50 Chairs Playbook: The Founder's Guide to Pitching
Ryan and Mike from the Veteran Fund reveal what really matters when pitching, fundraising, and building a company that lasts. Unpack actionable insights for founders looking to raise capital and build meaningful products.
Bet on the Jockey: What Great Investors Look For
Team Trumps Tech
At the early stage, VCs are investing in people, not just ideas. Show your domain mastery—why you're the right person to build this.
Relationship First
Build the relationship before the pitch. Lead with who you are and demonstrate follow-through, even in email responses!
"We're betting on the founder, not just the product."
Conviction is Contagious
The founders who win are those who believe so deeply in what they're building that others can't help but join. Be crystal clear on your why—what you're fighting for.
- Let your personal story anchor your pitch
- Make your conviction visible in how you speak, build, and show up
"Conviction turns the light on in others."
Investor Meetings Are Relationships, Not Transactions
Connect Personally
Use the first 2-5 minutes to build rapport
Structure Together
Ask how they'd like to structure the call
Create Dialogue
Make it a conversation, not a monologue
"This is a people business. Make it a conversation."
The Power of Persistence
The best founders follow up with clarity, professionalism, and purpose. It's not annoying—it's how deals get done.
- Send monthly investor updates—even if you're not raising yet
- Be politely persistent. One LP came in after the 12th follow-up
- Don't mistake silence for rejection
"Follow-up with class. It shows you're serious."
Build a Tribe, Not Just a Cap Table
Shared Values
Choose investors who share your values and vision. Great VCs want founders they can walk with for 10+ years.
Strategic Selection
Know who you want at your table before you raise. Consider: would you fly across the country for this person?
"We don't just invest in companies. We build a tribe."
The Perfect 30-Minute Pitch Meeting
1
Minutes 1-3
Build rapport. Ask about their background.
2
Minutes 4-6
Your founder story—why you?
3
Minutes 7-15
Walk through deck. Emphasize traction, vision, market.
4
Minutes 16-25
Open Q&A. Make it interactive.
5
Minutes 26-30
Confirm next steps. Set expectations.
Final Thought: VC is a Human Game
Whether you're pitching to the Veteran Fund or another firm, remember: conviction, character, and clarity win. This isn't just about raising money. It's about raising the right partners for the long haul.
Look out for Playbook #3, breaking down lessons from the next founder at the intersection of grit, vision, and real-world action.
© 2025 50 Chairs. All rights reserved.