Run the Numbers (CJ Gustafson)

Recent Episodes

1. How to Sell Your Company: A Multi-Time CFO's Full Playbook | Rick Smith

   Sep 17, 2026

   Rick Smith, founder of Bonfire Advisory and author of Six Months to the Sale, discusses the M&A process for selling a company. He covers valuation mechanics (ARR vs. EBITDA multiples), why being slightly profitable can paradoxically hurt a sale, the dynamics between strategic and PE buyers, and the human challenges CFOs and employees face during acquisitions. The conversation draws heavily from Smith's novel-based approach to teaching M&A, blending real deal experience with narrative storytelling.

2. Masterwork’s CFO Runs 12 AI Agents at Once | Nigel Glenday

   Sep 14, 2026

   Nigel Glenday, CFO and COO of Masterworks, discusses how AI is transforming day-to-day finance operations. He emphasizes that context engineering matters more than model selection, shares how his team processes 300,000 K-1 forms using Python instead of expensive off-the-shelf solutions, and explores how AI is reshaping the skills required for finance professionals in the age of intelligent agents.

3. How Oura Built a $1.4 Billion Business Around a Tiny Ring

   Sep 10, 2026

   CJ Gustafson breaks down Oura's S-1 IPO filing, analyzing the Finnish health wearable company's path to a $1.4 billion valuation on the back of 74% YoY revenue growth and profitability. The episode covers Oura's integrated hardware-plus-subscription business model, customer retention metrics, go-to-market strategy across DTC and retail channels, and key risks including Samsung's patent dispute, battery warranty liabilities, and concentrated customer receivables.

4. What 20 Years of Software Investing Says About AI | Matt Hedberg

   Sep 7, 2026

   Matt Hedberg, a sell-side equity analyst at RBC with over 20 years of software coverage, discusses how AI compares to the cloud transition and what separates winning management teams. He explores how traditional software moats are shifting in the AI era, the importance of technical leadership, and why customer relationships, data, cash, and organizational structure matter more than ever for companies adapting to AI.

5. Andy Ellis: How to Lead Without Becoming the Hero, the Villain, or the Bottleneck

   Sep 3, 2026

   Andy Ellis, leadership coach and former Chief Security Officer at Akamai, discusses counterintuitive leadership practices including why leaders shouldn't automatically backfill departing employees, the dangers of becoming indispensable, and how hero-villain narratives distort organizational decision-making. Ellis shares practical advice on delegation, budget allocation, metrics design, and making expensive time worthwhile, drawing from his book "1% Leadership."

6. 40 Years of IPOs with Jay Ritter: What the Data Actually Says

   Aug 27, 2026

   Jay Ritter, director of the IPO Initiative at the University of Florida and the leading academic researcher on IPOs, discusses 40 years of IPO data and trends. The conversation covers three waves of technology-driven IPOs (personal computers, internet, and AI), why companies are staying private longer, the economics behind underpricing and day-one pops, and what long-term IPO performance data reveals about market efficiency.

7. How AI Is Rewriting Product-Market Fit, Pricing, and Go-to-Market

   Aug 24, 2026

   CJ hosts a live panel discussion on a Soho rooftop with three AI-native founders: Rebecca Schwartz (Tabs), Fred Havemeyer (Fleet AI), and Rahul Rekhi (Rogo). The conversation centers on evolving product-market fit in the age of AI, scaling go-to-market strategies, pricing model experimentation (usage-based vs. subscription), and the operational challenges of managing token costs and customer success at rapid growth stages.

8. The Stripe Guide to Pricing, Billing, and Quote-to-Cash with Wisam Hirzalla

   Aug 20, 2026

   Wisam Hirzalla, Head of Product at Stripe Billing, walks through the complete quote-to-cash journey—from product packaging and pricing through quoting, contracting, billing, tax, collections, and revenue recognition. The episode traces how pricing decisions cascade into billing complexity, explores emerging pricing models driven by AI (hybrid recurring + usage, credits with auto-topup), and examines why billing has evolved from a back-office function into a core product and revenue strategy problem.

9. The CFO-COO Is Coming: Meredith Finn of Front on the Future of Finance

   Aug 17, 2026

   Meredith Finn, CFO and COO of Front, discusses the dual mandate that increasingly defines modern finance leadership. She explains how the CFO-COO role functions like an architect-general contractor partnership, explores how mature SaaS companies fund and incubate new AI-driven bets, and shares frameworks for budgeting AI token costs during rapid adoption phases.

10. Xero’s CFO: Why Finance Is Taking On More of the Business

    Aug 13, 2026

    Claire Bramley, CFO of Xero, discusses how the modern CFO role has expanded beyond traditional finance into strategy, operations, transformation, and technology. She shares her approach to building diverse, high-performing teams around her weaknesses, her philosophy on AI for small business owners, and why she frames diversity as a capital allocation and business performance decision rather than a compliance issue.