Jacques Benkoski (USVP): Money, Mentors & The Lost Art of Venture Capital

Jacques Benkoski, Managing Partner at USVP, joins the show for a candid, wise, and insightful conversation on venture capital, company building, and life.

Jacques opens up about:

• Growing up without money and raising kids young
• The emotional moment he finally felt financially secure
• Why are many serial entrepreneurs driven by unresolved childhood scarcity
• Why the venture industry has lost its discipline
• What “original venture capital” actually looks like
• Why founders must choose their customers
• The real role of a mentor (and the one line that changed his life)
• How he thinks about legacy, purpose, and what truly matters

📘 Jacques’ Book: The Market Entry Strategy
A practical, step-by-step guide to choosing customers, differentiating your product, and building a go-to-market motion that actually works.

If you’re a founder, operator, VC, or anyone who appreciates wisdom earned through decades of experience, this episode is for you.