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

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The Twenty Minute VC

Finance, Venturecapital, Tech News, News, Siliconvalley, Technology, Investing, Startups, Business

4.4 • 637 Ratings

🗓️ 18 September 2023

⏱️ 81 minutes

🔗️ Recording | iTunes | RSS

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Summary

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?

Transcript

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0:00.0	If you say, okay, Miles, what do you really look for when you're making a new investment?
0:03.9	I think the biggest one is what's changing, what's new either from their perspective, what's
0:08.7	a gap in the market that's opening up, change but gets the opportunity for new, but gets
0:13.2	the opportunity for dislocation.
0:15.0	I actually even think at early stages like data can be a trap.
0:17.5	The very best entrepreneurs are always making mistakes.
0:20.4	The really great ones are just making new mistakes each time.
0:23.1	Oh my god, I am so excited for this show. So seven years ago, I met Miles Grimshaw in London.
0:29.6	He was an investor at Thrive Capital in New York, not long out of Yale.
0:33.6	I was an unemployed podcaster about a hundred shows into 20 VC at the time, and I always remember the meeting.
0:39.7	Not only was at the start of a great friendship, but he's one of the most insightful and strategic thinkers in venture.
0:45.3	I've wanted to make this episode happen ever since that meeting seven years ago.
0:49.3	It's probably the longest wait time for a single episode, but I'm so thrilled to make this one happen.
0:59.0	Miles Now is a general partner at Benchmark, widely considered one of the best firms in venture. And before Benchmark, Mars was a general partner at Thrive Capital, where he led investments in Airtable, Monzo, Lattis, GitHub,
1:06.0	segment, Slack, and Benchling, to name a few. But before we dive into the show's day,
1:11.2	this episode is brought you by Teegas, the go-to research destination for bold investing.
1:16.1	Teegas curates expert insights, analysis and financial data to give you powerful perspective
1:21.4	for your investment decisions. With lightning fast access to over 60,000 transcripts across
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1:29.5	a wealth of unique insights to fuel your fundamental research, gain perspectives, synthesize
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1:38.1	As a 20-minute VC listener, try it for free at TIGUS.com forward slash gross.
	...

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