Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Postmates Founder Basti Lehmann on How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN, Why Great VCs Add No Value and VC Value Add is BS Marketing & Why The Biggest Companies in History Will be Born Today and Replace Incumbents About this episode Basti Lehmann is the co-founder and former CEO of Postmates, the on-demand delivery service that raised over $900M from the likes of Tiger Global, Founders Fund, Spark Capital and Andreesen Horowitz. Following Uber’s $2.65BN acquisition in 2020, Basti founded TipTop, a platform for fast tech sales which Marc Andreesen led the $20M seed round for. In Today’s Episode with Basti Lehmann We Discuss: From US Immigrant to Billion Dollar Founder How did Basti start his career hacking AT&T? How did early hardships shape Basti’s work ethic? What were Basti’s biggest challenges building Postmates? Lessons from Raising $900M How did Basti raise $20M from Marc Andreesen? How does Basti select which VCs to work with? Why does Basti think 99% of VCs are sheep? Why does Basti think great VCs add no value? Why does Basti think having to educate investors is a massive red flag? Selling Postmates for $2.65BN Why did Basti sell Postmates to Uber? How did the acquisition happen? Was there anything Basti would have done differently? What does Basti think makes Dara Khosrowshahi a great CEO? What is Basti’s biggest advice to founders on acquisitions? Future of AI: Startups or Incumbents? What does Basti think is the biggest challenge of LLMs today? Why does Basti think inference computing will be the future of AI? Why does Basti think incumbents can be replaced? Why does Basti think the biggest companies are being born today?
Transcript 11,985 words · 3 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 Here's another thing that I think people don't fully understand. We negotiated the deal so well, there was no color on the deal. By the time the deal closed, it was almost $5 billion. We had just under $100 million left in cash and our negative gross profit margin was, I think, single digits. Two or three quarters later, we were profitable as a company. Most companies fail because the founders give up, and that's it. We refuse to give up.
0:24 Harry Stebbings? This is 20 VC with me, Harry Stebbings, and what a show we have for you today, Postmates. What an incredible journey. It was acquired for $2.65 billion, but no, it actually turned out to be $5 billion with the stock price of Uber rising. The story of the acquisition, how it went down with all the details. Basti Lehman, Postmates founder and former CEO, in the hot seat today to reveal all. But before we dive into the show today, we're all trying to grow our businesses here, so let's be real for a second. We all know that your website shouldn't be this static asset. It should be a dynamic part of your strategy that really drives conversions. That's marketing 101, but here's a number for you. 54% of leaders say web updates take too long.
1:08 Harry Stebbings? That's over half of you listening right now, and that's where Webflow comes in. Their visual-first platform allows you to build, launch, and manage web experiences fast. That means you can set ambitious marketing goals and your site can rise to the challenge. Plus, Webflow allows your marketing team to scale without relying on engineering, freeing your dev team to focus on more fulfilling work. Learn why teams like Dropbox, IDEO, and Orange Theory trust Webflow to achieve their most ambitious goals today at webflow.com. And speaking of incredible products that allows your team to do more, we need to talk about SecureFrame. SecureFrame provides incredible levels of trust to your customers through automation.
1:50 Harry Stebbings? SecureFrame empowers businesses to build trust with customers by simplifying information security and compliance through AI and automation. Thousands of fast-growing businesses, including Nasdaq, Angel List, Doodle, and Coda, trust SecureFrame to expedite their compliance journey for global security and privacy standards such as SOC 2, ISO 2701, HIPAA, GDPR and more. Backed by top-tier investors and corporations such as Google, Kleiner Perkins, the company is among the Forbes list of top 100 startup employers for 2023 and Business Insider's list of the 34 most promising AI startups of 2023. Learn more today at SecureFrame.com. It really is a must.
2:32 Harry Stebbings? And finally, a company is nothing without its people, and that's why you need Remote.com. Remote is the best choice for companies expanding their global footprint where they don't already have legal entities. So you can effortlessly hire, manage and pay employees from around the world, all from one easy-to-use self-serve platform. Plus, you can streamline global employee management and cut HR costs with Remote's free HRIS. And hey, even if you are not looking for full-time employees, Remote has you covered with contractor management, ensuring compliant contracts and on-time payments for global contractors. There's a reason companies like GitLab and DoorDash trust Remote to handle their employees worldwide.
3:13 Harry Stebbings? Go to Remote.com now to get started and use the promo code 20VC to get 20% off during your first year. Remote: opportunity is wherever you are.
3:24 Harry Stebbings? You have now arrived at your destination.
3:26 Harry Stebbings? Basti, I've wanted to do this one for a long time, my friend. So first, thank you so much for joining me today.
3:32 Speaker 00 Same here. I think we had some scheduling bugs, but we figured it out.
3:35 Harry Stebbings? And we figured it out in the end, and we made it happen. I want to go back to your childhood. I think great entrepreneurs are shaped early. Take me to your parents and your teachers. If they were to describe a young Basti in Germany, what would they have said about you and how you were?
3:50 Speaker 00 Well, first of all, you know, in 1977, that's when I was born, 1980 in Germany. You have to understand, everything was still black and white. But what would they say? Probably very curious child, you know, I liked to play a lot. I think I was always on to something. As a matter of fact, I think I was out of the house most of the time. I think as soon as I could get out of the house, I would just be somewhere, play in the forest or run around, you know, we had a group of friends. We did exhibitions and, you know, that sort of stuff.
4:17 Harry Stebbings? I love that. Can I ask you? I always struck with the question of skill versus luck in life. How do you think about the importance of skill versus luck in life? What are your thoughts on that?
4:27 Speaker 00 I don't really believe in luck much, but I also don't have a definite answer. I think I believe in determination and grit and hard work.
4:34 Harry Stebbings? If we'd like isolate a point in your life that was a needle moving moment for your career. When you reflect, what do you think the most needle moving moment was? Was it the move to the US? Was it selling Postmates? What was that? Ah, that was the big move.
4:48 Speaker 00 Definitely moving to the US was a huge part. And I think it's important to understand, I wanted to be in the US almost all my entire life. I remember very vividly, this is actually a great story. So what happened is that I was obsessed with computers pretty much as long as I can remember. And I love the idea that I can just heck things and something comes back. So when we first got internet access, I incurred these bills of like ridiculous amounts of money. And I grew up in a fairly modest house and my mom had sometimes three jobs. So we didn't have a lot of money. And back then, if you remember, it's a dial up. So you pay per minute or you pay per hour depending on your plan. After a while, I decided that I could run a BBS, like a little software that allowed other people to connect to my computer.
5:30 Speaker 00 And obviously that was a very boring affair because only one other person could connect to your computer. Right? So you run this bulletin board and you designed it and I don't even know what you had on there. You had, you had probably photos of Claudia Schiffer. To that extent, content was available. And this person, his name was Annie Mello. He came online or that was his name and we started talking. He's like, well, what's your setup? And he had, I'm like, well, you know, just, I think I had a 14 4K modem. And, and I said like, you know, I, I don't really know much about the internet or anything. And I also can't be connected to the internet because it costs a lot of money. And he said, you don't know how to surf in the internet for free. And I'm like, no, I don't know. And he said, well, you need to get a US calling card.
6:11 Speaker 00 Cause how it works, he said, in the US they have like AT&T or they have MCI WorldCom. For long distance calls and collect calls or calls abroad, in the US they punch in this calling card number and a PIN code. And then they can use a telephone booth for free or they can, they can call when they're abroad and it gets charged to their account. So a week later, he wanted to come by and obviously I never, I never met this person. And it turns out he was like 40 something and my mom was very, very skeptical of, of this person. She's like, you leave the door open. But this guy was a complete nerd and he taught me literally what I had to do is I had to get a phone book from the US. Somehow. And then I had to call people in the US and had to tell them that I would be a, you know, a service agent from MCI or from AT&T and that there was a problem with their account.
6:54 Speaker 00 And that, you know, I needed to verify their calling card number and their PIN code. This is a true story. So at some point, my parents were divorced and here's the one good thing my dad did for me. He got me a phone book from San Francisco, a Pacific Bell phone book from San Francisco. And me and a friend of mine, we would hit the phone and we would call people in San Francisco and practice our American accent to sound like we're from MCI WorldCom or from AT&T, depending on the phone number. We would ask for their calling card number. And at some point, after weeks of effort, someone also gave us the PIN code without being too suspicious. So then what we would do, we would have that calling card number and the PIN code. We would call our dial-up provider. We would, so you would call a toll-free number from AT&T in Germany.
7:38 Speaker 00 You would punch in the calling card number. You would punch in the PIN code. You would then unplug the phone, plug in the modem, dial the number from your internet provider and you would surf. So in a way, my career probably has started embezzling TRMCI in San Francisco.
7:53 Harry Stebbings? They're going to come after you after this show. This is the retribution that they've been waiting for. Can I ask you a bit of a weird one? And I hope it's okay. You mentioned your parents' divorce. How old were you and did that impact you?
8:05 Speaker 00 Oh, yeah, I think it impacted me tremendously. I think I was six and my brother must have been like almost three.
8:10 Harry Stebbings? How did it impact you?
8:12 Speaker 00 I had a pretty perfect life up to that point. After that, it got a lot more, you know, complicated. We wanted to be with my mom. She has been there for us and she's the person I love the most in my life. And she was just a remarkably strong woman, never talked bad about my dad, even though there were a lot of things that he did that would have made it easy for her to discuss them with us. She just plowed on and I think she gave literally the next 18 years of her life to make sure that we are, grow up to be two capable, capable boys, right?
8:43 Harry Stebbings? Mothers are the most incredible thing. Can I ask, you mentioned the three jobs that she had there.
8:48 Speaker 00 Yeah.
8:48 Harry Stebbings? Is that where you think you got your grit and steeliness and ambition from? Where do you think about the source of where you got that muster?
8:57 Speaker 00 You probably got to suffer a little bit to be resilient. So it probably has to do with that. One morning I grew, I woke up and I must have been around 14 and my mom wasn't there. It was early in the morning. And I waited for her that, that she came back and, and she told me that she had to do another job in the morning to help clean a building somewhere. Because we just didn't have enough money at the time. And I couldn't believe it because you, you have to understand that when I say that we grew up modest. I'm not talking about a level that it was apparent to me every day. Things were limited, but I wouldn't walk around and feeling poor. But I think I didn't realize how tight things were until we talked about that and until she told me that. I, I remember that, that I said, you know, I will make so much money that my mom can have whatever she wants.
9:42 Speaker 00 And it was incredibly important to me to make sure that she has whatever she needs as soon as I could do that.
9:47 Harry Stebbings? We have some things in common, my friend. That makes me very happy to hear. Before we dive into the Uber acquisition, I spoke to Nabil before the show and I'm looking at my notes now. He said that you led a team that was in wartime mode the entire history under huge stress. And that you are not a cuddly CEO. What was the most memorable wartime moment in the company history of most stress that you remember?
10:13 Speaker 00 Oh, I think Nabil is right, but I, I want to say I enjoyed it. I enjoyed it tremendously. Because I really do believe that you have to measure yourself in life. And I think this journey of running that company for 10 years absolutely did that. The wartime was defined by us being so focused and so determined to create a successful company. You, you have to understand, I truly believe that everybody who worked at Postmates loved that company from the bottom of their heart. It was a group of people who couldn't drive us apart with whatever came at us. Any VC funding a competitor, Uber, threats, rumors, we were so focused on our mission. We were so focused because we love the company.
10:56 Speaker 00 I woke up 10 years in a row and every day I couldn't believe it. I'm like, I can't believe that I get to do this and that I can be with these people.
11:03 Harry Stebbings? What was the biggest oh shit moment?
11:05 Speaker 00 It was rough for a while when competitors raised bigger and bigger funding rounds. And look, we raised quite a bit of money. I think we raised around 900 million. So by no means small change, but it was really scary at times when you see the pace of which competitors raised money and did so very successfully.
11:23 Harry Stebbings? For founders listening, when your competitors raise a lot of money, should they raise it too? Or is it just a race to the bottom then on cash? What are your lessons on when comps raise that you give to founders?
11:35 Speaker 00 Well, I think it entirely depends on the situation. In our case, I think what happened is that we opened up this market of on-demand delivery. And by the time competitors came along and by the time competitors had their first funding round and by the time everybody saw the potential, there was an inflection point in the market when the only thing that mattered was more capital to do more advertising. You have to understand that this was, I think, the largest consumer battleground for five to six years. Billions of dollars deployed in advertising, in marketing, in grabbing market share. But, and this is something that from the outside was hard to understand, but it is the reason why ultimately almost every VC firm invested in one of the players.
12:16 Speaker 00 The fundamentals of the companies, I know this for us, but I have some insight in the other players. They were all pretty sound. And by that, I mean, there was a clear path to profitability. There was a clear understanding of the unit economics, how they work, where the gross margins need to be. All three companies, I think, had people that could execute very well against the goals. So that is a moment in time when you should raise a lot of money.
12:40 Harry Stebbings? Do you think that's actually the case, dude? Like, I, you know, I invest in the space, but I think the awareness that actually they were pretty tough business models to make work. The margins were super low. The density required was super high. The AOVs were too low, the labor costs were too high. I think that was a realization that they were bad business models.
12:59 Speaker 00 No, I think Tony and I knew from the start that this is a tremendous business. If you can scale. And every market that you had at scale was profitable for us. And I know that the same thing was also true for DoorDash. It is a misconception of that space in general. Look, it is a tough business. It's a lot. It's a lot tougher than a SaaS company where you just press a button and then you you go get a coffee. And you and you made a million dollars in revenues. We're moving about bits and bytes, moving things in the real world, right? You're programmed people. There's a million things that can go wrong. All of the things that you said are right, but it's important to realize the moment in time that I'm talking about. I'm talking about the moment in time when there was enough evidence, maybe around the series B or starting going into series C,
13:39 Speaker 00 that people that had the insights and looked at the numbers, we could clearly articulate how we would get there. When Postmates started out, this thing sounded so crazy that the only people that wanted to give us money were Brian Singman and Peter Thiel. And I think the only reason they gave us money is because nobody else said they would give us money. And Peter and Brian probably thought it's a smart thing to do.
13:58 Harry Stebbings? Dude, you're very vocal on VCs, which I always find an entertaining take.
14:03 Speaker 00 VCs are very vocal on on founders. So I think somebody has to, every once in a while, has to give some feedback.
14:09 Harry Stebbings? This is going to be a fun show, my friend. But when founders fund, invest in your series A and lead that as first institutional lead, how do you weigh the importance of VC brand is my question? Does it really make a difference to companies' trajectory when a tier one leads you around?
14:22 Speaker 00 Back then, it meant a lot to us that we had a known company as the lead investor. And I do believe that it sets up a signal, but I think a good signal can save a bad company. And it'll come down at the end of the day to your execution. A lot of times, even the great VCs and a lot of hype can't really change the outcome of a company.
14:44 Harry Stebbings? What was the hardest round to raise?
14:46 Speaker 00 Everyone, every single round.
14:48 Harry Stebbings? Do it to me. As we progress, the business matures, it gets larger. How did the Uber acquisition play out? We put it on Twitter. I got a lot of DMs being like, I want the story. Can you just take me to the story of how it played out?
15:02 Speaker 00 Dara called me and he said, do you want to, do you want to discuss merging the companies? And I said, yeah, let's do it. Fits in a tweet. That's how easy it was.
15:10 Harry Stebbings? You guys then meet? Where do you meet? How does the meeting go? What are the thoughts?
15:15 Speaker 00 It was during COVID. We met at Alta Plaza Park. It's sort of, I think it's a mean point between where we both lived at the time. A year and a half earlier. There were some preliminary discussions with the Uber team, so there was some familiarity. But ultimately, I think it wasn't the right time for either party. We raised more money and I think Uber had to explore more what they want and what they can do with Uber Eats. Ultimately, they had a change in leadership on the Uber Eats side. Pierre was now in charge and I think Dara was very bullish about Uber Eats, especially because of COVID, right? Their rights business was basically non-existent. And with DoorDash being clearly the market leader in most of the US, but not in California and certain regions that are very attractive, where we were the number one.
16:00 Speaker 00 They saw the great opportunity for consolidation and the whole thing was very pleasant, I have to say.
16:05 Harry Stebbings? Okay, so we have that meeting, we have that discussion. Again, you said let's smash this podcast, so I'm just gonna go for the questions and you can rip me if I'm going too far. Someone said that Postmates was running out of cash. This was like an emergency deal that landed super freaking well. Is that fair?
16:23 Speaker 00 No, no. Look, I actually love sort of defending the legacy here a little bit. You know, sometimes when you fight giants, you know, the war can get nasty and Infowar is definitely part of that. So first of all, let's just look at the facts. It's very easy. Uber obviously had to file an S4 at the time that they purchased Postmates and you can look it up. We had just under a hundred million dollars left in cash and our negative gross profit margin was, I think, single digits. Two or three quarters later, we were profitable as a company, positive cash flow. So we were in a position that we didn't have to sell. As a matter of fact, we were planning to go public and would have probably been one of the last companies to do so before, you know, the world ended. And we were excited about it.
17:07 Speaker 00 But when we looked at everything that was on the table, we had done the best job we could for 10 years to grow an amazing company. I think it was the furthest that we could have moved the company. We believed it was best as part of something bigger because the market needed to consolidate at some point.
17:27 Harry Stebbings? Why? Like, why could you not have done more, Basti? You're a steely founder, you're an ambitious guy, you're a great CEO. Was it tempting to go it alone?
17:35 Speaker 00 Yeah, absolutely. And I had a great belief that we could continue as a standalone company. But ultimately, I think I put the ego a little aside, and it's not easy. I wanted to be CEO of a publicly traded company. I was looking forward to that. And I think I would do a great job at it, and I may get another shot at it. But here's another thing that I think people don't fully understand. We negotiated the deal so well, there was no color on the deal. By the time the deal closed, it was almost $5 billion, which is amazing.
18:06 Harry Stebbings? It's reported to be 2.65.
18:08 Speaker 00 Yeah, that obviously, that was the price that was announced, but there was no color on the exchange ratio. And obviously, we benefited from the Uber share price that was, I think, in the, when we got the shares, the Uber shares were at around $31. When the deal finally closed and we got approval, it was at 53, I believe, or 55. The money returned to shareholders was almost 5 billion, and I have sold almost none of my shares. So I'm still rooting for Uber.
18:33 Harry Stebbings? Uber's share price today is 75.75.
18:36 Speaker 00 Yeah, it's a bit down, isn't it?
18:38 Harry Stebbings? Wow, that is insane. How did you come to the price? When you were sitting with Dara, how does one price the asset that is Postmates at that stage? Does he throw out a number? Do you throw out a number? What does that look like?
18:51 Speaker 00 Well, I think it's probably a mix of last valuation, and then you look at multiple on forward-looking revenue and sort of a mixed bag, really. And I think he came, he came out with a number that was, that was around 2.2 or something. And we negotiated it up a little bit, but I didn't want it to push too hard, because the two things that we negotiated for are no breakup, absolutely no way out, and no color on the deal, because we sort of knew that the street would probably appreciate the acquisition, and it did. So those elements were more important to us than pushing the price on paper, two or three billion, and maybe living with certain uncertainties.
19:30 Harry Stebbings? Fuck me. So how much of the company do you own, Basti? Like, 20%?
19:35 Speaker 00 I, it doesn't matter.
19:37 Harry Stebbings? Wow. What did the board say?
19:39 Speaker 00 I think Brian Singerman was excited to the extent, and he said, "You did it, Basti." I really think he said that exact same sentence, and that was sort of the end of the excitement. And that, I mean, meant, meant a great deal coming from him.
19:53 Harry Stebbings? Listen, that's as good as you're gonna get, so just embrace that.
19:56 Speaker 00 Yeah, I know.
19:57 Harry Stebbings? What are your biggest lessons then to founders on how to get acquired and how to sell your company the right way?
20:02 Speaker 00 Most companies fail because the founders give up, and that's it. We refuse to give up.
20:07 Harry Stebbings? You said before that Dara is one of the best non-founder CEOs alive. I'd love to unpack that. Why do you think that is? What makes him so good in your mind?
20:16 Speaker 00 So first of all, I think he has an ability to give the people that work for him a lot of autonomy. When I started working with him and see how he works, at first I thought that that was a weakness. And I had this feeling like, man, he's not really that involved in all of these things. But boy, I think it's just a great way of how he leads the company. And he is involved, but not to the extent that I was involved or that I thought people would be involved. But he rewards a group of people with trust. And he picked a lot of good people that ended up working for him, that executed very well. He's a very calculated risk taker. I think when he took over the job, I think he had a pretty good understanding that he can turn the company around and what needed to get done
21:01 Speaker 00 more so than than the street understood and would give him credit for. I think he has maneuvered legislation, any sort of cultural issues in the company, external expectations very well. And for a non-founder CEO, he really has, I think he has made this company his. And what is remarkable is if you have people two, three years ago that talk about it, they're like, nah, Dara, you know, at some point, maybe, you know, Travis comes back and this, the whole Apple thing. You know, we love these stories in Silicon Valley. We love it. It's the stuff that movies are made of, right? But you know, this guy just showed up at work, did his thing. You would have CNBC, you would have Bloomberg. They would just say nothing nice about it at all.
21:43 Speaker 00 And every, every moment in time that they could mention that Uber has not been, has not exceeded their IPO share price was good enough for it. This guy just keeps on executing. And now you turn on CNBC, you read Bloomberg, one of the best CEOs, incredible guy, unbelievable. Give him a billion dollar salary. Can he have done this? You know, here's a CEO that knows how to run a business. And it's sort of like, yeah, he did that.
22:08 Harry Stebbings? Can I ask you again, a final one, and then we're going to move to new company. Someone messaged me and said, basically, Dara's written off the Drizly in the Postmates acquisition. What does Bastian think? How do you think about that? And was that right? Does that feel good? What are the thoughts?
22:23 Speaker 00 So first of all, I couldn't care less about it because I'm not in charge at Uber and I don't run the company. And however, Dara wants to run the company, he probably will do what's best for the company. But I see no signs of the Postmates acquisition being written off because I think the brand is very strong. It continues to be very strong in L.A. And unless I haven't gotten the memo that they're shutting Postmates down, I think it continues to be a great brand. Maybe ultimately it is smart to consolidate to one brand. But when we discussed the merger, we sort of had this idea that you leave these brands, you start uniting the tech underneath, and then at some point, it's the same product, but it sort of has basically a different name. And that's literally like the one difference.
23:08 Speaker 00 And you can use these brands to maybe appeal to slightly different audiences. But if they change their mind, then that's fine. Maybe I can buy the domain back.
23:16 Harry Stebbings? So then we have the earn out and progressing through that. You then have a good amount of money and you're thinking about what to do next. Talk to me about the decision-making process there, Basti. You could have done anything. You could stay at Uber, you could be a big time exec. What was the decision-making process?
23:32 Speaker 00 Well, I tried to do nothing, but if you have a family, then it's hard to find time to do nothing. So for a while, I was just enjoying that. But if your mind keeps wondering about things that could be done and ideas that you could work on. I love building products and I love running teams and I love being in a room full of engineers and working on ideas and see things come to life. I try to do the investing thing and I do some investments, but it does not derive me the same amount of joy than actively building something.
24:03 Harry Stebbings? Now you start a second company then. What are the single biggest pros? If we start on positives, what are the biggest pros of being a second time founder, Basti?
24:12 Speaker 00 If you're a second time founder that has returned capital, I think you have a set of pros. It's very easy to raise money. You can select the people that you want to work with. It is fairly easy to assemble a team. And because you have done certain things, you don't know how to be successful again, but you know how to run a lot of the processes and a lot of the red tape and a lot of the things that would really consume you the first time around. Now you know how to do these things and so you can be fairly efficient in getting started.
24:43 Harry Stebbings? Often it's not knowing what to do right, it's knowing what not to do. The mistakes that one normally makes. You said about selecting the VCs and having the ability to. With the ability to select, how do you select the VCs you work with?
24:57 Speaker 00 If you ran a company for 10 years, you have met people that you maybe always wish you would have worked with. And for me personally, Mark Andreessen was one of my heroes. And this is a guy whose software I grew up with, whose browser arguably changed how we access information. I pitched him four times or five times the entire firm with Postmates. They were smart enough to say no, but it was amazing to be able to just reach out. And I think there was a mutual feeling from his side. He was excited to work with me as well.
25:25 Harry Stebbings? How did that round come together? You ping him and you're like, hey, I'm starting something new. Can I come meet you?
25:30 Speaker 00 He pinged me actually because a friend told him that I was working on something. And he called me and I said, I don't, I don't even know if that idea is good. And he said, do you want to do it again? And I said, yes, it's like, well, then I'm sure you figure something out. That was the extent of the fundraiser.
25:44 Harry Stebbings? So who did the price? Who did the negotiation? Like, how does that work?
25:48 Speaker 00 We didn't negotiate on the terms much. We just discussed what we believe to be reasonable for a cold start, series A, at a price that is not too high, and that's it really.
25:58 Harry Stebbings? What did you have in terms of company at that point?
26:00 Speaker 00 Three co-founders, a problem space that we've been looking at.
26:04 Harry Stebbings? Did you worry that it was too much too soon? One of the challenges is it's too easy to raise money and then you have the luxury of not being thrifty, being able to spend on whatever you want. Were you concerned about having too much too soon?
26:15 Speaker 00 Yeah, I still am, but only to the extent that I'm concerned about any of these things up to the point where I know that the new company is a success, right? So I don't think there's any set of circumstances that will necessarily dictate that outcome. If you have too little, you're worried that maybe you should have raised more. If you raise money, you may be worried that you have too much. And do you detect complacency somewhere? We will see.
26:42 Harry Stebbings? It's always one way. A lot of people say, oh, raise whatever you can and you just put it in a separate bank account on a rainy day. And I always find founders spend rainy day funds when it's not raining.
26:53 Speaker 00 We sort of raised an amount that would allow us to do three or four startups in one. If you think about it, something that Mark and I often talk about is if you run a company, you want to test a set of hypotheses. That's your job as a CEO, right? And you want to run down that list. And if you find that some of them work, you sort of want to increase the velocity and really get to the point where you know if this thing works or not. And I think the idea behind Tip Top is that we like the space, but we will explore it to the extent that if we believe that we have a tiger by the tail and that we see this thing moving in the direction that we like, we will continue testing hypotheses or we will move to a different space. And that would be, that will be no problem. And not for the team, not for myself, and I don't think for anybody who invested. The idea is that we'll figure something out.
27:39 Harry Stebbings? Where is the conviction bar on where you are with Tip Top? Is it like 50% proven, 30%, 70%?
27:46 Speaker 00 It's a great question. It's a very good idea. We're very convinced of that. It is a very slick product. We're very convinced of that. We are trying to understand the market size and the impact that we can have with our energy. We're not sure where that is yet.
28:03 Harry Stebbings? How do you determine when to cut something and move on? Is there a defining metric? Like if we don't have X number of users by X day, we kill it.
28:12 Speaker 00 You can do it that way. And I'm sure there are people that are like that. Who do I know who's extremely smart and would run a company like this? Patrick and John Collison. I think they're like the perfect example. I'm sure they have a metric. I admire them and we're very fortunate to call them friends. The most important thing to realize is that it doesn't matter. It doesn't matter. We tend to take everything way too seriously. Like, oh, if I fail, the world will think, nobody cares. It takes a minute for everybody to get over it, right? So something else will happen. Elon will tweet something and that's what we care about. The minute after somebody just thought about you. So it really doesn't matter. Like there is no right or wrong way. There is nobody who knows the master plan
28:56 Speaker 00 and it really does not matter.
28:58 Harry Stebbings? I find it incredibly reassuring to remember that you are not nearly as important as you think you are.
29:03 Speaker 00 Yeah, but nobody is, right? That's the thing. Nothing is.
29:07 Harry Stebbings? Can I ask you, I think one challenging or interesting element is financial position changes with your second company if the first was successful. You know, you no longer need it financially to work. How does starting a company rich change your mindset, approach, ambition the second time around?
29:25 Speaker 00 Well, that is a fair question. I had very little when I started Postmates and we put it all on that thing, right? And we felt like we had to push that little carriage up for up the mountain for 10 years, right? And at any moment, there were, there was not a moment in time when we were convinced that that we've made it. But we had the ultimate energy because we felt that this is what had to had to get done. But at least 50% of that was also a chip that we had on our shoulder that we wanted to prove that we can do this. And that is something that all the money in the world can't really compensate for. That's why people strive for greatness. That's why people strive to do certain things because there is a desire to do something.
30:05 Harry Stebbings? But how does starting a company the second time differ when you're starting it rich?
30:10 Speaker 00 Well, I don't, I don't need a salary, so I don't pay myself a salary. That sort of comes in handy.
30:15 Harry Stebbings? Are you more courageous in the bets that you take because you're not worried about the downside? Are you more fast moving?
30:21 Speaker 00 I think we as a company, and I've been very focused to not have any sort of external things influence our decision making. We try to be very humble. We try to be nimble. We try to move very fast. We try to write a lot of code, assess problems. We try to do that without the assumption that we're better off because of anything that happened before.
30:40 Harry Stebbings? I'm sorry for jumping around. When, when the money does land, does it land in one go? Do you get like, well, I'm being serious. So do you just get like a notification like here is like, you know, X million dollars? And you're like, wow, that's great. Or does it come in drip feeds? How long does it take? Like, just how does it work?
30:57 Speaker 00 What's really interesting is that you think it's this moment, but the whole thing almost takes a year. You sign a deal and then of course, you know, DOJ, in our case, the DOJ had a few questions and they submitted a request and, and we had to answer that and, and then. Then you get to go and then the deal closes. And then there is a company called Shareworks that deals with the transition of shares between two parties. And they take custody, you get access to it. And then there's a clawback. In our case, it was a, there was no clawback, I believe, company-wide clawback. But we just had a small amount of shares that did vest after like three months or something. So, but yeah, at some point, your bank calls you and says like, yeah, we got your shares.
31:41 Speaker 00 Do you want to see your bank account? I guess that's what they ask you, Em.
31:45 Harry Stebbings? How did you feel in that moment?
31:47 Speaker 00 The bizarre thing is that you prepare for that moment for a year, right? It's not like winning the lottery and you're like, and there it is, right? It's sort of like, we knew we had sold the company a year earlier. In your mind, you probably go over that moment then many times, right? But I was so focused at that moment in time was the transition of the company, right? So you have to understand up until the Department of Justice cleared the thing, there was a fair chance that this would have not been possible. There was no moment in time when we celebrated after we signed the paper because we had to run the company as a standalone company for, I believe, eight, nine months. So we had to hit our quarterly goals. We did not want it to have a scenario where we lose market share because now we're thinking that we're selling the company. So you run these things as very separate businesses.
32:31 Speaker 00 It's very anticlimactic, I would say. I wish there would have been a moment and on top of that, it was COVID. So the one thing that I'm extremely sad about is that I did not ever get to celebrate with our 2,000 employees at a party in a room and have a blast. That was a very strange feeling. Everyone walked away sort of in with masks and, you know, five feet distant. A very strange end to like a 10-year church-like community and being in the office for 18 hours most days, including the weekends. Like, it was very strange.
33:08 Harry Stebbings? But I'm sure your wife must have been thrilled when the cash landed.
33:12 Harry Stebbings? I do have to ask, as we said, you're very vocal about venture investors. As a venture investor, I agree with some and disagree with others. You said before that 99% of VCs are idiots, Basti. How do you find the 1% that are not? And do you really think that?
33:29 Speaker 00 I would probably today say that 99% are sheep.
33:33 Harry Stebbings? Why do you think they're sheep?
33:34 Speaker 00 That's probably enough to be somewhat successful. There is a mass sort of thinking and it's very self-informed. And there's very few people that understand where things should go and where the opportunities lie. And there is the majority of all people are just echo chambers of whatever that is. And, and there is a great desire in most VCs that I know to not bump in, bump around the edges too much and just do that thing and just, you know, follow that path. Whatever is the creed of the moment and whatever you want to discuss in regards to that,
34:15 Speaker 00 like it's rough to be a little different and try to convince people.
34:21 Harry Stebbings? Listen, I think it's the same with LPs. I quite often will say to LPs, you know, you get paid for the courageous bets that you take, not the safe decisions that you make. I think it's very much the same in venture, by the way. This is a business of anomalies and so I completely agree with you. I think one of the interesting elements is venture value add. A lot of founders say, oh, I'm thinking about this VC or that VC because they bring this and this and this. How do you think about venture value add? And you've said before, the best VCs in the world are humble enough to realise that they're not going to change the outcome. How do you advise founders on venture value add?
34:57 Speaker 00 Well, first of all, I think that statement is completely correct. It is my fundamental belief. The greatest VCs that I have met are the people that know this. When the company was bought, when the deal got closed, I remember having coffee with Brian Singeman and we both lived in Noe Valley at the time. So, and I was curious, I'm like, hey, how is it being a VC? What's, how do you do it at Founder's Fund? Do you think I could do it? And I think he said something, he said, I don't. I don't know if you can do it, but I don't think you can do it and I don't think you would be good at it. And I'm like, and I'm like, I'm like, why do you think that is like, well, you care too much. Like you're an operator, you wanna, you believe that you can change things and you can do that when you're running your company. When you're an investor, you have to realize that there is nothing you can do, it doesn't matter.
35:42 Speaker 00 So at Founder's Fund, they, they obviously believe in this very deeply. We just saw this obviously with, with Keys leaving there and, and being somewhere else. The belief is that there is very little you can do to actually move the needle other than writing the check. And then in the best case, you stay out of the way. And that's why they believe that board seats are, you know, all the downside and very little upside. All of it is rooted in this belief that why would you be the guy that knows best how to do something? And push these founders to do a certain thing. I believe the best VCs in the world believe that. I, I do not believe that Mark loses a sleepless night over what I'm working on. I, I believe that he may not even care.
36:25 Speaker 00 And that is totally okay with me because that is the job of the people running the company. And the investments that I have made, when I give someone a check, then I try to stay out of it. Because I think Brian Singerman is also one of the most intelligent people I know. And I think he, he's right. I think value add is a great marketing tool that VCs have discovered. That if they use it, they can attract talent, they can attract LPs. And by doing that, they also increase their own value in the chain of how money flows. That's mostly what it is.
37:01 Harry Stebbings? You said another thing, final one on fundraising. But you said, when you feel like you have to convince someone to really work hard on your space or to convince someone, walk away. Why is that? Why, why is having to educate your investor a bad thing?
37:16 Speaker 00 I'm a little jaded here, so, but one is allowed to be, to be jaded or influenced by one own experience. Even though I try to separate these things a lot, I do believe that there's unlimited amount of capital out there. And I believe that it is easier and it's better worth your time by focusing on the people that initially believe in that. Then, then trying to write two or three rounds with the same VC firm and spend two hours going into unit economics. Where the outcome of any of these meetings will evidently be that they write down the unit economics neatly. And then invest in your competitor. So it is very important to understand when a VC. Is trying to understand your business or when a VC is trying to understand your business to the extent of also another business at the same time.
37:59 Speaker 00 So oftentimes, when you spend a lot of time and you feel like every meeting you have to, you have to really dig incredibly deep. Again, if you are a VC that needs that much conviction, regardless of the check size, already a red flag. And I find it will only get worse from there. It will only get worse because good luck with the next board meeting and the subsequent board meeting and not hitting a number and losing a percent market share. We had all types of investors in the company. It's not fun. Did you enjoy board meetings? I was not really good at first at running board meetings. I grew up running this company and I don't mean like in the sense of from a, from a young buck to like a teenager, but I think as a businessman, when, when I started the
38:44 Speaker 00 company versus 11 years later, I grew up as a person and I obviously honed my skills. So the first couple of board meetings, I think were, I didn't have the headspace to even think about the board really. So I was, I was so focused into the daily operations of the company. It was hard for me to have even predictions or sort of to even focus on explaining things to someone else. And after a while, when we got external investors that were not just Scott Bannister, who was the first on the board and Brian, sort of I had to learn that part of that ultimately is also to align the board and to make sure that the, that it's not just in your head, but that you communicate it to the board. What I found to be a very good strategy is to actually have the board meeting and
39:28 Speaker 00 non-board meeting and do a dinner the night before with a presentation sent out a week, but at least a few days ahead of time. At the board dinner, you discuss any sort of tension that there may be hitting your numbers or beating them or fundraising or updates or whatever it is, competition, so that you can then have a board meeting that is very short, very focused on just a few things that people commented on in the week leading up to the board meeting with the board deck that you provided. And it also gives everybody this feeling that, oh, we just sat together last night, right? So a lot of anxiety is out of the room, you know, people got to be used to the quirks
40:10 Speaker 00 again that they may have forgotten about, because you know, it's, people are, I love people and we're all different, right? That, that worked very well for me towards the end.
40:19 Harry Stebbings? I love that and I really like that separation between the board dinner and the actual board meeting and actually segmenting the content in that way. I do have to go for some hot takes, Basti. It'd be wrong for me not to. And, you know, as you said, VCs are sheep.
40:32 Speaker 00 What could it be?
40:33 Harry Stebbings? Why don't we talk about AI? And you teased me with having some controversial hot takes, but you didn't actually go into them. And so you said inference computers and that was it. What's your hot take on inference computers?
40:47 Speaker 00 I think there were three sort of areas that I wrote down. I think personal AI is another one.
40:52 Harry Stebbings? Cost of LLMs.
40:54 Speaker 00 Yeah, great. I think that obviously AI or machine learning has opened this great new paradigm and way of thinking. And honestly, has given tech a much needed boost and enthusiasm, which I think is fantastic. I believe that one of the overlooked areas of the current state of AI and the large language models that we're using is that they're still very expensive. They're dramatically more expensive than a Google search. And as a result of that, we don't really have any great killer apps beyond the chatbot. And anything you build on LLMs is very expensive because compute is very expensive. And obviously there is even on the compute that's available, a shortage of that compute. Right? So now most of that goes into training these models, which is done in the cloud and which is done on large GPUs.
41:39 Speaker 00 And it's a fantastic use case for that. When it comes to AI and personal AI, we may be at a moment in time where there is there is an opportunity for a new computer and new type of computer that we may see in every home. A computer that runs your own personal AI on a chip that does not have to be as powerful as the most powerful Nvidia chips. As a matter of fact, it could be a chip just designed for inference and just designed for for doing that very specific work. And that computer is not a computer with a screen. It won't be a computer that you sort of even necessarily interact with, but it will be a piece that other devices could interact with and that powers a large language model, if you want to, hopefully an open source one, and that will behave like a platform
42:23 Speaker 00 that has your personal weights, your personal preferences.
42:27 Speaker 00 That is connected to the world in the way that you want to.
42:31 Harry Stebbings? Why would you need a computer separate in the home for that? Surely the preferences, the data would be stored in a cloud provider, very much like having an OpenAI account that has your personalizations and preferences baked into that.
42:44 Speaker 00 No, actually not, for two reasons. First of all, you want the inference to happen as closest to the source of data as possible. And I like to argue that once a model is trained, then you get all the signals from your house, from your life, and in that moment is actually when inference is the most powerful. If you have data in the cloud and you need to computing on that data, sure, but not if it's data that is maybe to do around your home, right? So inference is very powerful the closer it is to the source of data, given that if you think about a personal assistant, the personal assistant needs a lot of information about you and inputs, that's why you would see that at home. It also is the only way right now to do it cost effectively. If you have personalized weights, if you have personalized numbers, your LLM in the
43:27 Speaker 00 cloud will cost a lot of money and it can't even do things real time right now for you because of the cost. You can run it at home and the only cost is your electricity. That's another reason. I talked to a few founders about this over the last couple of weeks. A lot of folks are convinced that this is sort of when you had these huge time share mainframe and you had to go into them and you have to pay per minute and you have to pay per use and the thing came back. And then Apple came and Apple won and you had a board that you can hack against at home and that allowed you to do your own thing. So I may be wrong, but I think there is something here.
44:00 Harry Stebbings? Is Apple not best placed? If you think about being closest to the source as being fundamental, is Apple's monopoly on hardware and phone usage and device not putting them best placed to run these models locally on device?
44:14 Speaker 00 Yeah, a couple of more hot takes that most people will not agree with and I'm happy to be wrong. I think the phone is dead. That's the first problem that will happen very soon. I believe that AI happened too fast and Apple is caught in sort of the inventor's dilemma here. I'm sure that they could eventually put an additional chip in an iPhone that does inference and allows you to run these models more efficiently, but I doubt that it will be interesting enough for the group of people that I have in mind and want to tinker with the technology. So.
44:45 Harry Stebbings? Why is the phone dead?
44:46 Speaker 00 I think it had a good run, man, but I think we have to call it, we have to call it what it is. Look at us.
44:52 Harry Stebbings? What replace is there?
44:53 Speaker 00 I mean, ultimately, we will find a way to use implants to communicate or devices that are smaller. But I think we will see a world where people go to an operating system for L L Ms, maybe a voice operating system. I think there is many ways. That device may have not been invented yet and it may take obviously longer. You know, landlines are still around. So when I, when I call it dead, I don't call it dead in the sense of we won't use it anymore. But I think it, it has reached the peak of its importance in people's lives.
45:24 Harry Stebbings? Are you long or short on the Vision Pro?
45:26 Speaker 00 On the vision, as it, how it is today? Short.
45:29 Harry Stebbings? Because?
45:30 Speaker 00 I think it's a product in search of a market. It may have a fantastic application in science and in medicine, to a less degree in media. I think it is just a product that doesn't bring us together, regardless of all its neat technology and the fake eyes and, and all of these things. You know what? I think Apple knows this obviously, but they have incredible people working for them. The hardware that would change would just be in recognizable, different from your regular reading glasses. And it, and it would have unlimited battery life, overlay of information, anything that you can imagine in, in like a very subtle way. That would, I think it would be a great tool.
46:11 Harry Stebbings? Where do the benefits accrue? More to startups or more to incumbents in the next wave of A I?
46:16 Speaker 00 So in, in almost everything that we've seen, I think it is incumbents. I don't think that's too contrarian because it, it just makes a lot of sense, right? But there will be companies born today that will be larger in the field of A I than the companies that are the largest companies that we have today. And they will start as toys and they will start as something that is probably overlooked and something that is not most applicable and something that is not most obvious. That's my prediction.
46:50 Harry Stebbings? Quick debate with you, but we've never had incumbents who have such data advantages that these incumbents have. And we've never had incumbents who throw off three hundred and fifty million a day in free cash flow like Microsoft does, combined with the data advantage. Are these incumbents not too strong to use up?
47:05 Speaker 00 BlackBerry at some point owned the entire smartphone market. Grubhub ran pretty much all food delivery in the United States.
47:12 Harry Stebbings? Those are weak examples. You can do better than that, Basti. Come on. Like, they had BBM as a network retention mechanism, maybe. But I mean, the market itself was pretty small. Their market cap never exceeded a huge amount. Their free cash flow was never a monstrous amount. Grubhub was not ever global, not even comparable.
47:33 Speaker 00 What's your point?
47:34 Harry Stebbings? Is this incumbent set not more dominant than ever before? And actually, we're in a very different world of startup versus incumbent.
47:44 Speaker 00 I still don't buy it. I think in retrospect, it always looks like this. Ten years ago, Apple didn't produce their own chips. Like, everything looks like that. At some point, there is a market that looks penetrated, a thing that can't happen. At the same time, look, it, it, this is how it starts, dude. It's always starts like this. The things start to fall apart from the inside. Google already can't launch an AI without the original founders coming back and having meetings with people with T-shirts of boobs or sitting in a room somewhere in San Francisco. This is Google that you're talking about. And they shut the bed so hard. They literally just went from like the most respected company in the world to laughing stock in a matter of month. So I just don't buy it. And look, this is, this is a marathon.
48:29 Speaker 00 This is not just a sprint. But the cracks start to show on the inside. The Vision Pro, an effort inside the company that was Herculean, I was told, where everybody was involved, where people had to take meetings they didn't want to know, where two teams of hundreds of people were pitted off against each other to get that thing onto the market, and now it fails. Dude, this will be the first product for Apple where they have more returns than they have on any other metric. You, you can plot the graph and it's the, since Steve Jobs came back, this is probably the first thing that is a turd. So the stuff starts to happen from the inside. It's not only that there is smart kits coming along and they're, they're doing something, but it's a combination of both. And that I fundamentally believe in.
49:12 Speaker 00 At some point, the people that did whatever made that company Great. And even their direct reports and the people that believe that at some point that either shifts, moves away, and then it starts to feel a little loose on the edges. And when it starts to feel loose is exactly when there is opportunity for someone else. And sure, you can buy yourself out of this and you can M and A your way into whatever you want, but it can happen. And then it won't happen overnight. And it will look like a toy at first. Whatever it is will be ridiculed. Then people try to catch up. If they're lucky, they can buy someone. But every once in a while, there is a company that rises and becomes extremely, extremely big, even though the set of circumstances seem very unlikely.
49:56 Harry Stebbings? Dude, I love it. Question, one company that seems to have risen obviously above any other is OpenAI. Do you think foundational models get commoditized? And would you be a buyer of OpenAI at 90 billion?
50:06 Speaker 00 It's a fantastic research company, is how I would describe OpenAI. I think it remains to be seen if they can launch extremely successful products other than chat GPT. It will be a dominant player. And look what they did, by the way, coming out of nowhere, yet working on it for seven years, right? You didn't catch up with Sam every week to get the status on what they were working on for the last six or seven years. And suddenly there's this one product and off you go. So of course they're important. I think they're a great player that is now inspiring a lot of founders and entrepreneurs to do great things and have the audacity to to to sort of dream in a direction that for the longest time, mostly because it was a market where if you worked in ML, you you got a nice salary at Google,
50:51 Speaker 00 but the expectations was just that you please don't bother anyone too much, right? So and now suddenly you're like, you're in demand. People actually listen to you. They believe that these things can work. You know, everybody wants to know what a token is. They will be a big player. I think they will be a very large company. But there's other companies that I'm personally like more excited about, so.
51:09 Harry Stebbings? Which ones are they?
51:10 Speaker 00 Well, I don't know. I have my list here. I have certain, I have certain names. I divide companies into like the big stuff, useful and noise. And most of it is noise, obviously, right? That's just like someone who comes along and says like, we're developing a brain for robots. But I think what looks really good is Figure. I think the latest robots that we've seen from them, they're remarkable. I think they work with OpenAI. That's an OpenAI investment. I think that you see a lot of really remarkable companies coming on, working with smaller models, more dedicated models, models that may be a lot more trained for a specific purpose than sort of that giant call center that can do anything. But other than AI, I'm telling you, space, nuclear, count me in.
51:51 Harry Stebbings? Any startups that have had huge publicity and you're like, I don't get it?
51:55 Speaker 00 A lot of them, but that's okay. Technology is the absolute greatest thing. Faster, more enthusiastic into the technological future. That's what I believe in.
52:05 Harry Stebbings? Final one, you mentioned time scales actually taking longer. I am just intrigued. You said to me before, and you said, sorry, on Twitter before, not developing AI fast enough is what will kill us, not the other way around. What did you mean by that?
52:19 Speaker 00 We are already facing and we will continue to face dramatic challenges, obviously, as a country, but also as people. And on this planet, moving to a new planet, if we want to be multi-species. I think the challenges ahead of us, we need to develop all the technology we can to solve them, to engineer ourselves out of global warming, to make decisions based on data and guidance that we can get from better software, getting to Mars, all of that, I think it's essential that we make great strides in AI. The risk is not that there will be an evil AI that will kill us. I think the risk will be that by not becoming more intelligent and using these intelligent tools, we'll become extinct.
53:00 Harry Stebbings? Bold statements. I'm loving this. Glad we did that as a, as a quickfire on AI round, Basti. That's fantastic. I want to do a quickfire round more broadly. So I ping you with a statement, you give me your thoughts. Does that sound okay?
53:12 Speaker 00 Yes.
53:12 Harry Stebbings? What have you changed your mind on in the last 12 months?
53:15 Speaker 00 Again, technology. I, I mentioned it before. I think we were in a little bit of a slump there for a while. It seemed like everybody shut off the engines and we had to be very apologetic and it was sort of, now I think we're so back and I think it's great because I'm saying it again, like accelerate into the technological future as fast and as enthusiastic as we can.
53:36 Harry Stebbings? What are you most concerned about in the world today?
53:38 Speaker 00 What am I most concerned about? United.
53:41 Harry Stebbings? Go on.
53:41 Speaker 00 Going on a United airplane.
53:43 Harry Stebbings? Oh, wow. I, I thought, I thought you were like United. I was like, is that like, are we talking about like geopolitics?
53:49 Speaker 00 No, just flying United. I'd be very concerned about that.
53:53 Harry Stebbings? Well, you know, life is good then. You could get a PJ, Basti.
53:56 Speaker 00 There you go.
53:57 Harry Stebbings? Uh, single biggest way VCs and founders are misaligned?
54:00 Speaker 00 Expectations.
54:01 Harry Stebbings? Why expectations? VCs always just one more?
54:04 Speaker 00 No, it's, uh, expectations more in the sense when and sort of how, and I think there, there's a lot of friction there in general.
54:10 Harry Stebbings? What's the most lavish purchase you've made?
54:12 Speaker 00 Having two kids.
54:15 Harry Stebbings? What's the biggest piece of BS advice that you hear most often?
54:18 Speaker 00 The first X dollar in revenue is always the hardest or something like, there, there, there is a, there is a version of that coming out of everybody I've ever met. So yeah.
54:26 Harry Stebbings? What's the kindest thing anyone's ever done for you?
54:28 Speaker 00 You know, I think my co-founder Sean Place is one of the greatest humans that I know, and I am so thankful for his friendship because what he has done for the entire time while I was the CEO and ran the company and did a lot of the front of the office work and we often banged heads and I reserve the right to have the final decision on a lot of things. That guy has just been the greatest supporter you can imagine every day. And he showed up every day and he said, be, let's do it. And he drove us to the fundraisings. I think he has given 10 years of his life in something that I made him believe in. And so I think just that in itself is, is, is a remarkable gift.
55:09 Harry Stebbings? Other than Dara, which CEO do you most respect and why?
55:13 Speaker 00 Oh, man, I can only name one because if you if you now name another one, then it's a can of worms, right? Other than Dara, I believe that the world would be a better place if we had more founder CEOs. And I hope that the founder CEOs that we have, that they stay CEOs for the long time. Patrick at Stripe, Zach at Plate, Max at Affirm. These are all just remarkable, remarkable people that run their companies so well and that had to fight battles and and and overcome all sorts of challenges, whatever they are. I mean, in Zach's place, you were bought, the acquisition couldn't go through, you have to go back and build again. If these guys are ever in, well, Patrick in that case, and Zach, if they run their companies publicly,
55:57 Speaker 00 books will be written about their leadership style, I'm certain of that.
56:00 Harry Stebbings? Final one, 2034, why do you want to be then? Where's Basti in 2034?
56:05 Speaker 00 Well, realistically, probably at some sort of sport event with my kids. Whatever they play is probably where I will be, right? So I have two of them, maybe ballet or whatever they pick up. My oldest one likes basketball, so that's probably what I will do.
56:22 Harry Stebbings? Basti, I wanted to do this for a long time. I so appreciate you putting up with the prying. You've been fantastic, so thank you for joining me.
56:28 Speaker 00 Well, I had a great time.
56:31 Harry Stebbings? It's so funny, before that show Basti said, let's make this a really special one. I think he absolutely did that. That was such a fantastic discussion. If you want to see the full video, you can check it out on YouTube by searching for 20VC. But before we leave you today, one thing I hear from my listeners all the time is that marketing leaders are under more pressure than ever to deliver real business impact. You know, more conversions, lowering customer acquisition costs and bringing in more revenue. But that's impossible when you're stuck with tools that don't move as fast as you do. That's why companies like Dropbox, IDEO and Orange Theory all trust Webflow to power their web experiences. Webflow's visual-first platform empowers your team to own your most valuable dynamic marketing asset, your website.
57:15 Harry Stebbings? From launching a new site to optimizing for SEO and conversions, Webflow Gives you the tools you need to drive business growth fast. Learn how teams like yours are using Webflow to power their web experiences and unlock their site's full potential today at webflow.com. And speaking of incredible products that allows your team to do more, we need to talk about SecureFrame. SecureFrame provides incredible levels of trust to your customers through automation. SecureFrame empowers businesses to build trust with customers by simplifying information security and compliance through AI and automation. Thousands of fast-growing businesses, including Nasdaq, Angel List, Doodle and Coda,
57:56 Harry Stebbings? trust SecureFrame to expedite their compliance journey for global security and privacy standards, such as SOC 2, ISO 2701, HIPAA, GDPR and more. Backed by top-tier investors and corporations such as Google, Kleiner Perkins, the company is among the Forbes List of Top 100 Startup Employers for 2023 and Business Insider's List of the 34 Most Promising AI Startups of 2023. Learn more today at secureframe.com. It really is a must. And finally, a company is nothing without its people, and that's why you need Remote.com. Remote is the best choice for companies expanding their global footprint where they don't already have legal entities. So you can effortlessly hire, manage and pay employees from around the world,
58:41 Harry Stebbings? all from one easy-to-use self-serve platform. Plus, you can streamline global employee management and cut HR costs with Remote's free HRIS. And hey, even if you are not looking for full-time employees, Remote has you covered with contractor management, ensuring compliant contracts and on-time payments for global contractors. There's a reason companies like GitLab and DoorDash trust Remote to handle their employees worldwide. Go to remote.com now to get started and use the promo code 20VC to get 20% off during your first year. Remote: opportunity is wherever you are. As always, I so appreciate all your support and stay tuned for a fantastic episode this coming Wednesday with the godfather of New York tech, Kevin Ryan.
Previous 20VC: Oscar Health: How to Deal with a 94% Decline in Market Cap, "Why I Stood Aside as CEO" and The Rebound Journey to $5.8BN in Revenue with Mario Schlosser, Co-Founder @ Oscar Health Next 20VC: Are the Best CEOs the Best Fundraisers, Are the Best Founders Insiders or Outsiders to a Problem, Why Ownership Should Not Be a Focus in VC & The Biggest Lessons Scaling MongoDB to $26BN Market Cap with Kevin Ryan, Founder @ AlleyCorp Page updated October 26, 2026 · transcript and summary are machine-generated