Blackjack Taught Me Everything I Need to Know About Venture Capital Risk Today
Venture capital (VC) has long been seen as one of the most rewarding places to deploy investment capital. Yet today, a growing cohort of market participants are second-guessing whether VC even deserves a spot as a core asset class in their portfolios. In response, many active venture firms have turned to risk reduction strategies, dramatically slowing their pace of new investments.
As a VC myself, my first education in high-pressure calculated betting came not from finance classes, but from the blackjack table. I left the Soviet Union as a child refugee in 1979, and eventually built a new life in the United States. Years later, while studying at MIT, I joined one of the university’s famous blackjack teams. Through disciplined card counting, we won millions of dollars from casinos across North America, and our story inspired the book and hit movie 21. Our tactics were never illegal—casinos simply wanted us banned from their floors, for obvious reasons.
Card counting is neither against the law nor some sort of secret magic trick. It relies on nothing more than a basic probability model and elementary math. As long as every player follows the strategy the algorithm dictates, long-term results become predictable. It is no coincidence that many of my MIT blackjack teammates went on to found billion-dollar companies, or that I ended up building a career investing millions into early-stage tech startups. The core discipline of card counting shares far more in common with risk-taking, technology, and cutthroat entrepreneurship than most people realize.
I never stayed long in the flashy world of casinos. While we walked away with millions in winnings, blackjack is a zero-sum game, just like most trading activity on Wall Street. No new value is created for anyone outside the game. I found infinitely more gratification in investing in and mentoring founders whose products actually improve people’s lives, work that leaves customers genuinely grateful for our support. Fast forward to 2017, I launched my own VC fund focused specifically on startups founded by immigrant entrepreneurs.
Even so, the skills I built counting cards still shape every investment decision I make today—from vetting whether a new product solves a real unmet need, to assessing a founder’s ability to outperform competing teams. The only thing missing from my blackjack days was meaningful purpose, but the core lessons about risk carry straight over to today’s risk-wary VC climate.
At the blackjack table, you only ever see the few cards dealt in front of you—everything else about the remaining deck is unknown. But the gap between a casual gambler and a professional card counter is massive: one plays on luck and emotion, the other plays on data. Card counting doesn’t require superhuman talent, either. We only needed to think in probabilities, memorize simple arithmetic rules, and maintain a decent memory. Every visible card shifts the probability distribution of what’s left in the deck, and with that small set of data, you project the likelihood of different outcomes.
Our edge was extremely slim, usually just 1% to 2% of every dollar we put into play. But we knew one core truth: if we stuck to the disciplined process consistently over time, the math would work out, and we would come out ahead in the end.
