* Tell a good story (Investor Relations)* Deploy capital effectively (Capital Allocation)Most CEOs focus 80% of their time on the first two. Yet it's the third, capital allocation, that often has the highest leverage and the least guidance.You can read more about this topic at lookingforleverage.comThis week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai. Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

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