Right to Win Series EP.4: AMA with Lindsey Gray and Aaron Perrine - EP.277

In the fourth episode of the show's Right to Win series, host Alex Bridgeman is joined by Aaron Perrine and Lindsey Gray for an AMA-style conversation on search, investing, and operating small businesses. Drawing on real examples from recent deals, they unpack what separates strong searches from stalled ones, how investors evaluate searchers, and where value is actually created post-acquisition. The discussion blends tactical advice with candid reflections on boards, capital structures, and the realities of building durable businesses.

They discuss:

• How searchers can identify and narrow industry theses before and during fundraising
• What investors look for when evaluating searcher talent beyond resumes
• Signs that a search is progressing well, including compounding learning and quality seller meetings
• Common deal pitfalls around quality, valuation, and defensibility
• How boards create value for first-time CEOs and evolving companies

Links:

Pacific Lake Partners

Trilogy Search Partners

Topics:

(00:00:00) - Intro (00:01:54) - Fundraising and identifying industries (00:09:43) - Evaluating searcher talent (00:13:35) - Acquisition models and strategies (00:18:30) - Cap table construction and investor relations (00:20:28) - Navigating investor relationships (00:22:12) - Signs of a successful search (00:24:28) - Key metrics for searchers (00:27:14) - Lessons from recent deals (00:30:42) - Building an effective board (00:35:00) - Creating value in acquisitions (00:38:15) - Desert island CEO picks (00:39:48) - Sports rivalries and fun bets (00:41:45) - Conclusion and farewell