The former Postmates CEO built a company to 2,000 employees and a million couriers over 11 years, then learned the hard way that assembling IKEA furniture and handling payroll himself distracted from what mattered. Now at TipTop, he focuses on high-impact work and strong systems instead.
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But, you know, of course, you're also building TipTop now, you know, and started that more recently. So, you know, I guess, you know, looking back, you know, what were some of those learnings from Postmates, you know, as a first-time founder that you've then taken with you as a second-time founder to starting TipTop?
I think there is a question that you had in your document somewhere from, from someone on the chat that, that, that had, that had seen a podcast that I did, I think was Harry Stebbings, where I talked about some of the learnings, what's easier and what's harder. And I said some of the systems You learn more about how to run a company. Obviously, look, Postmates had 2,000 employees when Uber bought the company and a million Postmates that were doing deliveries. We had lawsuits against almost every state and the government. I've seen it all in 11 years as CEO. So what I'm referring to is When we started Postmates, certain things were just like, oh, gotta do payroll, gotta do it myself. And there were, so for her, you care a lot about things that are completely not important to the success of the mission, mostly because you maybe don't wanna hire for it or the tooling wasn't there at the time. But so there are just certain things that I cared about the furniture in the office. Right? What tables, you know? And I assembled the IKEA tables myself, right? I've spent an incredible amount of time trying to find used furniture. This is, this is an example on the smallest things. But if you do something for the first time, there is a lot of these things that you think you have to do, want to do, need to do. And the second time around, you're like, I don't care how this office looks like. Whatever. Let's just get the work done, right? Focus on the things that are extremely important. Focus on what you wanna build. Keep moving. And so it's just a bunch of these things, right?
