Episode summary
What Charlie Munger Taught Me About Venture Capital
How I Invest With David Weisburd
· · 32 min · Hosts: David Weisburd · Guests: Jamie Montgomery
Summary
Jamie Montgomery argues that venture capital is less about squeezing price and more about choosing the right long-term partner. He says March Capital looks for asymmetric upside, reasonable entry prices, and strong founder chemistry, because the real compounding comes from helping exceptional entrepreneurs build over many years rather than winning a negotiation by a few points.
He also ties good investing to self-awareness. When deciding whether to double down, he says he tries to separate conviction from recency bias, social proof, and valuation anchoring, then build a simple risk curve around downside, base case, and upside. That same mindset, he says, should apply to career building, board work, and even the conference he has grown into a major ecosystem event.
Montgomery is bullish on AI, but he thinks its bigger effect is forcing portfolio companies to reinvent themselves quickly. He believes the venture market has already gone through a 2021 peak, a 2022-23 trough, and a renewed 2024-25 upswing, and warns that liquidity is tightening as hyperscalers absorb more capital. He also argues that California’s growth has been undermined by policy mistakes, even as the state’s economy doubled.
Key takeaways
- Jamie Montgomery says venture returns come from asymmetric upside and alignment, not from winning the last 5% in price.
- He uses a "turkey sandwich test" to judge founder fit because venture requires years of repeated board meetings and close partnership.
- Montgomery says doubling down requires checking for recency bias, social proof, and valuation anchoring before deciding.
- He thinks AI is forcing portfolio companies to reboot operations, cut fat, and rethink growth trajectories.
- He expects venture liquidity to tighten because hyperscalers are pulling capital into infrastructure and away from other categories.
Notable quotes
“You could spend hours on that. I mean, I I think”
“do I want to have 20, 30 turkey sandwiches with this individual, he or she”
“It's important to understand the psychological forces that exist in in investing”
“AI the venture business was kind of going down the drain in 2022. you know, people put a lot of money to work and really bad investments”
How the episode opens
So Jamie, you have 1.65 billion AUM and you've been investor for the last 25 years after being a banker. You used to have a weekly meeting with Charlie Mer. What did you guys talk about?
He did most of the talking. I did a lot of listening. I was probably afraid to say anything for a couple years.
He's just an incredible intellect and he had so many ways of thinking about businesses and life. And uh we first got together uh I was uh at an age of where my father had passed away that year and his wife had passed away and we had a small group of us would get together and we thought well it'd be nice to have breakfast with Charlie and another good friend of his Rick Garren who's a very prominent investor and talented individual to talk about kind of what should we look forward to in life you know in the next 30 years of our lives and I think he was happy to have some younger friends as your turned 90, a lot of your friends have, you know, passed away or no longer active. And, you know, we I think, you know, we kept him young and he shared a lot of wisdom with us.
What did you learn from him? — You could spend hours on that. I mean, I I think — What surprised you the most to hear Charlie say? — Well, Charlie was in the last decade of his life and so he was probably more patient with us than maybe he would have been with people earlier in his life. And so, um, and I I I think he was always very consistent about knowing what your zone of competency is and sticking to that and and not compromising at all on any values or whatnot.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- venture capital relationships
- founder selection
- follow-on investment discipline
- capital cycles and liquidity
- ai impact on venture
Companies and tickers mentioned
- CRWD
- March Capital
- CrowdStrike
- ThoughtSpot
Watch the episode
Watch “What Charlie Munger Taught Me About Venture Capital” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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How I Invest With David Weisburd, this episode and its artwork belong to David Weisburd. Octagon is not affiliated with the show; this page is an independent summary.
