Skip to content
The Twenty Minute VCThe Twenty Minute VC

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

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

Miles GrimshawguestHarry Stebbingshost
Sep 17, 20231h 43mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Miles Grimshaw Redefines Venture, AI Copilots, And Founder Partnership

  1. 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.

IDEAS WORTH REMEMBERING

5 ideas

Anchor investing in the user, not in metrics or jargon.

Despite the abundance of SaaS metrics and frameworks, Grimshaw insists the core question is always, 'Who is the user and why do they care?' Data should validate a thesis, not be the source of it.

Think of venture as a long-term commitment, not a series of bets.

His 'five S’s'—sourcing, selecting, signing, supporting, summiting—center on deeply partnering with a founder through strategic planning and company-building, rather than optimizing a funnel of 'deals' and reserving for re-buys.

Will, passion, and rate of learning often trump current skill.

Drawing from Josh Kushner’s approach, he prioritizes 'will over skill' and passion because people who love the work will put in more hours, compound faster, and learn quickly—even if they lack certain concepts (like LTV) at the start.

Best founders don’t “need” VCs, but benefit from trusted, proactive partners.

He rejects the idea that great founders are better off alone; instead, he sees the VC’s job as helping them make a few high‑impact decisions better each year, grounded in trust, context, and proactive engagement (being 'first-to-call,' not just 'first call').

Regret often comes from underweighting markets or misreading how value scales.

His biggest misses (Figma, Plaid, Scale) came from either dismissing a market as too small (design seats) or over-intellectualizing how an ecosystem “should” work, rather than how incentives and real usage actually evolve.

WORDS WORTH SAVING

5 quotes

Kindness and competitiveness don't have to be oil and water in business.

— Miles Grimshaw

It should feel like planning an adventure, not a colonoscopy.

— Miles Grimshaw

I really think of it as making a commitment, not a bet.

— Miles Grimshaw

Copilot is an incumbent’s strategy. The opportunity for startups is to be orthogonal.

— Miles Grimshaw

We’ll move from selling software with an SLA on uptime to selling work with an SLA on outcomes.

— Miles Grimshaw

Miles Grimshaw’s background, early influences, and entry into venture capitalLessons from Thrive and Josh Kushner on talent, kindness, and will over skillBenchmark’s partnership culture, meeting style, and the ‘five S’s’ of ventureHow VCs can (and often don’t) add real value to foundersFounder/market/traction evaluation, regrets on missed investments (Figma, Plaid, Scale)Specialist vs. generalist investors and being a ‘biologist’ rather than a ‘physicist’AI and LLMs: copilot vs. control center, new architectures, and selling work not softwareInfrastructure vs. application-layer AI, LangChain’s role, and current AI investment qualityMarket timing, incumbents vs. startups, and where disruption may actually occurPersonal discipline, endurance running, and how family has changed his perspective

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome