Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061

ℹ️ EPISODE INFO

Released

September 18, 2023

Duration

1h 43m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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. ------------------------------------------- Timestamps: (0:00) Who is Miles Grimshaw? (5:10) Shopify vs Etsy (8:15) 3 Biggest Lessons from Josh Kushner (13:35) Joining Benchmark (17:11) The 5 S’s of Venture Capital (21:27) Benchmark’s Biggest Challenge Today (26:37) Do VCs do more harm than good? (31:16) Founder vs Product vs Market (37:46) How to Work With Your VC Partner (40:45) Where does Benchmark fit in the VC landscape? (43:28) Biggest Lesson from Wins (47:45) Biggest Founder Detection Error (52:32) Why Miles Missed on Plaid (54:29) Specialist vs Generalist (59:03) Investing in AI (1:31:00) Running Advice (1:34:55) Quick-Fire Round ---------------------------------------------- In Today's Episode with Miles Grimshaw We Discuss: 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? 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? 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? 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? ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Miles Grimshaw on Twitter: https://twitter.com/@milesgrimshaw Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact -------------------------------------------- #MilesGrimshaw #Benchmark #HarryStebbings #venturecapital

🎤 SPEAKERS

• Miles Grimshaw

  guest

• Harry Stebbings

  host

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Miles Grimshaw and Harry Stebbings, Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 explores miles Grimshaw Redefines Venture, AI Copilots, And Founder Partnership Miles Grimshaw, Benchmark partner and former Thrive investor, reflects on his path into venture, key lessons from mentors, and his philosophy on how VCs should truly partner with founders. He outlines his 'five S’s' of venture—sourcing, selecting, signing, supporting, and summiting—and emphasizes being a strategist and long-term partner rather than a deal-focused bettor. A major portion of the discussion focuses on AI, where he argues that current 'copilot' products are fundamentally an incumbent strategy, and that the real startup opportunity lies in a new architecture and business model: selling outcomes and work, not seats and uptime. Throughout, he uses case studies like Benchling, Monzo, Figma, LangChain, and Plaid to illustrate lessons on market timing, founder-market fit, and the importance of curiosity and respect in investing.

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