How to Pick the Right Investor with Jeff Bocan

Demo Day Podcast

In this episode of Demo Day, host Sean Goldfaden sits down with Jeff Bocan, Partner at Okapi Venture Capital, to dive deep into the founder-investor dynamic, red flags to watch for, and what truly sets top-performing startups apart.
🚨 Founders: Are you doing due diligence on your investors?
Jeff shares a wild story about a founder who raised a Series A just to remove a toxic investor—and why failing to check references on VCs is one of the biggest mistakes you can make.
This conversation covers:
1. The #1 trait Jeff looks for in founders (and it’s not experience)
2. The only real pattern he’s seen in billion-dollar companies
3. Why positivity is a secret weapon for founders
4. Where AI fits into startup efficiency—and where it doesn’t
5. Fundraising advice that could save your next round
Jeff also opens up about his own journey—from being thrown onto 10 boards in his twenties to scaling a startup from $50M to $250M before a successful acquisition.
If you're a startup founder, aspiring venture capitalist, or just obsessed with the inside game of entrepreneurship, this episode is packed with hard-earned lessons and practical insights.