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Most software companies try to maximize your time on their app to juice engagement. Ramp does the exact opposite. Ramp understands that no one wants to spend hours chasing receipts, reviewing expense reports, and checking for policy violations. So they built their tools to give that time back, using AI to automate 85% of expense reviews with 99% accuracy. And since Ramp saves companies 5%, it's no wonder that Shopify runs on Ramp, Stripe runs on Ramp, and my business does too. To see what happens when you eliminate the busy work, check out ramp.com/invest. OpenAI, Cursor, Anthropic, Perplexity
Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.
My guest today is Dara Khadrashahi, the CEO of Uber. Before Uber, Dara ran Expedia for thirteen years. We start with why he took this job in 2017, and a big part of that story is Daniel Ek, who told him that life is not about happiness, it's about impact. We talk about what the chaos felt like on day one and how his family leaving Iran when he was nine shaped the way he handles pressure today. We spend most of our time on autonomous vehicles and Uber's role as the demand aggregator in a world of physical AI. Dara explains why Uber is a supply led company, what it will take to win, and why he e
Yeah. So I've been in Expedia for thirteen years, CEO working with Barry Diller, and loved the experience and I loved where I was. At the time, Uber was in the news all the time. Right? It was in the business news if you're interested. So obviously, I was reading about the situation at Uber. It seemed pretty chaotic and pretty difficult. And then a headhunter called me out of the blue and said, are you interested in the Uber CEO job? And at the time I said, know, no effing way. Who would even think about it at the time? And I had a considerably lower profile as you can imagine. So I kind of bl
Wow. Okay. So you show up. There's a process. What is the impression on day one through 10 or something like this? Like, what did it feel like?
Complete chaos. Travis had not been at the lead of the company for some period of time. And there was a group of executives, a committee if you want to call that, who had been running the company for a few months. And obviously the company was in the public sphere in many, many bad ways. So lots of things going on both internally, externally. The business itself was very dynamic, hugely competitive. So it would have been difficult enough if there weren't any of the external distractions going on coming into the business, which I think fundamentally was strong, but was going through a lot of ch
How did you do that? You were teaching a college seminar or something, an HBS seminar on a leader bringing and establishing some order and structure in a chaotic situation. What is the how?
The most important how is simplifying the situation and breaking down what seems like an unassailable problem into its component parts. Vector mathematics. If you have a three-dimensional complex interaction, you can just break it down to each dimension. And if you solve each dimension and you bring it all together, you can actually solve pretty complex issues and equations into its component parts. And the same is true in business. When I got int
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