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August 18, 2025 39 mins

Frank Williamson, CEO of Oaklyn Consulting, joins Bruce Eckfeldt to explore what happens when a business stagnates—performing decently, but not meeting growth or exit expectations. He shares real-world insights on managing misaligned cap tables, preparing for strategic exits, and dealing with investor pressure. Frank offers clear tactics to transform underperforming assets into saleable opportunities, making this episode a must-listen for founder-CEOs navigating the murky middle of the M&A landscape.

Key Takeaways:

  • If your business can't run without you for two weeks, it's likely not a saleable asset.
  • Separate the "owner" and "operator" roles early to prepare for a successful exit.
  • Mid-performing companies need strategic storytelling and market testing to attract buyers.
  • Investor pressure often stems from their own fund timelines—not just company performance.
  • Framing early buyer outreach as partnerships creates rapport without prematurely signaling a sale.
  • Distinguish between VC (growth-focused) and PE (buyout-focused) when planning capital strategy.
  • A full sales funnel—multiple potential acquirers—is key to creating leverage in dealmaking.
  • Founders must proactively lead the narrative around exit timing, valuation, and deal structure.

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