Ben Gilbert & David Rosenthal in Conversation with Michael Grinich | Acquired Unplugged 2026

Thank you, Michael. Thank you. Yeah, and really, I mean, this venue is amazing. We've never been in this room before. This is like we couldn't ask for a better night. And it seems like half of the Bay Area startup community is here. So, awesome to see so many founders and builders and reconnect with people. So, to get started, you know, and please start thinking of your questions because I'm just going to kick things off here. Um, you know, Acquired, the name of the podcast, most people don't know the history of it. I was doing a little bit of research. It actually came from the early episodes where these guys were not researching the long-term durable companies. They were actually researching companies that in many ways failed. Companies that their outcome was they were acquired versus being failed. It's Instagram, Pixar. Well, that's my entrepreneur inside is showing, you know. Um, they failed to be like long-term independent durable with you. You know, they and um since then the episodes are really it's transitioned to focus on these companies that have been around for decades and in some cases, you know, 100 plus years. So, the thing I wanted to start off the conversation ask is what is the kind of unique essence that you see across these different businesses? Ones that, you know, don't necessarily just live for a certain era or just a certain eon. What is the quality that actually allows them to kind of become the dominant, you know, vendor in their category, but have something that transcends across multiple different, you know, technology eras or just kind of like macroeconomic global changes. You should give your first thought because I already know where your head is of like what do they all have in common?

Great. Well, I think I know what you're thinking of. I'm going to do two. So, maybe I'll be doing what you think of, too. We're like an old married couple. You guys have the same brain. It's incredible. Yeah. Well, you've done 200 episodes today. About 230. 230, 10 years of Acquired you to celebrate it, so. 11 now. Wow. Wow. Thank you. Um, I think if not 100%, but it is shocking how many of the companies that we cover. And we always aim to cover, like you say, like the truly greatest enduring, most outstanding companies in the history of humanity. Um, and a huge percentage of them are just deeply, deeply founder-led. You know, not just founded by the founder, but like the spirit of the founder, even in a company like Hermes that is 188, 189 years old. Like, and we were talking about it with several folks earlier. The generational stewardship that is imbued in that. It is like a, you know, it's not just a business to them. Like, this is their family. This is like a deep stewardship that they feel. Uh, and obviously most companies are not on their sixth generation. I doubt any company in this room is, you know, even beyond its first. Um, but I think it's really that mindset of, you know, which is cliché here in Silicon Valley. Every VC says they're looking for that. But like really it's pretty rare of companies that and founders that actually are like viewing this as their life's work and treating it as such. And I think the practical application of that, if you're a founder wondering how to do this in your company, is whether it's Ferrari or Hermes or Apple or trying to think of our Google from our Google series. Absolutely Google. Yeah. Each of these companies leaned into the thing that made them really weird rather than seeking ways to be more like other companies. I think each of them tried to own their differentiation. And that may be a path to failure because it's generally non-consensus. Um, but in order to be an outlierishly successful durable multi-generation company, it is required to be extremely different than. Yeah, this may actually just be correlation, not causation, that you need to be really weird on some dimension and the only way that you're going to survive as that when the world is trying to stamp out that weirdness is if you just care so deeply about it.

Does it feel like these companies therefore are more different than similar actually as you go deep and analyze them? That's what I was saying David up. They're different in their different ways. Yeah. David's a very annoying answer to this question usually is not annoying to me, annoying I think if you're looking for a satisfying satiating answer is there is nothing in common between these companies and actually the thing that makes them each unbelievably successful is so different from each other that it's actually quite hard to pattern match, but that's the pattern is owning the differentiation. With an audience of people that are, you know, they're CEOs of their own companies or founders, is there a nugget of advice in that? Is it just be weird? Embrace your weirdness. Again, I Be weird, but be right. Right. That's the important Be weird and profitable, you know. Weird is a necessary precondition to outlierish success, but it is not a guarantee of success. Like it's necessary, but not sufficient. I think both of you have worked either, you know, directly investing or at VC firms. Is this something that investors are looking for, the weirdness too? Like back propagate to be. They know they should and we're both ex-VCs, so like we knew we were, but then there's all these forces working against you actually betting on the weirdest founders and the weirdest companies. Yeah, weirdly the same dynamic applies to VCs. Um, yeah. Weird VCs investing in weird founders. Yeah, love it. Love it. Well, with that, maybe we have some questions from the audience. Any questions that have been burning to ask? Yeah, go ahead, James. Uh, the question was, do we think about curating the quality of our audience? Or do we just want to make a great product and, you know, we just think we'll put the product out and great people listen. Oh, we are obsessed with curating the quality of our audience. We weren't at first. We figured this out over time. Um, but when we're putting our I used to just sit in my own shoes when we were thinking about what episode to make, but now I'm picturing someone. Like I'm picturing this room and thinking you are so busy, you have access to amazing information. You're when you're catching up with your friends, your friends are like right on the cutting edge of what's interesting. You're having the most sophisticated conversations. Where can I possibly earn my space in the rare minutes of your life? And I think that is like absolutely the frame that we bring to every episode. used to purely just follow our own interests. And we still do, but we started thinking about merchandising um a number of years ago. Say more about what you mean by merchandising. Yeah, like curating the set of episodes and companies that we cover. Like it [clears throat] was sort of um it was a debate for us to do Ferrari right after F1. And ultimately because like the stories bled so well into one another, we decided to do it. But a big, you know, mark in the con category was like, hey, are auto racing, you know, companies in a row. What about all the, you know, probably majority of our audience who don't care about auto racing? The goal is pick up smart, curious, passionate people, and we don't care what industry. And so, one of our favorite growth strategies is just doing new industries because the format now is sort of honed to pick up smart, curious, passionate people, and we don't care if that's healthcare or automotive or Schwab, oil, higher education, or agrarian machinery, or any of the other things that we're thinking about for later this year. The question was, do we think about curating our sponsors as much as we think about curating the content? Um, and if I caught the second part right, it's how do we balance having cool sponsors like WorkOS versus giant boring companies? Is that That's right. We can take credit for the growth of Acquired. Yeah, that's right. The enterprise SaaS infrastructure ecosystem Right. directly bringing listeners. You heard it here first. Yeah. As soon as WorkOS signed on, then yes, lots of companies Yeah. JP Morgan, everyone wanted to get in on it, you know, like So, we like to merchandise the sponsors the same way that we merchandise our eight episodes throughout the year. We think of it as building an investment portfolio. There's reasons that each stock in your portfolio is there, and you're intentionally creating sort of a medley or a harmony portfolio. a portfolio. Um, and so, we want big public companies that have brands that we'd really want to associate with, that we think increase the perception of Acquired, increase the importance of Acquired in the world. Um, this is why we're writing in the Wall Street Journal. It's not a sponsorship, but it's that sort of what brands do we want to align ourselves with? Um, but we also are on the side of the innovators, and we need to have sort of a well-balanced portfolio of what are the next great companies. You know, we've been working with Anthropic the last couple of years. It's been awesome um and being partnered with them, watching their growth, like that's our favorite thing in the world is when you hear about something for the first time on Acquired or it helps legitimize a company where you're like, 'Oh, yeah, I've kind of heard of that.' And then you hear David and I talk about it for when we started working with Braintree a few years ago, they were like um I don't even know if they'd raised their Series B yet. Yeah. Yeah. So, which for us is early stage, but um yeah, we're obsessed with it. And we think we're going to be judged by the quality of our sponsors. Uh, it's sort of like you're known by the company that you keep, so we're really careful about the company that we keep.

So, we've spent some time with some Apple executives recently. We'd interviewed Mark Zuckerberg. Um, we spent a lot of time with early Microsoft people. And the thing that all of them had in common was a complete disinterest in looking backwards. Which is funny for us because that's all we do. So, the question was what is common among some of the people that we've interviewed at the highest level. We want to dig into 20 years ago you made this decision, help us dissect that decision, and how did it have all the downstream impacts on the company's success. Um, and we have to get find unique clever angles to make these people who are always looking forward, always, you know, they wake up every day thinking about how to stack the next S curve on their company. Um, it's like pulling teeth getting them to reflect on the history. It's gotten easier since we started covering luxury companies. I think um a lot of those people have come to understand that there is value in building your own myth in a way that I think a lot of the tech industry and tech executives didn't necessarily think that before. So, our task has gotten easier, but fundamentally that's the nature of these people, but they don't really want to. They're also different. I mean, that's the I keep we keep going back to it, but they're kind of idiosyncratic. Like Jensen is extremely willing to bet the company, and he does it over and over again. He goes all in at great scale, and it's very strange because there's a lot of other CEOs. I probably shouldn't I think this is going to be public, so I shouldn't say his name, but a founder CEO of a big five big tech company mag seven. I don't know what you of the biggest tech companies in the world. And he like looked at me in a private interview setting like this. We were doing a pregame to get ready to go on stage, and he goes that's stupid. You should never bet the whole company. Well, why would you need to? Like you know play with house money. Like make incremental bets, but you never push all your chips back in again. And it's just interesting how there's widely different philosophies, and they're both multi-trillion dollar companies.

Uh, pretty god exactly the same thing. Like, this is—I can't imagine anything better.

Yeah, we both feel like we're doing our life's work, and it's like unbelievably that we found each other to do it with. Yeah, we have... Thank you.

There's two amazing things about what we get to do. One is we truly would do this anyway, because we started doing this with no motivation. There was no ulterior motivation. It was just like, oh, we have an excuse to study business history and we get to do it together. We have so many friends and peers that are solo creators, and like I won't speak for Ben, but I just feel so lucky to have like a best friend to do it with. And we've had three kids between us and we've gone through life ups and downs and different cities and it would be impossible to do it alone.

Yeah, impossible.

Yeah. The tweak on this is Acquired didn't look the same 5 years ago. It didn't look the same 10 years ago. So, if it was exactly the same thing, I bet none of you would care because it would feel really stale. So, I think the only way to guarantee that it stays fun for me and interesting for you is that it's different and fresh and we kind of keep following what feels like a natural evolution of what we will be curious about then.

The question is, what has been the hardest thing recently that we've said no to because we are a team that enforces strict constraints. I will say after 10 years we finally broke one constraint and Cole, raise your hand. We have a chief of staff named Cole and he has been the most unbelievable month ever having him at Acquired HQ. Can we give a big hand for Cole?

There were so many things I was worried about giving up that I thought for some reason I had to do or David had to do and it turns out that bringing on someone smarter and ambitious and like who loves Acquired as much as we do.

Have three young children between him.

Yeah, like I didn't think it was—I, you've all built companies. You know how this feels. I had the classic founder thing where I was thinking nobody can possibly love our baby as much as us and it turns out other people totally can and they can make it much, much better. So, that's not a no, that's a yes we said recently that kind of violated our own strictness, but it took us 10 years to do it.