

Investor Stories 423. From Checklists to Leadership: Lessons from iFLY, DFJ Growth & Pismo Leaders (Shen, Schuler, Binatti)
Aug 28, 2025
Dive into the intriguing parallels between aviation and venture investing, where checklists play a crucial role in risk assessment. Explore the challenges faced by CEOs transitioning to investors, along with the rewarding experience of mentoring young entrepreneurs. Discover the vital importance of transparency in leadership, as personal stories illustrate how open communication fosters collaboration and engagement within teams. Each contributor shares their key lessons, making for an enlightening discussion on the nuances of leadership and investment.
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Checklists Before You Commit
- Han Shen compares piloting pre-flight checklists to venture due diligence as a personal heuristic.
- He often cancels flights or deals when he spots unexplained red flags on instruments.
Not Investing Is A Decision
- Assessing and mitigating risk matters more than loving risk when investing.
- Choosing not to invest can be as important as choosing to invest.
Coach, Don't Command Founders
- Treat founders as partners and use your scars to guide, not dictate, their decisions.
- Help teams arrive at answers by communicating in ways that make them want to respond positively.