The Diligent Observer Podcast Episode 50: "Crush the Cost of Diligence" | Serial Entrepreneur Wade Myers on Systematic Founder Scoring, 30 Years of Investment Lessons, and The Future of Angel Investing
Today's episode explores three ideas that caught my attention:
- Binary scoring reduce bias - Wade's yes/no questions (vs typical “tell me a story” questions) help address the "I like every founder" problem.
- Transaction fees align incentives - Wade's preference for paying only when deals close checks out with many other conversations I’ve had in recent years. Perhaps the next evolution for angel investing in community?
- Scarcity really does drive urgency - Wade's amazing “fax machine story” illustrates how scarcity and momentum create investor FOMO.
I explore these ideas and more with Wade Myers, Co-founder and General Partner at Eagle Venture Fund. Wade Myers brings a unique combination of military leadership, strategy consulting expertise, and 30 years of angel investing experience to early-stage capital allocation. As a former U.S. Army Airborne Ranger and Boston Consulting Group veteran with a Harvard MBA, he has invested in 150+ ventures while building systematic processes that filter through 20,000 annual pitches. Currently serving as chairman of a venture studio and partner in multiple investment funds, Wade has pioneered data-driven approaches to founder assessment that challenge the traditionally informal nature of the angel ecosystem.
During our conversation, Wade shares:
- Binary yes/no assessment questions that capture founder culture fit, perseverance, and business acumen without lengthy application essays.
- Why 90% of angel network inefficiency stems from poor founder-investor matching and how marketplace mechanics can solve this problem.
- The allocation strategy conversation every new angel needs - from calculating liquid net worth ratios to identifying where you can add immediate value beyond capital.
Connect with Wade
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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.