Podcast · Business

Run the Numbers

by CJ Gustafson · English · Business

Run the Numbers is a business podcast about financial metrics and business models for CFOs, aspiring CFOs, finance leaders, and ambitious people operating tech startups. Hosted by CJ Gustafson, CFO and writer of Mostly Metrics, the show shares lessons, frameworks, and operator insights from the tren

New episodes: Weekly
Typical length: 50 min
Latest: 12 Oct 2026
Language: English

Latest episode

12 Oct 2026 · 48 minNew

Inside the Food52 Bankruptcy | Heidi Robinson

In this episode of Run the Numbers, CJ sits down with Heidi Robinson, former CFO and COO of Food52, for one of the wildest CFO stories the show has featured. Heidi joined expecting to lead a modest turnaround and within weeks realized the company was in far deeper trouble than anyone understood. She walks through being the newest executive in the room and having to deliver that news and the Monday evening a lender swept the company's cash without warning. — SPONSORS: Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company.…

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Earlier episodes 29 most recent

8 Oct 2026 · 1 hr 7 min
Robinhood's CFO on Refounding & the Art of Capital Allocation | Shiv Verma
In this episode of Run the Numbers, CJ sits down with Shiv Verma, CFO of Robinhood, to unpack the company's 2022 "refounding". They dig into why Shiv personally signs off on every headcount and marketing dollar at a $100B+ company, and how Robinhood's capital allocation philosophy — no loss leaders, minimal variable costs, and a hard $100 million ARR bar for new products — shapes everything from prediction markets to private-market investing. — SPONSORS: RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid…
6 Oct 2026 · 15 min
Token Series Part 1 | How AI Created a New Budget
This is Part 1 of our new Token Series with Tabs. CJ calls up Ali Hussain to dig into one of the fastest-growing, least-understood line items on the P&L: AI inference and token spend. They debate whether AI costs ultimately belong to the CTO or the CFO, why the shift from "experimentation budgets" to real operating costs is forcing companies to rethink ownership, what's actually different about AI spend compared to the early cloud transition, and how tools like OpenRouter (acquired by Stripe) and Ramp's new offering are approaching the problem from opposite ends of engineering vs. finance. —…
5 Oct 2026 · 54 min
Why Owning Your Data Is the New Moat | Primary Venture's Emily Man
In this episode of Run the Numbers, CJ sits down with Emily Man of Primary Ventures to map out where value actually accrues in the AI economy. They break down the 5 layers of the AI stack and why Emily believes the next era of AI adoption will be driven by diffusion through apps rather than smarter models alone. — SPONSORS: Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and…
1 Oct 2026 · 48 min
Zuora’s COFO On Going Private and Pricing AI | Todd McElhatton
In this episode of Run the Numbers, CJ sits down with Todd McElhatton, CFO of Zuora, for a deep cut on pricing, packaging, and value in the age of AI. They dig into how companies are figuring out whether to charge for AI at all, why token-based budgets are starting to sit alongside headcount budgets, and why AI may be increasing — not decreasing — the value of deep expertise. — 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…
28 Sep 2026 · 50 min
LiveRamp’s CFO Rebuilt Pricing From Scratch | Lauren Dillard
CJ sits down with Lauren Dillard, CFO of LiveRamp, whose path to the CFO seat ran through investor relations, communications, and even a year as interim CMO. They dig into why storytelling and influence matter as much as technical finance chops, how LiveRamp tore down and rebuilt its entire commercial model — collapsing 25+ usage metrics into 5 and inventing the "token" along the way. — 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,…
24 Sep 2026 · 34 min
The NScale IPO | A Neocloud S1 Breakdown
Nscale just filed its S-1 to go public on the NYSE — and it might be the wildest IPO filing of the year. This UK-based "NeoCloud" is only 2 years old, is gross margin negative, started life as a crypto miner, and has somehow locked up over $100 billion in contracted value from Anthropic and Microsoft. CJ breaks down the entire S-1 line by line: what a NeoCloud actually is, how Nscale's "power to token" strategy works, why Nvidia shows up as its supplier, investor, guarantor, AND customer, and whether this is a durable business or a well-timed arbitrage on the AI compute shortage. — SPONSORS:…
21 Sep 2026 · 51 min
How Media Actually Makes Money | Blake Saunders
In today’s Run the Numbers, CJ sits down with Blake Saunders, founder and managing director at Core Advisors (an investment bank focused on media) and founder of The Joint, to go deep on how media companies actually make money — and how that's changing fast. If you're anywhere near advertising, media, or content monetization, this one's a masterclass. — SPONSORS: Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps…
17 Sep 2026 · 1 hr 7 min
How to Sell Your Company: A Multi-Time CFO's Full Playbook | Rick Smith
CJ sits down with multi-time CFO Rick Smith, founder of Bonfire Advisory and author of Six Months to the Sale , to break down what actually happens when you sell a company. They cover why buyers value some businesses on ARR and others on EBITDA (and why being slightly profitable can hurt you), how to negotiate banker fees, what buyers find when they dig into your balance sheet, and why every cap table Rick inherits is wrong. — SPONSORS: RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus…
14 Sep 2026 · 46 min
Masterwork’s CFO Runs 12 AI Agents at Once | Nigel Glenday
CJ Gustafson sits down with Nigel Glenday, CFO and COO of Masterworks, to talk about how AI is actually changing day-to-day finance work. They cover why context matters more than model choice, how Nigel runs a dozen Claude Code terminal sessions at once, and how his team solved a 300,000 K-1 problem with Python instead of a $300K tool. Plus: a detour into the 2026 art market and what securitizing fine art teaches you about scarcity and pricing power. — SPONSORS: Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a…
10 Sep 2026 · 34 min
How Oura Built a $1.4 Billion Business Around a Tiny Ring
How did Oura turn a tiny piece of wearable hardware into a $1.4 billion business? CJ breaks down the numbers behind Oura’s IPO filing and the surprisingly powerful business model hiding behind the ring. — SPONSORS: Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at…
7 Sep 2026 · 52 min
What 20 Years of Software Investing Says About AI | Matt Hedberg
In this episode of Run the Numbers, CJ sits down with Matt Hedberg, a sell-side equity analyst at RBC who has covered software for more than 20 years. They break down how AI compares to the cloud transition, why traditional software moats are changing, what separates management teams that will actually capitalize on AI, and why cash, customer relationships, data, and technical leadership matter more than ever. — SPONSORS: Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen…
3 Sep 2026 · 1 hr
Andy Ellis: How to Lead Without Becoming the Hero, the Villain, or the Bottleneck
In this episode of Run the Numbers, CJ sits down with leadership coach and former Akamai executive Andy Ellis. They break down why being indispensable can actually hurt your career, why managers shouldn’t automatically replace someone who leaves, how hero-villain thinking leads to bad decisions, and what great delegation and leadership actually look like. — SPONSORS: Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet…
27 Aug 2026 · 54 min
40 Years of IPOs with Jay Ritter: What the Data Actually Says
In this episode of Run the Numbers, CJ sits down with Jay Ritter. They break down what Apple, Nvidia, the dot-com boom, and today’s AI giants can teach us about IPOs, why companies leave money on the table on day one, why firms stay private longer, and what the data actually says about long-term IPO performance. — SPONSORS: Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn…
24 Aug 2026 · 45 min
How AI Is Rewriting Product-Market Fit, Pricing, and Go-to-Market
CJ sits down with Rebecca Schwartz of Tabs, Fred Havemeyer of Fleet AI, and Rahul Rekhi of Rogo for a live conversation about what it actually takes to build an AI-native company. — SPONSORS: RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj Pulley is an equity management…
20 Aug 2026 · 55 min
The Stripe Guide to Pricing, Billing, and Quote-to-Cash with Wisam Hirzalla
In this episode of Run the Numbers, CJ sits down with Wisam Hirzalla, Head of Product at Stripe Billing, to trace the full journey of a dollar—from product packaging and pricing through quoting, contracts, billing, tax, collections, and revenue recognition. — SPONSORS: Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can.…
17 Aug 2026 · 54 min
The CFO-COO Is Coming: Meredith Finn of Front on the Future of Finance
Front CFO & COO Meredith Finn joins CJ to explain why finance leaders are taking on more of the operator’s job. They break down the CFO-COO dual mandate, how Front funds new bets inside a mature SaaS business, why AI requires more coordination than simply handing everyone new tools, and how finance teams should think about the growing cost of AI. — SPONSORS: Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including…
13 Aug 2026 · 50 min
Xero’s CFO: Why Finance Is Taking On More of the Business
In this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology. Claire also shares how she builds teams around her weaknesses, what small businesses actually want from AI, and why she views diversity as a business performance decision. — SPONSORS: Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer…
10 Aug 2026 · 35 min
A CFO Explains Private Jets
On this episode of Run the Numbers, CJ and Ben trace corporate private jets from Sam Walton’s scrappy two-seater to Alex Karp’s $17 million jet bill. They break down when flying private actually makes business sense, how jets hit the balance sheet, the tax and accounting implications, what companies disclose to investors, and when executive travel crosses the line from productivity tool to corporate excess. — SPONSORS: Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and…
6 Aug 2026 · 50 min
The Business of Saving Lives: Inside RapidSOS
On this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster. They cover building AI fluency, combining FP&A with BI, monetizing vertical software, integrating acquisitions, and the leadership lessons Richard carried from entrepreneurship. — SPONSORS: Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising,…
3 Aug 2026 · 53 min
Building an AI-Native Finance Team with Plaid CFO Seun Sodipo
On this episode of Run the Numbers, CJ sits down with Plaid CFO Seun Sodipo. Seun explains how her team is using AI to improve speed, accuracy, and ambition; why finance leaders need both bottom-up experimentation and top-down direction; and how she approaches planning, network effects, and building a durable company. — SPONSORS: RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating…
27 Jul 2026 · 39 min
How to Tell a Demanding Founder They’re Wrong
On this special episode of Run the Numbers, CJ Gustafson revisits standout moments from past conversations with Alex Immerman, Curt Sigfstead, Daniel Kang, Adam Ante, and David Laptor. Together, their advice reveals how great CFOs earn trust, challenge founders, speak up when the data says something is wrong, and become true strategic partners without relying on the power of the purse strings. — SPONSORS: Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set…
23 Jul 2026 · 58 min
The Four Stages of World-Class FP&A with Datadog’s AJ Ljubich
On this episode of Run the Numbers, CJ sits down with Datadog SVP of FP&A AJ Ljubich to break down the four stages of a world-class finance team. — SPONSORS: Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics Anrok is the sales tax platform that watches your exposure everywhere, automates compliance,…
20 Jul 2026 · 1 hr 1 min
Dave McClure and Aman Verjee on Angel Investing at Scale, 500 Startups, and Practical VC
On this episode of Run the Numbers, CJ sits down with Dave McClure and Aman Verjee of Practical VC to talk about the evolution of startup investing — from the PayPal mafia and Founders Fund era to 500 Startups, YC-style scale, and today’s secondary market. — SPONSORS: Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and…
16 Jul 2026 · 37 min
Cumberland Farms S-1 Breakdown: Fuel, Snacks, and Debt
On this episode of Run the Numbers, CJ breaks down Cumberland Farms’ IPO filing and the surprising business behind it. — SPONSORS: RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com Pulley is an equity…
13 Jul 2026 · 1 hr
Token Economics, AI ROI, and the Future of Investment Banking with Rahul Rekhi
In this episode of Run the Numbers, CJ sits down with Rogo president Rahul Rekhi to unpack what AI actually changes in investment banking and finance. They dig into token economics, why adoption without ROI is a trap, how vertical AI wins, and why domain expertise still matter. — SPONSORS: Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at…
9 Jul 2026 · 28 min
Jersey Mike’s S-1 Breakdown: How a $4.2B Sandwich Machine Works
On this episode of Run the Numbers, CJ breaks down Jersey Mike’s S-1 and the franchise machine behind more than $4 billion in sandwich sales. He explains how an asset-light royalty model works, why franchise economics can be so powerful, what Blackstone saw in the business, and what the filing reveals about growth, margins, and the real money behind the subs. — SPONSORS: RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their…
6 Jul 2026 · 46 min
The CFO Who Was “Ill Equipped” to Save Lehman Brothers
What actually prepares someone to become a CFO? CJ revisits Erin Callan’s short, brutal run as Lehman Brothers CFO and pulls lessons from past guests on operational reps, simple communication, fast-moving bad news, budget mistakes, and why great finance leaders can’t just report the numbers, they have to shape them. — SPONSORS: Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay…
2 Jul 2026 · 40 min
How Finance Teams Are Actually Using AI | Opendoor, Datadog, PwC
In this episode of Run the Numbers, CJ goes live from Rillet Recon with Dana Decker (VP of Finance at Opendoor), AJ Ljubich (SVP, FP&A at Datadog), and Micah Richard (Principal, AI at PwC) to unpack how finance teams are actually using AI. — SPONSORS: Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics…
25 Jun 2026 · 43 min
Lime’s S-1 Breakdown: The $1.8B Scooter IPO
In this episode of Run the Numbers, CJ breaks down Lime’s S-1 as the scooter company heads toward the public markets. He gets into the $1.8B valuation, Wayne Ting’s turnaround playbook, Lime’s unit economics, the post-Covid recovery, and the debt wall that may be forcing the IPO window open. — SPONSORS: SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th…

About Run the Numbers

Run the Numbers is a English business podcast from CJ Gustafson. Melo plays each episode straight from the publisher's own feed — no ads added, no account needed — and remembers where you stopped, in this browser only.

Publisher: CJ Gustafson
Language: English
Category: Business
New episodes: Weekly
Typical length: 50 min
Latest episode: 12 Oct 2026
Feed: RSS — paste into any podcast app
Apple Podcasts: podcasts.apple.com/podcast/id1723787140
Rights: CJ Gustafson

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