Q: What is your approach to life, and how has it played into your success?
A: I have always prized efficiency. Life is short and precious. Know what you want, and then find the simplest, most direct way to accomplish your objective. That’s how I approach life, whether I am negotiating a business deal or scheduling my day. I think this is the most elegant way to think about the value of time. You have to be able to quickly zoom out and look at the big picture, and them zoom back in to focus on specific details. If you get hung up on something that is not important, you could waste a lot of resources and have little to show for it.
Q: You accomplished so much, at a crazy young age—from multi-million-dollar property deals, to two runs at the US Olympic Swimming Trials—all while obtaining a degree from Harvard. What gave you the conviction to act?
A: I forget about the conventional. For me, confidence comes from knowing where I am strong and where I am weak, and aggressively applying my strengths and humbly finding solutions for my weaknesses. This is something I realized very early in life. It’s all about knowing where you want to go and making the right decisions. Success can be non-random. Good decisions come from experience and knowledge, which are similar. Experience comes from repetition and mistakes. Knowledge can come from study. If, through study, you can find a way to make fewer, less costly mistakes, you can save a lot of time. I hate wasting time, so the course I charted at a very young age—maybe 7 or 8—was to study successful people who did the things I wanted to do and already made the mistakes. I read at least a hundred business biographies as a young kid, and that knowledge gave me the confidence to act.
Q: How did you get your start in real estate?
A: Real estate is an extremely opaque, illiquid, fragmented asset class with low barriers to entry, where someone with strong pattern-recognition skills can thrive. I recognized this early on, but didn’t come from a real estate family, so I had to teach myself pretty much everything. I started studying real estate finance on my own while I was in middle school. Leases, management contracts, levered and unlevered yields, mezz, pref, all that stuff. And then I started cold calling anyone in the business who would pick up the phone. The first guy to finally agree to teach me about buildings was a landscaper who owned some rental properties on the side. Eventually, I found a guy who owned thousands of apartment units and millions of square feet of industrial space. By sophomore year in college, I was doing deals on my own. Don’t get me wrong, I made a ton of mistakes. But I think studying the mistakes of others helped me make fewer of my own.
Q: You went to Harvard and studied history—that seems like a very non-standard major for someone with business aspirations. Why did you choose history?
A: I will admit that it is unusual, and you are not the first person to ask me this [laughs]. Investment analysis and historical analysis have a lot in common. History is all about looking for patterns and inconsistencies, and understanding why situations are the way they are, who is involved, what works, what needs to be fixed. It encompasses people, places, companies, buildings, everything really. If you want to make money, study the people who made and lost lots of money. And mirror those who got it right. Again, it’s non-random. There are some very successful, very well-known investors out there who were history majors. I know this because I studied a bunch of them.
