About Bob Gillespie

Bob Gillespie is a seasoned entrepreneur, investor, and startup advisor with over 30 years of leadership experience across technology, operations, and venture capital. He has played a pivotal role in launching and scaling startups, building venture portfolios, and leading high-impact accelerator programs across the U.S. and internationally.

Throughout his career, Bob has worked closely with more than 100 early-stage companies. He's known for helping founders master the intricacies of cap tables, pro forma models, pitch decks, term sheets, SAFEs, convertible debt, warrants, option pools, and distribution waterfalls. Beyond just creating deliverables, Bob is a teacher and thought leader—committed to helping entrepreneurs truly understand and confidently navigate their equity and investment structures.

Widely recognized as a leading authority on early-stage deal structuring, Bob brings a rare blend of technical depth, strategic clarity, and mentorship to every engagement. His expertise in modeling and capitalization strategy makes him a trusted partner to both founders and investors.

Today, Bob manages a portfolio of more than 70 investments and serves on the advisory boards of several companies. He's also a lot of fun to work with, bringing passion and energy to every engagement.