Dan Gray, Head of Insights at Equidam, dives into the intricacies of venture capital and its pitfalls. He discusses how top firms concentrate reputation and capital, potentially sidelining unconventional founders. From the perspective of LPs, Dan explores the dynamics of portfolio risk and the debate over whether VC behaviors stem from collusion or incentives. He also emphasizes the importance of 'legibility' in startups and shares insights on emerging managers and innovative funding strategies. Listen for his hot takes on shaping the future of venture.
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volunteer_activism ADVICE
Use Portfolio Size To Enable Contrarian Bets
Construct larger, more diversified portfolios to enable taking idiosyncratic bets without career risk.
Use portfolio math to allow contrarian investments that can produce outlier returns.
question_answer ANECDOTE
Would You Back The Rocket Early?
Grant asked whether Dan would have invested early in a now-obvious breakout rocket company in the 2010s.
Dan admitted he would like to think so, highlighting how non-consensus bets often become the best returns.
insights INSIGHT
Bifurcation: Nerds vs Venture Banks
Venture bifurcates into two strategies: small early-stage contrarian investors and large venture banks funding later legible winners.
Each serves a role, but mixing them causes misaligned incentives and poor outcomes.
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A deeper discussion on the shortcomings (and benefits) of venture
Today we’re interviewing Dan Gray, head of insights at Equidam. We’ve been following Dan’s work throughout the past year and decided to have him on as we begin talking to more LPs about their allocation strategies and perspectives.
Dan’s twitter account is a great follow — he frequently shares lots of data-driven insights and rebukes for a lot of the “tried and true” aphorisms. This episode is filled with hot takes, enjoy!
🔗 Dan’s Bio
Dan is the Head of Insights at Equidam, a platform for startup valuation that helps make unconventional and novel ideas more legible for investors. With two decades of experience in and around startups, Dan’s career spans industrial engineering, gaming, fintech, and animation. He has worked across the startup ecosystem—from startup hubs to accelerator programs—supporting both founders and investors in navigating the complexities of venture capital.
Dan is a prolific writer and commentator on the startup landscape, contributing regularly to Crunchbase News and sharing insights on his blog, credistick.com, as well as on X. His work focuses on demystifying fundraising, startup valuation, and the shifting incentives in the venture capital ecosystem.
Exploring what makes great companies and technologies work. Brought to you by Grant Gregory & Hammad Aslam. Grant is a Partner at Cantos where he focuses on physical world technologies. Hammad is a Partner at Kivu Ventures, Susa’s growth fund. Learn more about the hosts:
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