Sailing lessons for investing

Jacques shares sailing analogies: early leads can vanish when conditions change and timing matters more than early starts.

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Episode notes

On this episode of Invested, Michael sits down with Dr. Jacques Benkoski, a seasoned technologist, operator, and venture capitalist with a career spanning research, corporate, startups, and international investing.

As a partner at U.S. Venture Partners (USVP), Jacques brings decades of experience investing in the U.S. and Israel across cloud infrastructure, enterprise software, and cybersecurity. A speaker and mentor, he has taught his Market Entry Strategy seminar to over 5,000 entrepreneurs and released an expanded version of these materials in the eponymous book to help entrepreneurs turn vision into execution, and scale with purpose.

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KEY TOPICS

00:00 - Intro

03:59 - Riding the Dot-Com Wave

08:09 - Joining USVP & the Israel Strategy

12:06 - Bubbles Are Good

14:50 - AI Adoption Will Follow Workflows, Not Replace Them

17:44 - 95% of AI Projects Fail - and That’s Normal

19:21 - Israel’s Biggest Founder Weakness

20:45 - Why Being Founder-Friendly isn’t Helpful

24:16 - The Wiz Effect

31:20 - Jacques’s Market Entry Strategy