🎙️ Episode 22 is live! This time, we sit down with Bob Gillespie, a three-time founder, accelerator veteran, and “cap table expert,” to unpack the critical but often overlooked mechanics of equity, ownership, and investment structures.

If you’re building or backing an early-stage company, this episode is packed with actionable insights to help you avoid costly mistakes, structure your cap table properly, and prepare for funding or exits.

What do we cover?

1. Cap tables aren’t just paperwork. Bob explains why your cap table is a living, breathing document that requires diligence and ongoing updates—and what can go wrong if you neglect it.
2. Founder and early employee equity. Learn the importance of vesting, cliffs, share classes, and options to prevent “dead equity” and ensure fair ownership distribution.
3. Navigating accelerators and early-stage investors. Bob shares his insider perspective on setting clear goals, understanding option pools, and managing equity while scaling.
4. Avoiding the road to hell paved with good intentions. Missteps in equity allocation, informal promises, and friend-and-family investments can create long-term headaches. Bob breaks down professional approaches to safeguard your company’s structure.

🎧 Tune in for a candid, highly practical discussion on cap tables, founder dynamics, and professional approaches to raising capital.