Invested by Aleph USVP GP Jacques Benkoski on What Entrepreneurs Get Wrong About Go to Market, Building Value as an Investor & Why ‘Crossing the Chasm’ is Outdated
Dec 3, 2025
Jacques Benkoski, a partner at U.S. Venture Partners, has extensive experience in technology and investing. He discusses the evolving landscape of AI, emphasizing that successful adoption will hinge on adapting workflows rather than replacement. Jacques highlights the concept that bubbles can stimulate innovation, likening past tech bubbles to today's AI surge. He critiques traditional go-to-market strategies, declaring ‘Crossing the Chasm’ outdated, and stresses the importance of understanding true customer needs. His Market Entry Strategy is a vital resource for entrepreneurs.
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From Research To Dot‑Com Exits
- Jacques recounted joining startups after academic research and later leading Monterey Design Systems through the dot-com era and IPO.
- He described raising large rounds, pivoting products, and eventual acquisition by Synopsys as turning points in his career.
AI Echoes The Dot‑Com Buildup
- Jacques sees AI hype mirroring the dot-com buildup where infrastructure preceded adoption by years.
- He warns that rapid investment may outpace real demand, potentially creating a bubble.
Design For Evolving Workflows
- Expect workflows to evolve to leverage AI rather than AI having to perfectly fit existing workflows.
- Design products that assume customers will change how they work to exploit AI capabilities.
