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Five Founder Fails: Navigating Private Equity

Five Founder Fails: Navigating Private Equity

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In this 35‑minute episode, the hosts break down the five most common pitfalls that founders face when they bring a private‑equity (PE) firm aboard. From overlooked deal structures to the emotional reality of an eventual exit, the conversation is packed with hard‑won lessons, humorous anecdotes, and actionable advice for entrepreneurs who are looking to or already in a PE partnership.

“A founder’s job is to build a company. A PE partner’s job is to unlock value—so you need to know the difference.” – Ed Barton

Navigating private equity is less about groundbreaking innovation and more about precision, preparation, and clarity around expectations. The best strategies collaborate by anticipating disruption, understanding the deal, and being honest with themselves and their partners.

Don’t start with a belief you’ve navigated PE. Question it. Add these notes to your cheat sheet.

🔍 Key Takeaways
1️⃣ Understanding Deal Structures

  • Founders often underestimate the importance of knowing the deal structure.
  • Failing to understand exit strategies can trap founders, leading to economic uncertainty post-sale.
  • Financial modeling accuracy is critical; overly optimistic projections can hurt valuations and future compensation.

2️⃣ Shifting from Founder to Employee

  • After a PE deal, founders must shift from CEO to employee and accept decision-making authority shifts.
  • Leadership transitions can strain relationships if not communicated clearly.

3️⃣ The Trapped Money Trap

  • Founders may end up with trapped equity due to unfavorable deal terms or rollover options.
  • Negotiating clear payout structures upfront is non-negotiable to maximize returns.

4️⃣ Ignoring PE’s Professional Rigor

  • PE firms demand granular financial governance (KPIs, scenario analysis, forecasts).
  • Founders who resist these changes risk losing credibility and control.

5️⃣ Lack of Exit Strategy Awareness

  • Understanding the exit timeline (ranging from 5-10 years) helps founders plan post-sale.
  • Silicon Valley’s or similar PE firms do not mate for life—expect transitions.

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🎙 Podcast – Strategies, PE 101 & witty banter

📚 Book – On‑Ramp to Exit, full deal life cycle

🛠 Resources – Free templates, guides, tools

🔗 LinkedIn – Follow us for fresh PE insights

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Who Are We?

Three insiders. One mic. All things private equity — explained. Hi 👋 We’re Ed, Rory, and Emily — a CEO, a CFO, and a Chief of Staff — here to demystify the world of private equity. Between us, we’ve sat in the founder’s chair, run PE‑backed companies, and worked on the deal side, so we know the wins, the pitfalls, and the jargon (and we’ll explain it).

Through the Private Equity Experience Podcast, our book On‑Ramp to Exit, and a library of free tools and templates, we share real‑world stories, practical strategies, and insider insights to help you navigate every stage of the PE journey — whether you’re leading a portfolio company, joining a deal team, considering PE, or just PE‑curious.

🔗Connect with Ed

🔗Connect with Emily

🔗Connect with Rory

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