Expert Opinion

Mastering Cap Tables for Startup Success

Bob on a video interview at Raise & Exit Podcast: Episode 22

By Bob Gillespie Cap Table Expert

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?

  • 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.
  • Founder and early employee equity. Learn the importance of vesting, cliffs, share classes, and options to prevent "dead equity" and ensure fair ownership distribution.
  • Navigating accelerators and early-stage investors. Bob shares his insider perspective on setting clear goals, understanding option pools, and managing equity while scaling.
  • 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.