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?