Invest Like the Best with Patrick O’Shaughnessy
Business:Investing
This week we are replaying our episode with Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear. Please enjoy my great conversation with Doug Leone.
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For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
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Show Notes
[00:03:21] - [First question] - What Don Valentine’s heart was like
[00:06:30] - The most productive and unproductive parts of Don’s toughness
[00:10:55] - Why it’s so important to understand someone’s core motivations
[00:14:18] - Questions or topics he returns to when getting to know people
[00:16:44] - The most formative experiences he had prior to becoming an investor that impacted his investing the most
[00:20:37] - What venture looks like to him today relative to his prior career
[00:23:51] - His style of approaching emerging technology markets like AI as an investor
[00:26:37] - Whether or not he’d go into venture today if he was in his late 20s
[00:28:30] - Commonalities between the very best at going to market effectively
[00:31:11] - The key components of great product positioning
[00:37:15] - How interacting with companies early on has changed over the ears
[00:41:12] - Whether or not new entrants into venture should build firms with enterprise value
[00:46:14] - Sussing out the killer gene in somebody
[00:49:04] - How successful people can instill the lessons learned from hardship into their children
[00:53:52] - Whether or not his view on competitive advantage has changed
[00:55:21] - The early 2000s clawback at Sequoia and what navigating that period was like
[01:00:40] - The most interesting question an LP has ever asked him
[01:05:00] - Which dinner companions he’d pick to educate a newly successful founder
[01:07:59] - The kindest thing anyone has ever done for him
Madhavan Ramanujam - How to Price Products - [Invest Like the Best, REPLAY]
Daryl Morey - Systems Thinking in Sports - [Invest Like the Best, REPLAY]
Michael Ovitz - Knowledge Is Power - [Invest Like the Best, EP.359]
Erik Serrano - Investing in Investment Firms - [Invest Like the Best, EP.358]
Justin Ishbia - Lessons from Acquiring 586 Companies - [Invest Like the Best, EP.357]
Gavin Uberti - Real-Time AI & The Future of AI Hardware - [Invest Like the Best, EP.356]
A Conversation with Charlie Munger & John Collison - [Invest Like the Best, EP.355]
Peter Fenton & Victor Lazarte - Purpose and Partnership - [Invest Like the Best, EP.354]
Lior Susan - Leave the World Better than You Found It - [Invest Like the Best, EP.353]
Brad Jacobs - Think Big and Move Fast - [Invest Like the Best, EP.352]
Elizabeth Zalman & Jerry Neumann - Founder vs Investor - [Invest Like the Best, EP.351]
Palmer Luckey - Inventing the Future of Defense - [Invest Like the Best, EP.350]
Aswath Damodaran - Making Sense of the Market Pt. 2 - [Invest Like the Best, EP.349]
Patrick Collison & John Collison - A Business State of Mind - [Invest Like the Best, EP.348]
Strauss Zelnick - Playing to Your Strengths - [Invest Like the Best, EP.347]
Rick Buhrman & Paul Buser - Find Your X, Nurture Your N - [Invest Like the Best, EP.346]
Jack Altman & Miles Grimshaw - Building and Investing in Lattice - [Invest Like the Best, EP.345]
Michael Simanovsky - A Platform Approach to Real Estate - [Invest Like the Best, EP.344]
David Senra - In Service of Founders - [Invest Like the Best, EP.343]
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