Should founders spend time trying to win over skeptical investors, or focus only on those who already believe?

Matteo Franceschetti · published 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 · published 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 · published Nov 27, 2023

Founders should not try to educate investors; if an investor needs educating, the raise is too hard to be worth it

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 · published Nov 27, 2023 · hedged

If you find yourself educating an investor, either they recognize the insight and get excited, or 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 · published 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

Bastian Lehmann · published Apr 8, 2024

Founders should walk away from investors they have to convince or educate at length, rather than spending rounds trying to win over the same firm

Capital is unlimited, so time is better spent on people who already believe; deep diligence meetings often end with the VC neatly writing down your unit economics and funding your competitor, and a VC who needs that much conviction will only get harder at subsequent board meetings when you miss numbers

37:16 Walk away from investors who need convincing focus on believers