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Special: Acquired x My First Million Crossover

Limited Partner Episode

September 9, 2020
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Acquired teams up with the My First Million podcast for a “best of both worlds” crossover episode. First we go deep, “Acquired style”, on the wild story of MFM host Shaan Puri’s bought, sold, and then bought-again OG social networking site Bebo, and then we turn the tables and brainstorm startup ideas and investing themes “MFM style”. This episode was frankly a blast to do. We hope you have as much fun listening as we did recording!


  • Thanks to Quaestor for sponsoring this special episode. Quaestor is an investor relations platform for startups that gives every company and their investors the same level of tools and transparency as large public companies, regardless of their size and without a dedicated team of IR professionals. You can learn more and sign up for early access at: https://quaestor.com


We finally did it. After five years and over 100 episodes, we decided to formalize the answer to Acquired’s most frequently asked question: “what are the best acquisitions of all time?” Here it is: The Acquired Top Ten. You can listen to the full episode (above, which includes honorable mentions), or read our quick blog post below.

Note: we ranked the list by our estimate of absolute dollar return to the acquirer. We could have used ROI multiple or annualized return, but we decided the ultimate yardstick of success should be the absolute dollar amount added to the parent company’s enterprise value. Afterall, you can’t eat IRR! For more on our methodology, please see the notes at the end of this post. And for all our trademark Acquired editorial and discussion tune in to the full episode above!

10. Marvel

Purchase Price: $4.2 billion, 2009

Estimated Current Contribution to Market Cap: $20.5 billion

Absolute Dollar Return: $16.3 billion

Back in 2009, Marvel Studios was recently formed, most of its movie rights were leased out, and the prevailing wisdom was that Marvel was just some old comic book IP company that only nerds cared about. Since then, Marvel Cinematic Universe films have grossed $22.5b in total box office receipts (including the single biggest movie of all-time), for an average of $2.2b annually. Disney earns about two dollars in parks and merchandise revenue for every one dollar earned from films (discussed on our Disney, Plus episode). Therefore we estimate Marvel generates about $6.75b in annual revenue for Disney, or nearly 10% of all the company’s revenue. Not bad for a set of nerdy comic book franchises…

Season 1, Episode 26
LP Show

9. Google Maps (Where2, Keyhole, ZipDash)

Total Purchase Price: $70 million (estimated), 2004

Estimated Current Contribution to Market Cap: $16.9 billion

Absolute Dollar Return: $16.8 billion

Morgan Stanley estimated that Google Maps generated $2.95b in revenue in 2019. Although that’s small compared to Google’s overall revenue of $160b+, it still accounts for over $16b in market cap by our calculations. Ironically the majority of Maps’ usage (and presumably revenue) comes from mobile, which grew out of by far the smallest of the 3 acquisitions, ZipDash. Tiny yet mighty!

Google Maps
Season 5, Episode 3
LP Show


Total Purchase Price: $188 million (by ABC), 1984

Estimated Current Contribution to Market Cap: $31.2 billion

Absolute Dollar Return: $31.0 billion

ABC’s 1984 acquisition of ESPN is heavyweight champion and still undisputed G.O.A.T. of media acquisitions.With an estimated $10.3B in 2018 revenue, ESPN’s value has compounded annually within ABC/Disney at >15% for an astounding THIRTY-FIVE YEARS. Single-handedly responsible for one of the greatest business model innovations in history with the advent of cable carriage fees, ESPN proves Albert Einstein’s famous statement that “Compound interest is the eighth wonder of the world.”

Season 4, Episode 1
LP Show

7. PayPal

Total Purchase Price: $1.5 billion, 2002

Value Realized at Spinoff: $47.1 billion

Absolute Dollar Return: $45.6 billion

Who would have thought facilitating payments for Beanie Baby trades could be so lucrative? The only acquisition on our list whose value we can precisely measure, eBay spun off PayPal into a stand-alone public company in July 2015. Its value at the time? A cool 31x what eBay paid in 2002.

Season 1, Episode 11
LP Show

6. Booking.com

Total Purchase Price: $135 million, 2005

Estimated Current Contribution to Market Cap: $49.9 billion

Absolute Dollar Return: $49.8 billion

Remember the Priceline Negotiator? Boy did he get himself a screaming deal on this one. This purchase might have ranked even higher if Booking Holdings’ stock (Priceline even renamed the whole company after this acquisition!) weren’t down ~20% due to COVID-19 fears when we did the analysis. We also took a conservative approach, using only the (massive) $10.8b in annual revenue from the company’s “Agency Revenues” segment as Booking.com’s contribution — there is likely more revenue in other segments that’s also attributable to Booking.com, though we can’t be sure how much.

Booking.com (with Jetsetter & Room 77 CEO Drew Patterson)
Season 1, Episode 41
LP Show

5. NeXT

Total Purchase Price: $429 million, 1997

Estimated Current Contribution to Market Cap: $63.0 billion

Absolute Dollar Return: $62.6 billion

How do you put a value on Steve Jobs? Turns out we didn’t have to! NeXTSTEP, NeXT’s operating system, underpins all of Apple’s modern operating systems today: MacOS, iOS, WatchOS, and beyond. Literally every dollar of Apple’s $260b in annual revenue comes from NeXT roots, and from Steve wiping the product slate clean upon his return. With the acquisition being necessary but not sufficient to create Apple’s $1.4 trillion market cap today, we conservatively attributed 5% of Apple to this purchase.

Season 1, Episode 23
LP Show

4. Android

Total Purchase Price: $50 million, 2005

Estimated Current Contribution to Market Cap: $72 billion

Absolute Dollar Return: $72 billion

Speaking of operating system acquisitions, NeXT was great, but on a pure value basis Android beats it. We took Google Play Store revenues (where Google’s 30% cut is worth about $7.7b) and added the dollar amount we estimate Google saves in Traffic Acquisition Costs by owning default search on Android ($4.8b), to reach an estimated annual revenue contribution to Google of $12.5b from the diminutive robot OS. Android also takes the award for largest ROI multiple: >1400x. Yep, you can’t eat IRR, but that’s a figure VCs only dream of.

Season 1, Episode 20
LP Show

3. YouTube

Total Purchase Price: $1.65 billion, 2006

Estimated Current Contribution to Market Cap: $86.2 billion

Absolute Dollar Return: $84.5 billion

We admit it, we screwed up on our first episode covering YouTube: there’s no way this deal was a “C”.  With Google recently reporting YouTube revenues for the first time ($15b — almost 10% of Google’s revenue!), it’s clear this acquisition was a juggernaut. It’s past-time for an Acquired revisit.

That said, while YouTube as the world’s second-highest-traffic search engine (second-only to their parent company!) grosses $15b, much of that revenue (over 50%?) gets paid out to creators, and YouTube’s hosting and bandwidth costs are significant. But we’ll leave the debate over the division’s profitability to the podcast.

Season 1, Episode 7
LP Show

2. DoubleClick

Total Purchase Price: $3.1 billion, 2007

Estimated Current Contribution to Market Cap: $126.4 billion

Absolute Dollar Return: $123.3 billion

A dark horse rides into second place! The only acquisition on this list not-yet covered on Acquired (to be remedied very soon), this deal was far, far more important than most people realize. Effectively extending Google’s advertising reach from just its own properties to the entire internet, DoubleClick and its associated products generated over $20b in revenue within Google last year. Given what we now know about the nature of competition in internet advertising services, it’s unlikely governments and antitrust authorities would allow another deal like this again, much like #1 on our list...

1. Instagram

Purchase Price: $1 billion, 2012

Estimated Current Contribution to Market Cap: $153 billion

Absolute Dollar Return: $152 billion

Source: SportsNation

When it comes to G.O.A.T. status, if ESPN is M&A’s Lebron, Insta is its MJ. No offense to ESPN/Lebron, but we’ll probably never see another acquisition that’s so unquestionably dominant across every dimension of the M&A game as Facebook’s 2012 purchase of Instagram. Reported by Bloomberg to be doing $20B of revenue annually now within Facebook (up from ~$0 just eight years ago), Instagram takes the Acquired crown by a mile. And unlike YouTube, Facebook keeps nearly all of that $20b for itself! At risk of stretching the MJ analogy too far, given the circumstances at the time of the deal — Facebook’s “missing” of mobile and existential questions surrounding its ill-fated IPO — buying Instagram was Facebook’s equivalent of Jordan’s Game 6. Whether this deal was ultimately good or bad for the world at-large is another question, but there’s no doubt Instagram goes down in history as the greatest acquisition of all-time.

Season 1, Episode 2
LP Show

The Acquired Top Ten data, in full.

Methodology and Notes:

  • In order to count for our list, acquisitions must be at least a majority stake in the target company (otherwise it’s just an investment). Naspers’ investment in Tencent and Softbank/Yahoo’s investment in Alibaba are disqualified for this reason.
  • We considered all historical acquisitions — not just technology companies — but may have overlooked some in areas that we know less well. If you have any examples you think we missed ping us on Slack or email at: acquiredfm@gmail.com
  • We used revenue multiples to estimate the current value of the acquired company, multiplying its current estimated revenue by the market cap-to-revenue multiple of the parent company’s stock. We recognize this analysis is flawed (cashflow/profit multiples are better, at least for mature companies), but given the opacity of most companies’ business unit reporting, this was the only way to apply a consistent and straightforward approach to each deal.
  • All underlying assumptions are based on public financial disclosures unless stated otherwise. If we made an assumption not disclosed by the parent company, we linked to the source of the reported assumption.
  • This ranking represents a point in time in history, March 2, 2020. It is obviously subject to change going forward from both future and past acquisition performance, as well as fluctuating stock prices.
  • We have five honorable mentions that didn’t make our Top Ten list. Tune into the full episode to hear them!


  • Thanks to Silicon Valley Bank for being our banner sponsor for Acquired Season 6. You can learn more about SVB here: https://www.svb.com/next
  • Thank you as well to Wilson Sonsini - You can learn more about WSGR at: https://www.wsgr.com/

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Transcript: (disclaimer: may contain unintentionally confusing, inaccurate and/or amusing transcription errors)

Ben: Welcome to this special unnumbered crossover episode of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I’m Ben Gilbert.

David: I’m David Rosenthal.

Ben: And we are your hosts. This episode is a crossover between Acquired and My First Million podcast. A podcast from The Hustle for business builders, schemers, and dreamers. The show is hosted by Shaan Puri and Sam Parr. This crossover episode was just Shaan and us. Shaan works on special projects at Twitch and was most recently the CEO of Bebo, a once massive part of the consumer internet in the early 2000s. Shaan was also the CEO of Blab.im, which some of you may have used a few years ago.

Our episode today has two parts. First, we had Shaan take us through what it was like to buy Bebo out of bankruptcy many years after its heyday and build something new with the assets, eventually selling it to Twitch. This is the first time on our show that we’ll be talking about a company that was sold and not bought. Which for those of you who have ever been through an exit know that is the far more common scenario.

The second part of the show is more of the My First Million format where David and I spitball startup ideas and talk tech trends with Shaan. Also, we should say that while Acquired is normally a family-friendly show—at least for families who love analyzing business histories together—this episode has a bit of profanity.

As always, if you love Acquired and want to hone your own craft of company-building, you should join the community of Acquired Limited Partners. You’ll get access to the LP show where we dive deeper into the fundamentals of company building and investing in addition to our monthly LP calls where we talk with all of you directly, and of course, our Book Club and Zoom calls with the authors. The most recent episode in the feed is the recording of our Book Club Zoom with Will Thorndike, author of The Outsiders.

If you aren’t already a limited partner, you can click the link in the show notes or go to acquired.fm/lp and all new listeners get a 7-day free trial. Also, if you want to hang out with the Acquired community and discuss all things tech news, strategy, and ideas, you should join us in our Slack at acquired.fm/slack. Now, over to David for our special sponsor for this episode.

David: A special sponsor indeed. Today’s sponsor is Quaestor, an early-stage startup that’s still in beta but is building something super relevant for a lot of the Acquired community. And it’s one that I’m so excited about that I even invested in the company personally. My friend in Quaestor’s Co-Founder and CEO, John Melas-Kyriazi, is here to tell us a bit about it. John, I’m so excited you’re here.

John: Thanks for having me.

David: Of course. Can you tell everyone a little bit about what Quaestor is and also how you spell the name.

John: Sure. Quaestor spells Quaestor and we’re an investor relations platform for startups and VCs. Our goal is to give every startup and its investors the same power and sophistication that a public company like Netflix or Zoom or Amazon has in their quarterly earnings report and IR toolkits. And we want to give investors unprecedented visibility, instant performance in the health of their portfolio companies.

David: Awesome. Thank you for spelling the name for everyone. The question here is all of that sounds great, but what’s the real problem with startup investor relations today, and how do you guys change that for everyone?

John: Yeah. I think you and I both saw from our years in the venture capital world that startup investor relations today is really all about playing defense. Everything from oh yeah, we have a board meeting next week, we should put together a deck. To oh, my VC just sent me their quarterly data request for our financials. I’d better forward that to our outsource CFO to get on it. That makes sense.

As a founder, you should be focused on building the product and the business. Investor relations is a lot of work. But the problem is that it gets neglected, and that leads to reactive and low-quality communication. Sometimes even board members don’t know how a company is performing. If you’re a smaller investor, good luck if you even get an email a few times a year. We want to automate a lot of that work and help companies and investors shift to playing offense.

Jeff Bezos famously said, “You get the shareholders you ask for.” Which is true. But the way you keep your shareholders aligned and engaged is to regular, high-quality communication. Through software, we help startups do the same things that Amazon IR does. But without a dedicated team of professionals.

David: Indeed. When you first told me about this idea, it was such a no-brainer to me that this should exist. I remember—when I was a VC of various firms—sending out all the financial data requests to our portfolio companies every quarter. It was just so painful and it didn’t help anyone make better decisions about the business. You guys are so much better and I can’t wait until all the companies I work with use it. I’m excited to be an investor and get to watch your guys’ journey from the front row.

As we mentioned, Quaestor is in beta right now. But for VCs and venture-backed founders in the Acquired community, just shoot John a note at john@quaestor.com, and he’ll help you get early access. You can also visit their website at quaestor.com to sign up for the beta. Thanks to John and Quaestor for making all this happen and now, back to the episode.

Ben: We also want to give a shoutout to our banner sponsor for all of season seven, Tiny. If you own a wonderful internet business that you want to sell or know someone who does, you should get in touch at tinycapital.com. And now, over to our crossover episode with Shaan Puri of My First Million. Hey Shaan, are you open to telling us a little bit about the story of Bebo? Because I think listeners of Acquired probably don’t know your background and might know an element or two of that story. But I think getting a little bit of context around all that would be totally fun.

Shaan: Sure.

David: Have you even told it on your show?

Shaan: No, I haven’t. One of the reasons I was initially pretty worried because when you get acquired, there’s this pretty strict about what you can disclose and not disclose. I’ve overtime figured out, okay, I can’t say certain numbers. That’s fine, no problem. But I can just generically tell the story of what our company was, how this all came about, and the twists and turns of the story.

The hard part is I’m the host so it’s almost awkward. What am I going to do, interview myself? This is perfect. You guys can ask me questions.

David: This is great, we’re hosts too.

Ben: That’s why you have two interviewers.

Shaan: One of the companies that I can talk about is Bebo, which is the company that most recently I ran. Bebo actually has a really funny story, and I only came in halftime. I’ll tell the first half of the story, but the key disclaimer is I was not the CEO and founder during that first period, which was a way bigger exit. I wish I were the CEO and founder back then, but my partner, Michael, was the CEO and founder of that time.

For those who don’t know—

David: With his wife, Xochi, right?

Shaan: Michael and Xochi are actually a husband and wife duo who had built multiple companies together, actually. Bebo was their biggest hit. I’ll tell you the quick version then we could dive in. The quick version is, did you know there was this company back in the day when MySpace and Facebook were taking off. Facebook at the time was still in colleges. MySpace was actually the biggest network and was famous, and celebrities, musicians were all using it.

Michael, when he tells me this story because I’ve asked him a bunch of time, “Dad, can you tell me, what was it like back then? Tell me these internet horror stories.” Let me finish the short story version, and I’ll tell you the whole thing. The short version is, built a social network called Bebo, got really popular but it became clear to him that Facebook was going to win this war. Where he was now was more the top, and was like, look, I should start looking at a certain exit here for us.

Ben: At what year is this?

Shaan: This might have been 2007, 2008. I think the deal closed in 2008, so let’s say 2007—started thinking along these lines. Facebook had been out for three years, had expanded out of colleges at this point. It was at a high school level, I think. Basically it was like, look, we’ve built a co-product. Bebo was big in certain markets like Europe, New Zealand.

David: Yup. UK and Ireland.

Shaan: If you’re in Ireland, Bebo was more traffic than Google at the time. Sells the company for $850 million to AOL. Huge exit at the time. Sold for more than MySpace did. Amazing exit for Michael and Xochi, and they went on to do a bunch of great things—both philanthropically as well as in business.

David: They own 70% of the company.

Shaan: They own 70% of the company at the exit. I’ll go into why they were able to own that if we want to go into that detail too. They sell it then. Fast forward a few years, Facebook takes over the world. AOL basically wrote off Bebo a year and a half later, as a tax write off of like, it’s worth nothing to us now. We write it essentially as zero. Product dwindles (obviously).

Now it’s five, six years later. Michael comes to me and at this time, I’m running his Idealab. A startup studio that he had built that he and Xochi were funding themselves. Michael originally was the CEO and then I joined to work with him. I came to San Francisco to work with him, and then a few months later he put me in charge of the lab. He’s like, I’ll go to the board. Me and Xochi, we’re going to do cool billionaire [...]. You go run this thing. I was like, hey, more power to you. That’s what I would do too. I don’t know if I would bet on me. I’m a 25-year-old kid. But thank you, I’ll try my best.

He comes to me at a certain point and he says, “Hey, we actually have the opportunity to buy Bebo back.” Bebo had traded hands or a private equity guy had bought it off of AOL. He had invested in that, and he knew that he’d gone nowhere. I didn’t even really do anything. And then he’s like, “He knew it was going to go into bankruptcy and it was going to get bought by somebody.” He’s like, “We have the opportunity to buy it back. Would you be interested? We’re already building social consumer products anyway, that’s the point of the lab. Maybe we could use this brand name, maybe we could use the email list, maybe we could use the servers. Whatever is there, would this help us in any way get better distribution for one of our product ideas?”

Again, this is the longest short story I’ve ever told. We go buy it back for a million dollars. We go to this crazy-ass auction (I can talk about), buy the company back for $1 million. Sold for $850,000, bought it back for $1 million. A couple of years later, we now sold it again to Twitch. We got acquired by Twitch, which is owned by Amazon. I’m currently at Twitch.

Ben: When you’re buying for $1 million, does it come with all of the data it’s ever had? All the email addresses from every epoch of the company?

Shaan: It comes with whatever is still there. Some [...] gets lost along the way, you can’t recover that. In theory, yes. We got like an 80 million person email list, which is one of the assets. Now, what we found when we got that 80 million email list was it looks like this email list might have been bought and sold before or something. Because this does not have a great send rating (essentially).

The other key component was, Bebo had started back when Hotmail and AOL were the rage, and then Gmail came and everybody switched. What we had was, essentially 80 million emails of which approximately 40 million were my teenage Hotmail address that I never check and will bounce or just go into the abyss.

David: Or AOL emails or whatever.

Shaan: That turned out to be a lot less useful. I don’t know how much of this I can share. But the funny thing was, one of the things in buying it was we actually bought two assets. We bought the company, that brand, the domain, the email list, and all that stuff for $1 million. But in that same auction, we bought the legal rights to sue the previous owner for $50,000. They won the suit for multiple millions of dollars. That asset turned out to be really, really valuable and has a great ROI.

Ben: No way.

Shaan: And then the domain and email list turned out to be a little less valuable than we originally had hoped.

David: Wow. Did you guys use—to our previous conversation—an SBA loan at all in financing the purchase?

Shaan: No. Michael and Xochi were like, “Hey, straight cash.”

Ben: All-cash buyer.

Shaan: I don’t think it will qualify necessarily. It didn’t have a positive cash flow. It didn’t have a lot of things that you would need. It was kind of a hairy deal going through bankruptcy. You need it to be an all-cash buyer to buy it.

Ben: I catch off a little bit. Where is it eventually now, how did it get there, and why?

Shaan: Okay. Let me try and pick it up. Where is it eventually now? We got acquired now. The whole team that was working on it—the majority of the team, 95% of the team—is at Twitch and got bought because we had built a whole bunch of things.

One of the things when we bought it—I also have to tell the story. It's an interesting entrepreneurial story. When we were going to buy, I got split opinions. I asked a few smart friends, hey, do you think we should buy this back? 50% of people were like, don’t touch it with a 10ft pole. Internet companies don’t get revived. That’s not really a thing. The brand is stale, it might be more baggage than it’s worth. It’s just going to be constant confusion if you’re launching a new thing under that old brand name. You don’t need it. Why would you go pay for this? Go put the million dollars into ads and you’ll get the same amount of users.

And then the other people were like, I don’t know what’s going to happen, but what a challenge. What fun if you did it? And you are also going to get a lot of people who are curious to check out what it became. Whether they’re actually going to adopt it or not.

David: It’s a good start.

Shaan: The analogy is like, you go back home to your parent’s house after you’re 30 years old. They say, hey, we renovated your old bedroom. You’re like, oh, I want to go see. What did you do with my stuff? What does it look like now?

Ben: Dude, I downloaded the Digg Reader in 2016. Of course, I did. I had to see what they did with Digg.

Shaan: Right, exactly. Even if you come in thinking, I’m never going to [...] use Digg, you want to see what are they trying to do with Digg and laugh at it. We were like, okay, at the very least we’ll get that. Better than complete obscurity (I suppose). When we bought it, we did one smart thing, which was we had some predefined ground rules. We’ll just bring it back as another social network. We had seen MySpace try that and we’re like, no, that game is over. Facebook has won that game. Don’t try to be like, hey, we’re cool again 10 years later. That doesn’t work.

We also didn’t have a new product. But we had to close the deal given the timeline of the acquisition. We had to close the deal, we had to announce it, and we had to turn off the existing product. Because it was going to cost a whole bunch of money every month to run.

David: I saw this, yeah, yeah.

Shaan: We were like, okay, we’re going to do three things. First, we’re going to turn it off. Second, we’re going to preserve the SEO because it has amazing SEO. We’re like, how do we lower the cost by 100X while keeping the SEO—everybody’s profile page alive? Because you Google someone’s name, their Bebo profile was in the second or third.

Ben: Static pages?

Shaan: Yeah. We created these static, frozen pages that remain indexable. I don’t know anything about it, but nine engineers in the room were like, there’s no way. And then our youngest engineer was like, well why don’t I just do this? And then all the other engineers begrudgingly like, well yeah, if we just want to do that, we could do that. I’m like, that accomplishes the goal. Of course, we want to do that simple thing that accomplishes our goal. Anyways, shoutout to Quinn for coming up with that.

The last thing was we came up with this video. We shot it in a weekend and it was basically an announcement video of, hey, the original founders bought it back. It was kind of tongue-in-cheek. It looked like serious corporate stock video of like hi, I’m Michael, and I’m the original founder of Bebo. We had this vision. Over the years, it grew. The video starts to make fun of the old Bebo. It’s like, we had a great time and it’s basically pointing fun at people used to go on each other’s profile page and draw dicks on the whiteboard feature. He’s like, we have the largest repository of hand-drawn dicks on the internet. This video goes viral, which was our hope.

While the 80 million email list was dirty and pretty much unusable—we couldn’t send from it. We got a million new people to sign up to see what’s the new Bebo. We’re like, okay, that’s cool. And they signed up thinking like, this was funny. I like this guy.

David: This is like the Dollar Shave Club video.

Shaan: Exactly. That was our intent. Now, it wasn’t as successful as that but it was close. That was the goal there. Then we were like, okay, we still don’t know what product we’re going to do and I was still of the mindset of we need to test. We don’t want to come back with this big bang that’s a one-shot thing.

I started creating a little sublist—groups of 50,000 people that was like, hey, we’re going to launch three new things. I want you to try them. You’re going to be our focus group. You’re going to tell us if this is any good or if this is dogshit. Whatever comes out of this will be the new Bebo, but you’re sworn to ultimate secrecy and blah blah blah.

We created this little list, and we’d launch different products to them. One was this messaging app with crazy avatars that looked like Bitmoji. And then this other one was Blab, which you used as just this video chat platform. We were launching them under other names to test them first. The idea was, if it ever works, we’ll brand it as Bebo. We’ll email the whole list.

The last thing we did was we took the live-streaming tech we had built and we built an esports platform. We’d built essentially high school esports. The way you can go play in a football league, soccer league, or baseball as a high school student.

Ben: It’s like what, PlayVS?

Shaan: Just like what PlayVS was doing. They were our competitor. You could sign up to be in a Fortnite league. We were like, dude, Fortnite’s more popular than baseball. There should for sure be a way to join a team for your school or as a high schooler and play with other high schoolers, compete, and play in tournaments. Because we had built all this streaming tech, we were like, this is cool. Not only are you playing, but your friends or your family can watch you play. That was really cool. We were running the biggest high school esports league in the country at the time.

And then a couple of the platforms came knocking and we told them, hey look. Honestly, I’m a realist. This is cool. The students love it. The platforms are happy because we’re bringing on tens of thousands of new, young teenage streamers streaming for the first time who would have never otherwise streamed because they don’t want to be a streamer. They just want to play in tournaments. Now they’re getting the joy, the thrill of streaming for the first time. We’re like, all the value is occurring to them. We should go try to sell this to one of them.

We went to YouTube, Facebook, Twitch, and all the others. We basically said, hey, who wants to buy this thing? Ran a process—a pretty tight process over 45 days, closed the deal, and ended up selling the company.

David: That’s awesome.

Ben: Had you already closed down the other experiments at this point? Was Blab still potentially a thing?

Shaan: No, we did them one at a time. We had learned that lesson the hard way running the startup studio in general, which is parallel entrepreneurship. Splitting focus is very, very dangerous, not to be done unless you are someone much more skilled than me. We were doing one experiment all in, and if it didn’t work, we would then cycle and pivot to the next thing. We had shut them down by then.

Which was hard. Blab had 4 million users and was growing. Some people loved it and used it for eight hours a day. I got death threats. It is actually funny. Somebody sent to the office a 200-page script for a play that was using me as the central character, my CTO as the second central character, our designer, head of community, and other people whose names they knew. It’s kind of like The Office. It was us being dipshits—making bad decisions. Because they were so angry we’re shutting this down that they sent us a full play of our total ineptitude. I read the thing and I was like, wow. Someone took this much time to do this. That’s awesome.

David: Why did you shut that one down? Was it that other messenger where it’s like a Facebook-style situation?

Ben: By the way, can I take a stab at explaining Blab from my recollection?

Shaan: Please do.

Ben: I guess the three modern comms would be sort of like Zoom meets Twitch meets Clubhouse. Where it’s like video collaborative chat in real-time that has a broadcast component.

Shaan: The experience was like this. There are three of us on a Zoom call right now—three little squares. We would be doing this, but where our chat is on the side of Zoom, Zoom is just for private communication. Blab was public. It was like a talk show. We could have live people watching this, listening to this, and typing in questions. We could pull the question, put it on the screen, and address it. Anybody could call in like an old radio show and join the conversation. It’s like if Google Hangouts had their audience, or if Zoom had an audience. That was the premise.

We organically had a bunch of people use it. Like I said, the UFC used it when they wanted to do a virtual fight announcement. We had Tony Robbins come on. He would let people call in, tell him their problem, and he would help them, workshop them live just like he does at his big 7000 person events. The Jonas Brothers did that with their fans. ESPN would use it every Friday for their basketball show.

But the problem was, there were two groups of people using it. There were all those cool things I just talked about that make it sound legit. But those people who would use it once a week for an hour. They’re like, okay, I’m doing my live interactive fan thing that’s hard to do. I’m on the spot, but it's a super deep connection with people. They love me if I do this. So I’ll do it once a week for an hour, Fridays at 3:00 PM. That’s when my live show happens. We were like, cool. Fridays at 3:00 PM are awesome. What happens every other hour of the day? How are we ever going to feel this up with good content?

David: Same problem as Facebook Live.

Shaan: Same as Periscope, Facebook Live, and Meerkat. We were all at the same time. They were like a monologue. You hold up your phone and you just talk, which we thought was really hard to do. We were like, dude, dialogue is way easier for people to create content, which is true. But the hard part was, for any given category—let’s say a business talk, sports, or whatever—you had to have 24/7 interesting content to build a habit for a viewer to come and show up when they’re bored.

If you just try to get people to show up on demand, they were like, dude, I’m busy. I don’t show up on a schedule anymore. I order things when I want it, and I get what I want when I want it. This is the Postmates era. I don’t want to have to show up when the creator decides to go live and I’m in the middle of dinner.

That was always a challenge. And then on the other side, we had people that just used this as a Clubhouse. They just use it as a room to chill in. People would meet each other. They become friends. And then every day, some number of them would get online, they would trigger notifications to the other friends, and then the party would just rage on all night. You would just dip in and out as you were free. Or you were busy—you would leave, and you’d come back and a different set of people would be hanging out. It was this hangout platform.

The cool thing about that was these guys were super sticky. We wanted people on all the time, they were on all the time. They would fall asleep on the platform. But the problem with them was the core value they were getting was they were making friends. They didn’t bring any friends to the platform. That side was not growing.

The celebrities grew but were totally using it for one hour a week. The people using it 40 hours a week, got no friends. Those two groups did not co-exist at all. They didn’t even understand why the hell they’re on the platform.

Ben: Crazy.

Shaan: That was the problem that we were never able to solve and why we ended up pivoting.

Ben: Wow. Bring it at home. Twitch buys it. What’s the main reason? What’s the repurposed asset here? Is it mostly the team? Or is there technology or learning?

Shaan: Yeah, all three. I always differentiate. A company can either get bought or it’s sold. We were sold, not bought. Bought is your Instagram—you’re hot, you’re the next big wave. Everybody recognizes it, and people are banging down your door trying to buy you. We were sold in the sense that I approached a bunch of companies. I threw conversations. I was able to suss out what are the things that are important to them, what are their big top three strategic priorities as a company, and is my little company an answer to any of those problems?

Ben: That’s a great framework.

Shaan: I was doing some Yoga poses to try to make that fit where I was like, oh, you really care about this?

David: Yeah. You’re doing instead of customer discovery, buyer discovery.

Shaan: Exactly. Because I need to sell this company. It’s not going to be the mega home run we think, but there is some value here. I don’t want to stay and work in a medium-sized business for five years, nor do I want to shut this down—walk away from millions of dollars of value. I need to learn a skill I don’t know, which is how to sell a company.

David: By the way, as a long time venture capital, you are falling into the 80% thick middle of entrepreneurs here—venture-backed entrepreneurs. This happens way more often.

Shaan: I asked six entrepreneurs who have done this before. I was like, hey, how do I do this? And they gave me some tips. They became what I call my deal doulas, which if you’ve ever had a baby, a doula is somebody who helps you birth that baby. These were the guys who helped me birth this deal. They helped it go all the way from the tough part of labor all the way to the happy part at the end.

Essentially, I found out what their top strategic priorities were. First, I’ll try to be really smart about this. Then I realized oh, here is how this market works. You have Twitch, which is the market leader. They have strategic priorities about how to grow their business. Those are very specific to Twitch. I got to find those out. I took some people to beers, I asked them a bunch of questions, and sussed out that oh, there is this program that they’ve realized. I’ll give you the round down, which was they were in the category of Twitch has gotten really, really big in the same way that Netflix got really big. But then the content costs start to go up. People start demanding more money. Famous streamers want more money. Esports tournaments want money.

David: Going to get those exclusive deals.

Shaan: They want exclusive deals.

David: Ninja moves over to Mixer.

Shaan: Exactly. You got streamers getting paid tens of millions of dollars to switch platforms, so that drives up prices. Netflix had a smart idea, just create original content. Hey, this is stuff we own. I realize that Twitch really needed original content, and it needed content that it could control its cost better and drive a ton of viewership. Internally, they had been doing this program totally manually. They had no technology to do it.

We were lucky that they themselves have been thinking similarly, had been running a program very manually, and had come to the conclusion that, hey, this works. We need to scale this using tech. They looked inside the company, they’re like, [...], where am I going to get a leader that I trust to do this really hard thing? We need engineers that know how to build this.

David: Yeah, nine engineers.

Shaan: And we need this now, not 18 months from now. That’s a great spot to get acquired in because you say, hey, I’m a leader. If you meet me and believe in me as a person, you think I could be one of the 10 leaders of your company. You can’t hire me. I’m a non-hirable person. You got to buy me to get a talent like that. Also, I come with 12 engineers that have been working on this for two years, and we’ve already gone through the learning curve and figured out everything. You get the code and you get the learnings.

In our case, we didn’t have revenue or a big user base that would matter to them. But they were like, don’t worry. We already have revenue and users, we just need the rest. I figured out for Twitch that was the solution. For everybody else, I realized that the core problem was we want to beat Twitch. I was like, oh, this makes it really easy. I just need to pitch this as a way that you could potentially overtake Twitch. I need to spin that story and then I need to tell you that Twitch wants to buy this. That will automatically get you interested.

That became the game you play as an entrepreneur to try to get multiple bidders involved. Part of it is persuasion. But you can’t just persuade. These are no dummies. These are CEOs of billion-dollar companies. They know what the hell they’re doing. It’s not about convincing them of something that they don’t want to do and making them do it. It’s about finding out what they already want to do. Cutting away the fat of our story and just being the solution for that, and then connecting on a personal level and saying, would you want me as one of the senior leaders of your company? Would you want me on your extended exec team? If so, great. Let’s do a deal.

Ben: Fascinating.

David: It’s so funny. We don’t have time to go into it, but that process is the exact same process of raising money from a venture cap. You want to have a hot round? You want to have VCs competing for every deal? You do exactly what you just said.

Shaan: Right, exactly.

Ben: Shaan, I think we’d like to have you on the LP show at some point to be our deal doula to help listeners understand what are the levers you can pull? What are the ways you can message different things at different times and different parties? Putting that aside, thank you for sharing the Bebo story.

Shaan: Yeah. For sure. I kept every email I sent and things like that because I want to help the next entrepreneur who’s going to be like me—needs this. This is seven years of effort that they just need to cash in on, and they need a successful outcome. They deserve it, but they’re going to be totally clueless. You don’t get a ton of reps at doing this.

I know when I googled Ford, I couldn’t find jack [...]. Everything was about the bought use case which is should I sell my hot company when I have all these offers, or should I stay independent? Yeah, there’s a ton of content about that because VCs love to talk about that, and they’ll tell you to stay independent. And then this is the other side that’s a little bit less sexy, usually results in failure. But if you could thread the needle, it’ll be life-changing for you, your investors, and your employees. There should be more content about this.

I wouldn’t make a course out of this probably because there’s just not that many people who need to know this. It’s a niche of a niche. But I saved it in case people knock on my door and they’re like, hey, can you help me? Yeah, here are some templates that I used. Here’s what worked for me.

David: Amazing. And now you have a podcast.

Shaan: Now I got a podcast. That’s actually how the podcast started. The funny thing is, when you’re running your company, you just get so worn down. You’re just so tired over time, especially when it’s not a breeze when it isn’t taking off or whatever. Then as soon as the sale process started, my creativity muscles just started firing again. I started having all these ideas. I was like, well, this is the worst time to have a startup idea when I’m trying to sell my company. I need to shut the lid on this and not get tempted to go start something.

I was like, oh, maybe I can start something that’s safe—a podcast. I started the podcast just for kicks during that time to keep myself busy because otherwise, I was going to damage my own deal.

David: Little did you know what it would become.

Ben: All right listeners. Now we shift to the second part of the show which—time for a secret—we actually recorded first to talk startup ideas, trends, and internet businesses with Shaan. We’ll talk about a side project idea I have been kicking around. What our smart friends are dabbling in on the weekends, and a bit more on SPACs. Let’s dive in.

Shaan: Let’s do a quick intro. I’ve actually never met you guys, but like most people from this podcast, I’ve heard you guys talking. And actually, just to say five words into your mic. Your mic setup is godly. I don’t know if it’s your voice or your mic, but something is perfect.

David: It’s all Ben.

Shaan: Listen to that.

David: If I were running the tech side of Acquired, we would still be talking into our Macbooks.

Ben: Yeah. Fortunately, we have David’s dulcet tones and buttery voice that complete the equation.

Shaan: And Ben, you have the soundproof panels in the background and stuff like that. I just roll out of bed, push go, and see if it works. All right. We have David and Ben here with us. These guys host the Acquired podcast. We’ll talk a little bit about that. You do that. You’re also venture capitalists, from what I understand (if I remember correctly from the podcast).

David: Correct.

Shaan: 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 office at our startup named Jason. 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. But the one thing that Jason was always the punching bag in the office was he would always have his facts wrong. He would be like, oh, they got bought by this company, and we’re like, no, it was this other company. Or they had raised this number, and it’s like, nope, that’s not the right number.

He was always getting fact-checked. And then one day, Jason started coming in with just this knowledge bombs. We were like, that’s not right. Wait, that is right. I was like, “How did you know that backstory? Did you research this?” I didn’t understand. And then I realized the secret. He was listening to your podcast.

Basically what you guys do is you tell the story of great acquisitions in tech history. You go through it very methodically. You research it well and you tell a very good linear story with no plot holes. Jason all of a sudden had this superpower. He was telling these perfect renditions of what went down. I was like, what the [...] is going on?

David: This is amazing.

Shaan: That’s when I was like, okay, what’s this podcast that you listen to? I listened to a few of them. I haven’t listened recently. I know you guys have pumped out a ton of them.

David: You got to hop back in because we’re not just acquisitions anymore. We realize these stories we were limiting ourselves with just acquisitions. We’ll get into this with you.

Shaan: What did you expand to?

David: The acquisitions are a limited part of the universe. We just did Epic Games. We did SpaceX.

Shaan: It’s just success stories in addition to acquisition stories type of thing?

Ben: Yeah. The goal is that we tell the very deep story of any great company, but then also try and understand the playbook of why it worked.

Shaan: I love them. I listened to a bunch where you had a three-parter. I’m like, oh man. This is so deep. I love it. Anyway, that’s my genuine shoutout for the Acquired podcast.

David: We got to say too, your guys’ show is awesome. We love it. One of the reasons, A) you’re just good. You guys have great flow, chemistry—you’re awesome. B) It’s such a good counterpart to what we do on Acquired. We tell this certain part of the internet history as it exists and it’s these big huge flashy companies. But there are a million ways to skin the cat. There are so many other good businesses out there and so many other people working, doing amazing things that are never going to be SpaceX. But that’s cool. Your Golden Hippo episode, I love that one.

Shaan: On one hand, you have the story of SpaceX. And then the other hand, you have this guy who’s in Iowa who’s doing a drone light show company and just local rural Iowa, making $2 million a year. He quit his job as a construction worker before that. That’s the other end of the spectrum of cool success stories that are just different flavors.

David: It’s so cool you guys find these. You bring these folks on the show. This was awesome.

Shaan: We can agree, our podcasts are great. We love it. Sorry, go ahead, Ben.

Ben: I was going to say, I also just like that it feels more like classic entrepreneurship. We’ve lumped in entrepreneurship to become this thing that involves tons of money, a winner takes all market, in all likelihood—failing and flaming out fabulously. By telling everyone they should go do that, you just set most people up for failure. As long as you’re really focused, you’re really listening to your customers, you really iterate, and you’re really capital efficient. Going and achieving a million dollar a year top-line business, lots and lots and lots of people who do that can do that and should think they can do that. I love that reminder in our lives.

Shaan: I would say, Naval has this really money line. I don’t know who he stole it from. I think it was Nassim Taleb or something. He was like, what’s your political stance? He’s like, with my family, I’m a communist. With my friends, I’m a socialist. With my city or my town, I’m a democrat. I’m a libertarian at the federal level (or whatever). It’s just a money quote.

But I have a similar thing in entrepreneurship. It’s the poor man’s version of that which is, if I invest, I go for 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 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 a lot of people can love. I don’t have to have employees or an office. That’s my dream. There are these different flavors. Each is good for a different purpose and for a different person. Anyway, that’s my view on it.

You guys reached out the other day and you were like, hey, it’d be fun to do a crossover episode. I think that’s a great idea. 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. I want to jump in and riff through a bunch of these.

Normally, the way me and Sam do it is just like you have here. We just have a sheet with a bunch of bullet points. You don’t even understand the full idea just from the bullet point. And we’ll just say, 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 going.

David: This is going to be so fun for us because we don’t get to do this on Acquired anymore. This is awesome.

Shaan: This is like when a successful business person goes to Burning Man, Mardi Gras, or something. It’s like, oh, I get to let my hair down and just shoot the [...] on half baked ideas that will totally not work (most likely). Yup, that’s what this is.

When you guys get excited about ideas or some of the stuff you sent over, what’s on your mind? What are you guys seeing as interesting? Let’s jump in with some of these different ideas you got.

Ben: Yeah. I’ll start. Your Naval quote inspired me. I have a very bifurcated lens on the way that I look at ideas. And I don’t think I realized it until recently. I should give a little bit of background. I started a thing called Pioneer Square Labs five years ago. We’re a startup studio where we spin-out companies all of which go on to get venture-backed. We’ve done that 24 times in the last 5 years, and we’re based on Seattle. Really looking to make a dent in the entrepreneurial ecosystem in the Northwest. We’re coming up with ideas all the time.

David: And you guys are investors now, too.

Ben: Yeah. Then we also have the venture fund—PSL ventures—where we invest in early-stage companies in the Northwest. Many that we have nothing to do with starting. I sit on both sides of the house coming up with ideas and also evaluating ideas that are not my own. I have 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.

It’s privy engineering background. I put on my blinders real quick and just go heads down. I had to fight every instinct. David will be like, hey, I think there is this really big way we can move the needle for Acquired. And pitch me this big grand plan. I’ll be like, yeah, but I need to fix the way that headers look on our website. I have a really good idea about how to do that. Sorry, I need two hours now. I have a massive bias towards things I can fully conceive of and will be satisfied with the value of.

David: I think this idea you have is a really good one.

Ben: The way that I think about or evaluate other ideas is definitely, Shaan, in that same that you thought about is this winner take all? Is this going to be a massive thing? Is this a moonshot idea? The scary part that always comes along with that is 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?

That’s almost disheartening because then you scope down the universe super narrowly. And most of the time, what you’re doing is saying, no, I’ll wait for the next one. That’s a frustrating and sometimes disheartening job. But I think finding that spot in the middle where you can 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 the things you’re being pitched to things you come up with, that’s where the magic lies in the middle.

Shaan: I would agree. Also, when you said that thing about the way you two are different, it reminded me of this framework that I heard one time that has always stuck with me. I don’t know if you guys have ever heard this but, Bill Gross, who’s the founder of Idealab. He’s like an internet OG. He gave this talk once and he’s talked about (have you heard this) the four personalities that come together to make a company?

Ben: No.

Shaan: Basically he says, every company needs these four personalities. They come in a certain order. It’s called EPAI. Not a great acronym, but it works. EPAI. E is the entrepreneur. He gives this analogy. You’re sitting in a classroom. One kid is going to look out the window and 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. We all come to school every day and parking is such a hassle. There should be a parking lot there. It could be six stories high. We should build a parking lot. Entrepreneur comes up with a vision, sees something before it exists based on a pain point or a personal dream.

Then they have P, which kind of sounds like you, Ben, which is the producer. Producer is somebody who gets along strangely well with the E. They’re not usually the one necessarily to come up with the visions every single time, but they’re very good at downloading the vision. They hear the vision, they say, yup, 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 whatever. Immediately, their brain starts building that vision out, and they’re going to be able to take words and turn it into some form of action. He draws these curves.

If it’s just the E alone, there’s this initial value because they come up with a vision, and then this 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, your venture will be a mess because you need the A, which is actually an administrative type of person. A type of person says, okay, great. We have a vision. We have 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, and if nobody is writing things down about our plan, we’re screwed. We got to get organized here. 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, it’s just looking at the other three people being like, you guys need to learn how to work together. It’s the integrator. The I is this amazing person who can figure out, okay, how do we get this group of talented people to be cohesive over time? One person is thinking one thing. Another person is thinking another thing. How do we get alignment?

I found this in my startups too. The reason I bring it up is because it’s really useful to know which one you’re great at, which one your superpower is. Then you’ll know who to partner with and win to partner with them. I at the beginning does nothing for you. But an I is great at the end of that cycle. Same sort of thing. I just wanted to share that.

David: That’s awesome. When do you think you need the As and Is?

Shaan: From my experience, you don’t need them unless you hit product-market fit. Sometimes, the E is totally off base. You didn’t need the parking lot at all. Or you build the parking lot, but you didn’t have a plan to get customers. Once your products have been pulled by the market. Once the demand is pulling 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 thing. That’s when you start to need A and then you need I as the team grows to a certain size. Because a two-person team, you don’t even need meetings. You’re just constantly in sync. You’re just sharing a brand.

Once you even get to six, six is like, oh [...], 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 every time the size of your team doubles, the communication required is like a square. As you get from 6-12, you don’t need double the communication. You need to quadruple the communication or whatever. I assume that to be true

Ben: In a perfect world or in an easy to model scenario where every person in the organization must communicate equally with everyone else in the organization, then the number of communicating lines is proportional to the square of the number of people in the organization.

Shaan: Exactly, because it’s a network. Every node needs multiple connections to all the other nodes, or at least to different hubs. It creates all these different lines that you need to work on. That’s where the A and I help a lot. Because the A is like, hey, let’s write things down so other people can read this. The I is like, hey, here is a common way to write things down, so we’re all saying the same thing and have the same bar for what it takes to say yes to a project or whatever it is.

David: That’s awesome.

Shaan: Framework hour over.

Ben: Everyone, come back from business school.

Shaan: Exactly. I get real academic about these things. In reality, you don’t need to know any of this [...]. You just got to go. 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. It doesn’t work that way. Anyway, you guys had a bunch of ideas. Let’s riff off the first one. What do you got?

Ben: We thought about talking about some of the stuff that’s more directly related to our show here. People seem to come on your show and then throw out their latest brainstormed ideas and shoot the [...] about it. I figured that would be a fun thing for us to do here. I try to apply my own criteria of what’s a thing that occurs to me that I want in the world, that the time is now, and I can see a path how to accomplish it. The gist of the idea is I want to book an Airbnb or a Vrbo and all it tells me is whether it has the internet or not. That is completely useless in the world of I sit on Zoom for eight hours a day.

This is a totally bootstrappable, maybe even no-code thing. It’s basically Waze for WiFi where whenever you’re somewhere, you upload the geo coordinates. Maybe you put the address in, and we’d have to figure out some security stuff around that. But you just take a screenshot of a speed test, and then we just have this big database of all these different places and anyone who stayed there and the screenshots they’ve uploaded. That’s the basic gist.

Shaan: It’s basically solving the problem of I need a great internet because everything is done through Zoom. When I’m out and about, I need a trusted source to know where my internet is going to be good versus okay versus whatever I have.

David: Particularly when you’re travelling, working remote. We did this, my wife and I went to Santa Barbara for a month, rented an Airbnb for a month. Ben, you’re doing this [...]. Tons of people are doing this now. Sam is doing this, right?

Shaan: Yeah. Sam’s nomadically bouncing around every two weeks or three weeks, I think.

Ben: It’s this classic cold start problem of what a useless website you’ve created, Ben. There are zero entries on here. You got to figure out some way to bootstrap that cold start problem. But I think the data entry is really easy, and you could do cool stuff over time like charting how it’s gone up and down. At the very least, you can probably create 5-10 spots in every city where super nerds who saw this on Product Hunt uploaded data for the first time. It has a pretty low bar for minimum efficient scale.

Shaan: Would you literally build it based off of what Airbnb inventory is? Airbnb tells you if it has WiFi or not, which is kind of useless. If it doesn’t have WiFi, just take it off the site. If it has WiFi, okay, that doesn’t tell me if that’s going to work for what I need.

Ben: It could be the Sightglass coffee argument of oh, we created this experience for you that is WiFi-free. But yes, that’s not at all what we’re looking for.

David: It’s funny. Ben put this on the list last night where we were brainstorming these ideas. I was like, holy [...], did you talk to—this guy we both know who’s super awesome in Seattle—because I just talked to him yesterday afternoon. He was also thinking about this idea. And Ben was like, oh no, I didn’t. It just speaks to the timing and needs for this is so acute right now. Of the four of us on our two shows, three of us have done this in the past couple of months, we’re going to do it now in COVID. This went from yeah, it’s really nice when I get good WiFi at my Airbnb to no, I need this.

Shaan: Yes. WiFi is up there with food and water, as far as I’m concerned. Forget COVID. I always need great WiFi. And if I don’t, I have to take a time out for five minutes and be like, am I really this upset about the WiFi? Yes, I am. I have to bounce back.

David: Here’s what I think is cool though—totally doable. You could stand this up on Webflow and do a little bit of other no code stuff in the background. Maybe a little bit of code that you add over time. This could be a wedge into something more interesting though. On its own, great. You can build this. It’s a little product. Maybe you charge for it. You probably better monetize this with affiliates for Airbnb listings, Vrbo listings, and the like.

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—Ben and my buddy were calling it work-cations. You’re doing this. Here is where the best places for this are. You start to onboard a little bit of that supply, and maybe all of a sudden it becomes its own network. Just like Hipcamp has offloaded a lot of true camping-type experiences and glamping off of Airbnb. Maybe you can start to disaggregate it.

Shaan: Right. The two ways I was thinking about this because you just wrote a very simple thing—a WiFi site for Airbnb. I didn’t know what that meant. My brain actually went to a different thing. I didn’t know you meant WiFi website. I thought you meant WiFi site.

My first thought was around Hipcamp which is like, is there just a cool outdoor area where I can be outdoors, sitting, and comfortable but have amazing WiFi? I don’t actually want to go camping, but I don’t want to be not in my room anymore. Could I be outdoors and have great WiFi? I love outdoors, I love great WiFi, and they rarely come together. If you could create these WiFi sites that were awesome, that were just comfortable places to go sit, maybe there’s little food trucks around there, I think you could build this weird outdoor coworking thing. I’d love to see somebody take a shot of trying one of these.

David: Yeah, that’d be awesome.

Shaan: The other angle I thought you guys might be going is like that Boingo Wireless. They went to airplanes. There’s a version of this for coffee shops which is like, hey look, everybody who comes here wants WiFi, and better WiFi than you're providing. We will give free WiFi in exchange for their email. You could potentially do that with an Airbnb host.

You can basically say, hey, we will boost your WiFi through either those mesh network routers, or just provide WiFi where you don’t have WiFi. In exchange, basically run this little service. Either you charge $5 a night for WiFi. Or you get that, plus their data, and then you use that the way Boingo does. That’s actually what I thought you were initially saying. But I don’t know if there’s a [...] there.

David: I think that’s a valuable service itself. But if you’re 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 WiFi. That’s how you can onboard the supply.

Shaan: Right, exactly. That’s an interesting point of how do you either onboard new supply? Okay, you’ve got a backyard. Now, backyards are cool. Or it’s how do you give supply that is unviable, how do you make it viable with some investment that you can pay back in two-night visits? Could you pay that back in that short amount of time? Hard space, but there might be something there. Let’s jump to a different one. I’m going to pick a random bullet.

Ben: Wait. Can I go meta on this one for a second?

Shaan: Go for it.

Ben: I guess this is moving to a different idea. But I love that we wrote down WiFi site for Airbnbs and there are three different ideas that came out of that. Purely because there’s insufficient information, so you apply creativity and fill in the gaps. It reminds me of the very first time I did anything not worthy on the internet. I made this website called itsthisforthat.com as a joke at a startup weekend. Because every single pitch was, well, it’s this for that in 2009. It was the first time I got TechCrunch.

We still maintain the website. It’s my buddy, Eric and I. It just comes up with random X for Y pitches. As you click to refresh, it’s like a startup meme generator. I’ve come up with some pretty decent ideas after looking at very few words and then trying to extrapolate from there.

Shaan: Dude, I’ve been to this website. I just went to it now. I’m going to do it. The first one is, basically it’s like Airbnb for stolen goods. The next one is, so basically, it’s Salesforce for coffee shops. Don’t know what that means? Can you make it up? Actually, we’ve played a similar game. There’s a game (I don’t know if you’ve ever heard it) called PowerPoint Karaoke.

Ben: Yes.

Shaan: I think there are different variations of how you do this, but there’s a startup variation of it which is somebody gets up, there’s a PowerPoint deck behind them, and they don’t know what it is. They come in totally cold. They see the first slide and they just have to start talking as if this is their presentation, and the next slide comes up and they have to connect it to whatever the hell they were saying about the previous slide and create a cohesive story. It’s a good muscle to exercise. It’s like improv for business.

You could do this with startup pitches as well. You could literally just remix. Take one deck of cards, which is successful internet companies, and another deck of cards which is just niches. You could just pull two different cards then pitch it. It’s surprising how some pretty viable ideas come out of it.

Ben: Someone should do that as a startup comedy podcast.

Shaan: I think you guys are ready to spin it off.

Ben: I guess that’d have to be video.

David: What do we get up next?

Shaan: You have one in here, SPAC index fund. Tell me what you’re thinking.

Ben: Hear me out on this. I don’t know how long the opportunity exists to do this. But at least for the moment, there is this rush of everyone who has sufficient 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.

You’ve probably talked about SPACs on your show. We’ve talked about it in our LP program. I don’t want to go into too much detail about the mechanics. But I think if you were to bet on SPACs as a whole and say 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 untouchable. 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.

In general, I think we’re going to see 20+ of the series C (or later) startups go public through this mechanism of SPACs in the next couple of years. There are two levels of appreciation here. There’s the first one where you buy in at $10 a share and then there’s a pop when they announce who they’re going to buy. 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 2020, 2021 vintage, and hope that there’s a Zoom in there? To me, it feels like a reasonable upside super mitigated downside type of way to index.

Shaan: Yes. I loved this idea when I saw it. This is the opposite where there are no question marks about what this idea was. I was like, good idea, interesting. 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? Do you need to be a certain person? Is there a certain bar? How does that work? Do you know?

Ben: Oh damn, someone should create an angel list for public equity indexes.

Shaan: Right, is it just so simple?

Ben: I maintain an index and get some carry.

Shaan: A bunch of people try to do this on Robinhood or public.com—this new website where it’s like this new app. I go invest in a basket of stocks. You can follow me. It’s a social network. But [...] the social network part. I think that’s a little bit weak, honestly. I think that more interesting is, I listen to this podcast. I’m like, wow, Ben and David are so smart. You know what I want to do? I just want to own whatever stocks they own. I want to basically buy the index that they created and just roll with them and their portfolio.

Like a money manager, but if you guys were busy curating an index over time, I think it would be interesting if you could create an angel list-like platform where it was very trivial for somebody to create their own index and let others invest into it.

David: Totally.

Shaan: I might have also just invented a mutual fund. I’m not sure.

David: 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 and Dow Jones is part of News Corp. While I was there, we sold the indexes business. The Dow Jones index is now owned by one of the big Chicago companies.

Ben: Which is a garbage index, and no one should pay any attention to it.

David: But it was a billion-dollar business within Dow Jones. Billion-dollar top line, basically no expenses. It was all just pure money. What it was, it was just a marketing thing. You get to use the Dow name. It’s like licensing.

Shaan: It’s like a license, essentially.

Ben: That is absurd.

Shaan: 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: That’s a good question. I don’t know exactly the answer. I don’t think CNBC 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, then you got to pay that licensing fee. Or if you want to use the brand.

Shaan: It might also be the data stream.

David: Dow Jones was a powerful brand. The Dow Jones XYZ, whatever mutual fund blah blah blah.

Shaan: Right. That’s interesting. 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 the Nasdaq. Maybe the New York Stock Exchange. I was like, wait Nasdaq has a CEO? Okay, that makes sense. So Nasdaq? Wait what the [...] is Nasdaq? Because I had just always heard of Nasdaq. It's kind of like Dow Jones. This is just a name we give to track the market. At that time, I had no idea that first of all, there are multiple exchanges that are highly competitive with each other. They hate each other, and they're constantly trying to find different IPOs.

I kind of knew that part, but the part I didn't know was they licensed their technology. They're like, yeah, we power the stock exchange in Sweden and 40 other countries. 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.

I was like, wow, this is a great business actually, because it has this ultra-powerful brand in the US, and they built this technology stack. There are very few competitors to it, and then it becomes the end of one company around what should I use to run our stock exchange. There's going to be no switching, I bet. I bet nobody wants to switch their full-stack they’re using to run their stock exchange.

Ben: Totally.

Shaan: Crazy, right? You have extreme pricing power. I was like, wow, this is an amazing business. Could you compete with this? That was around the time that Eric Ries [...] Long-Term Stock Exchange.

David: Oh, yeah. We’ve had him on our show. It’s great.

Shaan: Exactly, which is just an amazing idea. It seems like it’s been a little bit slow to market as you would maybe expect.

Ben: Turns out, taking a stock exchange to market is not just putting up a website and measuring clicks.

Shaan: Yeah, exactly. Ironically, for the Lean Startup Guy to do the...

Ben: I know right.

David: Yeah, we’re talking some ultimate irony.

Shaan: Exactly, no quick MVP. Just a landing page with smoke and mirrors. 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 anyway, I think the whole idea of stock exchanges is 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 like the idea of an angel list, but for creating private equities instead of venture funds. Somebody out there is just doing a SPAC newsletter right now. Just taking advantage of all these SPAC keyword searches and probably has built a 50,000 person—pretty valuable email list.

Ben: There is. Spacresearch.com. The founder is an Acquired community member. It's a paywalled business. It’s either some sort of trial or some sort of premium thing. But yeah, he's building a real business on it.

Shaan: Yeah. I think totally you could do kind of the Motley Fool or whatever. Basically this is an old solution, new problem. This paid newsletter—that's an old solution. New problem— everyone wants to know about SPAC, and there's not a definitive place to go find it. I remember in the crypto boom, I ran into this guy who is—

Ben: You're referring to this past tense crypto boom?

Shaan: Yeah. The boom was a very specific time when the money was flowing freely, and my aunt in Virginia was like saying the word Ethereum in her Indian accent. I was like, oh, [...]. What the hell is going on? But there's this guy, his name is Shakil Khan. He's kind of this international man of mystery. He worked at Spotify, and he did a bunch of random things. Nobody knows who he is, but he's just friends with the CEOs. They hire him for a special project.

David: He’s the Wolf from Pulp Fiction.

Shaan: Yeah, exactly. He's the Wolf. He's the one they call in. During the initial Bitcoin run-up, when it was going from $10-$1000, everybody was trying to figure out how 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 first things first, let's create Bloomberg or CNBC for Bitcoin.

I was like, oh man, such a simple idea that could be executed because you're nimble and you're very responsive to where the world is going.

David: Totally.

Ben: Yeah. For anybody who hasn't read this thing, it's quite hard to discover because it's an archive of an old website. It's pmarchive.com and it's Marc Andreessen’s. It's a play on his handle, and it's his old blog before he started Andreessen Horowitz. 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, you can't plan your career, so I refuse to give you any advice. But if I were to, here are five articles on it.

One of the things is, if your five smartest friends are getting together at 2:00 AM in the morning and going to Denny's because of something exciting that they're thinking about or something new in the world, go with them every time. And it's such a good litmus test for if pro rata 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.

Shaan: Right. 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 five years from now, the Chris Dixon thing. 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.

What do you guys think would be that right now? If I just think about my smartest friends and what they're doing, I think I know one answer to what I would say. But there are lulls where there's just no clear answer, and then there are 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: 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.

Shaan: That's right.

Ben: I think we can talk about GPT-3, we can talk about crypto stuff. There are other frontier technology things at the moment, but probably five times in the last couple of months, I've had a really smart people that I've tried to recruit to start something with me to join a PSL company who are saying, actually, after doing some reflecting, I'm going to go work on some climate stuff.

There's no capital structure to support that. David, we did that deep dive into how breakthrough energy stuff gets funded, which is completely broken.

David: I've got a company to talk about, but keep going.

Ben: Anyway, that's definitely the thing that occurs to me of my smartest, most well-intentioned, and people with means.

Shaan: I'll throw out a couple of names that I've seen. These aren't even people I know. I know Jason Jacobs has launched a rolling fund for the climate. I know that Josh Felser left Freestyle 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 of years now.

David: He was the CEO of Reddit, right? At some point, either before or after Ellen Pao.

Shaan: He was the CEO of Reddit. He was kind of like early-ish Facebook, and then he became the CEO of Reddit for a while. He's got this very simple website. I think it's just Yishan Wong, which is hard to spell.

Ben: He should give it a shot at being CEO Twitter for a little bit just to mix it up.

Shaan: Just to round it all out.

David: I’m so long Reddit, by the way.

Shaan: He's buying a plot of land in Hawaii and doing some radical experiment.

Ben: Oh awesome.

Shaan: There's also this guy. The guy who created Control Labs (I think), which got bought by Facebook.

Ben: Did he leave Facebook?

Shaan: I think he left Facebook. I don't know if he's working on this, but I saw him talking about or tweeting about, we really could just go put solar panels into space and harness the sun's energy that way and then beat it to the earth or something crazy. What would it take to throw a giant set of solar panels into space? I was like, what the [...] is this guy talking about? People with brain power ten 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: What's super exciting to me on this is I have a friend who just started a company. This is a double-edged sword, but it's just reality. The problems are finally starting to get real with climate. I think one of the reasons why there is no good funding structure for it and Cleantech failed. Everybody knows that this wave of awfulness is coming.

Shaan: Winter is coming.

David: But the tip of the spear is fires in California. Those are real, real problems that we can't go outside. It's just terrible. People are losing their homes and properties. I have a buddy who started a reinsurance business for fire risk in California. The insurance industry is so backward on this. They use old stochastic models from past history of there's a terrible fire in California once every 30 years. No. It happens every year now. Okay, let's deal with this problem. That's going to be a great company.

Ben: That's going to be a great value capture mechanism. How does that help us not burn down the planet?

David: But you can't get insurance for fire in a lot of places in California anymore. This is a serious problem.

Ben: Yeah. It's a way to address the symptom of a problem.

Shaan: You know what you also can’t get insurance for?

Ben: That makes the symptom much less painful for lots of people, but it's still not addressing the problem.

Shaan: You're not solving the fire problem. You're solving the my house burn down problem.

Ben: Which is great and admirable to solve downstream problems.

Shaan: Also, speaking of insurance, I tried to get insurance for an ecommerce business I own. Dude, you can't get ecommerce insurance. I don't know what the hell's going on. You can't get business insurance for ecommerce, it was so painful. I thought I'm going to start typing the word biz and then Google's going to be like, oh, you want business insurance? Cool. Here are 10 leads that we'll just call you incessantly.

Instead, it was the opposite. It was like business insurance for an ecommerce business. Called twelve different companies, emailed a bunch of them, and they're just like, oh, it’s ecommerce. It's not physical retail? Oh, that's going to be tough. Another is like, "Is it manufactured in China?" I was like, "Everything is manufactured in China. What are you talking about?" They're like, "Oh yeah, it's going to be really, really tough."

Ben: You're like, who is this for then?

Shaan: Right.

David: [...] fraud? Why is it going to be tough?

Shaan: They would just email me. They'd be like, unfortunately, we can't find any underwriters that will underwrite this business. I was like, I haven't even told you anything specific or scary. I've just said ecommerce and made in China. That's everything. That's most things, as far as I'm concerned. And they were just like, yeah, we don't do much ecommerce. I'm like, who does [...] ecommerce then? I don't know if I'm just a terrible googler.

Ben: How does Shopify not have a preferred partner for this?

Shaan: Yeah, I don't know. How does Shopify not just provide this as a service?

David: They totally should.

Ben: Totally. It's a nice high-margin. This could float a bunch of their investments.

David: Insurance is the best business ever. I won't do a spoiler alert, I'll do a teaser.

Ben: The mere fact that you said you won't do a spoiler alert means people are going to know what we're talking about.

David: Probably our season finale this year on Acquired is going to be a well-known insurance business. But it's the best business in the world. You get free money. You literally get the money that you can invest that you have to pay back at some point, but it's free money.

Ben: To continue, David, because you've given away so much of the story now that we may as well round it off. If you have a large insurance business that allows you to have a nice big float, you can invest that float in other things. If you have a good capital allocator…

Shaan: It’s the Buffett model, right?

Ben: Yeah. It's an amazing way to just go buy a bunch of other businesses, make more investments in non-insurance products. It actually seems like a no-brainer for Shopify because they do want to build more and more and more technology and that's going to cost cash.

Shaan: Right. If it's not Shopify, then somebody needs to go do ClearBank for ecommerce insurance and do it extremely well. I finally got one provider, but the fact that I even had to try means there's money on the table for someone somewhere for this type of thing.

I think the thing you said is really, really interesting. It really resonated with me when you said that if your friends are going to Denny's at 2:00 AM in the morning, just go with them. That's literally the best career move you can do. I totally agree. I [...] this up a ton in college. I wasn't really even excelling in class, but I always just thought, okay, the class is where I should go. That's where the value is going to be. That's what I'm supposed to be doing.

I ignored all these people. I actually literally laughed at a whole bunch of people who I knew were just working on random [...]. They weren't going to class. They weren't going to parties. They were just building. And now, I'm begging them to invest in their companies here in Silicon Valley because I'm like, oh, dude. Sorry I made fun of you in the hallway.

David: You went to Duke, right?

Shaan: I went to Duke.

David: Were you there with Steven from Cameo?

Shaan: Yeah, he was a couple of years older than me. The funny thing is, Duke is this school in Durham. Durham, at the time at least, wasn't a very cool city. There was only one club that anybody could go to. One off-campus bar, basically, called Shooters.

David: I've been to Shooters several times.

Shaan: Did you go to Duke?

Ben: David, Why have you been there?

David: I have performed a wedding at Duke Gardens. My sister and brother in law went to Duke. We went to visit them a bunch of times and then they got married there.

Shaan: Of course they take you to Shooters. It's the only [...] place to go. Steven from Cameo

David: Shooters’ in Wayne Manor. My brother in law was in Wayne Manor.

Shaan: Right. He used to just host parties at Shooters. He was just a party promoter. I literally knew this guy as like [...] boy number one. He was just throwing parties at Shooters. He was always texting people trying to hype up parties. He was good at it.

David: Of course he was.

Shaan: And now he's the CEO of a billion-dollar company.

Ben: It's the perfect company for him to be CEO of. Its pattern matches perfectly.

Shaan: Exactly. He's a funny guy. Anyway, I forgot where I was going with this. What I was going to say is to follow your smart friends. Step one, have smart friends that actually do this kind of thing. If you just do that, you're 90% of the way there. The last 10% is to listen to them, follow them, and be interested in their things that seem just like random toys right now because one of those is going to become a big deal soon.

I'll throw out three that I've seen as trends among my friends. I have basically tech friends and then I have smart business friends. Of the top 1% of my friends, the tech friends are all about GPT-3, and they're all about DeFi, which is this crypto infrastructure. I don't think these guys own a stock, but they're like, oh, yeah. I'm in this DeFi system where I'm staking, I'm yield farming, and I'm creating these really complex lending mechanisms.

I'm like, what the hell is going on? When did you turn into a finance guy? It's because all of a sudden, engineers who like money are like, oh, I can use my engineering to make a lot of money.

David: The crypto boom probably fueled this because people were just making millions of dollars.

Shaan: They're all flush with wealth that is in Ethereum, in Bitcoin, or random ass [...] coin. They don't want to take it out. They're not ready to leave the crypto game. But they're like, I was just trying to invest $10,000 into Ethereum, and now I have $1.1 million. Okay, cool. This is a way I can stake my Ethereum, or I can lend Ethereum, and I can get 12% a year doing this. This is great. And I can control the whole thing from my terminal and my computer. That's awesome.

Ben: It's the same game that multigenerational wealth has been playing within trusts in the US for a couple of hundred years. But now these crypto millionaires have the exact same problem of like, I'm sorry, I have to pay taxes if I pull this out into cash? Well, how do I roll it into something that can spit off exactly as much cash as I need to live and I can leave it as an illiquid asset the rest of the time?

Shaan: Exactly. That is what's happening. Maybe more stuff needs to get built that's the equivalent of a trust or like the 1031 exchange of crypto. That's where a lot of potential is. This is why the ICO boom happened. So many people had made so much money off Bitcoin and Ethereum. To them, they're still thinking about their $10,000-$20,000 investment. But now it's $200,000, $500,000, $700,000, and $1 million. They were like, okay, cool. Maybe I could do that again. First, false confidence that I could do that again. I can invest in this new small thing and I could also—

Ben: With skill, not luck.

Shaan: Right, exactly. It was skill, not luck. Then the other is, I don't want to pull this out. When the Fed pumps in a bunch of money and the stock market goes up, that's basically what happened for crypto and why there was so much slush money to put into random ICOs.

Ben: All right, new idea is opportunity zones for crypto millionaires. Do you know about the tax treatment on that? On the opportunity zones.

Shaan: I've been hunting for ways to avoid paying taxes over the past year. People keep telling me about opportunity zones and how I should be investing in them. I only understand 20% of it so far.

Ben: I'll give you a very small amount that I know for sure and leave everything else unsaid so I don't say anything wrong. I know you can roll appreciated stock in, which I think is similar to a 1031 exchange without paying tax on it. So it's a new investment.

Shaan: Right. Let's combine the climate change and tax idea here into one with an idea I've been noodling on. I actually have said this on the podcast before, but I need to say it again because I'm still thinking about it, which is not true of 99% of the ideas I say.

One of the best simple ways to reduce your tax burden is to do a solar installation. There's a solar tax credit that the government gives. You have a house, you put solar panels on. Yes, you pay the upfront investment, but then you save on your utilities, and you get the tax credit that you can use to eliminate a whole bunch of your earned income. Essentially, you could do it for free as long as you have the money to put up front.

I've been looking to basically do this. I need something bigger than just my house. Your house might have a $30,000 or $50,000 project. I don't know exactly what it is. Can I get like $1 million of tax credits for this? Can I do $1 million worth of solar?

David: You want a farm.

Shaan: I want a farm, yeah. I was driving with my father in law, and he was telling me about this. In every school, you see these solar panels on the parking garages just outside the school. He's like, "Yeah, this is part of Chevron Energy. Chevron installs all these." From what I gathered was they both have a service provider. I think they're a vendor. They get paid for that. But the bigger thing is they'll be like, hey, school. You don't need to put up $2 million for the solar installation. We will do it—Chevron—out of our profits from oil and gas.

They get to say they're doing clean energy things. They get to reinvest profits into something that they're going to be able to get favorable tax treatment on. They get to help a school have solar power. Then they become a long-term lessor of the solar panels. And the school pays out a small monthly fee, but they are there from day one saving money on their utility bill. For them, it's like a net gain anyways even if they pay for this. They’re just paying less for the utilities.

I was thinking, why isn't there a marketplace where I don't have to buy a building and I do this whole solar plan, but I just had dollars. Please invest that into the solar projects for me, give me my tax credits back, and give me my monthly recurring income from—this is going to go on some farm in Idaho.

Ben: Yeah, it's an asset manager. It solves the same problem of like, I don't want to do the dirty work of finding those investments and operationally putting the money in, but I will pay you something if you do it on my behalf.

Shaan: Exactly. Let’s say supply is capital and the demand is people who want solar. Whether this is commercial buildings, schools, farms, factories, or whatever. Places that could use solar that don't want to put a $250,000 investment into their solar. They are going to buy another machine to run their factory better or whatever. But they're happy to take a lower utility bill. On your side, you're happy to get monthly income plus tax credits. So it seems like there is a business there.

David: That is solar installed.

Shaan: Yeah, exactly. And we're helping the environment. I like all of that. Now, somebody who is more knowledgeable than me probably in five seconds could tell me why this is not a viable thing. But for now, I'm going to say it out loud until somebody points that out or builds it.

David: I love it. This is part of—I don't know the exact history, but Solar City looked a lot more like this before it combined with Tesla. Which was weird all in and of itself. But now, I think Tesla's solar projects are much more about the solar roofs and power walls

Shaan: Right, for sure. Climate is one. The other one I said was buying businesses. Going more, forget this venture capital game. I'm just going to buy all these profitable businesses or the internet.

David: Our mutual buddies, Tiny capital.

Shaan: Yeah. Tiny capital is probably the thought leader and has the longest-running track record of doing this of people who are public on Twitter about it. Then there are others like Constellation Software. There's a whole bunch of different folks that do this. But a lot of my smart friends are going down this path of, hey, I'm going to buy and then build rather than play the lottery and hope I find product-market fit with a brand new invention.

Ben: It became so sexy to be—to use the finest term—an early-stage manager, emerging manager, as people would call it—solo capitalists in the startup parlance, do a rolling fund, or something like this. There's been so much of a rush to, I want to invest in my friends and relationships who are starting early-stage companies that we're now into year five or so of the boom of that, and people realizing how crazy hard it is to produce a market-beating return.

Let's say better than that—a top decile, top quartile return for your investors. Unless you're really really differentiated—and I think most people are kidding themselves on how differentiated they are in the deals that they have access to. Unless you're incredibly differentiated, you probably should go play a lower beta game. Where you can put in some sweat equity like having to use your PM or dev talents to rehab a business that is available to you for a below market price.

Much like the way we started this podcast talking about classic entrepreneurship versus shoot your laser at the sun and hope (I don't know what I'm talking about there)—go big or go home. I was trying to make a metaphor.

David: You’re like a Bond villain.

Ben: I think people are just realizing how crazy hard it is and they're like, wait a minute. If what I'm trying to get is an X% annualized return, gosh, I know way better ways of doing that that don't involve this crazy power law.

Shaan: Yeah, I think that's true. If I was saying, hey, over the next 7-10 years, I have to end up with this amount of wealth or I die. That's the path I would go, right? Because it's really de-risking the market fit side, and it's all about execution and growth because the financing is so favorable. Most people don't realize this. A lot of people listening to this are working at a job and they make a great salary. They might be making $200,000 a year, and then they're paying like income tax on that. Now they're taking home $120,000 or whatever it is.

David: Absolutely, if they live in California.

Shaan: Yeah, exactly. What most people fail to realize is that for either no money down or you could put down 5%-10%, you can buy a million-dollar business with an SBA loan. By the way, if you buy it before September 27th, the first six months are going to get paid for you by the SBA. The first six months’ payback is taken care of.

David: Not to mention seller financing. There are so many ways to do this.

Shaan: The seller is going to carry 10% of it themselves. That's how you get to 15% down the total. You put 5%, they put 10%, and then the SBA loan covers the rest. Every month, half the profits are going to go towards paying back your loan. The other half is going to go to you. Within 12 months, you paid off that whole thing. By the way, if you improved operations doing one of three stupidly obvious things, you've now created an asset that is worth two, three times what you bought it for.

David: It's like buying a house, except instead of you paying the mortgage, the mortgage is paying you.

Shaan: Yes, exactly. Unlike a house, it can appreciate at a rate that is uncommon. I have a friend who bought a business for $300,000 on one of these websites. He was the first guy. I was like, "You [...] buy off these random ass websites?"

David: Love it. He used one of these marketplaces.

Shaan: You go to Flippa and stuff like that. He's like, "Oh yeah, I bought a bunch of stuff." I'm like, "What?" It's because he didn't have connections. He's like, "I didn't have funding, and I didn't have connections. I just go to these places where I don't need a reputation or connections. I can get funding from these like very simple pools of capital. But I have to buy profitable businesses, otherwise, nobody will lend me the money. So I'm not taking big risks."

He bought this company that was small but profitable, and that company is going to do $30 million this year in revenue. He's going to literally take it from $300,000.

David: He 100x it.

Shann: Yeah, he basically 100x his business. I was like, "Dude, take me back. When you were looking at this business..." I 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?" He's like, "Yeah, I talked to the owner. He was just always thinking about operations, how to do the shipping, and the warehousing."

He'd never ran a Facebook ad. He never did any marketing. And also his SEO was a little screwed up, and I realized that. There's a lot of potential there. He didn't launch one new product in four years. Just Facebook ads plus new products plus improving the content SEO game and this insane lift. He'll sell this company for over $100 million that he bought on one of these Flippa type websites. It’s insane.

Ben: Shaan, I'm curious. Do you think there is an opportunity—if your skillset is like an amazing growth marketer—to get really surgical about running ads against other people's products and trying to get data back from like, oh my God? I know something they don't.

Shaan: Send them traffic.

Ben: It's hard because you don't own the pixel on their website, but maybe as a part of like, hey, I'm interested in doing the deal. Would you throw this pixel on so I can test some stuff and then I can tell you what I can afford to pay?

Shaan: Yeah, I think that's a great way to diligence things. But honestly, you don't even have to get that smart. There's a lot of these that they're just not doing one channel. And if you know that that channel works, if you have experience in that channel. Let’s call it Facebook ads, Google AdWords, or influencers. Whatever's your growth thing. You know the characteristics of the type of business that works there.

Let's say it's Facebook. You know that the types of products that work are scroll stopping products. It has to be visually appealing. You have to understand the value through a visual in less than three seconds.

Ben: The slow-mo of a Theragun beating against a thigh, making the ripples.

Shaan: Exactly. It does well like a baby. It does well. These things just do well on social networks. So you're like, okay, cool, I'm going to do that. And maybe a little less B2B thing that's not going to resonate in the same way.

Ben: The spreadsheet will change your life.

Shaan: Exactly. The spreadsheet beating against your leg doesn't do the same.

David: You guys get these ads of like two MIT grads got together and X.

Shaan: Dude, all my ads are crazy because it's only for businesses that I'm looking at buying. I try to get myself covered in their pixels and then I'm like, yes, retarget me. I want to watch everything you're doing. I want to see your ads and all the stuff. Facebook thinks I’m a 40-year-old woman.

Ben: I'm just picturing you bathing in D2C pixels.

Shaan: Yeah, exactly.

Ben: It's very strange.

Shaan: Anyway, I think if you know the channel really well, it's really not that risky. You'll know which type of products will work. You just know how much they have invested in doing this channel. Okay, you can think about the lift you're going to get. You could say, hey, I’d love to run a trial. But what you risk is educating the operator of how good this is going to work. I think it's a little bit dangerous to do that. You're better off betting on yourself in that way. There are other funny ways you can do it, but I won't go into those that are slightly in the grey area.

Listen, this was fun. Good dual episode. I appreciate you guys coming on. I feel like we didn't get to half the ideas on the list, so there's definitely more ammo if we want to do this again sometime. I appreciate you guys coming on my show. Thank you for having me on your show.

David: We got to do both shows here. It's great. We tasted both.

Shaan: Yeah. I like it. Thank you everybody for listening and that's it. That's a wrap.

Ben: That's it for today. If this is your first time listening to Acquired and you like what you hear, you should subscribe. And feel free to check out My First Million wherever fine podcasts are distributed.

As always, if you love Acquired and want to hone your craft with company building, you should join the Acquired Community of Limited Partners. You'll get access to the LP show where we dive deeper into the fundamentals of company building and investing in addition to our monthly LP calls where we get to talk with all of you. And of course, our book club and calls with the authors like recently Will Thorndike from The Outsiders.

If you aren’t an LP, you can click the link in the show notes or go to acquired.fm/lp. Everyone gets a 7-day free trial. So great to have so many of you in here. It's a blast. With that, thank you to our brand new very special sponsor for this episode. David, could you tell us about it one more time?

David: Of course. Thank you to Quaestor. Thank you to John for joining us at the top of the episode. If you want early access to their investor relations platform for startups, you can send John a note at john@quaestor.com or go to their website at quaestor.com.

Ben: Awesome, and with that, we will see you next time.

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