Doug Leone - Lessons from a Titan

**Patrick O'Shaughnessy** (0:00)
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Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts and you can access all our podcasts, including edited transcripts, show notes and other resources to keep learning at joincolossus.com.

**SPEAKER_2** (2:08)
Patrick O'Shaughnessy is the CEO and founding partner of PositiveSum and the CEO of O'Shaughnessy Asset Management. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum or O'Shaughnessy Asset Management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
Clients of PositiveSum or O'Shaughnessy Asset Management may maintain positions in the securities discussed in this podcast.

**Patrick O'Shaughnessy** (2:37)
My guest this week is 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 $150 million early stage fund to 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.
Doug, I've heard you interviewed elsewhere and I wanted to start our conversation somewhere a little bit more unique. I'd love you to talk about the heart and mind of Don Valentine. I've learned a lot about him, obviously someone that was influential on you and a key figure in the history of this style of investing, of our style of investing. Maybe start with his heart. What was his heart like?

**Doug Leone** (3:41)
It's truth be known for the first 20 years, I did not know whether he had a heart. It was all pure business. It was all for the cause of generating returns for our clients, most of which are endowments and foundations. So for the first, I would say 15, 20 years, he was visionary, but extremely tough and certainly dedicated to the cause. At his eulogy, I was very amused and interested to find out from his kids that they spoke of him as having his huge heart when he went home. And it was really interesting how he segregated his work life from his home life.
As he got older and developed a sense of history and put himself in perspective of other leaders, there were certain things he did not want to do. He did not want to be one of the older folks that stuck around too long. He had images and knowledge of other leaders, his age or a little younger that were falling asleep in meeting and they're starting to be a drag on their partnerships. He was very cognizant of not wanting to do that. The other thing he was very cognizant of is, boy, how do we leave Sequoia in the best possible place for the next generation? It was interesting that he chose, and I say chose as if he's pointed us out, he had his own subtle way of choosing, assigning Carrie, maybe two of us at 10% more than the other folks. That's how he chose leadership.