Think Like an Owner Right to Win Series EP.4: AMA with Lindsey Gray and Aaron Perrine - EP.277
Feb 6, 2026
Lindsey Gray, investor at Pacific Lake Partners who advises searchers on fundraising and board-building. Aaron Perrine, investor/operator at Trilogy with deep experience in evaluating searchers and post‑acquisition value creation. They discuss how to pick and narrow industry theses, what signals investors look for in searchers, signs a search is progressing, common deal pitfalls, cap table and board dynamics, and where value is created after acquisition.
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Prove Commitment Not Checkboxes
- Ask yourself why you're doing a search and whether you accept the hard journey ahead.
- Demonstrate past success, curiosity, relationship-building, and grit rather than specific resume boxes.
Prepare For Deep Interviewing
- Expect intensive behavioral interviews that probe drive, EQ, and thesis strength.
- Ask investors what matters to them and what they seek in the partnership.
Structure Should Follow Strategy
- New acquisition labels often mask similar underlying economics and tradeoffs.
- Design the capital structure to fit the strategy, not the label.