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Ben Gilbert
Co-founder & Co-host, Acquired

The Obsessive Craftsmanship Behind Acquired Podcast

📅 Aug 28, 2025 Glue Guys Podcast 80 MIN 2122 VIEWS 385 SEGMENTS · 3 SPEAKERS
Ben Gilbert and David Rosenthal, hosts of the mega-hit podcast Acquired, join Glue Guys to share their incredible journey from side hobby to multi-million dollar business. They reveal how they've doubled their audience every year for 10 years through purely organic growth, discuss their intense research process, and explain why they architect surprises for each other during recording. From grading tech acquisitions to telling the stories of business legends, Ben and David explain how they've created podcast royalty through obsessive craftsmanship and authentic chemistry. #Acquired #Podcas...

Questions asked in this interview

12
  1. 3:00So how did you architect the research process?
  2. 9:34Like a—I mean, I know you said hobby, but was there a problem you guys were like trying to solve?
  3. 18:09So, David, when did you go full-time?
  4. 27:45Can I—can I do the thing now, like of just like two takeaways for me that are like bumping around in my head as you guys are talking?
  5. 32:29Like again, my former teammate, but like there's so much power in his ability to create content, right?
  6. 36:47Like yeah, Joe is like—this is a, you know, I think it's a moment that a ton of people look for pregame every game. What's he wearing?
  7. 38:23And then yeah, the commissioner walks up and I'll never forget—like there's this—there's a phone in the middle of like the table, right?
  8. 45:35I, you know, like literally from growth and, you know, monetization and what content style, what do you guys want?
  9. 48:24Rather than like their real versions, you know?
  10. 53:08It was crazy and like it was clear that you like weren't scripted, you know?
  11. 1:01:14You guys just had Brett and Clay on, you know, Act Two, right?
  12. 1:06:20I have a strong sense of some of the people that might have written you on the Indian Premier League cricket episode and it's like, man, like those people are really busy, right?
Ben Gilbert 0:00 ↗
A thing that has been true all of Acquired—it's doubled every year since we started 10 years ago, and all the growth has been organic.
Alex Rodriguez 0:07 ↗
Would you invest, RVI?
Ben Gilbert 0:08 ↗
The thing—I mean, listen, why do you think they're on this podcast right now? I mean, you know, wait till we go to the end and be like, 'All right, like here is the term sheet,' you know?
Alex Rodriguez 0:17 ↗
Live pitch.
David Rosenthal 0:18 ↗
Live pitch. Great.
Alex Rodriguez 0:27 ↗
All I will say is we have podcast royalty with us today, Alex. You know, these are the most—I don't know. I think that they're the only podcasters that I know that have been on the front page of the Wall Street Journal saying something like all the important people in the world listen to them. And so this is to me a little bit like Kobe going and playing at Rucker Park or something with a bunch of amateurs. And so we appreciate you guys. Thank you for joining our pickup game. You know, we hope that we get, you know, some of the reflection from the Acquired listener base. You know, today is deep, you know, very humbling with honesty and—
David Rosenthal 1:06 ↗
We love it. The stakes have gotten so freaking high with every Acquired podcast that it's amazing to play some pickup. Like, and we get to—we get to be creative again. We get to, you know, experiment.
Ben Gilbert 1:16 ↗
Yeah. The higher the stakes get, the more fun stuff like this gets. Well, we—Alex and I were talking before, and there's like a ton of things actually we want to talk to you guys about. So, we hope we get to everything, but like a bunch of stuff you just said actually is included in our topics that we hope to hit on. Like one, like you guys do have a lot of fun on the episode, and it's interesting. And then also the other thing is, all jokes aside, Acquired has gotten so popular, but it wasn't always that way, you know? And so we want to talk about that. But one thing, I guess, just to jump into it that I am genuinely curious about is on the stories you guys tell—you guys do sound like you're having a lot of fun, and there sounds like there's real moments of like delight and surprise. Like I was listening to the—re-listening to the Costco one the other day, which is just the best, right? I don't know what your best one is, but it's in the discussion. Costco's in the discussion—it's so good. But there was this moment where I think, David, you were like, 'Do you know who ran the all-hands after Sol Price got kicked out?' or something, and Ben's like, 'No, I don't.' And then you're like, 'It's Jim Sinegal.' And there's genuine surprise from you, Ben, on like, you know, that it was Jim. And so how does that happen? Like when you guys are doing the episodes and you have these moments of genuine surprise with each other, like how do those come about?
David Rosenthal 2:35 ↗
So we are not good actors, so those are genuine surprise moments, and we realized it's part of what makes the show great. So we architected our research and prep process to keep things from each other so that we get to have those, and that's why when we come together for recording day, that's the only take we get because we can't fake those moments by redoing it later.
Alex Rodriguez 3:00 ↗
Yeah. So tell us—tell us about the research process then. Like, how do you actually architect it? What do you do? I think we like getting into details from people that are excellent, and I genuinely believe it's like one of the aspects of the show that make it so cool and interesting and kind of makes it—you're enthusiastic to listen for hours because there are moments like that. If it was just you guys narrating, it would be less interesting and, you know, less durable. So how did you architect the research process?
David Rosenthal 3:27 ↗
Well, we can totally talk about the research process, but the other thing on the fun—I'm so glad you picked up, like, it genuinely is fun. No matter how crazy everything gets, how big the stakes get, like every time we get in the studio and we record, like it's just like—it's like the first time, you know? It's like it's genuinely like we love it. Like it's so fun. I could be so stressed out in the research process like, 'Oh my god, I don't know, we're going to land the plane'—and then we just get in the studio and we're like, this is genuinely really fun, right? We picked doing this—that like this was a hobby before it was the thing we do. But yeah, Dave, start with your side of research because you're—you tell the story. I mean, you're the one who writes a 70-page effectively script that guides the story.
Oh, wow. Well, I mean, it's evolved so much and it constantly evolves. So, I mean, when we started it was like—yeah, I mean, we were basically picking a topic like hours beforehand.
Ben Gilbert 4:23 ↗
That's true. We would—so we worked at Madrona at the time, and we would say, 'Let's record at 6:30,' and at 5:00 we would pop down our computers, start researching for the episode, and be like, 'All right, I feel like I have a pretty good sense of why Facebook bought Instagram, got some good facts.'
David Rosenthal 4:41 ↗
This is how we ended up grading the YouTube acquisition as a C-minus, maybe, originally. Yeah. Everything we're about to say has been this very iterative thing that has never changed that much from episode to episode, but is, you know, a ship of Theseus. It's unrecognizable from the way it started. My end—and then Ben should tell his end too because it really is separate. I mean, we live in separate cities. We talk every day, multiple times a day, but we don't talk about—like, beyond the basic scaffolding, we don't talk about what we are researching and what we're going to say in the episode. So it really is like a whole month of independent research from each of us. We spend a whole month doing it. I usually—I like to start with books. So usually the companies we're covering, there's anywhere from one to, you know, 20 books about them.
So I used to be—I made a mistake a couple years ago, especially on the Nike episode, where I was like, 'I got to read every book.'
Ben Gilbert 5:38 ↗
Together, we read 12 books about Nike.
David Rosenthal 5:40 ↗
Yeah, that was too much.
Alex Rodriguez 5:44 ↗
Are there—if there are books about Nike other than Shoe Dog that are worth reading in addition to listening to your episode? I would love to do that because I love Nike, but like—separate conversation.
David Rosenthal 5:54 ↗
Yeah, Rob Strasser's book for sure. Yeah. Totally different perspective.
Alex Rodriguez 5:58 ↗
Awesome. He's the—I can't remember if he's the villain in Air or just one of the other characters.
David Rosenthal 6:03 ↗
Yeah. Air is great. Not entirely historically accurate, but Rob has a very different perspective that's worth reading. Anyway, since then I dialed it back and realized that like, you know, when you read 12 books, it's just—you're overwhelmed. It's like you prepped too much for the test.
Alex Rodriguez 6:19 ↗
Yes.
David Rosenthal 6:20 ↗
So now it's like spend a little bit of time, figure out what are the one to three like books to read. Like in the Nike case, it should have read Shoe Dog and Strasser's book.
Alex Rodriguez 6:30 ↗
Yep.
David Rosenthal 6:31 ↗
That have the best primary-source account of what happened by the people who were really in the room.
Alex Rodriguez 6:35 ↗
Yep.
David Rosenthal 6:36 ↗
Yep. And there were a few years there—Nike episode around that era, you know, probably 2020 to 2023, early 2024—where that was it. Like, read the books, take a lot of notes. I read physical books, hard copies, with a pencil. I'm underlining, I'm making notes. Go through, read them, and then enter into like note- and script-writing mode where I'm going back through all my notes, translating that into like, okay, what's the story I want to—what's the narrative I want to weave? What are the beats? How is this going to flow? What sets up what? That used to be it. Now, though, that's like—I don't know, what would you say, Ben? Half of what we do, maybe less. We're doing so much primary-source research now. Like, there ends up being about 50 sources per episode, and we put all those in a link in the episode.
Alex Rodriguez 7:28 ↗
And 50 sources, you mean like interviews with, you know—
David Rosenthal 7:31 ↗
So that doesn't count the interviews.
Alex Rodriguez 7:33 ↗
Yeah.
David Rosenthal 7:34 ↗
We end up doing about 10 to 20 primary-source interviews in addition to the few books that we read. And then, you know, sources 4 through 50 are like articles that were important at the time but people have long forgotten. I think this is a huge key to research: is how were people describing in the press when Facebook launched the News Feed? Totally different than the way people talk about it now. And that's part of what makes the episode great is David speaks in present tense as he goes and he says, 'Okay, so it's now 2004. Facebook is launching the News Feed. People are saying...' And I think that that's a—I don't want to call it secret sauce.
Ben Gilbert 8:24 ↗
Yeah. By getting to go and read all that day-of primary-source reporting, we can like feel in our guts as we almost transport ourselves there. And you find stuff like in our Alphabet episode we just did—Q4 2005 earnings for Alphabet, first year the company was public—or from Google then, first year the company was public. Revenue is growing like a rocket ship and profitability is down, earnings are flat because they're investing in all these new products. Stock drops 27%. There are all these press articles about like, 'What is Google doing? These guys are messing it up. Like, this is awful,' like, you know, etc., etc. Like, now nobody remembers, but like that actually sets the stage for, you know—so anyway. And now if you look at a stock chart, it's—you know, it all rounds to zero. So it's not like you can even tell if you're trying to examine the data from today. So yeah, then there's the primary source, the interviews we do. I mean, yeah, the Google series has been probably 30, 40 people we've talked to, you know, from the highest levels all the way down to like engineers who are actually building the stuff.
Alex Rodriguez 9:27 ↗
Quickly to go back to the very—I take you back. Let's go back to the very first episode. What was the—what year was it?
David Rosenthal 9:33 ↗
2015, October.
Alex Rodriguez 9:34 ↗
2015. Okay. What was the genesis of this for you two? Was it literally a passion? Like a—I mean, I know you said hobby, but was there a problem you guys were like trying to solve?
Ben Gilbert 9:45 ↗
Alex, just before they answer, when was the first time you listened to a podcast? What year?
Alex Rodriguez 9:49 ↗
I have no idea.
Ben Gilbert 9:50 ↗
I mean, well after 2015, right? Like—
Alex Rodriguez 9:53 ↗
Yeah.
Ben Gilbert 9:53 ↗
This is what I'm saying. Like, if you asked me what a podcast was in 2015, I don't think I would know. And so this is why it's so crazy. I want to hear this. But like, if you made me guess, it might be like 2020 was the first time I listened to it. Like, literally first time I listened to a podcast was five years later. Probably didn't know they existed till 2018 or 2019. And so it's so crazy to think about 2015 in this thing. Please.
David Rosenthal 10:16 ↗
The total addressable market for podcast advertising, because that was the only revenue stream for podcasts then, the year we started was $40 million—with an M, million dollars.
Alex Rodriguez 10:32 ↗
Yeah.
Ben Gilbert 10:32 ↗
So yeah, the way it started was I was a big Apple nerd. I was a software developer and I'd been building iPhone apps. And podcasting—Serial, I think, had just come out, but before that, podcasting was kind of a thing people did who were tech nerds. There was MacBreak Weekly and the Leo Laporte world, John Gruber and Daring Fireball, Marco Arment, who was an iOS developer, wrote—he did Build and Analyze. I mean, it was nerds talking about nerd stuff, and it was deeply tied with the Apple ecosystem because podcast—the iPod. The funny thing is that was actually 10 years into podcasting in 2015. Podcasts actually first appeared in iTunes all the way back in 2005. And so David and I were co-workers-ish. I worked at Madrona in the Labs group. He was a proper investor. We were friendly but not super close friends, but we just knew we liked spending time together. And I was just rattling off my list of, 'Here's a bunch of different projects that sound interesting.' Some were apps, some were like ideas for blog posts, some were podcast ideas. And David just leapt at this one and was like, 'Not only do I think this Acquired idea is a good one—if you want to do it, I will do it with you.' And we recorded a pilot shortly thereafter.
Alex Rodriguez 11:49 ↗
Really? Okay. So then you start—keep going because I think again, like one of the things we talk about a lot is like—I mean, this is—it's so funny to say this to you guys because you tell stories of incredible companies, but like one thing for us is like if you go to people, it feels sometimes like people that appear successful from the outside, like you guys certainly do, it was so inevitable and it was so obvious and it was like—that does not seem like the story of Acquired. Even the name, right, is not what you guys—yeah. Yeah. So like, take us—go deeper. Is 2015—you know, you guys are—I mean, at least, Alex, for you, like you grew up playing football. It's like people know football is a thing. Like nobody probably questioned why you were playing football. Like we got questioned for a long time. 'Why the hell are we doing this? What is this? What is a podcast? This is a distraction. This is worthless. This is—you know, like what are you doing?'
David Rosenthal 12:42 ↗
Yeah. So it wasn't a business. I don't think we made money until maybe year three. We got our first check—I can't remember exactly. I think it was—
Ben Gilbert 12:52 ↗
$2,500.
David Rosenthal 12:54 ↗
10 episodes, something like that. So it wasn't about making money. It wasn't a business. It was purely, I think, this would be fun. The format was incredibly structured. It was take a deal—a very good tech acquisition—and analyze why it was incredibly value-creative for the acquirer, and then grade it. And it actually wasn't as much about story as it was about the analysis and the grade. You know, basically comparing everything to the Instagram deal.
Ben Gilbert 13:23 ↗
To the extent that we had a motive beyond just—like, the primary motive was hanging out. The secondary motive, such that it existed, was we were VCs and like, 'Oh, I guess like, you know, we should try and invest in companies that get acquired for a lot of money. So let's study how that happens.'
Alex Rodriguez 13:40 ↗
This is—this is crazy.
Ben Gilbert 13:41 ↗
Yeah. This is crazy. This is crazy. And by the way, RVI tries to sell us on that it's just time to hang out, you know, this is, you know, regardless of anything, which it's been effective so far. But I mean, again, like on this whole like not-obvious thing, right? Like you're in a—you're in a—you guys are dabbling in a field that is nascent, right? Like it's—it's not even what it's going to become. Did you guys have an idea that it was going to become something? And then for three years, like there is this concept of like, are we just like, you know, like talking into the void, right? Like I mean, is this—there—did you guys—there had to be—
David Rosenthal 14:19 ↗
We got feedback from like our immediate social circle saying, 'Oh, I listened, it was cool, I agree with you, you said this.' So even though the numbers weren't big, you get enough like passing comments at a—
Ben Gilbert 14:30 ↗
Start getting fans too that we didn't know. I mean, it was small, but like we could tell it was working. People really like this.
Alex Rodriguez 14:36 ↗
Is it kind of like the—you know, the Paul Graham, like, you know, a hundred or a thousand people that really love it, you know, type—whatever the numbers are—the idea of like there's real passion from a small group of like, 'We're on to something.'
Ben Gilbert 14:49 ↗
A thing that has been true all of Acquired, which this is crazy—it's doubled every year since we started 10 years ago, and all the growth has been organic. Like truly 100% year-over-year growth for a decade.
Alex Rodriguez 15:00 ↗
Would you invest, RVI?
Ben Gilbert 15:01 ↗
The thing—I mean, listen, why do you think they're on this podcast right now? I mean, you know, wait till we go to the end and be like, 'All right, like here's the term sheet,' you know?
Alex Rodriguez 15:10 ↗
Live pitch.
Ben Gilbert 15:12 ↗
The thing—the thing that's been true the entire time is people don't listen because they're interested in a topic. People listen because they're interested in the show. And there's something about the concept, the format, David and I, our chemistry, whatever it is—when you tie a bow on that package, it's a thing where a huge amount of people just listen to whatever we say rather than saying, 'Oh, I like healthcare. I'll listen to Novo Nordisk.'
Alex Rodriguez 15:40 ↗
Well, okay. On that note though, you even said like obviously the early parameters of the show are not even close to what they are now, right? Like from the research, the storytelling. When was—was there an unlock at some point? Like when did it happen that you guys got to this? Was it—was there an episode? Like did you guys even have your own like Acquired moment? Does that make sense? Like what—I—I don't know. I'm just asking. Or was it like—
David Rosenthal 16:02 ↗
There probably were some moments we can think of, but I think also like the industry just kind of birthed around us.
Ben Gilbert 16:10 ↗
AirPods came out. Yeah.
David Rosenthal 16:11 ↗
It became acceptable to just like listen to other people talk in your ears while you're wandering around the world, which wasn't true in 2015.
Ben Gilbert 16:18 ↗
Yeah.
David Rosenthal 16:19 ↗
And then we started—you know, meeting all these other shows and just being in the ecosystem—and we started realizing like, crap, this might be a lot bigger than we thought, or the potential might be bigger. I mean, Patrick O'Shaughnessy, you guys know, we got to know him. We went on his show, he came on our show. This is what, 2020—
Ben Gilbert 16:37 ↗
21, somewhere in there.
David Rosenthal 16:38 ↗
Yeah, somewhere 2020, 2021. And we were chatting with him about, you know, what his show is like, the amount of numbers he was doing and listeners and revenue. And we were like, geez—
Ben Gilbert 16:51 ↗
Maybe we could do that too.
David Rosenthal 16:52 ↗
He was two to three times—like the best was two to three times Acquired in listenership, but like 25 times or something in monetization.
Alex Rodriguez 17:00 ↗
And this is what year?
David Rosenthal 17:02 ↗
2020, I think.
Alex Rodriguez 17:04 ↗
So right around that time that you were like podcasts were becoming a thing. You were, you know—
Ben Gilbert 17:08 ↗
And so at this point, when did you guys make this your full-time jobs?
David Rosenthal 17:13 ↗
The funny thing is I didn't go full-time till last year.
Alex Rodriguez 17:16 ↗
What? Oh, really?
David Rosenthal 17:17 ↗
Isn't that nuts?
Alex Rodriguez 17:18 ↗
It's—it's pretty nuts.
Wait, no, that—Ben, that cannot be true. Sorry. Like, say that. Give me some more details on this.
David Rosenthal 17:25 ↗
It's funny. I can hear my wife talking in the other room. If you ask her, I basically have just always worked two jobs since we met. We met and Acquired started the same week.
Alex Rodriguez 17:34 ↗
Oh, wow. Okay.
David Rosenthal 17:36 ↗
And so basically, like it's just always been a normal thing in my life that I had a job and then I also spent another 40-plus hours doing Acquired. Ben is the best partner ever because you just genuinely love working.
Alex Rodriguez 17:50 ↗
What was your guys' cadence early on? Recording?
David Rosenthal 17:54 ↗
We used to make a lot more episodes, but they were a lot shorter and they were a lot less researched.
Yeah. Early on, I mean, gosh, we were doing probably a show every two weeks. Does that sound right, Ben?
Ben Gilbert 18:06 ↗
Yeah, that's about right.
David Rosenthal 18:07 ↗
Yeah. Yeah.
Ben Gilbert 18:07 ↗
And for many years that way.
Alex Rodriguez 18:09 ↗
Okay. So, David, when did you go full-time?
David Rosenthal 18:11 ↗
2020.
Alex Rodriguez 18:12 ↗
Okay. So full-time 2020, you're—
David Rosenthal 18:15 ↗
2020 is when the business—after that conversation with Patrick, we were like, oh wow, we should just stop doing everything else and like this is like—this is the thing.
Ben Gilbert 18:26 ↗
The insight was we're not a podcast the way that a true-crime podcast is, where we're selling mattress ads for the same price as mattress ads. What we've done is create a trusted relationship with the most valuable subset of people in the world who want to study business history and the lessons you can learn.
David Rosenthal 18:46 ↗
And so we should completely divorce ourselves from like, oh, we're selling ad slots, and instead think about, okay, what's the right price, package type of relationship, durable partnership with companies that—so we completely rebuilt the revenue model.
Alex Rodriguez 19:01 ↗
Is that from—because a little bit of that I, you know, from the Patrick—you know, you think about Patrick O'Shaughnessy's audience, like his listenership, like it's not—to your point, that's not the same people that are listening to like fantasy football podcasts.
David Rosenthal 19:15 ↗
Well, there probably are people who are listening to both, but not everybody who listens to a fantasy football podcast listens—
Alex Rodriguez 19:20 ↗
Right, like there's a different value.
Ben Gilbert 19:21 ↗
Alex, you got to be careful. I think the fantasy football listener is part of your demo, which, you know, we got to—we like people that listen to fantasy football podcasts.
Alex Rodriguez 19:28 ↗
Okay. Listen, I play. I'm just saying you're not being sold Bud Light on Acquired.
Ben Gilbert 19:36 ↗
And we actually have a, you know, sort of quasi-policy, to the extent we have policies at all, of like we don't do consumer brands. We only do B2B. We only do super-high-LTV B2B. Like if your—if the product that you're selling is targeted at SMBs or not a, you know, big enough annual contract value, it's just not going to make sense. Like most of our sponsors are landing, you know, million-dollar, tens-of-million-dollar type deals at a pop, and that's what we're great at.
Alex Rodriguez 20:06 ↗
Okay. But we're hiding the ball on some of this inflection-point stuff. There's business inflection points, which is what we talked about there, and we talked with Patrick, and—but there's also these content inflection points, most of which came from David. David, you've come to me a number of times saying, 'I think we have more latitude from the audience than we think.' And first that came in the form of, what if it wasn't just acquisitions? What if it could be IPOs?
David Rosenthal 20:28 ↗
So we did—was it the Facebook IPO?
Ben Gilbert 20:30 ↗
Facebook. Facebook was the first one. Yep. That we recorded the evening of the 2016 election.
Alex Rodriguez 20:35 ↗
Oh, wow.
David Rosenthal 20:36 ↗
Before—before like when everybody thought Hillary was going to win until like 10:30 p.m. I mean, I think that night—I think it was when Wisconsin flipped. There's basically like a moment late in the evening where it's like, 'Oh, this is going to go differently than most people thought.' Okay. Yeah. Anyway, and obviously that event changed Facebook's, you know, and Mark Zuckerberg's fortunes hugely.
Ben Gilbert 20:59 ↗
Yes. We didn't—we actually didn't re-record the episode. We sort of released it as is with some tongue-in-cheeky comments in there, which we probably wouldn't do today. Then in 2019, David came to me again and said, 'What if it's not about grading transactions? What if, you know, we've leaned so much into story in addition to analysis? What if we just tell the story of Tesla as a company without a transaction?' And it's not about the IPO, it's just about Tesla. And that was our biggest episode ever when we did that. And then the same thing, you came and said—you were talking to your wife and she said, 'I feel like you guys could do Taylor Swift. Like, why—she's not a corp—or there might be a corp in there somewhere, but the story is Taylor as a person. Could you do a person?' And then Taylor Swift was one of our biggest episodes ever. So I think there—it turned out that this format of conversational storytelling, us telling a story not through narration but through dialogue and then having some analysis baked in and after, applies to a much broader set of things than an acquisition.
Alex Rodriguez 22:03 ↗
So okay, so this is awesome. This is exactly what I was hoping to like learn. And so, okay, so when you—David, when you decide to go full-time, right? Are there people that like you love in your life being like, 'What are you doing?' Like, I mean, dude, you're like an investor at like a super legit venture capital firm, right? Podcasting is still not—it's like it's on the up. Okay. But it's not obvious that it is going to be as a career. It's not—it's not as obvious that it could be a career the way it is now, like a super awesome career. And so, was it hard? Were there people that you know you cared about that were like, 'Dude, like let me sit you down and have an intervention right now, like your partner's not even going full-time,' you know?
David Rosenthal 22:42 ↗
Uh, yes.
Alex Rodriguez 22:44 ↗
Okay. And so, how did you—
David Rosenthal 22:46 ↗
Everybody.
Alex Rodriguez 22:47 ↗
Everybody. Okay, cool.
David Rosenthal 22:48 ↗
Well, part of it was circumstantial in that it was just—just sort of, you know, how fund cycles work. And it was just sort of the right time to be like, all right, am I going to be an investor for the rest of my life or am I going to do something else? And this was just what I loved. And I was like, you know, it's funny—as the more we did Acquired, for me—I don't know if you had experienced this, Ben—I used to think that being a VC was like my dream in life for 15 years. If you met me, I would say all I want to do is be a great venture capitalist. I'm so obsessed.
Alex Rodriguez 23:26 ↗
Oh, wow. Okay. Fascinating. We started the show—
Ben Gilbert 23:28 ↗
Before you were in the industry. I mean, this is—you were like an investment banker at UBS saying that, living in New York, never even being on the West Coast.
David Rosenthal 23:34 ↗
From the time I was a senior in college until 2020, it was all I wanted to do. I was dreaming—dreaming about Sand Hill Road.
Alex Rodriguez 23:43 ↗
Yes. Yes. Yes. Yes. That was my like—that was my NFL. You know—
Ben Gilbert 23:48 ↗
You had a needlepoint pillow with a Michael Moritz quote.
David Rosenthal 23:52 ↗
Yes.
Ben Gilbert 23:53 ↗
What quote?
David Rosenthal 23:54 ↗
That my wife got me for my birthday one year.
The quote was, 'Focus on your winners.'
Alex Rodriguez 23:58 ↗
Oh my gosh, that's amazing.
David Rosenthal 24:00 ↗
That is how obsessed I was. I was so obsessed.
But then we started the show, and I swear to God, like as the show went on, you know, my interest and desire to be a VC just started like slowly going down, and my interest and desire to do the show started slowly going up. And at a certain point, you know, earlier than 2020, probably 2018, 2019, that, you know, before that, that intersected, and it just—and now today, you know, we still do plenty of investing, but like the last thing in the world I want to do is like be an actual day-to-day—no, no offense to you, Robbie, like I take it—like listen, I want—we want the truth, you know, that's it. It just became like I realized I was wrong about what I was sort of born to do in this world, and was like, I just want to tell stories.
Alex Rodriguez 24:49 ↗
Take me to that moment when you finally like told yourself like, fuck it, this is what I want to go do. This 15-year dream and journey that I've been on—like that's a big moment in life, right? Like to have the courage to go do that. Like what was that process like? And then the freedom, I'm assuming afterward, to like again go deep on this thing that you made this decision, right? Like—I don't know, I admire that so much.
David Rosenthal 25:11 ↗
Me too.
It was—it was, yeah, very, very, very stressful, as you could probably imagine, you know, on all fronts—family, friends, professional. You know, pretty much everybody thought it was crazy.
Ben Gilbert 25:27 ↗
You set a six-month clock.
David Rosenthal 25:28 ↗
Yeah. Yeah. Yeah. I mean, even my wife Jenny, who is the most supportive—you know, she's great, she's got her own great career. We've been together since we were—she was 19, I was 21 when we got together. We've been together—
Ben Gilbert 25:38 ↗
David and I bonded on this because we both met our wonderful wives when we were in college, you know. So—and even she was like, you know, okay, like, you know, I support you, but like we got to have a plan here. Like, you know, what's the—when's the money going to run out? Like what, you know, what's the clock? How long do you have for this to work? And so we settled on—
David Rosenthal 25:57 ↗
It was—I think it was—no, I think it was more like eight months. I think it was kind of like the rest of—if by the beginning of 2021 we hadn't—this was a few months into 2020 when I was sort of like kind of coming to this realization. So then I was like, okay, all right, I got the rest of the year. Let's prove that we can like actually make this into a real business. Ben, what did we do 2020? No—
Ben Gilbert 26:19 ↗
2019.
David Rosenthal 26:20 ↗
2019 we did 70,000 in revenue.
Ben Gilbert 26:24 ↗
Yeah. Total to the business. 70,000.
David Rosenthal 26:27 ↗
And we were VCs, you know, we weren't like, you know, partners, but like we were making hundreds of thousands of dollars in our day jobs.
Ben Gilbert 26:34 ↗
And then in 2020, when David made this basically ultimatum—because to me it was like, oh my god, if you have to go like get a new job and like become a high performer at this new job, you're not going to have time to do Acquired. Existential for the whole franchise that we build a business out of it such that David gets to keep it.
David Rosenthal 26:53 ↗
I bet you were right there with me the whole time. I mean, you were doing two full-time jobs, but like—
Ben Gilbert 26:57 ↗
Right.
David Rosenthal 26:57 ↗
I mean, this is the like greatest thing anyone's ever done for me—is you were like, 'Hell yeah, let's go.' And then in 2020 we made around somewhere between 200 and 250,000. So it was like still—I think the run rate was higher.
Ben Gilbert 27:11 ↗
Obviously we weren't making our day jobs, but—
David Rosenthal 27:14 ↗
Yeah, and then we had line of sight to 2021 when it had a huge multiple of that, where that's when we had the conversation with Patrick, realized we're thinking about this completely wrong, completely changed the sponsorship model.
Ben Gilbert 27:27 ↗
And then 2021, it became a multi-million-dollar business.
David Rosenthal 27:30 ↗
And it's one of these crazy things where like in 2020 at the beginning it seemed like there's no chance this could support us. By late 2020 we were like, oh, maybe it could be equivalent to our day jobs, and then within 12 months we were like, this is a no-brainer.
Alex Rodriguez 27:45 ↗
Can I—can I do the thing now, like of just like two takeaways for me that are like bumping around in my head as you guys are talking? One, dude, like I have so much admiration for this idea of you like leaving some room for serendipity in your life rather than just like being committed to one path come hell or high water. Like—dude, like I was talking to actually like a family member there, a young family member, like, you know, and he was—he just started college and he was like, 'Man, like, you know, should I join this business thing?' And I was like, 'Hey man, like listen, like you don't need to know what you want to do yet. It's okay. Like you just like be good and you'll figure stuff out.' And it's so easy as like the old guy to say that, but I think that like, dude, you got a needlepoint pillow with a Mike Moritz quote and you have a venture capital job. It'd be really easy to just be like, 'This is what I'm meant to do. This is what I said I was going to do.' But I like give you so much credit for the like—'No, man. Like let's see. Let's see what I actually love.' And so I think that's like amazing. And then I think the second thing is like by making yourself desperate, you know, it kind of like changes the trajectory of the thing. Like totally, totally right. Like that's so cool. Like the burn-the-boats, like, okay, like let's do it. And I think there's a thousand reasons not to do it, or I don't know however much money we're making, that many reasons not to do it. And it's really cool, dude. Just like—
David Rosenthal 29:06 ↗
There are a couple hundred thousand reasons not to do it.
Alex Rodriguez 29:08 ↗
Yeah. Like not to do it. And it's like, you know what? I'm going to do it anyway. Like and Ben, that's super cool on your side that you like were there with him, but also still on your side of like, look, I'm not ready to leave my job yet. And that—but I'm still going to get desperate with you. Like I don't know. It's like there's so much team stuff in there as well as like being who you are. Like I give you guys a lot of credit for when hearing that.
Have you guys ever done—I know you've covered obviously the NFL and NBA. Have you guys ever done one on an athlete? And if you—if you have, you ever thought about that and/or an acquisition?
Ben Gilbert 29:44 ↗
Taylor Swift, and then Michael Jordan's obviously a big part of the Nike story. And we had initially thought—we were like, oh, we want to do the Jordan Brand, and then we're like, well, you can't really extricate this from like—it is Nike.
David Rosenthal 29:58 ↗
Yeah, I'd say a big—a big chunk of the Nike episode is the history of the Jordan Brand. But yeah, on an athlete, I mean, that would be really interesting. And especially, you know, an—you know, not Michael Jordan, but Michael Jordan, Inc., and figuring out who the candidates are. Who—who are the five?
Ben Gilbert 30:13 ↗
Tiger Woods, Tom Brady.
David Rosenthal 30:16 ↗
It's not crazy that you could do LeBron. I mean, you could do—
Ben Gilbert 30:19 ↗
We could go back to the original thesis of the show and the New England Patriots acquiring Bill Belichick.
Alex Rodriguez 30:25 ↗
Alex, I bet you also internationally—like I don't know, like they could be like an F1 driver or something. Like I think I read one time like was it Michael Schumacher or somebody like the highest-paid people sometimes are, you know, in like—they're not, you know, necessarily like US athletes. And so I don't know, like I—that would be interesting. Taylor Swift is like a phenomenon though, and so I don't know, you got to think about whether there's a story that's worth telling that's as good.
David Rosenthal 30:51 ↗
The most impressive thing about Taylor is that we thought that was true in 2020, maybe 20—
Ben Gilbert 30:58 ↗
January '22. Yeah.
David Rosenthal 31:00 ↗
Okay. When we did the episode, and the impressive thing is her staying power as a phenomenon. I mean, she is a multiple of her prior phenomenon now with the Eras Tour, with the merger with the NFL, with these album drops. It's—it's really impressive.
Ben Gilbert 31:17 ↗
Big on the athletes though. I mean, to think of it—Travis Kelce, there's no way to know for sure—for us to know for sure, obvious, but I get the sense that athletes today, the top athletes, are making decisions about their careers through a much wider lens than just like, what is my contract with my team.
Alex Rodriguez 31:37 ↗
For sure. What you know, where you're playing, what your narrative is—like feels like way more important. Well, you guys just did this—you guys just did the episode on Alphabet, right? And like the YouTube thing is unbelievable. And even our journey into podcasting, like I assumed everybody just listened to podcasts on their Apple or maybe Spotify, you know, and you realize this like YouTube is this monster, like behemoth. They just—they just bought into the NFL, right? They had the Sunday Ticket. They have games this year. But to that point, like sports as a media property is the only thing in this country that brings people together at the same time, right? Like you no longer tune in Thursday night to watch Seinfeld, right? Like those days—100% broadcasts were—
Ben Gilbert 32:26 ↗
They're all football and most of them the NFL. Yeah.
Alex Rodriguez 32:29 ↗
They're all football. And so I do think there's been this empowerment, right? Like Travis is a great example of this. Like again, my former teammate, but like there's so much power in his ability to create content, right? Like obviously his own podcast is a monster.
Ben Gilbert 32:44 ↗
He's making way, way more money from New Heights than he is from the Chiefs.
Alex Rodriguez 32:47 ↗
Yes. So I think there is this—there has been an unlock, especially in the last I think five years, for athletes and their power, obviously off the field, to in different ways to create—I think generate income. And certainly YouTube, I think, being a part of this.
David Rosenthal 33:02 ↗
Especially interesting for the NFL. I mean, you know, we did episodes on the NBA and the NFL, and one of the key differences when we did these a couple years ago that we thought between the leagues was that in the NBA, players, you know, you're not wearing helmets, so the, you know, the fans see your face. So like you're much more able to build your brand and have a voice and have influence off the court. And then in football, it seemed like both culturally within the NFL and then just kind of elements of the game—it's so much bigger, team, etc., etc.—that was less true. But now it feels like that's converging.
Alex Rodriguez 33:36 ↗
Yeah.
I also think, you know, I was listening actually to Patrick's episode with the Skims founder, you know, Jens—I think his name is. And he was talking about how—why he went into business with Kim Kardashian. He basically was like, look, if you want to start like a tequila brand tomorrow, okay, and he's like, and you just want to start from scratch, he's like, you could spend like $2 billion on performance marketing and on billboards and all stuff. Like I don't know if it gets off the ground, like who knows. He's like, if you start one with The Rock, like it will sell. Like there is a set of stuff that will happen that is equivalent to some very high amount of marketing dollars. And he's like, and like even though The Rock has a great brand, I bet you he undervalues it in terms of like the fact that it is certain to get off the ground. There is something there. And I think that that same point that you guys are making on the athlete side—like Ben, the thing you said about the broadcast, that's all true, and that's like without some of the gambling stuff that's now coming in as hard. Like there's another factor that's going to make simultaneous watching even more pronounced, right? And I think that a lot of the people that are associated with the NBA, NFL, etc., I think they still believe that like many athletes are dramatically undervaluing their brands because like the fact that you watch what the NBA players wear when they walk into the stadium—like I don't know, is there—what is that analogous to? Like there is like real stuff that like is not fully monetized yet from these folks.
Are most NFL, NBA players buying their own outfits that they're walking in, or are they—
Ben Gilbert 35:13 ↗
There's no way.
Alex Rodriguez 35:14 ↗
Are they sponsored? Like—
Ben and David, I bought my own outfits. You know—
You were telling the story. I loved it. Of—was it—who was—was it Jim Harbaugh who said like, now we're traveling in the shirts and sweats? That wouldn't fly today, right? Because like everybody needs their fit for the social media.
Ben Gilbert 35:37 ↗
What do you think it's worth to a Gucci if they get that week's Joe Burrow walk-in photo?
Alex Rodriguez 35:42 ↗
Yeah, Joe Burrow. Totally.
David Rosenthal 35:45 ↗
No, a lot more than the cost of the suit. That's for sure.
Alex Rodriguez 35:49 ↗
Well, to your guys' point, the other thing is like I don't know. So I was watching it on Quarterback, right? Burrow like going to like the rack of like figure—he has got like a stylist, like, 'What am I wearing today?' But then the thing that was cool was the juxtaposition—like this dude, I think Joe Burrow is from Ohio if I'm not mistaken, like his family like hanging out in the box afterwards. He's wearing some like leather shirt with like a zipper that's like half open, and like his mom or somebody comes up and is effectively like, 'What the fuck are you doing?' you know. And but it's just great because like you can kind of see the full thing. Like I guarantee you if Alex—like having met like your parents, like if you at some point had decided to go more in the like fashion side, you know, like I mean how much shit would you be taking from the people around you? Like your sister.
I'm the complete opposite. Like I actually have this history, unfortunately, drafted in an era where it was like still the Carmelo Anthony like draft-day suit.
Ben Gilbert 36:45 ↗
Oh, the big—the big suits. Yeah.
Alex Rodriguez 36:47 ↗
Seven buttons and baggy. And so like no, no, my history is like the exact opposite. Like these pictures from my journey, it's like, what the fuck were you wearing? Like what were you thinking? Right? Like this is not—even remotely close to style. Like I didn't put any thought into this. Like this is all part of that same storytelling again—the power of these athletes. Like yeah, Joe is like—this is a, you know, I think it's a moment that a ton of people look for pregame every game. What's he wearing?
Ben Gilbert 37:11 ↗
Alex, did you wear a pink shirt on draft day?
Alex Rodriguez 37:14 ↗
Draft day. I wore a pink suit then. It was embarrassing. It was so big. So bad. I had these long sideburns—the video sideburns because like the only facial hair.
Ben Gilbert 37:25 ↗
You did it to look older, right?
Alex Rodriguez 37:28 ↗
I was a baby. I was 20. Was trying to look older.
Ben Gilbert 37:31 ↗
Projecting. I'm projecting.
Alex Rodriguez 37:33 ↗
Okay, this is—this is good. What was your—what was your mindset going into that day? Like what do you—did you know you were going to be number one?
I knew that week I was going to be number one. From the time that you found out you were going to be number one until the actual moment, it was like, holy fuck, how long until they find out they made a mistake? Like you know, like how long until—I mean it was—it was insane. Surreal. How did I get here? Like I mean I grew up watching the draft and you're like all of a sudden you're backstage in New York City. I got this ridiculous suit on that someone gave me.
Ben Gilbert 38:06 ↗
Was it at Radio City?
Alex Rodriguez 38:07 ↗
It was not Radio City. It was the Javits Center that year.
Ben Gilbert 38:09 ↗
Okay.
Alex Rodriguez 38:10 ↗
And so you're backstage. I got all my family. I got—I have an agent, right? Like all of a sudden you're sitting at this table. I mean, the commissioner, all these people I've grown up watching are like around. I mean, it is this insane.
Ben Gilbert 38:22 ↗
And you were only 20 years old.
Alex Rodriguez 38:23 ↗
I was 20. Yeah. It was this insane media frenzy, right? And then yeah, the commissioner walks up and I'll never forget—like there's this—there's a phone in the middle of like the table, right? And you're like, 'How did this phone get here?' And then it rings, you know, then all of a sudden I'm talking to the owners and you know, commissioner walks out and announces your name and it just like—I mean literally an out-of-body experience.
Ben Gilbert 38:46 ↗
Wow.
Were they doing back then? I mean now there's so much content captured around draft day. Were they doing that then?
Alex Rodriguez 38:53 ↗
We did a full like two days in New York. Me and Aaron Rodgers are like traveling around New York City going to different sites and there's cameras with us. It's like NFL Films and we're like—we go visit monuments and we're like throwing footballs around in our suits and it was like not—nothing like today, but they tried. Yeah.
Ben Gilbert 39:09 ↗
NFL Films, by the way, sidebar—
Alex Rodriguez 39:12 ↗
Greatest gift to like America.
Ben Gilbert 39:14 ↗
So great.
Alex Rodriguez 39:15 ↗
Yes. Unbelievable.

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APA

Gilbert, B. (2025, August 28). The Obsessive Craftsmanship Behind Acquired Podcast [Interview transcript]. Glue Guys Podcast. CEOInterviews.AI. https://ceointerviews.ai/interview/3055050/

MLA

Ben Gilbert. "The Obsessive Craftsmanship Behind Acquired Podcast." Glue Guys Podcast, 28 Aug. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3055050/.

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@misc{gilbert2025_3055050,
  author       = {Ben Gilbert},
  title        = {The Obsessive Craftsmanship Behind Acquired Podcast},
  howpublished = {Interview transcript, Glue Guys Podcast. CEOInterviews.AI},
  year         = {2025},
  month        = {aug},
  url          = {https://ceointerviews.ai/interview/3055050/},
  note         = {Speaker-attributed transcript with timestamps}
}