Investing Insights and Personal Reflections

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.

Listen to Founders Podcast

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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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