Run the Numbers

Wealthfront’s CFO on Automation, Compounding Growth, and Going Public

In this episode of Run the Numbers, CJ sits down with Wealthfront CFO Alan Imberman to unpack automation as a strategy, the compounding power of retention and trust, and how to balance elite profitability with continued investment. They also discuss why Wealthfront went public earlier than many peers and what’s really happening in fintech right now.—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/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.comBrex 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/CJ—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/alan-imberman-cfa-aab2371/Company: https://www.wealthfront.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:37 Welcome and guest intro3:11 Wealthfront overview4:38 Automation as core philosophy6:50 55K clients per support rep example7:45 90% gross margins and $1M revenue per employee8:46 Optimization vs. exploration framework9:58 Data flywheel: the Path product10:43 Cash account insight from customer data11:26 Home lending insight from wire data13:33 Sponsors — Rillet | EY | SpendHound16:45 Product led growth and referrals18:11 Incentives vs. paid marketing20:46 Compounding philosophy and 120% NDR22:07 Long term thinking vs. public market pressure22:40 No guidance decision26:26 Sponsors — Brex | Aleph | RightRev29:44 Serving the wealth builder: 80/20 in wealth management31:45 Decision to go public at $339M revenue33:46 Does size matter for IPOs?34:46 Fintech's moment: Chime, Klarna, Circle36:49 Non-monetary benefits of going public38:30 Memos over slides40:31 Hedge fund early career: spreading 10-Ks in Excel46:45 Don't lose the forest for the trees in modeling48:31 Lightning round48:43 Screwed up: de-annualizing a fee rate49:55 Advice to younger self50:32 Finance software stack51:14 Craziest expense story: $100K coffee tab53:11 Credits#RunTheNumbersPodcast #CFO

How Strategic CFOs Get It Wrong

On this week’s Run the Numbers, CJ sits down with Steve Isom of Bloomerang to break down what a “strategic CFO” really is. They cover the shift from reporting to operating, why customer orgs drive SaaS value, and how AI is reshaping the finance role. —SPONSORS:RightRev 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.comBrex 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/run—LINKS: Steve on LinkedIn: linkedin.com/in/steveisomjrCompany: https://bloomerang.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview1:25 Intro2:55 Welcome Steve Isom3:13 CFO to COO promotion5:02 Having a pulse on every function6:51 Defining "strategic CFO"7:19 Tying strategy to value creation9:27 Being embedded in the rhythm of the business10:55 Finance leaders as commentators vs. team captains12:25 Sponsors — RightRev | Rillet | EY15:33 Killing projects as a core skill18:14 Activity doesn't equal impact19:16 Project Steve killed20:39 Taking over the customer org at Bloomerang22:18 Why acquisition is a cash-losing exercise23:07 LTV lives post-sale24:39 Most vulnerable area: customer success25:24 Ruthless CSM segmentation26:30 Nonprofits don't think about your software29:21 Sponsors — Spendhound | Brex | Aleph32:43 CFO running ops35:52 Metrics vs. humans37:18 Skip levels and what they reveal39:01 Incentives drive the wrong outcomes40:22 Customer-introduced delays as a key sub-metric40:27 Unit economics become tangible when you're accountable42:17 Going deep on AI45:13 Motivating your team to experiment with AI46:02 AI for personal projects47:05 Resource allocation in a vibe-coding world48:42 Does AI efficiency just mean more work?50:32 What excites Steve about the future of finance leadership52:08 Finance leaders who don't use AI won't get hired52:13 Credits#RunTheNumbersPodcast #CFO #StrategicFinance #SaaSFinance #FinanceLeadership #CFOtoCOO

CFO Explains: The Rise of Secondaries and the Death of the IPO Path

Secondaries aren’t a niche anymore — they’re the main event. In 2025, the secondary market hit $233B, outpacing IPOs 5:1. This episode breaks down how we got here, why companies stay private longer, and how employees, investors, and CFOs actually navigate liquidity. From Facebook’s wild west to structured tenders and continuation vehicles — this is the new playbook.—SPONSORS:Aleph 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.comBrex 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/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comBen on LinkedIn: https://www.linkedin.com/in/slackerstuff/Slacker Stuff: https://www.slackerstuff.com/—RELATED EPISODES:IPOs Are Being Replacedhttps://youtu.be/oGuZf83pdREThe $10T Question: Who Needs Wall Street?" | Scott Vosshttps://youtu.be/szCIZmTs3SQDriving revenue without selling | Greg Henry of 1Passwordhttps://youtu.be/f5FsNoG8A3EFinance vs. Marketing: Who’s Really Right About ROI? | Brandon Sullivanhttps://youtu.be/ivcht5N7uRQDo the things spreadsheets can’t do | SeatGeek’s Teddy Collinshttps://youtu.be/jn0L5KkmMI4—TIMESTAMPS:0:00 The $233B market replacing IPOs2:57 What is a secondary?4:24 The dot-com hangover5:48 The wild west era8:58 Sponsors — Aleph | RightRev | Rillet12:21 Why companies stay private longer13:56 The three stakeholders18:57 When is it too early?20:42 How to run one of these things23:57 Sponsors — EY | SpendHound | Brex27:04 Not all shares are created equal31:08 The good, the bad, and the ugly34:23 GP-led continuation vehicles36:19 The whole game changed37:34 Credits#RunTheNumbersPodcast #PrivateMarkets #SecondaryMarkets #VentureCapital #CFO

Fanatics CFO on CAC, LTV, and Capital Allocation Across Verticals

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

AI Pricing and the Hidden Growth Lever Most CFOs Ignore

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