VCs don’t know how to pick unicorns nearly as well as they claim.
Mahendra Ramsinghani, founder and managing partner of Secure Octane and author of The Business of Venture Capital, joins Brian Bell to challenge the conventional wisdom of venture investing.
We discuss:
Why a cybersecurity startup that raised over $100 million and approached $30 million in revenue was ultimately sold for $1.
How a chance introduction at the RSA Conference eventually produced an 8x investment outcome.
Why a $50,000 check into Demisto generated a 16x return, and how much of that opportunity depended on relationships and timing.
Why VCs who claim exceptional unicorn-picking abilities may be rationalizing luck after the fact.
How an institutional LP rejected Mahendra because investing in his fund threatened the LP’s career.
Why the traditional 20 to 30 company venture portfolio deserves scrutiny rather than unquestioning acceptance.
“Nobody knows. Nobody knows.”
If venture returns depend so heavily on luck, should investors prioritize portfolio diversification over concentrated bets?
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