Invest Like the Best with Patrick O'Shaughnessy
· Gokul Rajaram
In fact, I'll never forget, in AdSense, I think we had some of the largest publishers in the world sign up and start using us on a self-serve basis. And then we engage with them after that. And I think companies like Atlassian… Square, I think we had Nike, signed up for a Square device and self-serve onboarded and started using it in one of their stores. It does two things. One, it makes your product better because these folks, they use the product in ways that you don't expect or anticipate and it forces you – because what is the definition of self-serve? The definition of self-serve is that the customer can onboard, not just use, but onboard and use the product without ever talking to or engaging with a single member of the employee base of the company. So when you do that, that means you have to think about how do they actually get set up with the product. So it really puts a lot of effort into onboarding. Because onboarding is one of those things where most people drop off, if you don't do a good job. And then you've got to get them to a moment of delight very quickly. All of those things, if you're not building a self-serve product, you don't even think about. In a self-serve product, you think about it every day. It's like a consumer product or a self-serve business product. And then second, what it does for you is it opens up the aperture to your customers. Because with, say, 100 salespeople, yeah, you can reach maybe 10,000 customers. But with a self-serve product, with the right word of mouth, you can reach millions of customers. Look at Cursor, for example. It is used in every large company, I bet. Only maybe 1% of companies uses maybe the top-down motion. 99.9% of companies, some engineer got it. Great example is a company, is Figma, actually. After I invested in Figma, I joined Square one and a half years later, I tried to basically push Figma top-down into the design team, because I didn’t design. I said, "You've got to use Figma." Designers refuse to use it. They're using a tool called Sketch. And they said, "We're not going to use it. Sketch is much better." And so I felt, okay, it's not my place to tell them what to use. So I backed off. Two years later, a mid-level design manager came in and they brought in Figma from their prior company and they got it to be used across, and it kicked out Sketch.
· Gokul Rajaram, Patrick O'Shaughnessy
So I think with self-serve, you can get into these things where even there's an incumbent, but you can infiltrate and be an insurgent in a unique and powerful way, which direct sales motion could never produce that. [00:00:00] S0: One of the other dimensions that's changing fast is careers. I'm curious what you think about the sorts of people that will thrive best in this new era. So if you're a person hiring someone, what are the sorts of things that you would place extra emphasis on now in the AI era?
· Gokul Rajaram
[00:00:00] S1: The number one thing I think is going to be the focus on doing and building. I think CEOs have gotten too comfortable over time, and I think this is changing. Hiring middle management very, very quickly and hiring C-level people. Instead, I think you're going to see the rise of AI agents doing a lot of work, but then humans who manage the AI agents and are ICs. So I think what the number one skill that is going to be relevant two years from now, probably even one year from now, is to become a functional expert that knows how to build AI agents to do that function and orchestrate an army of AI agents to do that function well. There was a great article the other day I read about a PM at Meta who's non-technical, but who basically built a bunch of AI agents to do his job as a PM so well that even his engineers are like, "Teach me how to use AI agents well." And so I think that's what you want. You want somebody who is essentially acting as a manager. Not of humans, but of AI agents. And management has to be a full-time job. What I mean by that is if you manage three, five, 10 people, that's not enough. You either need to be managing 50 humans or you need to be an IC. There is something called span of control, which means how many people you manage. And so a span of control of less than 10 should not be allowed at any company at this point. Because think about it, if you're managing even 15 people, maybe you meet with them once a week, that's 15 hours. What are you doing for the other 25, 30, 40 hours? You should be working. So I think you've got to go back to doing. So, I literally – and on the company side, don't hire managers as long as possible. Hire doers, hire builders.
· Patrick O'Shaughnessy, Gokul Rajaram
[00:00:00] S0: What is your favorite way to assess whether or not someone is that? Interviewing them, or learning about them? [00:00:00] S1: Best way is to give them a work project. Engineering does a great job. Engineering has always been a great job. Every company I've been at, they would have engineering coding interviews, programming interviews. [00:00:00] S0: Do stuff.
· Gokul Rajaram
[00:00:00] S1: Yeah, do stuff. Everywhere else, you can just BS your way without doing stuff. So at Square, we established work projects where even for Corp Dev, our work project was give me one company that Square should buy, and analyze the company, and tell us why we should buy it, and tell us what the synergy should be. So the best candidates had to do that. Every function needs to have a work project that you need to put them in a room without AI and get them to do the project, get them to do the work that is ideally very similar to the work they're going to do. For product managers, we would take a product we were thinking about and we would just say, "Here's a product we're thinking about. Figure it out. Should we build it?" The first and most important thing you want for these kinds of things is, especially for customer-facing roles, they need to take the voice of the customer. In other words, they need to justify the why. The best PM candidates rejected the premise completely and they did it in a beautiful way. They went and talked to 10 customers on the street. So brilliant. They said, "I talked to 10 customers. They were all Square users and we found that none of them want this Premium Insights product. So we don't build it. We're going to build this other thing instead." It was amazing. That's what you want to see. You want agency. You don't want people to just say, "Give me what to do and I'll do it." You want people to reject the premise or question the premise in the first place. "Square should not buy a company." That would be great. Why? Tell me why. And so that's the kind of thinking you're looking for.
· Patrick O'Shaughnessy, Gokul Rajaram
[00:00:00] S0: What was Tony's thing? [00:00:00] S1: DoorDash had the best work project ever. He would give people either $10 or $20 and ask them to acquire a thousand customers. A thousand customers for DoorDash consumers. And literally some people would say, "I'm not going to take this challenge. I'm not ready for it or something." And great, if they literally opt out of it. And then some people would take it. Nobody even came close to acquiring a thousand or even a hundred, I think. But the goal was to see how many different things they were able to try in the course of a few hours. Someone went to the gym, printed flyers out and gave it out. People tried all kinds of things, but it was a brilliant way to just filter out people who didn't want to do stuff. [00:00:00] S0: Is there any other advice that you would give the person building the career? We talked about evaluating, and be a builder, and all these sorts of things. How should one think about managing a career in the AI era?