Uploaded December 2025 | Updated September 2026, 1 day ago
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38:49 - Why ‘Crossing the Chasm’ Is Obsolete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: 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: youtube.com/@aleph-vc
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: linkedin.com/in/mieisenberg
Follow Aleph on Twitter: twitter.com/mikeeisenberg
Follow Aleph on LinkedIn: linkedin.com/company/aleph-vc
Follow Aleph on Instagram: 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
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: 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: youtube.com/@aleph-vc
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: linkedin.com/in/mieisenberg
Follow Aleph on Twitter: twitter.com/mikeeisenberg
Follow Aleph on LinkedIn: linkedin.com/company/aleph-vc
Follow Aleph on Instagram: 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
