Run the Numbers

In this episode of Run the Numbers, CJ sits down with Glenn Schiffman, CFO of Fanatics. They break down the economics of sports IP, how Fanatics approaches CAC, LTV, and capital allocation across merchandising, collectibles, and betting, and the negotiation lessons Glenn learned from decades in investment banking and leading finance at IAC.—SPONSORS:Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/glenn-h-s-51440521/Company: https://www.fanaticsinc.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:13 Welcome and guest intro2:38 Football at Duke and college businesses5:40 Predecessor to DoorDash story7:10 IP monetization explained9:22 All deals are snowflakes10:36 Partnership KPIs13:21 Sponsors — Brex | Aleph | RightRev16:40 Buy, bet, collect: CAC and LTV17:15 Single view of the fan18:39 Multi-business customers spend 4.7x20:32 Fanatics credit card launch22:13 AI for personalization23:01 DTC vs. wholesale margin profiles24:05 Budgeting process26:07 Infinite vs. finite: focus on revenue26:37 Sponsors — Rillet | EY | SpendHound29:47 Starve your losers, feed your winners32:58 Capital compounding: revenue, EBITDA, FCF33:56 Buybacks at IAC37:02 First negotiation at Lehman39:17 Outlasting the other side39:56 Listening in negotiations40:03 Long-Ass Lightning Round44:25 Credits#RunTheNumbersPodcast #CFO #SportsCommerce #CapitalAllocation #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Kunal Agarwal, CFO of Gorgias, to unpack how AI is reshaping pricing and operations. They discuss outcome-based pricing, how to forecast LLM-driven costs, and why order-to-cash isn’t just back-office plumbing—it can be a true growth lever when designed correctly.—SPONSORS:Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/agarwalk/Company: https://www.gorgias.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:14 PE to venture incubator4:39 Operational empathy from zero-to-one4:45 First paying user feeling5:40 Jet ski customer support story8:49 Hanging with IC sales reps12:24 Sponsors — Tabs | Abacum | Brex15:44 Finance as the decision engine17:36 Gorgias overview20:20 Pricing structure and iteration22:11 Outcome based / resolution pricing24:48 AI success rate as key metric25:33 Sponsors — Metronome | RightRev | Rillet28:57 Pricing value split — $1 per resolution31:17 Vertical specificity as AI moat33:27 Managing LLM costs35:41 Falling token costs and model mix39:28 Order to cash as growth engine43:31 Auditing order to cash at 25M ARR44:09 Manual choke points46:32 Learning density over titles48:30 SurveyMonkey as the most formative period50:07 Lightning round50:17 Listening to respond vs. listening to learn51:04 Advice to younger self52:02 Finance software stack52:45 Cortex — internal AI decision tool54:21 Craziest expense story54:52 Credits

In this episode of Run the Numbers, CJ sits down with Federico Acabbi, investment banker at RBC, to break down what’s happening across cybersecurity, infrastructure, and the broader software market. They cover why horizontal software is under pressure while security spend holds up, what it really takes to go public today, and how the IPO process actually works behind the scenes—from diligence to pricing.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNFederico: https://www.linkedin.com/in/federicoacabbi/rbccm.comCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro2:36 Software investability right now6:46 Cyber — CFO's #2 investment priority8:17 AI turbocharging attacks9:08 DevOps disruption10:30 Sponsors — Rillet | Tabs | Abacum13:55 IPO landscape overview14:33 Revenue and market cap benchmarks19:24 Founder share sales at IPO22:28 Secondary market vs. IPO market23:14 How many IPOs can the market digest?24:20 Investor mix for larger vs. smaller IPOs25:04 Sponsors — Brex | Metronome | RightRev28:23 Role of mutual funds in IPOs30:00 What banks actually do on an IPO31:49 Book building and allocation32:43 Research coverage35:52 NDRs and testing the waters38:59 Roadshow format — then vs. now40:41 Direct listings explained43:57 How banks make money on IPOs44:56 Fee splits between banks47:36 IPO vs. M&A — which is more attractive?51:02 Junior banking story — Nokia and the Vespa54:31 Craziest expense story56:08 Credits

In this episode of Run the Numbers, CJ sits down with financial historian and PayPal Mafia member Aman Varejee to explore the recurring patterns behind economic bubbles. Drawing on research from his upcoming book “A Brief History of Financial Bubbles”, Aman explains what defines a bubble, the psychology that fuels speculative manias, and why major technological shifts—from railways to the internet to AI—often coincide with periods of extreme market speculation.—SPONSORS:RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNAman: https://www.linkedin.com/in/aman-verjee/https://practicalvc.com/Aman’s book: https://bigbubbletrouble.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:38 Welcome and guest intro3:48 Defining a bubble6:03 Cognitive biases behind bubbles10:27 Sponsors — RightRev | Rillet | Tabs13:56 Do bubbles produce breakthroughs?14:35 Dot-com bubble — winners and losers16:00 UK railway bubble21:24 Bubble warning signs25:30 Sponsors — Abacum | Brex | Metronome28:47 Do bubbles attract grifters?31:11 Role of government in bubbles35:59 Bubble duration vs. severity37:32 2008 — roots go back to 199240:27 Are bubbles connected through time?43:38 Are we in an AI bubble?45:06 Nvidia vs. Cisco valuation comparison46:52 Circular finance in AI49:16 FP&A at PayPal under Thiel and Musk52:02 PayPal's referral campaign and LTV/CAC54:40 Book plug55:09 Credits#RunTheNumbersPodcast #Fintech #EconomicBubbles #FinanceHistory #CFO

In this episode of Run the Numbers, CJ sits down with Jason Lee, CFO of Faire, to unpack the economics of wholesale marketplaces. They break down how Faire connects independent brands with local retailers, the key metrics that matter in marketplace businesses, and ROI as a decision-making framework. Jason also shares lessons from scaling Square through its IPO and how finance leaders navigate valuation resets in private markets.—SPONSORS:Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNJason: https://www.linkedin.com/in/jason-lee-11787020/Faire: https://www.faire.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro3:01 How Faire serves retailers5:49 Revenue model and retention metrics8:21 Recurring vs. reoccurring revenue11:54 Sponsors — Metronome | RightRev | Rillet15:17 Input vs. output metrics17:13 The business equation19:08 Metric ownership22:07 Killing metrics: signal to noise23:21 800 metrics at Faire24:51 Customer count as a misleading metric26:04 Sponsors — Tabs | Abacum | Brex29:25 Planning cadences at Faire32:41 When to reallocate resources36:40 ROI as a framework40:25 Portfolio view of investments43:53 Discipline is knowing where to say yes47:11 Faire's valuation reset50:49 Tender offer mechanics55:33 Screwing up IR at Square IPO56:52 Advice to younger self58:44 AI at Faire59:32 Claude connected to data warehouse1:00:16 Tariff analysis with AI1:02:38 Credits#RunTheNumbersPodcast #Marketplace #CFO #SaaS #FinanceLeadership