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Jason Droege: preference

9 Oct 2025 Lenny's Podcast First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege

“I think the way that I look at it that might be additive to the discussion is I look at the underlying incentives of the customer.”

— Jason Droege

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Speaker
Jason Droege
Attribution
Verified speaker
Claim type
preference
Recorded
9 Oct 2025
Publisher
Lenny's Podcast

Transcript context

…This episode is brought to you by Mercury. I've been banking with Mercury for years, and honestly, I can't imagine banking any other way at this point. I switched from Chase and holy moly, what a difference. Sending wires, tracking spend, giving people on my team access to move money around so freaking easy. Where most traditional banking websites and apps are clunky and hard to use, Mercury is meticulously designed to be an intuitive and simple experience. And Mercury brings all the ways that you use money into a single product, including credit cards, invoicing, bill pay, reimbursements for your teammates and capital. Whether you're a funded tech startup looking for ways to pay contractors and earn yield on your idle cash, or an agency that needs to invoice customers and keep them current, or an e-commerce brand that needs to stay on top of cashflow and access capital, Mercury can be tailored to help your business perform at its highest level. See what over 200,000 entrepreneurs love about Mercury. Visit mercury.com to apply online in 10 minutes. Mercury is a FinTech, not a bank. Banking services provided through Mercury's FDIC-insured partner banks. For more details, check out the show notes. Okay, let's move on from AI. This could be an endless discussion about AI, but you've got a lot more lessons to teach us. You've helped build Uber Eats, you've had a couple startups in the past. We talked about Scour for a bit. I've talked to a bunch of people that have worked with you over the years, and I got a lot of really interesting insights into the stuff that you're extremely good at. So I'm just going to go through a bunch of these. One is your obsession with being close to customers, talking to customers, and I love this topic because it's something everybody thinks they're great at, and they feel like they completely understand how this is important, why this is important. They all feel like I'm doing this, don't worry about... Everyone else is not doing this, but I am. Talk about just what you think maybe people miss about how this looks when you're doing it well, and just why this is so important. I mean, I probably fall in the category of what you just described, which is maybe part of the hubris you need to start anything new. But I mean, I don't think it's a clean process. I think my process is I'm constantly questioning every single thing that I'm hearing at the beginning of anything. I don't take what a customer says literally. And there's been a lot talked about on this topic from a product management standpoint in terms of like, oh, don't do what they say, do what they mean, and look at the real problems and underlying things. I think the way that I look at it that might be additive to the discussion is I look at the underlying incentives of the customer. And the underlying incentives of customers are not always financial. Sometimes it's ego, sometimes it's career growth. If you're selling enterprise software to someone, there's an executive sponsor as an example, that person needs to trust that you're going to do a good job for them. How do you get them to jump with you on this big project? Well, that's part of the journey of not just the product, but what do they need to hear from us? What do we need to supply them? What do we need to do to actually unlock the opportunity to implement the product? So I think there's an incentives alignment baseline. I'm a big believer that it's cliche, but show me the incentive and I'll show you the outcome. I think that's absolutely true. And even when customers will tell you things, I'll give you an example. I've been out of the game for a while so I can be open about it, Uber Eats. So when we launched Uber Eats, I looked at the business in terms of being close to the customer. We actually couldn't get a restaurant tour. I knew nothing about this industry. So at Uber, my job was to figure out what other businesses we should get into. And so, we looked at a billion businesses and Uber Eats, food delivery was the one that we thought was most interesting, which turned out to be right so good for us. Very right.…

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