20VC: Benchmark General Partner, Miles Grimshaw on The Five Pillars of Venture Capital, Why Data Can Be a Trap When Early-Stage Investing, Investing Lessons from Missing Figma and Plaid & The New Business Model for AI & Why Co-Pilot is an Incumbent Strate

Miles Grimshaw is a General Partner @ Benchmark, widely considered one of the best venture capital firms in history. Prior to joining the Benchmark Partnership, Miles was a General Partner @ Thrive Capital where he led investments in Airtable, Monzo, Lattice, Github, Segment, Slack and Benchling to name a few.

In Today's Episode with Miles Grimshaw We Discuss:

1. Straight into VC From University: From Yale to Thrive

• How did Miles come to land a role with Josh Kushner and Thrive right out of Yale?
• What are 1-2 of his biggest lessons from working with Josh @ Thrive for 8 years?
• What does Miles know now that he wishes he had known when he started in venture?

2. The Pillars of Venture Capital: Sourcing, Selecting, Servicing:

• What does Miles believe are the 5 core pillars of successful venture capital?
• 1-5, what is his strongest and what is his weakest?
• Does Miles really believe that VCs add value today?
• What are the most clear ways that Miles have seen VCs destroy value in portfolio companies?

3. Investment Decision Making: From Github to Segment:

• What is the single most important question that Miles has to answer to say yes to an investment?
• How does Miles think about both market sizing risk and market timing risk?
• What have been Miles' biggest hits? What did he learn from making those investments?
• What have been Miles' biggest misses? What did he learn from missing Figma and Plaid?
• What have been 1-2 of Miles's biggest lessons so far from working with Bill Gurley and Peter Fenton?

4. AI: What Happens Next:

• Does Miles believe we are in an AI bubble today? How does he assess the landscape?
• Why does Miles believe that the "Co-Pilot" strategy is an incumbent strategy?
• Where does Miles believe the value will accrue; the application layer or the infrastructure layer?
• What does Miles mean when he says the future is in "selling the work and not the software"?
• What business model disruption and adoption disruption does Miles believe AI will enable?
• Why does Miles believe that the analogy of AI to the rise of mobile is wrong?