Right to Win Series EP.4: AMA with Lindsey Gray and Aaron Perrine - EP.277
From Think Like an Owner by Alex Bridgeman
February 6, 2026 · 42 min · Season 1 · Episode 277
About this episode
In this episode, Alex Bridgeman hosts an AMA with Aaron Perrine and Lindsey Gray discussing search, investing, and operating small businesses.
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…
People in this episode
Host: Alex Bridgeman
Guests: Aaron Perrine, Lindsey Gray
Topics covered
- search
- investing
- operating small businesses
- fundraising
- evaluating searcher talent
- creating value in acquisitions
Keywords
- AMA
- small businesses
- investors
- searchers
- acquisitions
- capital structures
- board value
Mentioned in this episode
Organizations: Pacific Lake Partners, Trilogy Search Partners
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