Uncomfortable IPO Moments and Real-World Stories

In this episode of Run the Numbers, CJ sits down with Jeff Bernstein, managing partner at Riveron, to unpack what really happens when a company decides it might be time to go public. Jeff draws on his experience across banking, hedge funds, operating roles, and advisory work to break down IPOs, dual-track processes, and the surprising realities behind price discovery—including why a 20x-oversubscribed book isn’t what it seems. He also dives into the re-emergence of SPACs, what’s different this time, and the key considerations CFOs should weigh before choosing that route. From IPO-readiness must-haves to building the muscle memory needed for public-company life to the sketchiest EBITDA adjustment he’s ever seen, Jeff brings stories, frameworks, and hard-won lessons for any finance leader thinking about the road to the public markets.

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LINKS:

Jeff Bernstein on LinkedIn: https://www.linkedin.com/in/jeff-bernstein-498a23158/

Company: https://riveron.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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RELATED EPISODES:

Grindr’s $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantz

https://youtu.be/ijFIMmtpLNw

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:59 Sponsors – Tipalti, Aleph, Fidelity Private Shares

00:06:20 The Mechanics of Going Public at Riveron

00:09:59 The State of Tech Capital Markets

00:11:19 Comparing the Internet, Mobile, and AI Waves

00:14:11 Understanding Dual Track Processes

00:15:34 Sponsors – Metronome, Mercury, RightRev

00:19:35 Why Companies Choose to Go Public or Sell

00:23:02 Why Price Discovery Is Harder in Today’s Market

00:26:05 The Pros and Cons of Direct Listings

00:29:16 Balancing Fairness Between Employees and Investors

00:30:47 Inside the IPO Pricing Process

00:34:26 How Banks and Investors Game Allocations

00:41:22 The Return of SPACs and Why They’re Back

00:43:46 Key Considerations for CFOs Evaluating SPAC Mergers

00:47:53 The Most Successful SPACs to Date

00:49:00 Building Public Company Readiness

00:52:03 Developing Muscle Memory for Quarterly Reporting

00:55:31 The CFO’s Role as Chief Communicator

00:57:47 Long-Ass Lightning Round – Overhyped Metrics and Sketchy EBITDA

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SPONSORS:

Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.

Metronome 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.com

Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.

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#RunTheNumbersPodcast #IPOmistakes #CFOinsights #SPACs #FinanceLeadership

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