Invested by Aleph podcast

USVP GP Jacques Benkoski on What Entrepreneurs Get Wrong About Go to Market, Building Value as an Investor & Why ‘Crossing the Chasm’ is Outdated

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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. Please rate this episode 5 stars wherever you stream your podcasts! 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isn’t Helpful  24:16 - The Wiz Effect 31:20 - Jacques’s Market Entry Strategy 38:49 - Why ‘Crossing the Chasm’ Is Obsolete 47:19 - War Doesn’t Affect Investment in Israel 52:00 - Israeli Trait That Hurts Sales 56:16 - The Galapagos Syndrome RESOURCES Follow Jacques on LinkedIn: https://www.linkedin.com/in/jacques-benkoski-ab9133 “The Market Entry Strategy” Book: https://a.co/d/etw96SX Subscribe to Invested here: https://content.aleph.vc/invested Learn more about Aleph: aleph.vc  Sign up for Aleph’s monthly email newsletter: https://newsletter.aleph.vc/ Subscribe to our YouTube channel: https://www.youtube.com/@aleph-vc/ Follow Michael on Twitter: twitter.com/mikeeisenberg Follow Michael on LinkedIn: https://www.linkedin.com/in/mieisenberg/ Follow Aleph on Twitter: https://twitter.com/mikeeisenberg ‍Follow Aleph on LinkedIn: https://www.linkedin.com/company/aleph-vc/ ‍Follow Aleph on Instagram: https://www.instagram.com/aleph.vc/ CREDITS Executive Producer: Erica Marom  Producer: Myron Shneider, Sofi Levak Video and Editing: Ron Baranov Music and Creative Direction: Uri Ar  Content and Editorial: Kira Goldring Design: Rony Karadi

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