Should founders pitch investors who do not already understand their market?

Matteo Franceschetti · Nov 20, 2023

You should raise only from investors who already hold your thesis about how the world will change, because deals are lost when you have to convince someone of the underlying belief

Hundreds of people passed on Eight Sleep but their eventual investors all already believed technology would dominate sleep — Keith had been talking about it for a decade — so the only question left was whether this was the right team; investors lacking that belief are where he loses the pitch

23:49 20VC: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | What Makes Truly Great Leaders and How They Give Feedback | Do VCs Really Add Value; Lessons from Hard Fundraises with Matteo Franceschetti, Co-Founder @ Eight Sleep

Harry Stebbings · Nov 20, 2023

Founders should avoid having to educate investors, but must still ground a bold long-term vision in unit economics and expanding LTVs through ancillary products

Pitches that require educating the investor are too hard to sell, and the dislocation between vision and reality shows up in the unit economics

25:09 20VC: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | What Makes Truly Great Leaders and How They Give Feedback | Do VCs Really Add Value; Lessons from Hard Fundraises with Matteo Franceschetti, Co-Founder @ Eight Sleep

Harry Stebbings · Nov 27, 2023

Founders should not try to educate investors — if an investor needs educating on your space, the deal is too hard and you should walk

The gap is just too large to close in a fundraise conversation

44:32 20VC: Keith Rabois and Mike Shebat on Creating an Olympian Mindset to Work Ethic, Why First-Time Founders are Better Than Serial Entrepreneurs, Why Remote Work Does Not Work, Why the Best Founders Always Start in their Teens & Why Companies are Cults?

Keith Rabois · Nov 27, 2023 · hedged

If you find yourself educating an investor, either they notice and immediately get excited, or they don't and you should simply avoid them

44:38 20VC: Keith Rabois and Mike Shebat on Creating an Olympian Mindset to Work Ethic, Why First-Time Founders are Better Than Serial Entrepreneurs, Why Remote Work Does Not Work, Why the Best Founders Always Start in their Teens & Why Companies are Cults?

Harry Stebbings · Jun 20, 2026

If you have to educate an investor on the market, they are not the right investor for you

Scope: Ryan counters that this is tricky when you're doing something genuinely unique

54:25 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport