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
Dev Ittycheria - The Database Evolution - [Invest Like the Best, EP.373]
Nico Wittenborn - Finding the Adjacent Possible - [Invest Like the Best, EP.372]
Mitch Rales: The Art of Compounding - [Art of Investing, Forever Episode]
Marc Lasry - Making Bucks in Credit and Sports - [Invest Like the Best, EP.371]
Bill Gurley & Michael Mauboussin - Putting Theory into Practice - [Invest Like the Best, EP.370]
Tim Ferriss - Curating Curiosities - [Invest Like the Best, EP.369]
Ken Langone - The American Dream - [Invest Like the Best, EP.368]
Robin Dunbar - Optimizing Human Connection (Dunbar's Number) - [Invest Like the Best, EP.367]
Sean Feeney - Reinventing the Restaurant Business - [Invest Like the Best, EP.366]
Dave Fontenot - The Monastery of Code - [Invest Like the Best, EP.365]
Anne-Marie Peterson - The Capital System - [Invest Like the Best, EP.364]
Aravind Srinivas - Building An Answer Engine - [Invest Like the Best, EP.363]
Ali Hamed - Building an Investment Firm - [Invest Like the Best, EP.362]
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, EP.361]
Danny Meyer - The Power of Hospitality - [Invest Like the Best, REPLAY]
Chuck Akre - The Three Legged Stool - [Invest Like the Best, REPLAY]
Alex Telford - Unlocking Innovation in Pharma - [Invest Like the Best, EP.360]
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]
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