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, a General Partner at the prestigious Benchmark, shares his invaluable insights from years of venture capital experience. He discusses the five core pillars of successful VC, emphasizing the most critical aspects of sourcing, selecting, and servicing investments. Miles reveals his biggest lessons learned from missed opportunities like Figma and Plaid, highlighting the pitfalls of relying too heavily on data. He also delves into the transformative power of AI in business models and the emerging trends shaping the tech landscape.
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Early Inspiration
Miles Grimshaw's stepfather founded an e-commerce software company, inspiring his interest in startups.
Witnessing his stepfather's entrepreneurial journey fueled Grimshaw's passion for working with founders.
volunteer_activism ADVICE
User-Centric Approach
Focus on the user and their needs, not just metrics and jargon.
Write a hypothetical product launch announcement to stay grounded in user value.
insights INSIGHT
Kindness and Competition
Kindness and competitiveness can coexist in business.
Belief in someone's potential is a powerful gift.
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This book recounts Cathy Freeman's journey from a little girl who loved to run to a world champion athlete. It includes her experiences growing up in a loving family, her relationship with her severely disabled sister who inspired her, and her rise to the top in athletics. The book also touches on the challenges she faced, including racism and personal losses, and how she overcame them through hard work, self-belief, and the support of her family. The narrative is honest and simple, making it relatable to young readers. The book is accompanied by black and white photos, some of which are family shots, adding a personal touch to the story[2][4].
Working Backwards
Insights, Stories, and Secrets from Inside Amazon
Colin Bryar
Bill Carr
Working Backwards provides a detailed look at Amazon's approach to culture, leadership, and innovation. The book is written by Colin Bryar and Bill Carr, who collectively have 27 years of experience at Amazon. It outlines the company's 14 leadership principles and how they are applied in practice, focusing on customer obsession, long-term thinking, and operational excellence. The book is divided into two parts: the first part explains the leadership principles and practices, while the second part includes case studies on the development of products like Kindle, Amazon Prime, and Amazon Web Services. The authors provide practical steps and insights that can be applied to any business, regardless of size or industry[2][4][5].
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?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 
