Run the Numbers

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.

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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 spre...

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.

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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 comp...

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.

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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 posts 98% of transactions directly to it...

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.

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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...

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.

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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...

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.

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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 sl...

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.

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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 fo...

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.

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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 yo...

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.

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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 Mercor...

On this episode of Run the Numbers, CJ breaks down Cumberland Farms’ IPO filing and the surprising business behind it.

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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.righ...

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.

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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 re...

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.

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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...

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.

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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...

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.

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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 ht...

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.

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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...

On this episode of Run the Numbers, CJ sits down with Confluent CFO Rohan Sivaram to talk goal setting, prioritization, consumption-based pricing, hybrid zero-based budgeting, and the frameworks finance leaders use to scale companies. Rohan shares why he carries his 12-month goals with him, how he evaluates opportunities through TAM, technology, and team, and why usage-based pricing changes the entire operating model.

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EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across st...

In this episode of Run the Numbers, CJ sits down with Jake Kornreich, CFO of CoLab and former CFO of Own, live from the New York Stock Exchange. Jake breaks down the six-part framework behind Own’s $2.1B sale to Salesforce, why “control your destiny” matters, how CFOs should think about IPO readiness, board communication, share price theater, and why great finance leaders operate beyond the spreadsheet.

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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 nati...

In this episode of Run the Numbers, CJ sits down with Dan Bettes, CFO of SoundCloud, at the New York Stock Exchange. Dan breaks down how SoundCloud operates as a two-sided music marketplace, how he thinks about liquidity between fans and creators, and why great finance leaders need to make forecasting feel owned by the business

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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 mo...

In this episode of Run the Numbers, CJ breaks down Bending Spoons’ F-1 filing and the acquisition machine behind AOL, Evernote, Vimeo, Eventbrite, and more. He unpacks the company’s playbook: buy under-optimized digital businesses, transform operations, raise prices, reinvest earnings, and repeat — while asking the core question: how much was built, and how much was bought?

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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 calcu...

CJ Gustafson sits down with Marten Abrahamsen, CFO of Vercel, at the NYSE to talk about running finance inside a hypergrowth AI company. They cover AI use cases in finance, rev rec, forecasting, KPI dashboards, PLG, consumption pricing, and Marten’s “speeding tickets vs. parking tickets” framework for moving fast without losing control.

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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 tim...

In this episode of Run the Numbers, CJ breaks down how stock exchanges became the operating system of modern capitalism. From ship captains raising voyage money, to the Dutch East India Company’s first tradable shares, to coffee house traders, the Buttonwood Agreement, market crashes, Robinhood, and GameStop, this is the story of how markets turned ownership into something liquid, global, and very, very human.

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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...

In this episode of Run the Numbers, CJ sits down with Ryan Roccon, CFO of Zapier, to cover AI hiring standards, automating month-end close, measuring ROI on AI spend, and why determinism still beats agents most of the time.

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SPONSORS:

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build th...

In this episode of Run the Numbers, CJ sits down with Aurélien Nolf, CFO of Navan, to unpack how to pre-align before budgeting, how to think about portfolio construction inside a company, when to fund or kill internal bets, how IR is becoming more connected to FP&A, and where AI actually works inside finance teams.

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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...

In this episode of Run the Numbers, CJ breaks down SpaceX’s S-1, unpacking what the filing reveals about Starlink, xAI, X, common control accounting, revenue, losses, CapEx, and Elon Musk’s Mars-linked compensation structure.

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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/CJ

Rillet is an AI-native ERP built for modern...

In this episode of Run the Numbers, CJ sits down with ParkerGale Operating Partner Paul Stansik to break down five ways CFOs can help build a better sales engine: making the budget mean something, improving forecasting, sharpening metrics, getting involved in key RevOps moments, and building real trust with sales.

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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...

In this episode of Run the Numbers, CJ sits down with Figure Technologies CFO Macrina Kgil to break down how Figure’s business model works, why traditional lending remains so bloated, and how speed in origination and funding flows through financial performance. They also cover stablecoins, blockchain as invisible infrastructure, AI in accounting, and scaling finance with fewer than 35 people.

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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...

Cerebras is going public with the largest commercial chip ever built, $510M in 2025 revenue, and a $24.6B backlog mostly tied to OpenAI. CJ breaks down the company’s wafer-scale AI bet, why inference changed the story, the strange customer-investor-lender relationships behind the IPO, and the big question: is Cerebras the next NVIDIA-style infrastructure winner, or a concentrated hardware company with a very expensive cloud pivot?

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SpendHound 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 pric...

David Bell, co-founder of Idea Farm Ventures and early investor behind Warby Parker, Harry’s, and Diapers.com, and CJ break down how consumer investing works. They cover why durable consumer companies require more than clean unit economics, how to apply SaaS-style thinking to businesses without contracts, and why the best opportunities often live in boring gray space.

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SPONSORS:

EY 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 buildi...

CJ turns the mic on the people behind Mostly Media for a special behind-the-scenes episode of Run the Numbers. Michelle, Callie, Sarah, Matthew, Ben, and Steve share what it’s like building the company, scaling media, talent, sales, production, and operations, and dealing with CJ’s scooter lore, calendar quirks, and chaos along the way.

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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 financ...

In this episode of Run the Numbers, CJ Gustafson breaks down the diamond industry as a business model: how De Beers controlled supply, engineered demand, and built one of the most powerful pricing machines in history. From the Central Selling Organization to “A Diamond Is Forever” to the rise of lab-grown diamonds, this episode unpacks monopolies, scarcity, pricing power, and what happens when technology forces transparency.

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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 upgrad...

In this episode of Run the Numbers, CJ Gustafson sits down with Angela Chen, former CFO of The North Face and Mars Veterinary Health, to unpack how finance leaders build and scale iconic consumer brands. Angela shares how to measure brand equity, why the CFO should act as an architect of growth, and how capital, talent, and strategy connect inside a scaling business. They also get into humanistic leadership, consumer-margin tradeoffs, and what a 39-cent Taco Bell taco can teach finance teams about growth.

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Aleph is a modern FP&A platform built fo...

In this episode of Run the Numbers, CJ sits down with PSG Managing Director Chris Nesbitt to unpack how great deals are actually found, how investment decisions are really made, and why narrative often matters more than most investors admit. They also dig into forecasting, boardroom authenticity, simple vs. complex models, and the roles of market, product, and leadership in driving outcomes.

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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 mo...

In this episode of Run the Numbers, CJ sits down with Manu Diwakar, CFO of Virta Health, to unpack why health tech breaks traditional SaaS thinking. They get into the realities of running a business where outcomes matter, half the company are medical professionals, and efficiency can’t come at the expense of care. It’s a conversation about sustainable scaling, smarter reinvestment, and building for durability over hype.

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SPONSORS:

SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all yo...

In this episode of Run the Numbers, CJ sits down with Praveer Melwani, CFO of Figma, to unpack the financial model behind one of tech’s most iconic product-led companies. They cover viral growth, forecasting without a traditional sales pipeline, AI credit pricing, margin tradeoffs, and the metric Praveer believes matters most in the long run: free cash flow per share.

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SPONSORS:

EY 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 f...

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.

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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...

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. 

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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/CJ

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.

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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 fas...

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.

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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. Jo...

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.

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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 sp...

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.

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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 operat...