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David Rosenthal
Co-founder & Co-host, Acquired

#108 with Ben Gilbert and David Rosenthal - Brainstorming with the Acquired Podcast

📅 Jul 10, 2026 BlackNova Productions 87 MIN 23 VIEWS 224 SEGMENTS · 4 SPEAKERS
Shaan Puri (@ShaanVP) hosts the pod today with guests Ben Gilbert (@gilbert) and David Rosenthal (djrosent) from the Aquired podcast (@acquiredfm). In today’s episode you’ll hear: Shaan asks Ben and David to give some background on themselves and the Acquired podcast (0:30), Shaan gives four personalities that every company needs to succeed (11:00), the Acquired guys pitch an idea for an Airbnb that says whether or not the location has wifi (18:00), the Acquired guys talk about making your own stock index (29:10), Shaan talks about putting solar panels into space and beaming energy back down t...

What David Rosenthal said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

David Rosenthal, co-host of the Acquired podcast, discussed the evolution of the show beyond acquisitions to cover any great company story, citing recent episodes on Epic Games and SpaceX. He praised the host's show for highlighting smaller, capital-efficient businesses as a counterpoint to the venture-backed moonshot narrative. Rosenthal brainstormed several startup ideas, including a Waze-for-Wi-Fi service for Airbnb rentals, which he noted faces a cold start problem but could bootstrap with minimal data. He discussed a SPAC index fund, explaining the mechanics of SPACs and the potential for a basket of startups going public. Rosenthal shared insights on the insurance business, calling it 'the best business in the world' due to the float, and mentioned an upcoming Acquired season finale on a well-known insurance company. He also discussed the trend of smart people moving into climate tech, citing a friend starting a reinsurance business for California fire risk, and the appeal of buying small profitable businesses with SBA loans, sharing an example of a friend who bought a company for $300,000 that grew to $30 million in revenue.

Key takeaways

  1. Acquired podcast expanded beyond acquisitions to cover any great company story, like Epic Games and SpaceX.
  2. A Waze-for-Wi-Fi service for Airbnbs faces a cold start problem but could bootstrap with minimal data.
  3. Insurance is 'the best business in the world' due to the float, with an upcoming Acquired season finale on a well-known insurance company.
  4. Smart people are moving into climate tech, including a friend starting a reinsurance business for California fire risk.
  5. Buying small profitable businesses with SBA loans can yield outsized returns, as a friend's $300,000 purchase grew to $30 million in revenue.

Numbers and commitments

FigureWhat it refers toTypeAt
$300,000 Purchase price of a friend's business that grew to $30 million in revenue metric 58:07
$30 million Projected revenue this year for a friend's acquired business metric 58:24
20-plus Number of Series C or later startups expected to go public via SPACs in the next couple years metric 27:04
$10 a share Typical trading price of SPACs before acquisition announcement price 27:04
12% a year Yield from staking or lending Ethereum metric 47:33
5 to 10% Down payment required to buy a million-dollar business with an SBA loan metric 57:00
September 27th Deadline to buy a business and have the first six months paid by the SBA timeline 57:00
10% Portion of the purchase price the seller typically carries metric 57:00
12 months Timeframe to pay off an SBA loan for a business purchase timeline 57:00
2 to 3 times Potential appreciation of a business after operational improvements metric 48:32

Chapters

  1. 0:00Podcast crossover and show evolution
  2. 4:57Classic entrepreneurship vs. venture moonshots
  3. 17:27Waze for Wi-Fi for Airbnbs
  4. 26:59SPAC index fund idea
  5. 30:06Index licensing and stock exchange business
  6. 37:25Climate tech and smart friends trend
  7. 41:34E-commerce insurance gap
  8. 54:19Buying small businesses with SBA loans
  9. 1:02:09Bibo acquisition story
  10. 1:20:18Selling a company to Twitch

Questions asked in this interview

12
  1. 0:00Or this is going on your podcast or both?
  2. 5:43And we'll just say like, okay, what you got?
  3. 11:18... amazing person who can figure out, okay, how do we get this group of talented people to be cohesive, uh, over time, and how do we, you know, one person's thinking one thing, another person's thinking another thing, how do we get alignment?
  4. 19:52So Airbnb tells you, does it have Wi-Fi or not?
  5. 25:41Don't know what that means. Can you make it up?
  6. 38:52Was he the CEO of Reddit, right, at some point?
  7. 41:34I was like, everything's manufactured in China, what are you talking about?
  8. 44:04That's where the value is going to be, right?
  9. 58:55I was like, first, this is very uncommon, you don't usually get this type of lift, but I was like, did you know that there was this much room?
  10. 1:02:52The hard part is I'm the host, so it's always awkward like what am I going to interview myself?
  11. 1:09:21Why would you pay for this?
  12. 1:20:31And then is my little company an answer to any of those problems?
Sean Pancere 0:00 ↗
And this is for our podcast, correct? Or this is going on your podcast or both?
David Rosenthal 0:04 ↗
Good, good question. Like, we're open to whatever.
Ben Gilbert 0:06 ↗
Yeah, I think we should record it and see what fits. But like, by default, I think it'll definitely work on our feed. If you guys feel good about it on your feed, I think great. Just dual purpose it.
Sean Pancere 0:14 ↗
Great. I love it. Okay. Uh, are we rolling then?
Ben Gilbert 0:17 ↗
Uh-huh.
Singer 0:22 ↗
I feel like I could rule the world. I know I could be what I want to. I put my all in it. On the road, let's travel. Never looking back.
Sean Pancere 0:33 ↗
Let's do a quick, uh, quick intro. So, uh, I've never, I've actually never met you guys, but like I think most people for this podcast, I've heard you guys talking. Uh, and actually just say like five words into your mic. Your mic setup is like godly. I don't know what, I don't know if it's your voice or your mic, but something is perfect. It's all been, we, uh, if it were like, if I were running the tech side of Acquired, we would still be like talking into our, into our MacBooks. So, uh...
David Rosenthal 0:57 ↗
Yeah, but fortunately we have David's, uh, dulcet tones and buttery voice that kind of complete the, the equation.
Sean Pancere 1:04 ↗
And Ben, you have the, uh, like kind of soundproof panels in the background and stuff like that. I, I just like roll out of bed and push go and see if it works. All right, so we have David and Ben here with us. These guys host the Acquired podcast, which is, we'll talk a little bit about that. So you do that. You're also a venture capitalist from what I understand, if I remember correctly, from the podcast. Correct.
And, um, the podcast, I, so I used to listen to a bunch of it at the beginning because I'll tell you a funny story. We have a guy in our, in our office at our startup named Jason. And, um, Jason is great in all these different ways. He's super enthusiastic. He's a go-getter. He'll make [__] happen. He's very creative. Uh, but the one thing that Jason was always, uh, like kind of the punching bag in the office was he would always say the wrong, like he would always have his facts wrong. So he would be like, oh, um, you know, that's, you know, they got bought by this company, and we're like, no, it was this other company, or they raised this number, and it's like, nope, that's not the right number. So he was always like getting fact-checked, and then one day Jason started coming in with just these knowledge bombs, and we were like, that's not right. Wait, that is right. And I was like, how did you know that backstory? Like, did you research this? Like, I didn't understand. And then I realized the secret. He was listening to y'all's podcast, and he was, you know, basically what you guys do is you tell the story of great kind of acquisitions in tech history. And, um, and you go through kind of like very methodically. You like research it well, and you tell a very good linear story with no plot holes. And so Jason all of a sudden had this superpower where he was telling these perfect renditions of what went down. And I was like, what the [__] is going on? And so that's why I was like, okay, what's this podcast, uh, that you listen to? So I listened to a few of them. I haven't listened recently. I know you guys been, you pumped out a ton of them.
David Rosenthal 2:47 ↗
You got to hop back in because we're not just acquisitions anymore. We realized these stories, like we were limiting ourselves with just acquisitions because we'll get into this. So what did you expand to?
Ben Gilbert 2:56 ↗
You know, acquisitions are a limited part of the universe. So we just did Epic Games, uh, we did SpaceX, like those are like...
Sean Pancere 3:02 ↗
So it's just like success story in addition to acquisition story type of thing.
Ben Gilbert 3:06 ↗
Yeah. The, the goal is that we tell the story of like the, obviously the very deep story of any sort of great company, but then also try and understand the playbook of why it worked.
Sean Pancere 3:16 ↗
Right. I love, I loved them. I've listened to a bunch where you had like a three-parter, and I'm like, oh man, this is so deep. I love it. And then I was like, and then I sort of switched my habits in general, uh, where I was like, um, okay, I don't want to get smarter. I just want to escape. Uh, so now my podcast listening is like, I need junk food. Uh, that's how I listen to my podcast now. And so totally, I, I just go for like more entertainment, less information. But I know there's a bunch of people who listen to this that would actually really dig that because they want to hear the stories. They want the real information, and that's what you guys provide in a very good, good way. So anyways, that's my, my genuine shout-out for the podcast.
David Rosenthal 3:53 ↗
Your guys' show is awesome. We love it. And one of the reasons, A, you're just like good. You guys have great flow and chemistry. Like you're awesome. Uh, but B, it's such a good counterpart to like what we do on Acquired. Like we tell this, like this, like certain part of like the internet, like history and like as it exists, and it's like these big, huge, flashy companies, but like there's a million ways to skin the cat, and like there's so many other good businesses out there, and so many other people working, doing amazing things that are never going to be SpaceX, but like that's cool. Like, you know, Ben, like your Golden Hippo episode, I loved that one.
Ben Gilbert 4:27 ↗
Right, yeah. On one hand you have the story of SpaceX, and then the other hand you have like, you know, this guy who's in Iowa who's doing a drone light show company and just local, you know, rural, rural Iowa, and, uh, you know, making $2 million a year, and, you know, he quit his job as a construction worker before that. You know, that, that's the sort of other end of the spectrum of like cool success stories that are just different flavors.
Sean Pancere 4:48 ↗
Yeah, it's so cool you guys find these and you, you know, bring these folks on the show, and this is awesome.
David Rosenthal 4:53 ↗
Okay, so we agree. Our podcasts are great. We love it. Sorry, go ahead, Ben.
Ben Gilbert 4:57 ↗
I was going to say like I also just like that it feels more like classic, I'll say classic American, but classic entrepreneurship. Like we've lumped in entrepreneurship to become this thing that involves tons of money, a winner-take-all market, in all likelihood failing and flaming out, you know, fabulously, and by telling everyone they should go do that, you just set most people up for failure. Whereas it's not, as long as you're really focused, you really listen to your customers, you really iterate, you're really capital efficient, like going and achieving a million-dollar-a-year top-line business. Like lots and lots and lots of people do that and can do that and should think they can do that. And so I, I love that reminder in our lives.
Sean Pancere 5:43 ↗
Yeah. I would say like, um, Naval has this really like money line when he's talk, or I don't know who he stole it from. I think it was like Nassim Taleb or something where he was like, you know, um, they're like, you know, what's your political stance? He's like, well, with my family, I'm a communist. With my friends, I'm a socialist. With my, you know, my city or my town, I'm a Democrat. And, you know, I'm a libertarian at the, at the federal level or whatever. And it's just a great, yeah, it's a, it's a, it's just a money quote. But I have sort of a similar thing in, in entrepreneurship. It's the, the, you know, the poor man's version of that, which is, you know, if I invest, I go for the billion-dollar, the potential billion-dollar companies. If I'm advising somebody to start something, I advise the types of things we brainstorm on the podcast all the time, which are these, you know, small niche businesses that can generate a ton of cash flow. And then when I do it myself, I just go solopreneurship and I just create content that I think, you know, a lot of people can love, and I don't have to talk to, I don't have to like have employees or an office. That's my dream, right? And so there's, there's these different flavors that each is good for a different purpose and for a different person. So anyways, that's my view on it. And so you guys reached out the other day and you were like, hey, it'd be fun to do kind of a crossover episode. I think that's a great idea. So you came on and I was like, okay, what are we going to do? Are you guys going to come on and tell great stories? And I'm just sitting here with my popcorn because I'm down for that. But actually, you guys came with a bunch of ideas. And so I want to jump in and, uh, riff through a bunch of these. And like normally the way me and Sam do it is just like you have here. We just have a sheet with like a bunch of bullet points that like you don't even understand the full idea just from the bullet point. And we'll just say like, okay, what you got? And then one person will riff on one, and then when we're bored of it, we just say, all right, I got another one. And you just keep...
David Rosenthal 7:16 ↗
For us, because it's like we don't get to do this on Acquired anymore. Like we anti-Acquired.
Sean Pancere 7:21 ↗
This is awesome.
David Rosenthal 7:22 ↗
This is like, you know, when like a successful business person goes to Burning Man or Mardi Gras or something. It's like, oh, I get to let my hair down and just, you know, shoot the [__] on half-baked ideas that will totally not work most likely. Yep. That's what this is.
Sean Pancere 7:35 ↗
Uh, cool. So, so when you guys get excited about ideas or, you know, some of the stuff you sent over, you know, what's on your mind? What are you guys seeing as interesting? Let's, let's jump in with some of these different ideas you got.
Ben Gilbert 7:48 ↗
Yeah. So I'll, uh, I'll start because I, I have your, your Naval quote sort of inspired. Um, I have a very bifurcated lens on the way that I look at ideas, and I don't think I realized it until recently that, um, so I should give a little bit of background. So, uh, I started a thing called Pioneer Square Labs five years ago. We're a startup studio where we spin out, um, companies, all of which go on to get venture-backed. We've done that 24 times in the last five years. Uh, and we're based in, in Seattle. So I'm really looking to make a dent in, uh, in the entrepreneurial ecosystem in the Northwest. So we're coming up with ideas all the time too.
Yeah. So then we also have the venture fund, PSL Ventures, where we invest in early-stage companies in, in the Northwest. And so, uh, and many that we have nothing to do with starting. And so, uh, I sort of sit on both sides of the house of coming up with ideas and also evaluating ideas that are not my own. And I, I have, um, a massive bias with my own ideas where I'm excited about it no matter the market potential if I can fully conceive of how to build it in my head and how it will deliver value to me as a customer. And like, I, it's probably the engineering background, but like, I, I put on my blinders real quick and just go heads down. And I have to like fight every instinct. Like David will be like, hey, I think there's this really big way we can move the needle for Acquired, and pitch me this big grand plan. And I'll be like, yeah, but I need to fix the way that headers look on our website, and like I have a really good idea for how to do that, and sorry, I need two hours now. And so like, I have a massive bias towards things I can fully conceive of and, and will be satisfied with the value.
David Rosenthal 9:32 ↗
The idea you have is a, is a really good one.
Ben Gilbert 9:36 ↗
But the, I think, I think the way that I like think about, um, or evaluate other ideas is definitely, Sean, in that same way that you thought about like, you know, is this, is this winner-take-all? Is this going to be a massive thing? Is this a moonshot idea? And, and the scary part that always comes along with that is like, well, if this is a really good idea and now just happens to be the perfect moment in time where someone can do this, are these people the people that are going to pull it off out of all the other people who are also thinking of this rare moment in time where there's a good idea that hasn't yet been done? And like, that, that's almost disheartening, right? Because then you scope down the universe super, super narrowly. Um, and, uh, and you know, most of the time what you're doing is, is saying, no, I'll, I'll wait for the next one. And that's a frustrating, um, and, and sometimes disheartening, uh, job. But, uh, I, I think that finding that spot in the middle where you can sort of believe in other people's ideas as much as you do your own that you get excited about and apply the same amount of skeptical rigor that you do to things you're being pitched to things you come up with, that's sort of where the magic lies in the middle.
Sean Pancere 10:48 ↗
Yeah, I, I, I would agree. Uh, also when you said that thing about like kind of the way you two, uh, are, are different, it reminded me of this, um, you know, all right, take a shot. I said framework, framework that, um, uh, that I heard one time that has always stuck with me. I don't know if you guys have ever heard this, but, uh, Bill Gross, who's the founder of Idea Lab, he's kind of like, you know, internet OG, he gave this talk once and he talked about, have you, have you heard this about the four kind of personalities that, that come together to make a company?
Ben Gilbert 11:17 ↗
No. No.
Sean Pancere 11:18 ↗
So, so basically he says every company needs these four personalities and they come in a certain order. So it's called EPAI. So, uh, not a great acronym, but it works. And so EPAI, so E is the entrepreneur. So he gives this analogy. You're sitting in a room. So say you're sitting in a classroom and one kid is going to look out the window and it's just, you know, there's just a, there's just grass outside, but somebody's going to look at that grass and say, you know what? There should be a parking lot there. And, uh, you know, we all come into, we all come to school every day and parking is such a hassle. Um, there should be a parking lot there. It could be six stories high. We should build a parking lot. And so entrepreneur comes up with a vision, sees something before it exists based on, you know, a pain point or a personal dream. Then they have P, which kind of sounds like you, Ben, which is the producer. So producer is somebody who gets along extremely well with, with the E. Uh, they're not usually the one necessarily to come up with the, the kind of visions every single time. Uh, but they're very good at downloading the vision. They hear the vision. They say, yep, got it. Makes sense. And their brain immediately goes to, oh, by the way, six floors. No, no, no. What it should be is two different structures that each have this, you know, whatever. They start immediately, their brain starts building, uh, building that vision out, and they're going to be able to take words and turn it into, you know, some form of action. So he draws these curves. Like if, uh, if it's just the E alone, there's this initial value because they come up with a vision, and then it sort of peters out and goes nowhere because there's no production. But then if you have the E and the P, the P jumps in after the initial value is created and takes it to the next level. But then if you just have the two of them, um, your, your venture will be a mess because you need the, uh, A, which is actually an administrative type of person, a type of person who says, okay, great, we have a vision, we have a, a, a plan of production, we're actually going, we have six employees. But if no one's doing payroll, if no one's feeding anybody, if nobody's like writing things down about our plan, like we're screwed. We got to get organized here. And so you need A. A takes it to the next level. And then the last one is I. I is the student who's not even looking out the window, is just looking at the other three people being like, you guys need to learn how to work together. It's the integrator. Um, and so the I is this amazing person who can figure out, okay, how do we get this group of talented people to be cohesive, uh, over time, and how do we, you know, one person's thinking one thing, another person's thinking another thing, how do we get alignment? And so I, and I found this in my startups too, and what the reason I bring it up is because, uh, it's really useful to know which one you're at, which one your superpower is, so then you'll know who to partner with and when to partner with them. An I at the beginning does nothing for you, but an I is great kind of at the end of that cycle. Um, you know, same sort of thing. So anyways, I just wanted to share that.
Ben Gilbert 13:54 ↗
That's awesome. When do you think you need the A's and the I's?
Sean Pancere 13:57 ↗
Um, so from my experience, you don't need them unless you hit product-market fit. So sometimes the E is totally off base. You didn't need a parking lot at all, or you know, you, you build the parking lot, but you didn't have a plan to, you know, get customers. Uh, so it's once your, once your product is being pulled by the market. So once the demand is pulling, uh, more of the product faster than you can produce it, or asking for more features than you can keep up with, but they're actually using your, your thing, that's when you start to need A. And then you need I as the team grows to a certain size, right? Because a two-person team, you don't even need meetings. You're just constantly in sync. You're just sharing a brain. And then once you, once you even get to six, it's like, oh [__], uh, we all are doing different things. We all need to talk more. And then there's this rule, I forgot what it's called, but like every time the size of your team doubles, the communication required is, is like a square. So like, um, as you get, you know, from six to twelve, you don't need double the communication. You need, you know, quadruple the communication or whatever. Uh, and I've seen that to be true.
David Rosenthal 14:56 ↗
In a perfect world or in a, uh, easy-to-model scenario where every person in the organization must communicate equally with everyone else in the organization, uh, then the number of communicating lines is proportional to the square of the number of people in the organization.
Sean Pancere 15:12 ↗
Exactly. Because it's a network, right? So every node needs multiple connections to all the other nodes, or at least to different hubs. And so it creates all these different lines that you need to, to work on. And that's where the A and the I help a lot because the A is like, hey, let's write things down so other people can read this. And the I is like, hey, here's like a common way to write things down so we're all saying the same thing and have the same bar for, you know, what it takes to say yes to a project or whatever it is.
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David Rosenthal 17:04 ↗
Everyone, uh, come back from business school. Let's, uh, actually...
Sean Pancere 17:06 ↗
Yeah, exactly. Uh, I get real academic about these things. In reality, you don't need to know any of this [__]. You just got to go. And, you know, when you look back on it, you'll say, oh, yeah, that matches up to what I did. But it's not like you go forward saying, I got to be a better P. You know, it doesn't, doesn't work that way. So, uh, anyways, you guys had a bunch of ideas. Let's, let's riff off the first one. What do you got?
Ben Gilbert 17:27 ↗
So, uh, we thought about talking about some of the stuff that's more directly related to our show here, but people seem to come on your show and then throw out their latest like brainstormed idea and, uh, and shoot the [__] about it. And so I figured, well, that would be a fun thing for us to do here. And so I tried to apply my own, um, criteria of what's a thing that occurs to me that I want in the world that the time is now, uh, and I can see sort of a path to how to accomplish it. And the, the, uh, the gist of the idea is I want to book an Airbnb or a VRBO and all it tells me is whether it has internet or not. And that is completely useless in the world of I sit on Zoom for eight hours a day. And so, uh, I'm thinking this is like a totally bootstrapable, maybe even no-code thing where you just say, uh, hey, to get access to, um, uh, it's basically Waze for Wi-Fi where whenever you're somewhere, you, you know, upload the geocoordinates, maybe you put the address in. We'd have to figure out some, um, security stuff around that, but you just take a screenshot of a, of a speed test, and then we just have this big database of all these different places and, uh, anyone who stayed there and the screenshots they've uploaded. And, um, yeah, that's, that's the basic gist.
David Rosenthal 18:47 ↗
So it, it's basically solving the problem of I need great internet because everything is done through Zoom. And so when I'm out and about, I need trust. I need a trusted source to know where my internet is going to be good versus okay versus whatever, you know, whatever I have. Particularly when you're, uh, when you're like traveling, working remote. Like, uh, we did this, my wife and I went to Santa Barbara for a month, rented an Airbnb for a month, and you're doing this later, like tons of people are doing this now. Isn't Sam's doing this right?
Sean Pancere 19:14 ↗
Yeah, Sam's, you know, nomadically, you know, bouncing around every two weeks or three weeks, I think.
David Rosenthal 19:20 ↗
Yeah, I mean, it's this classic cold start problem of like, what a useless website you've created, Ben. There's zero entries on here. So you got to figure out some way to sort of bootstrap that, that cold start problem. Um, but I think the data entry is, is really easy, and you can do cool stuff over time like charting how it's gone up and down. And, um, and at the very least, you can probably create like five to ten spots in every city where like super nerds who saw this on Product Hunt uploaded data for the first time. So it has like a pretty low bar for minimum efficient scale.
Sean Pancere 19:52 ↗
Right. Would you literally build it on, uh, like based off of what Airbnb inventory is? So Airbnb tells you, does it have Wi-Fi or not? Which is kind of useless. Um, it's like, yes, if it doesn't have Wi-Fi, just take it off the site. If it has Wi-Fi, uh, okay, that doesn't tell me if it's going to work for what I need.
Ben Gilbert 20:08 ↗
It could be the Seinfeld coffee argument of like, oh, we, we've created this experience for you that is Wi-Fi-free, so you can... But yes, that's not at all what we're looking for.
David Rosenthal 20:16 ↗
Right. Right. So it's funny. So Ben put this on our list last night, uh, where, where we were brainstorming these ideas, and, um, and I was like, holy [__], did you have, did you talk to this guy we, we both know who's super awesome in Seattle, uh, because I just talked to him yesterday afternoon. He was also thinking about this idea. And I was like, oh, no, I didn't. And, uh, I think it just speaks to like the timing and the need for this is so acute right now. I mean, of the four of us on our two shows, three of us have done this in the past like couple months or going to do it now in COVID. Like, this, this went from like, yeah, like it would be, you know, it's really nice when I get good air, good Wi-Fi at my Airbnb to like, no, I need this.
Sean Pancere 20:59 ↗
Right. Uh, yeah, Wi-Fi is, you know, up there with food and water as far as I'm concerned. So forget COVID. I always need great Wi-Fi, and if I don't, I'm like, you know, I have to like, you take, take a time, time out for five minutes and be like, am I really this upset about the Wi-Fi? And I'm like, yes, I am.
David Rosenthal 21:15 ↗
So here's what bounce back.
Totally doable. You could stand this up on Webflow and, you know, do a little bit of other no-code stuff in the background, maybe a little bit of code that you add over time. Um, this could be, this could be a wedge into something more interesting though, right? Like, you know, on its own, great, you can build this. It's a little product. Maybe you charge for it. I think you probably better monetize this with affiliate for, um, uh, for Airbnb listings and VRBO listings and the like. Um, I wonder though if you could actually use this to bootstrap inventory of places and have it then become its own network of like, oh, you want long-term, you know, uh, Ben, my buddy was calling it workations. You know, you're, you're, you're doing this like, here is where the best places for this are. Well, you start to onboard a little bit of that supply, and maybe all of a sudden it becomes its own network, just kind of like Hipcamp has kind of offloaded a lot of the, uh, the, you know, true camping type experiences off and glamping off of Airbnb. Maybe you can start to disaggregate it.
Sean Pancere 22:17 ↗
Right. You know, the, the two ways I was thinking about this when you, because you just wrote a very simple thing like Wi-Fi site for Airbnb. I didn't know what that meant. I thought my, my brain actually went to a different thing. I didn't know you meant Wi-Fi website. I thought you meant Wi-Fi site. So like, first, my first thought was around Hipcamp, which is like, is there just a cool outdoor area where I can be outdoors and sitting and comfortable but have amazing Wi-Fi? And it's like, I don't actually want to go camping, but I do want to be like not in my room anymore. And so like, you know, could I be outdoors? Could I have great, I could be outdoors and have great Wi-Fi? Like that already is like, I love outdoors and I love great Wi-Fi, and they rarely come together. And so if you could create these Wi-Fi sites that were awesome, that were just comfortable places to go sit, uh, maybe there's little food trucks around there or whatever, um, I think you could build kind of like this weird outdoor co-working thing. Um, I'd love to see somebody like take a, take a shot of trying one of these. The other, the other angle I thought you guys might be going is like sort of that Boingo Wireless or whatever that's called, which is like, you know, they went to, you know, airplanes or, um, you know, there's a version of this for coffee shops, which is like, hey, look, everybody who comes here wants Wi-Fi and, uh, better Wi-Fi than you're providing, we will give free Wi-Fi in exchange for, you know, their email. And, um, you could potentially do that with Airbnb hosts. So you could basically say, hey, we will boost your Wi-Fi, um, through either those kind of mesh networks, mesh network routers, or just like provide Wi-Fi where you don't have Wi-Fi. And, um, in exchange, we, so basically run this little service, either you charge five bucks a night for the, for Wi-Fi or you get that plus their data, and then you use that as like kind of the way Boingo does. So that's actually what I thought you were, you were initially saying, but, um, I don't know if there's a, there.
David Rosenthal 24:00 ↗
That's a, that's a valuable service itself. But if you did the, like, if you were trying to build your own network of longer-term rental properties, this would be a great growth hack. You'd say, come on my network, I'll pay for you to upgrade your Wi-Fi. Uh, and, uh, and then that's how you can onboard the supply.
Ben Gilbert 24:21 ↗
Right. Yeah. Exactly. Yeah. That, that's an interesting point of like, how do you either onboard new supply, like, okay, you've got a, whatever, you've got a backyard, and now that, now backyards are cool. Um, or it's how do you give supply that was like unviable, how do you make it viable with some like investment that you could pay back in two, two-night visits? You know, like, could you pay back, uh, could you pay that back in that short amount of time? Um, I don't know, hard space, but there's, there might be something there. Uh, let's jump to a different one. I'm going to pick a random...
Wait, can I go meta on this one for a...
Sean Pancere 24:52 ↗
Yeah, go for it.
Ben Gilbert 24:53 ↗
I love, I guess this is moving to a different idea, but I love that we wrote down Wi-Fi site for Airbnbs, and there was three different ideas that came out of that purely because there's insufficient information. So you like, you apply creativity and fill in the gaps. And the, uh, it reminds me of, um, I, the very first time I did anything noteworthy on the internet, uh, was I made this website called its-this-for-that.com as a joke at a startup weekend because every single pitch was, well, it's this for that, in like 2009. And, uh, it was like the first time I got TechCrunch'd. So we still maintain the websites, my buddy Eric and I, and it's like, it just comes up with random X for Y pitches, and as you just like click to refresh, it's like a startup meme generator. And I've like come up with some pretty decent ideas after looking at very few words and then trying to extrapolate from there.
Sean Pancere 25:41 ↗
Dude, I've been to this website, so I just went to it now. Uh, so I went to it. The first one is, so basically it's like Airbnb for stolen goods. The next one, the next one is, so basically it's Salesforce for coffee shops. Don't know what that means. Can you make it up? And so actually we've played a similar game. We, uh, there's a, there's a game, I don't know if you ever heard of it, called PowerPoint Karaoke.
David Rosenthal 26:03 ↗
Have you ever played this?
Sean Pancere 26:05 ↗
It's, I, I think there's different variations of how you do this, but there's a startup variation of it, which is, you know, somebody gets up, there's a PowerPoint deck behind them, and they don't know what it is. They, they, they come in totally cold. And so they see the first slide and they just have to start talking as if this is their presentation. And then the next slide comes up and they have to connect it to whatever the hell they were saying, you know, about the previous slide and like create a cohesive story. Uh, it's a good muscle to exercise, like improv for business. And, um, you know, you could do this with startup pitches as well. You could literally just remix, you know, take one deck of cards which is like successful internet companies and another deck of cards which are just like niches, and you could just like pull two different cards and pitch it. And, uh, yeah, it's kind of surprising how some pretty viable ideas...
David Rosenthal 26:46 ↗
Do that as a like startup comedy podcast.
Sean Pancere 26:50 ↗
Although I guess...
David Rosenthal 26:51 ↗
I think you guys, I think you guys are ready. You guys are ready to spin it off.
Sean Pancere 26:55 ↗
Oh boy.
David Rosenthal 26:56 ↗
All right. What's we got? What we got up next?
Sean Pancere 26:59 ↗
So you have one in here. SPAC index fund. Tell me what you think.
David Rosenthal 27:02 ↗
Another Ben special.
Ben Gilbert 27:04 ↗
So, uh, hear me out on this, and I don't know how long the opportunity exists to do this, but at least for the moment, there's this rush of everyone, um, who has sufficient, uh, connection to capital, raising that capital into a SPAC and hoping in the next two years that they can leverage relationships with entrepreneurs to get a deal done and take someone public. And I, you've probably talked about SPACs on your show. We've talked about in our LP program, so I don't want to go into too much detail about the mechanics, but, um, I think if you were to bet on SPACs as a whole and say, you know, they're, they're, they all go public, they trade right around $10 a share because they're effectively worth exactly the amount of cash that they have in the bank, which is a trust in the Cayman Islands or something that's like untouchable. And then at some point they announce an acquisition and you either can redeem and get your money back or you can roll it into the acquisition. And so in general, like, I think we're going to see 20-plus of these sort of like Series C or later startups go public through this mechanism of SPACs in the next, I don't know, couple years. And, um, there's two levels of appreciation here. There's the first one where, you know, you buy in at, at $10 a share and then there's a pop when they announce who they're going to buy. So you could play the pop game if you want to and then just cash out immediately after that. Or you could play the longer-term game and say, do you want to hold the basket of startups that went public in the 2020-2021 vintage and, and hope that there's a, a Zoom in there? And I think it'd be, uh, to me it feels like a reasonable upside, super mitigated downside type of way to index.
Sean Pancere 28:51 ↗
Yes. Uh, I love this idea. When I saw it, this is the opposite where I had no, um, there was no question marks about what this idea was. I was like, oh, good idea. Interesting. Um, also, I was curious. I don't know if you guys know what are the mechanics of starting an index. Can I create an index? Uh, do you need to be a certain person? Is there a certain bar? How does that work? Do you know?
David Rosenthal 29:11 ↗
Oh, damn. Someone should create, uh, AngelList for public equity indexes.
Sean Pancere 29:15 ↗
Right? Like where I index and get some carry.
David Rosenthal 29:19 ↗
Yeah. Because like, you know, a bunch of people are trying to do this with like, you know, on Robinhood or Public.com, this new website or whatever, where it's like this new app where, you know, I go invest in a basket of stocks. You can kind of follow me. It's a social network. Like, [__] the social network part. Like, I think that's a little bit weak, honestly. Um, I think that more interesting is I listen to this podcast. I'm like, wow, Ben and...
Sean Pancere 29:39 ↗
David, you're so smart. You know what I want to do? I just want to own whatever stocks they own, and I want to basically buy their index that they created and just roll with them in their portfolio, kind of like a money manager. But if you guys were basically curating an index over time, I think that would be interesting if you could create an AngelList-like platform where it was very trivial for somebody to create their own index and let others invest into it. I might have also just invented a mutual fund. I'm not sure.
David Rosenthal 30:06 ↗
This also feels like... so I don't know the answer to how you do this, although I should, but I used to work at Dow Jones, which the Wall Street Journal is part of Dow Jones. It's part of News Corp. And while I was there, we sold the indexes business. So the Dow Jones index is now owned... garbage index, and no one should pay any attention to garbage index, but it was a billion-dollar business within Dow Jones. So billion-dollar topline, basically no expenses, like it was all just pure... and what it was, it was just a marketing thing. It was like, you get to use the Dow name, like that's...
Ben Gilbert 30:47 ↗
So it's like a license.
David Rosenthal 30:48 ↗
It's like a licensing thing. Yeah.
Ben Gilbert 30:50 ↗
That is absurd.
David Rosenthal 30:51 ↗
Yeah, totally.
Ben Gilbert 30:52 ↗
And who's paying for that license? Who pays to be able to put the Dow Jones? Is it like CNBC has to pay to put the Dow Jones index on their screen or what?
David Rosenthal 30:59 ↗
I don't know exactly the answer. I don't think CNBC or media properties have to pay for it because I think that's just public. But I think if you want to incorporate that index in your data of whatever product you're using or whatever, then you got to pay that licensing fee. Or if you want to also be the data stream, like... hey, you know, Dow Jones was a powerful brand, like the Dow Jones XYZ, whatever mutual fund, blah blah blah.
Sean Pancere 31:28 ↗
Right, that's interesting. You know, this reminds me, I had this meeting once where this guy came to our office and he was like, yeah, I'm the CEO of NASDAQ. I think it was NASDAQ, maybe New York Stock Exchange. And I was like, wait, NASDAQ has a CEO? I guess, okay, that makes sense. So NASDAQ, like, what the [__] is NASDAQ? And he's like, well, you know, because I just had always heard of NASDAQ through the kind of like, it's kind of like you hear Dow Jones, it's like, oh, this is just a sort of a name we give to track the market. And I didn't really fully at the time, I had no idea that first of all, there's multiple exchanges, they're highly competitive with each other, they hate each other, and they're constantly trying to fight for different IPOs. And then, but the part I didn't know was that they license their technology. They're like, yeah, we power the stock exchange in Sweden and 40 other countries and we make a billion dollars a year or whatever the number is, just licensing our stock exchange technology to other countries for their stock exchange. And I was like, wow, this is a...
David Rosenthal 32:26 ↗
This is a great business actually because it has this ultra powerful brand in the US and then it just becomes like, you know, and they built this technology stack, there's very few competitors to it. And then it becomes kind of like the end-of-one company around what should I use to run our stock exchange and there's going to be no switching. I bet nobody wants to switch the sort of full stack they're using to run their stock exchange. That would be crazy, right? So, you have extreme pricing power. And I was like, wow, this is an amazing business. I was like, could you compete with this? And that was right around the time that Eric Ries launched the long-term stock exchange.
Sean Pancere 33:00 ↗
We had him on our show.
David Rosenthal 33:01 ↗
It's great.
Sean Pancere 33:02 ↗
Exactly. Which is like just an amazing idea. Seems like it's been a little bit slow to market as you would maybe expect, but...
David Rosenthal 33:08 ↗
Turns out taking a stock exchange to market is not just putting up a website and measuring clicks.
Sean Pancere 33:12 ↗
Yeah, exactly. There's no sort of, you know, for ironically for the lean startup guy to do kind of...
David Rosenthal 33:18 ↗
Yeah. It's like the ultimate irony.
Sean Pancere 33:21 ↗
Exactly. No quick MVP, you know, just a landing page with, you know, smoke and mirrors where there's no product behind it. You can't do that. Eric Ries will be in jail telling people about the lean startup in there. But anyways, I think the whole idea of stock exchanges is just a very interesting thing. I think a SPAC index fund is interesting and I want to know how you create an index fund. I also kind of like the idea of AngelList but for creating private equities instead of venture funds. Also, I just think like who out there, somebody out there is just doing like a SPAC newsletter right now and just taking advantage of all the SPAC keyword searches and probably has built like a 50,000-person pretty valuable email list.
David Rosenthal 33:58 ↗
There is, it's called SPAC, is it SPAC Report? Let me look this up real quick. Spacresearch.com. The founder is an Acquired community member and yeah, I think he's got, it's a paywalled business. There's either some sort of trial or some sort of premium thing but yeah he's building a real business on it. Yeah, I think totally you could do kind of the Motley Fool or whatever. You know, basically this is old solution, new problem, right? Okay. Niche newsletter, paid newsletter. That's old solution, new problem. Everyone wants to know about SPACs and there's not a definitive place to go find it, right? Like I remember in the crypto boom, I ran into this guy who...
Sean Pancere 34:36 ↗
You're referring to this past tense crypto boom.
David Rosenthal 34:39 ↗
Yeah, yeah, crypto. Oh no, the boom was a very specific time when, you know, money was flowing freely and my aunt in Virginia was like saying the word Ethereum in her Indian accent and I was like, oh [__], what the hell's going on? But there's this guy, his name Shaq, Sha Khan, Shaquille Khan, and he was like, he's kind of this international man of mystery. He worked at Spotify and he did a bunch of random things that like nobody knows who he is but he's just friends with all the CEOs and like they hire him for like a special project of whatever that means. He's the wolf in Pulp Fiction.
Sean Pancere 35:10 ↗
Yeah, he's exactly. He's the wolf. He's the one they call in. So during the initial Bitcoin run-up when it was going from like $10 to $1,000, everybody was trying to figure out how do we create Bitcoin products. And he just created CoinDesk. He was helping create CoinDesk. He's just like, oh yeah, we should just create the news and information site and then we'll figure out from there what other opportunities we want to go to. But like first things first, let's create Bloomberg or CNBC for Bitcoin. And I was like, oh man, such a simple idea that could be executed because you're nimble and you're, you know, very responsive to where the world is going.
David Rosenthal 35:43 ↗
Yep.
Sean Pancere 35:44 ↗
Totally.
David Rosenthal 35:46 ↗
Yeah. I mean, it definitely fits into that. For anybody who hasn't read this thing, it's really quite hard to discover because it's an archive of an old website, but it's pmarchive.org, and it's Marc Andreessen's, it's like a play on his handle, and it's his old blog before he started Andreessen Horowitz. And one of the amazing pieces of content on there, it's like a five-piece thing, is his career advice, which of course starts with like, you can't plan your career so I refuse to give you any advice, but if I were to, here's five articles on it. And one of the things is like, if your five smartest friends are getting together at 2 in the morning and going to Denny's because of something exciting that they're thinking about or something that's new in the world, go with them every time. And it's such a good litmus test for...
Sean Pancere 36:34 ↗
If Pratta has written about SPACs every single morning for the last two weeks, then it's probably a good time to start a SPAC media business if you feel well positioned to do so.
David Rosenthal 36:44 ↗
Right, right. Yeah, that's a great call. There's the other one that's like, what nerds are doing on the weekends, we'll all be doing, you know, five years from now. The Chris Dixon thing. And you know, wherever a nerd engineer is spending their free time on the weekends tinkering, that's the area of innovation because they just can't help themselves. And what do you guys think would be that right now? I think I know if I just think about my smartest friends and what they're doing, I think I know one answer of what I would say, but there are lulls where there's just no clear answer and then there's like clear periods where something emerges. Do you guys have something in mind or do you remember a time when that was happening and you either were aware of it or you missed it?
Ben Gilbert 37:25 ↗
So, I have, I mean there's some, I'm going to give a little bit of a different answer than I think we're looking for here. My smartest friends who have means are working on climate problems right now.
David Rosenthal 37:38 ↗
That's right.
Ben Gilbert 37:39 ↗
And I think like we can talk about GPT-3, we can talk about crypto stuff, we can talk about, there are other sort of frontier technology things at the moment, but probably five times in the last couple months, I've had really smart people that I've tried to recruit to start something with me to join a PSL company who are saying like, actually after doing some reflecting, I'm going to go work on some climate stuff. And there's no capital structure to support that. I mean, we have a whole, David, we did that deep dive on how energy breakthrough, energy stuff gets funded, which is completely broken, but I...
Sean Pancere 38:19 ↗
I've got a company to talk about, but keep going.
Ben Gilbert 38:23 ↗
Anyway, that's definitely the thing that occurs to me of like my smartest, most well-intentioned people with means. And yeah, throw out a couple names that I've seen. These aren't even people I know, but I know Jesse Jacobs just launched a rolling fund for climate. I know that Josh Felzer left Freestyle I think to work on climate problems. I know that Yishan Wong, who's one of the smarter people, I like to read his writings on stuff. He's been talking about this, working on this for a couple years now.
Sean Pancere 38:52 ↗
Was he the CEO of Reddit, right, at some point? Either before...
Ben Gilbert 38:55 ↗
He was the CEO of Reddit. It was kind of like earlyish Facebook and then he became the CEO of Reddit for a while. And he's got this very simple website. I think it's just Yishan Wong, which is hard to spell.
Sean Pancere 39:05 ↗
You should give a shot at being co-CEO of Twitter for a little bit just to mix it up.
David Rosenthal 39:08 ↗
Round it all out.
Ben Gilbert 39:12 ↗
So yeah, he's like buying a plot of land in Hawaii or something like that and doing some radical experiment.
Sean Pancere 39:18 ↗
There's also this guy, the guy who created Control Labs, I think, which they got bought by Facebook. They're kind of like... Facebook. I think he left Facebook and I don't know if he's working on this, but I saw him talking about or tweeting about like, you know, we really could just go put solar panels into space and harness the sun's energy that way and then beam it to the Earth or something crazy like what would it take to throw a giant set of solar panels into space and then... Yeah. And I was like, what the [__] is this guy talking about? Like, people with brain power, you know, 10 orders of magnitude more than mine. I'm like, oh wow, I can't tell if you're joking or if you're serious. You're probably serious. And it sounds like a joke to me. That's how big the knowledge gap is here.
David Rosenthal 40:01 ↗
Yeah. What's super exciting to me on this is I have a friend who just started a company that like, there's, I mean this is a double-edged sword, but it's just reality. Like the problems are finally starting to get real with climate. Like I think one of the reasons why there's no good funding structure for it and cleantech failed and all this is just like everybody knows that this wave of awfulness is coming but nobody, winter is coming yet, you know. But the tip of the spear is fires in California, like those are real, real problems that we're all like, can't go outside, like it's just terrible and like people are losing their homes and properties. So I have a buddy who started a reinsurance business for fire risk in California. He's like, yeah, the insurance industry is like so backward on this. They use old stochastic models from like past history of like there's a terrible fire in California once every 30 years. It's like, no, it happens every year now. So like, okay, let's deal with this problem and like that's going to be a great company.
Sean Pancere 41:04 ↗
That's going to be a great value capture mechanism. I don't know. I mean, how does that help us not burn down the planet?
David Rosenthal 41:11 ↗
Well, it's like, there's a serious, but like you can't get insurance for fire in a lot of places in California anymore. So like this is a serious problem.

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APA

Rosenthal, D. (2026, July 10). #108 with Ben Gilbert and David Rosenthal - Brainstorming with the Acquired Podcast [Interview transcript]. BlackNova Productions. CEOInterviews.AI. https://ceointerviews.ai/interview/3018973/

MLA

David Rosenthal. "#108 with Ben Gilbert and David Rosenthal - Brainstorming with the Acquired Podcast." BlackNova Productions, 10 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3018973/.

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@misc{rosenthal2026_3018973,
  author       = {David Rosenthal},
  title        = {#108 with Ben Gilbert and David Rosenthal - Brainstorming with the Acquired Podcast},
  howpublished = {Interview transcript, BlackNova Productions. CEOInterviews.AI},
  year         = {2026},
  month        = {jul},
  url          = {https://ceointerviews.ai/interview/3018973/},
  note         = {Speaker-attributed transcript with timestamps}
}