Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy, Josh Kushner
[00:00:00] S0: To the extent that you have, how do you help usher people from the spark of motivation that comes from insecurity to the more abiding source of motivation that comes from passion or joy? [00:00:00] S1: Just from personal experiences, I've seen a couple of times – whether it be through some of my family's troubles or association with politics – that external validation can be very dangerous and it also can be very fleeting. What is the point in trying to prove something to someone else or caring about what other people think in reality, if they don't really care that much at all? A lot of the people that are at the firm I think have made that transition. They all started with this desire or feeling like they had to prove something to someone else. One of the things that I've been able to impart on people is you'll never win if that's the ultimate goal. [00:00:00] S0: Maybe a click more about the culture of Thrive. It's so interesting that Miles was with you from the beginning, went to one of the other great venture firms, Benchmark, came back to Thrive. I'm so curious about the ways that you can keep the culture to its most essential elements.
· Patrick O'Shaughnessy, Josh Kushner
[00:00:00] S0: Maybe a click more about the culture of Thrive. It's so interesting that Miles was with you from the beginning, went to one of the other great venture firms, Benchmark, came back to Thrive. I'm so curious about the ways that you can keep the culture to its most essential elements. [00:00:00] S1: We've always believed that artists like to live in artist colonies, and it's our job to ensure that we have the right people within the organization that are constantly pushing us forward, and pushing us to learn as much as we can. The things that we look for in the people that are at the firm are very similar to the things that we look for in the founders that we hope to partner with, which is self-awareness, humility, drive, ambition. One of the things that I'm most proud of within the organization is this incredible open-mindedness to the idea that we have just a tremendous amount to learn. Many people view vulnerability as a sign of weakness, but if you are willing to say, "I don't know the answer", that is actually the most extraordinary sign of confidence. We've always had this orientation that the only way to have a team is to have a small team, and the only way to have a small team, is to have a group of people that everyone mutually respects. If you respect everyone else around the table, the conversations are really oriented towards trying to get to the right answer. It's impossible for us to make the right decisions every time, but we can ensure that we have the right conversations.
· Josh Kushner, Patrick O'Shaughnessy
[00:00:00] S1: We've always believed that artists like to live in artist colonies, and it's our job to ensure that we have the right people within the organization that are constantly pushing us forward, and pushing us to learn as much as we can. The things that we look for in the people that are at the firm are very similar to the things that we look for in the founders that we hope to partner with, which is self-awareness, humility, drive, ambition. One of the things that I'm most proud of within the organization is this incredible open-mindedness to the idea that we have just a tremendous amount to learn. Many people view vulnerability as a sign of weakness, but if you are willing to say, "I don't know the answer", that is actually the most extraordinary sign of confidence. We've always had this orientation that the only way to have a team is to have a small team, and the only way to have a small team, is to have a group of people that everyone mutually respects. If you respect everyone else around the table, the conversations are really oriented towards trying to get to the right answer. It's impossible for us to make the right decisions every time, but we can ensure that we have the right conversations. [00:00:00] S0: Why are small teams such a key concept for you? Why do you think they're so powerful? Why don't you have a hundred person investment team?
· Patrick O'Shaughnessy, Josh Kushner
[00:00:00] S0: Why are small teams such a key concept for you? Why do you think they're so powerful? Why don't you have a hundred person investment team? [00:00:00] S1: Since the early days, I really wanted Thrive to feel like a company. I think there's always been this dynamic that has existed within investment organizations, that the investment team is what matters and other people mattered less. Our core belief is we wanted every single person within our organization to be the best possible person in that role. In order to have that, you need to give everyone incredible transparency around everything that you're doing. Give them the autonomy and the responsibility to ensure that, even if they're not within the investment organization, they're helping us get to the right decisions. The reason why we've been able to stay so small, not just as an investment team but as an organization is because across every dimension of our business we have these 10x people. Whether it be in legal, finance, compliance or engineering organization, our portfolio support and impact team. I think people feel like they're responsible for every decision that we are making. They feel pride and authorship around the decisions that we're making.
· Patrick O'Shaughnessy, Josh Kushner
[00:00:00] S0: I was having a conversation last week with a friend about the state of the venture ecosystem and which firms had differentiation. My friend said that he thinks that there's only two firms that have true differentiation, his firm and yours. And that the reason that yours did was that there was no one else willing to make the size of bet, the conviction of the bet, at the stage of the company, at a price. By doing that early, you were the person that people called for this specific thing. How much of that was deliberate? Ooh, there's an opening here to be the only provider of capital in this specific part of the market, versus it just being a natural consequence of you doing you. [00:00:00] S1: It was a natural consequence of the firm being intuitive around where we thought that the world was moving. We think of ourselves as a service provider. We were not looking to put meaningful capital to work. The companies that we were partnered with needed to raise meaningful capital, and in order to be the best possible partner to them, we needed to do whatever we needed to do to support them in that capacity. [00:00:00] S0: But there wasn't some grand meeting of, “No one's providing a billion-dollar check to these big companies, we should do it.” It was more bottom up, it was more company specific.
· Patrick O'Shaughnessy, Josh Kushner
[00:00:00] S0: But there wasn't some grand meeting of, “No one's providing a billion-dollar check to these big companies, we should do it.” It was more bottom up, it was more company specific. [00:00:00] S1: Stripe needed to raise $6 billion or else they had to go public, and it was our job to find a way to get them that capital. OpenAI is a very capital intensive business. It was our job to get them that capital. Same with Databricks. We did not view it from an output orientation. It was an input orientation, which was – our job is to serve these companies. [00:00:00] S0: I think it'd be really fun to review some of the iconic deals that maybe people scratch their heads about through Thrive's history. It seems like when you tell the story of the business and of your investment arc, there are these hash marks of incredibly defining things that you've done. The first one that really, really caught my attention was GitHub, which I think was in Fund Four or something like that. It turned out to be a huge percent of that fund and a very large return, but probably at the time, people were scratching their heads about it. Can you tell me that story in as much detail as possible since it seemed fairly formative?