19: Managing Mid-Performer Assets: A Tactic for Founders Facing M&A Stagnation

Frank Williamson, Founder, CEO, Oaklyn Consulting

In this episode of From Angel to Exit, host Bruce welcomes Frank Williamson, founder and CEO of Oaklyn Consulting, a specialized M&A advisory firm focused on complex, smaller deals often overlooked by traditional investment banks. Their discussion dives deep into the underexplored territory of businesses that fall in the middle—not breakout successes, but not failures either.

Frank explains how these companies create challenges for both founders and investors. Often, they’re not structured to be sellable, behaving more like high-paying jobs than scalable assets. This distinction is critical—without separating the roles of owner and operator, founders risk building companies that are difficult to exit. Frank provides litmus tests to help leaders recognize this early.

The conversation also uncovers how investor dynamics shift over time. Early expectations of exponential growth fade, and pressure mounts when projections go unmet. Frank outlines how founders can respond: by identifying strategic buyers, initiating exploratory conversations framed as partnerships, and building a roadmap toward an exit—even if it's 12–24 months away.

He emphasizes that founders don't need to wait for investors to dictate their next move. Instead, they can take initiative, conduct structured buyer outreach, and craft narratives that create urgency—mimicking sales processes but aimed at potential acquirers. Frank also breaks down the distinctions between venture capital, private equity, and strategic acquirers—helping founders better align with the right buyer personas.

Whether you’re in the early planning stages or facing an underperforming portfolio company, this episode offers actionable strategies and mental models to guide your exit journey with clarity and confidence.

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.

Contact Information:

• LinkedIn: https://www.linkedin.com/in/fwilliamson/

• Website: https://oaklynconsulting.com/