Startups
Helped
Helped
100+
Companies
Portfolio
Portfolio
70+
Years of
Experience
Experience
30+
Cap Table Expert for Founders:
SAFEs, Convertible Notes & Option Pools Done Right
Avoid costly dilution mistakes, prevent investor disputes, and know your founder ownership before you sign any term sheet.
Cap Table Services for Early-Stage Founders
📊
SAFE & Convertible Note Modeling
Understand how your SAFEs and convertibles will convert and impact founder ownership
🎯
Pre & Post-Money Option Pool Planning
Structure your option pool correctly to minimize founder dilution
📈
Pro Forma Ownership & Dilution Analysis
Model future fundraising rounds and see exactly how your ownership changes
💰
Exit & Liquidation Waterfall Scenarios
Understand who gets what in acquisition or IPO scenarios
✅
Investor-Ready Cap Tables
Clean, professional cap tables for fundraising and M&A due diligence
Don't Let Your Cap Table Break Your Startup
Confusing SAFEs or stacked notes?
Multiple convertible instruments can create unexpected dilution
Unexpected dilution reducing founder ownership?
Option pools and conversion ratios can surprise you at the worst time
Investors questioning your math?
A messy or incorrect cap table kills deals and wastes months
What Clients Say About Working With Bob
Real feedback from founders and companies who've transformed their cap tables
Startup Founder
"Bob is a genius on this stuff. He just knows exactly what's going on—and let's face it, cap tables are not the place to make mistakes. You can't go wrong with Bob. 15 on a scale of 1 to 10!"
Company Founder
"Bob is an amazing professional, with exceptional deep knowledge of cap tables, startups, deal structures, funding, and finance. Our specific situation is complex, and Bob helped us untangle things."
Entrepreneur
"Great working with Bob! He really knows his stuff. Something that seemed very complex, he managed to get done within a few hours."
VC Partner
"Bob is a fantastic VC who gives back to his community and helps up-and-coming companies succeed with his insight. He is very easy to work with, and this was an educational experience."
CEO
"Excellent service with a consultative approach. It felt like working with a partner and not a freelancer. Bob's work exceeded expectations with unparalleled professionalism."
Tech Founder
"Bob clearly knows his stuff. A few hours of his time will definitely pay dividends. I recommend all people looking to raise funds to have a chat with Bob."
Not Ready for a Call?
Get Bob's checklist
"Top 10 Cap Table Mistakes Founders Make (and How to Avoid Them)"
Get Bob's Free Cap Table Essentials Checklist
Instant access. No spam. Learn from 30+ years of cap table expertise.
Meet Bob Gillespie
Your Cap Table expert with deep experience in helping startups and growth stage companies manage their cap tables
✓
3x founder (CEO, COO, CFO)
✓
Expertise in varying equity instruments and
structures
✓
Expertise working with companies from formation
through growth equity fundings
✓
Deep knowledge working with SAFEs, convertible notes, options, warrants,
proforma cap tables and equity deals
✓
University of Chicago Booth MBA
Bob Gillespie
Cap Table Expert Consultant