Semyon Dukach, the Founding Partner at One Way Ventures, serial entrepreneur, and former leader of the famed MIT Blackjack team, joins me to share his extraordinary journey from arriving in the U.S. as a Soviet refugee to becoming one of New England’s top venture capitalists. We discuss his path from leading the MIT Blackjack team to startup founder to prolific investor. One Way Ventures invests only in immigrant founders and we discussed how he developed that thesis.

We also talk about personal growth, overcoming imposter syndrome, and what it really takes to become an exceptional founder and leader.

Where to find Semyon:

Timestamps:

(00:00) From Pacman to Blackjack: A Unique Journey

(02:58) Lessons from the MIT Blackjack Team

(05:54) Transitioning from Operator to Investor

(08:52) The Immigrant Experience and Entrepreneurship

(11:46) Building Trust in High-Stakes Environments

(14:36) The Power of Immigrant Founders

(17:44) Branding and Recognition in Venture Capital

(28:18) Building a Strong Network for Deal Flow

(31:39) Recognizing Undervalued Immigrant Founders

(34:19) Traits of Extraordinary Founders

(37:07) The Importance of Customer Focus

(38:53) Growth Through Partnership and Experience

(42:23) Navigating the Challenges of Venture Capital

(44:56) Turning Disappointments into Opportunities

(46:19) Dealing with Imposter Syndrome

(47:32) Lessons Learned on the Entrepreneurial Journey

(51:03) The Inner Drive of Entrepreneurship

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#108 Semyon Dukach— MIT Blackjack Team Former Leader, Current VC, Invests Only in Immigrants

From Start-Up to Grown-Up