YouSaid · the spoken record

Jason Droege

lines on the record: 93
first: 2025-10-09
most recent: 2025-10-09
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Yeah, thank you. Yeah, yeah, honored to be a guest here. You know, super excited to be with you, especially so early in the journey, or at least my journey here, Lading Scale.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, we didn't sign one. We signed two in one month. So, yes. No, our federal business is doing well. Our enterprise business is doing well. Our international government's business is doing well. There's a lot of demand out there.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, yeah, absolutely. Just go to scale.com, go to our careers page, and we have 250 open roles to the point about we're in business and we're growing. You were hiring a ton of people. Our applications business, our data business is growing, our applications and services business is growing like crazy. And so we're going to need a lot of people to help us on that journey.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, absolutely. I'm at J Drogi, JDR E-G-E at on X. That's probably the easiest way to follow me. Keep up with things. And you can shoot me a DM if you like. And so I think that's how you would keep in touch. And sorry, what was your other question?”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, more practically, we will order mixed greens or tender greens or something like that on a day-to-day basis. But I think the more notable, surprising thing is that despite my initial aversion to working with a global chain, it's a good treat once in a while. You just shouldn't have it all the time.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I order a shocking amount of McDonald's actually, despite original story, it's sort of the family treat in the house. I would say that that's That's probably the tough thing that we order.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Like, I'm gonna wake up tomorrow. Like, this isn't the end. There's another end somewhere. I just find that to unlock me, to be like, okay, there might not be a perfect solution. There might be like an imperfect solution, but it's a solution. So let's just keep going.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, the end is never the end. That's like my favorite internal saying. And it goes to the comments before about survival being a precursor, surviving being a precursor to thriving. You got to survive before you thrive, which is your brain tells you, and along these entrepreneurial journeys, I think this is most applicable. I mean, this is the hardest journey anyone can go on. Like if you go on this journey for five years, like you are mentally harder than like 99.9% of the population, like people don't understand the Chinese water torture of like having self-doubt and like having things go wrong, et cetera. And so, you know, more tactically, you get this when you're working out and, you know, like in a day, like, oh, I'm too tired. Like, I need to stop. But the truth is, is you can keep going and the world's going to keep spinning. So I find in the moments where it's just like the hardest. Where you have this hard decision that seems impassable and your body, you're having this visceral reaction to like, this is not just to remind yourself.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I was actually talking to someone who was working on VO3 and I told him the script thing, and he goes, Oh, actually scripts, yeah, no, like the way the data is formatted in a script, that would actually be very good because, you know, they start with like, you know, set looks dark, interior, this character says it in this raspy voice. And so it gives you all the instructions in the script.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Was shocked. I was just like absolutely shocked that you could just take a picture of a script. And so now I'm thinking about that for like, you know, how do I use these tools for like family videos, like, you know, Some of the grat tools now with making live images more active, I think are like really interesting. I think they need one more step of iteration. But I think those are going to be really like emotionally life-changing for people because just like a little bit of movement in an image from a grandparent or a relative or whatever you haven't seen in a while, it really does make a big emotional impact on you.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“VO3, right? Not totally new, but when I was in high school, I wanted to be a screenwriter. I actually grew up in the Bay Area and everybody was an engineer, but like I wanted to be a screenwriter. And so I went back and I got the first page of one of my old scripts, which not good scripts, but like, you know, I got the first page. I took a picture of the script and I fed it to VO3. And I said, make this scene. And it got it right.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, the formula movie I thought was really good. I mean, you know, it's a classic, you know, classic action movie. I don't think it informs anything in AI or business, but it's good to check out from the craziness of tech once in a while.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“See, I find myself checking myself whenever I get super convicted on something now, I will like be like, okay, what is the list of things that I'm like inclined to do to try to like catch myself? Because I think we're most inclined to have these bad decisions impulsively.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, I think selfish gene road less traveled. I've read more than once. Just, I mean, it's just one of the classic human psychology book. And then I think in business, I think good to great. It's not the read that you're going to be most excited to enjoy on a vacation. But like, it's pretty much right. And I think we should take advice from people who have analyzed these business problems before because not a lot's changed, but we keep acting like everything's changed.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, yeah, absolutely. I mean, I think the really important reason why I'm doing this, the reason why one wants to spend time here outside of wanting to be on the show for a while and being a long-term listener is a long-time listener, excuse me, is there's a lot of amazing work going on at scale. The teams are working super hard. We're delivering a ton of value for our customers. The public narrative has not represented the work that the people here are doing and the work that our customers are doing with what we're doing for them. And I just think that deserves the respect and reward that all those people are putting in. And, you know, we.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“And I'm shocked. And then I'll read it and just double check. But I'm shocked at how good it is. It's just pulling out. There's so much in organizations that is like, I don't know what you want me to say. And I don't know what I need to know. But we each have our own agendas. And so this matching of, and so then there's like this huge broadcast problem where it's like of all of the information you might want to receive, like what's actually important to you. And so I use it a lot for that too.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think number two would be I'll take the internal documents and I'll ask what's the most important thing in this document?”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Talk to it on my way into work. So I think that's probably like the most impactful thing that I use it for that's also relevant to this topic.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Honestly, like when I came into scale, so my history was in consumer and I'd done some application level stuff with government and this space is moving so quickly. AI is my, you know, I use it as a tutor. As these new concepts come up, I have a lot of people in the company who can educate me on the nuances of the technicals of like all of the technical nature of the data and the products, but they only have so much time. And honestly, there's new concepts coming up all the time and I need to stay on top of it. So it might sound crazy, but a large percentage of my job is not dealing with the engineering issues related to AI. I'm managing an organization, but I love understanding it. It's like one of the most enjoyable rewarding parts of my job is to learn from all these AI researchers, but they don't always have the time to do it. So I use it as a tutor. I turn on voice mode and”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I don't think that the core rise of humanity will change. And I think that these things are pretty core to how humans have been successful for a long time.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, but can they learn it? Like, I learned it. So you do have to kind of believe in people a little bit, which is my job, not necessarily their job. And so, you know, I mean, these are people systems. They're not, they're not straightforward rules-based things you can apply.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Can you work across people? Like, are you humble enough to work across? And are you a good leader? And if you just do those three things, you know, I think you have a pretty high chance of success, at least in an organization that I'm running. Because the world's changing, right? So you do need people that are adaptable. So all the experience is not necessarily like one-to-one relevant. And then the working across to your team point, this actually came up with Uber Eats. So like when I was building the Uber Eats management team, I'm not sure if this was mentioned to you from that group. But whenever I would hire people, I was trying to compose almost like an organism of strengths and then like minimize the conflicts. That management team for the most part outside of some of the operations side, but like for the most part, that management team was the same management team from day one when we had nothing to $20 billion. And I just believed that the team knowing each other's strengths and weaknesses and being able to compensate for each other was more important than the classic advice you get around like, well, that person hasn't seen this much scale. And you're like, well.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“As of late, I've developed a more nuanced view of this, which is for certain roles, you absolutely need the right experience in this current market. You see this with researchers, right? Because the market's moving so fast, you don't have time to train up some people. So you actually have to go find people either who have the right relationships with customers that you want to get, or you have to, who might not check other boxes, but like are awesome at that, like might not check the classic boxes that I think you're referencing of like, they're a problem solver. They can grow with a company. They have a high trajectory, et cetera. I would say that that's like 5% of the roles in a company, but like very important whenever speed to market is important. And then for interviewing, I just interviewed for three things and I have to interview across all kinds of like expertise, which is hard. You know, I can't be an expert in everything. And so I reduce it down to just three things, which is like, are you a curious problem solver? And can you articulate that verbally?”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, and it's just like it's madness to actually think about the practicality of that. And so I just didn't spend the time thinking. And then I ended up in this business. The business was profitable. It got to a couple million of revenue or whatever. It paid me a dividend for a while. But it was painful the entire way.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“And I was making real money, and I might have learned more from this business than any other because I started on eBay. And like I was 22 and I didn't really understand that my marshes would come down because anyone can do this. But I was one of the first ones to do it. So I was making a ton of money. And then I built this business. And then I just failed to recognize. I had a lot of hubris. I was like, oh, if I could just buy all the used golf clubs in America, I can be the market maker for prices. And don't do that.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, this is where it nits together on why I try to be so, I think you can spend a little bit of time thinking up front to save yourself a lot of pain downstream. I had this business not worth detailing it. But after the bubble burst in 2001, I'm like, I'm going to self-fund a business. I'm going to build a profitable business. I want to prove that I can do this. And we had started Scour, which had all the things we talked about.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, you ever get on the other side of a high reward high risk decision? It is so painful because you are just cooked. You are done. And often there's no way out”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“And so then the question is when you're in a hype cycle, I would argue that we are right now, everyone wants to go for it and then go for it more and then go for it more and go for it more. And you don't realize like, guys, all of our customers are going to be around in five years. Like they just want us to solve their problems. Like we have to be around to solve their problem for them. And so survival is a precursor to that. So let's not put ourselves in position that could potentially like compromise the enterprise along the way. Doesn't mean don't take risks, but think about how you calculate.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“And there's more to unpack there because I actually think taking highly risky decisions and then having it work out is a weird cultural thing too because then having you train people to do that because it's a very hard thing to take high risk decisions and be right enough because it creates a lot of volatility. But it goes back to my comment about like the most important thing in founders, which is just this ability to persevere through, right? Survival is just part of the game. And most people just give up before they could get their timing right, before they get the right insight with the customer, before they get the right product in the market. And life can change quickly in tech. You can go from being a dog to being a hero in like a very short period of time, but you're on this very, very long journey, but you have to survive for that condition to be met.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Tech is a culture where portfolios are built by investors. And a lot of the narrative is controlled by investors, frankly. Founders obviously participate, but this idea that you should just go for it is consensus. Just go for it. Who cares? Well, I don't know if it's my life and I only have one moment every, you know, to like take a shot, I might want to just not just go for it. Like I might want to think for a little bit and I think the best entrepreneurs I have no data to back this up, but just these are my friends. This is my friend group. I think the best entrepreneurs and the best business owners look at the risk profile of the decisions that they're making and they try to make asymmetrically positive decisions like all along the way. And so oftentimes I feel like we forget about the risk of a decision.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, that's right. I mean, they're playing a slightly different game. Not an expert on Costco. I have spent some time with the company. But they use price as a way to get to scale. Right, and so they're basically saying if we discount, same with Walmart, right? Like, we will get so much volume that we will just take the air out of the room for all of our competition. And so then the question of, okay, so if you have a low gross margin today in two or three years, once you land one of these centers in a market, why won't your margins get eroded? The answer is because we will have already absorbed all of the demand. You try to go to 8% versus 10% gross margin, which I roughly think is what they're gross margin is. That's going to be a really hard business if you already have a habit with a customer. They have already built their weekly trips around you. You already have relationships with suppliers. You already have general managers that know how to stock inventory. That's not a straightforward exercise. So they are first to scale. And then good luck competing with them.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, exactly. And like I said, it's meant to disqualify just like, you know, you're doing these large for larger companies and everybody has ideas. And so you just, it's like it's a way to cut through. Like, do you understand like the machine that is going to need to be in place in two or three years? Like you might have a 70% gross margin now because the next question is why can't someone else do this? And if you have an answer of like, well, they can now, but they can't in two years if we run really fast. Okay, we might have something. If they can now and they will be able to in two years, you're going to have margin compression.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Is yeah, gross margin is super low right now, but here's the dynamic I'm going after. And then you're like, oh, okay. And sometimes it's like, we'll just make it up with volume and then the gross margin will go negative for a while. And you're like, wait, wait, this doesn't work.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“This business, and I think we can charge this, and it will get us to a 40% gross margin. And then my next question is start at a 60% gross margin. Why does that not work? And they go, oh, well, the customer, and immediately you short circuit to like what the real problem is. Oh, the customer has an alternative. Oh, okay. Well, who's the alternative? Oh, it's some offshoring company. Well, what's their ghost margin? Oh, we don't know. You go find out. It's like 20%. And they've been around for a long time and they have scaled operations. And you're like, okay, so like your gross margin is going to go from 40 to 20 quicker than you think. And you're going to be in a world of hurt unless you do something to differentiate. So I take gross margin as just like a very coarse instrument, not a perfect instrument to think about, am I adding enough value? Am I differentiated? It's not perfect, but it's like a very quick short circuit filter to like even to see if someone's pitching you an idea, have they thought through this dynamic? Because if the response.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, look, it's one filter like many filters. There are certainly businesses that have low gross margins that are great businesses, Costco, Walmart, et cetera. Amazon talks about this all the time of like there's companies that increase prices and there's companies that lower prices. But I would say that by and large high gross margins combined with healthy churn curves are a very healthy sign for the business. I mean, think about it. Like if I were to sell you something and I can't market up a lot, how much value am I adding beyond what's in my hand? And if I'm not adding that much value, then what am I in the business of doing? And I'm in business of adding value. And it's not quite that simple, right? This is just a litmus test of like when someone comes to me and they go, especially in a new business, and we deal with this. I dealt with this Uber. I've dealt with it everywhere. Someone comes up with an idea and they go, we can get into.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think that's the story he would be referencing. And then the onboarding of it was crazy because, you know, we basically went global with them in like six months. And at this point, the business was less than two years old. So, you know, activating this, you know, I don't even know, 80 year old company that expects processes to be in place. And we have like two of our offs managers in New York managing it. It's just mayhem.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Months later, the business just like started hockey sticking again at a different level. And my team is just like, dude, you were so stubborn on this point. But I think it actually ended up being in that benefit because we got a great deal with them.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“And they're like, hold on a second. Like, we have like 80 million consumers a day. We don't want to do this together. I'm like, it's not really like our vibe right now. And so I push them off for like four or five months until my team is like, you're insane. Like these people are going to put marketing behind it. They really want to do this. They want to lean in. So we actually had a we because of that, I think it's hard to correlate these things. Like we ended up with this exclusive relationship with them. got an insane number of customers. Of chains at this point actually weren't really on food delivery networks because everybody was so worried about the unit economics because they're so sensitive to the basket size. And my approach was like, eh, figure it out, right? Which is a very Uber culture thing. Like, okay, the basket's $17. It's our job to make that work, reduce the radius on the delivery, figure out the economics, maybe mark up some of the food someplaces. There's always a way to figure it out. So we did it and then, you know, three months.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so it was kind of interesting. And this just goes to maybe like where sometimes ignorance leads you to accidentally the right answer. So we had launched Uber Eats and Uber had a global footprint and we were the only food delivery network with a global footprint excluding China. And so Uber was everything at Uber needed to be launched globally. That was a very big part of the culture, et cetera. Which is a lot of work and you can spread yourself too thin and cause other problems. But in this way it was good. And so my vision was, okay, let's help the little guy compete with all these chains. They have these systematized food systems and food is what makes a city amazing. And no one talks about the chain restaurant that they visited in Paris. They talk about the local place that they found. And like, let's be part of that. That's who we want to be. And so McDonald's actually approached us and they said, hey, we'd love to do food delivery with you. And I said,”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Luck is part of the game. That's the other thing that's important to realize. Luck is part of the game. So do not begrudge people for luck like this industry is hard. All these things we're doing are really, really hard. Luck is just part of the game.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Something Yeah, of course. Well, we launched it in December of 2015 in Toronto, and within like two hours we had done like $20,000 for the sales. It was crazy how quickly we saw that it was the right idea. And the unit economics for good. And then four and a half years later, I was an Uber for about six years, but it took us about a year and a half to figure this out. Four and a half years later, it was about $20 billion. So 0 to $20 billion in four and a half years, which is pretty good. Uber was very good at scaling things, but competitive market. Others did well. We beat a lot of people. Some people beat us. And then now I think it's pushing 80 billion. And that's been for another four and a half years since I left. I think COVID turned it from 20. I left right before COVID. Total coincidence. 20 to 50 in like a year. So yeah, I mean, ride sharing went this and, you know, food delivery just went like to Pluto.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“But we tried like 15 versions of all these things before we eventually just said, okay, the food delivery thing is just popping off on all signals. And we can make the unit economics work. People seem to want it. It's a super cool problem because we can like enable independent restaurants with like all these tools and allow them to compete with the big guys. We can take the real estate out of the equation so you can have a real estate location that's non-prime. But if you have prime food, then you get to compete. So we're like, oh, this is a very interesting problem and we can really help local economies.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Felt like 250 skews in them. And I mean, Crickets is an understatement of how bad it was. I mean, we did, we couldn't get an order to save our lives. And what we realized was that we hadn't really done the research on what convenience stores really were. It was, you know, if you didn't have cigarettes, you didn't have beer, you didn't have slurpes, you didn't have these things. Like, for example, like you didn't bring people in to sell all the other things. So we didn't know anything about retail. We were clueless. So that's like one idea. We looked at grocery, but honestly, the unit economics just terrified me of like all the pickpacking and everything like that. I think Instacart did a remarkably good job at getting the uneconomics to a good spot in like probably the hardest operational problem you could tackle. We did generalized delivery like point to point delivery. What's now, I forget what Uber's product is called, but like Uber Direct, I think it's called, where you have something that needs to go point to point in the city. That was kind of a flop from the beginning because the truth is like how consumers don't really have this needs. Business sort of have this need. And in 2014, when we were doing this, no one had this need.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I am definitely not the smartest person in the room when it comes to like figuring these things out. And so I keep a very, very wide aperture on ideas for as long as I can until I'm like, okay, everything is coalescing. And I think there's a bunch of reasons why you have to keep an open aperture on considering ideas that might seem bad at the start, but you just keep digging and see if you're right that they're bad or you're wrong. So just as a general philosophical principle, I'll start there. We looked at, we did some crazy stuff. We put, you know, like I went walking around San Francisco one day and I looked down Market Street and there was like a CVS, a 7-Eleven, a CVS, a Walgreens, a 7-Eleven. And I'm like, how many SKUs could possibly be inside one of these things that people want? And couldn't you just put that into a van and like, you know, you hit the button on the van, the van comes around and you get whatever convenience items you have. And they're convenience items. So like, why would that be a problem? And we launched that in DC. We put like 10 of these trucks on the road.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Operate, which is marketplaces are good businesses. SaaS, at least historically, we'll see how this changes. But like SaaS historically, great businesses, recurring revenue businesses, sticky businesses, network effect businesses. And if you look at what the top VCs invest in, yes, there is a lot of like portfolio building, but there are similarities in terms of the types of business models that they believe could be worth tens of billions of dollars and they have network effects. They have lock-in. They are more valuable at scale, a big scale than low scale. If you just take a filter on a new business, this is what I did at Uber, which is like if you just have a filtering mechanism on a new business, it doesn't take that long to eliminate the bad ideas. And then of what's left, you can pick, oh, I'm very passionate about this, even though it might have more problems in this other thing that on paper looks better.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“If you want to give yourself the best chance, and this isn't always how it works, but if you're like in my position 25 plus years in their career, if you want to give yourself the best chance, I think there's two ways that companies end up working out. And the first way, which is probably the most important, quite frankly, is that the founder is just a force of nature over a long duration of time because you're going to have to pivot. You have to have that energy to pivot. You have to go years and years and years with it being hard. And that's probably the most important thing. But the second most important thing is that you can easily educate yourself on like what are good business models? What are bad business models? What are good markets? What are bad markets? And even if you're this force of nature, having the knowledge, if you're going to go into a bad market with all your energy, you should at least know maybe ignorance is bliss because you just throw yourself into it and it just kind of works out with time. But like, that's not how I.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Thinking is that you can't fall in love with your ideas. And I do not proclaim to be the world's greatest independent thinker for what it's worth. These are what you've been told, but it's just like part of that is basically throwing away who you are, who you've been, all your ideas for the mission that you're on, which is like trying to accomplish something for our customers.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It truly is about what insight do I have because why am I so lucky to have this insight? Why in a world of a million entrepreneurs who are thinking, who are smart, who are trying everything? Why am I in the position where I likely have an insight that others do not? And then why am I the one to do it? And like the answer might be I'm in this narrow far flung place. The other answer might be like I am inherently a contrarian personality type. So I'm just constantly looking for the thing that's true that people don't believe is true, which sometimes works. But then the second part of that's super important, which is like, why do I want to work on this problem for five to ten years? And like people get this wrong all the time. They go and talk to a customer and they go, they have a problem. I'm going to go solve it. And it's just like not a great way to like start a business. Like you really have to have this burning desire to constantly be questioning yourself. The other thing about independent.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think as a founder's job, and I mean, I stretch that term because at Uber, we had all of the benefits of Uber, so I wasn't really a founder. I just sort of started the business there. But there are some elements of founding there is you're looking for alpha in the market. When we started our first company in 1997, it wasn't that cool. Like it might have been cool in Silicon Valley, but it was definitely not cool in LA. Now it's super cool to start a business. So as a result, everyone's kind of trying everything. So how do you get alpha on that market? You know, if you're just your research is highly influenced by what the world is saying around you, you're not going to have an independent insight. Like you kind of have to go off and do your own thing. And this is why from an entrepreneurship standpoint, like I have a very strong feelings about what the approach to founding a company should be. And it's probably very particular to me.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, yeah. I mean, if you want to do a restaurant, they would tell you a bunch of things. They would say, oh, labor schedule is an issue. They would say my rent is an issue. They would say all these, you know, my ingredients prices are an issue. That's 20 or 30%. If you could shave off 3% of that, that would be huge. You might then take that and go, I'm going to go build a business that's going to save you 10% of your ingredients cost. But that doesn't actually get into their head on like what's truly important day to day. That might be important for them on an annual basis, but on a daily basis, what are they doing? They're looking at their numbers. They're looking, do people show up? Did I make money yesterday? Am I going to make money tomorrow? So like the urgency, I think the biggest thing people miss when they're building new products is the urgency of the buyer part of it. You can build something that provides a lot of value, but if it's not the top thing that the customer is thinking about in their busy days, then you're just going to have a long road to a small town.”
2025-10-09 · 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 · IDENTIFIED FROM THE TRANSCRIPT · source