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.

Links & Resources

• Frank Williamson

  LinkedIn: https://www.linkedin.com/in/fwilliamson/ Website: https://oaklynconsulting.com/

• Subscribe to the Podcast:

  • Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode.

• Newsletter & Exclusive Content:

  • Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates.

• Connect with Bruce & the Community:

  • LinkedIn: Bruce Eckfeldt

  • Instagram: @bruce_eckfeldt

  • Email:

    • podcast@eckfeldt.com

    • bruce@eckfeldt.com