Run the Numbers

In this episode of Run the Numbers, CJ breaks down Anthropic’s S-1: the revenue growth, 900% net revenue retention, compute costs, gross margin, and whether the company is actually profitable. We also cover the risk factors, the five-class share structure, executive pay, and what a roughly $2 trillion valuation implies next to other recent IPOs. — SPONSORS: RightRev is a revenue recognition platfo...

In this episode of Run the Numbers, CJ welcomes back Sid Kumar, who has led go-to-market through perpetual, cloud, SaaS, and consumption models at CA, AWS, HubSpot, and now Databricks. They cover how consumption changes the sales org, why customer success has an identity crisis, how to build a commission stack, and what ARR actually means. Sid also shares how AI is reshaping capacity planning and...

In this episode of Run the Numbers, recorded live at Brex Mode in Chicago, CJ sits down with Craig Bealmear, CFO of Oklo, who spent nearly 30 years at BP before moving into nuclear. They cover raising billions before meaningful revenue, why cash matters more than the P&L, and how he hires the finance team Oklo will need two years from now. Craig also looks back at leading through the Deepwater...

In Part 2 of our Token Series with Tabs, CJ and Ali Hussain ask how much AI is too much in finance. They cover why finance may be the most AI-forward function after product and engineering, how MCP became its “ChatGPT moment,” and why headless agents need a leash. They also get into where to start with governance and why deterministic layers still matter. — SPONSORS: Tabs is an AI-native revenue p...

Episode Description:  In this episode of Run the Numbers, CJ sits down with Erica Dorfman, CFO of Brex, to trace her path from capital markets at SoFi to product to the CFO seat. They cover why Brex moved away from lending, what happened behind the scenes during the SVB collapse, and how Erica keeps reinventing her role and her team as the company scales. — SPONSORS: Cloud Capital helps you say go...

In this episode of Run the Numbers, CJ welcomes back Jim Cook, a multi-time CFO (Intuit, Netflix, Mozilla) turned coach, author, and newsletter writer. They dig into “return on compute,” the metric Jim believes every finance leader needs in their vocabulary, and why surprise AI bills echo the early days of the cloud. They cover how to budget for tokens, the “frontier convergence” idea for ramping...

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...

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...

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...

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 p...

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 a...

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. —...

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&#39...

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...

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 t...

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...

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...

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 mo...

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 bui...

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...

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. I...

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...

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 plat...

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...

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 corpora...