Sam and Shaan go host-only and cover five business ideas: Play Street Museum (kid-friendly play spaces doing $30K/mo profit), 260 Sample Sale (pop-up clearance for fashion brand samples), and HostShare (vacation rental swaps between Airbnb hosts). Sam pitches an AI Santa deepfake side project. Shaan does a deep dive on Vice Media’s bankruptcy and founder Shane Smith’s wild story, then spins off into Emerson Spartz’s viral content engineering and the TrueMed FSA/HSA startup.
Speakers: Sam Parr (host), Shaan Puri (host)
Cold Open [00:00:00]
Shaan: This is such a good idea, by the way. This is a phenomenal idea. This is a 10 out of 10 opportunity. Dude, he pitched me — why haven’t I invested in this?
Intro: Just the Two of Us [00:00:10]
Shaan: All right, what’s up. We got a banger, we got a doozy. We got a two-man trio here — it’s just me and Sam, no guest today. Sam, what’s up?
Sam: Nothing. I’ve liked having guests actually. Normally I hate it, but lately I’ve enjoyed it.
Shaan: What’s the difference?
Sam: So we should do more. I like the people we’ve chatted with. It’s been better.
Shaan: Yeah, not like those other crusty guests in the past.
Sam: I have a meaty topic. It looks like you have four good ones but they’re smaller — is that right?
Play Street Museum: Chuck E. Cheese for Good Parents [00:00:45]
Shaan: All right, I’m gonna tell you about a business I think is kind of interesting. Ben put this on my radar yesterday. He goes, “Dude, your sister should open a Play Street — a Play Street.” I was like, what the hell’s a Play Street? So I look it up. Have you ever heard of this thing, Play Street Museum?
Sam: Probably not. You don’t have little kids.
Shaan: Basically, imagine a good-for-you version of Chuck E. Cheese. I’ll start with that as the analogy. Chuck E. Cheese is, you know… it’s like, “Come eat rat pizza at my child casino.”
Sam: Dude. My parents used to — I always thought the Chuck E. Cheese near my house had burnt down, but they just said, “No, it burnt down, we can’t go anymore.” When I got my license and drove by and it wasn’t burnt down, I realized that was just their excuse. I just believed it when I was five.
Shaan: Totally. My father one time said, “Real men don’t drink with straws.” He was referring to a Jack and Coke. So for years I was like, oh, we’re not allowed to drink from straws. It’s like the Chuck E. Cheese burnt down story.
Sam: The Chuck E. Cheese on Chippewa burned down, you know. It’s not there anymore.
Shaan: Too good. All right. So Play Street is basically you go there, it’s a nice clean place — like a dream playroom for your kids. They’ve got a giant train set, learning games, the floor is all child-safe, beautifully done. And you basically pay and get to play for an hour and a half.
Ben goes, “Yeah, I’ve been going to this place and I think they’re doing $50 grand a month.” I forgot the exact numbers but it’s like seven sessions a day, $15 each, maybe 25 kids per session. At 75% occupancy you do the math and you get to roughly $40K plus. They also host birthday parties in the evenings and weekends — maybe another $8 to $10K of event revenue per month.
When you look at costs — rent is probably like $5K, and then you have your staff, your sort of supervisors overseeing the play space and resetting and cleaning it between sessions. I’m pretty sure this thing nets around $25 to $30K a month in profit. And they have tons of locations. They’re franchising.
Sam: I wouldn’t be surprised. My sister owns some preschools in San Francisco and the numbers are somewhat similar. That’s different — they pay more — but for regular schooling it’s interesting that these play spaces can do so well.
Shaan: It’s weatherproof. With me, like — I know we go to Target three times a week. You might ask, Shaan, what do you need from Target so much? Can’t you order online? And what I’ll tell you is this is daycare for me. Sean goes to Target so much that in his home you have this Target checkout playset, a Target mini grocery cart. You had to find it because it was like a collector’s edition, all sold out everywhere — you had to buy it on eBay at a markup.
Sam: Yeah, exactly. These Target mini grocery carts — kids love them because they like to do anything they’ve seen their parents doing.
Shaan: I go there often to kill time. How do I kill 90 minutes in a way that’s enriching? In a worst case scenario we go to Starbucks or Target. This would be better. I would gladly pay $15 for my kids to play in a place that’s not a park, which is weather-dependent.
I think these are really cool ideas. The Play Street franchise could do decently well. Where are the locations?
Sam: Texas. There’s basically none in California or New York. It’s like a blank commercial space — no food stuff, just like regular retail.
Shaan: Yeah, I mean their branding is pretty good. It’s kind of like how escape rooms work — escape rooms require no specific real estate, small footprint, two staff to run all day. They were fairly good franchise businesses for a period. But unlike escape rooms, where you wonder if it’s a fad, these you kind of know are going to stay popular. Every parent’s got this problem.
260 Sample Sale: Fashion’s Hidden Waste Stream [00:07:30]
Sam: All right, let me tell you about another thing like this. Another problem you haven’t really thought about. There’s a business called 260 Sample Sale — have you ever heard of this?
Shaan: No.
Sam: It’s a cool New York thing. So what they do is — any e-commerce or fashion brand has a ton of photo samples or product samples they get from their manufacturer. They use them in photo shoots to create the pictures on the website, for advertisements, for marketing. Then those don’t live in the warehouse — they live wherever the photographer is or where their office is, and you just end up piling up boxes and boxes of photo samples over time.
Most fashion brands have thousands of SKUs. For each SKU you had a sample made before the production run — and not just one sample, you had each size made because you needed it for the photo shoot to show the range or cast different types of models. So you get a ton of these samples over the years that you can’t really — it’s not worth your time to get rid of.
So this business popped up. There’s an empty crevice in this market for getting rid of these samples. What they do is — 260 Sample Sale — they say, send us your brand and we will host a pop-up where we’re going to sell your stuff along with a bunch of other brands, all at a great markdown. These are samples, so you’re not training your customer that this is like TJ Maxx discount. It’s a good story — these are samples you’re getting for less. And they’ll give the brand a commission back, so every time they sell something of yours you get a small commission. Better than nothing, takes it out of your space.
Shaan: How’d you find this? This is totally out of your wheelhouse.
Sam: They’re only in LA, Miami, and New York, and the pictures are like smoking hot women and a huge line out of a warehouse in SoHo. I’m in the e-commerce world, I have my own brand, and I know about this problem. I heard about this solution and I think it’s very clever.
I think like an aspiring hustler could do this by vertical — go get a bunch of health, wellness, and fitness brands or beauty brands. Have stations where you can demo them and sample them and then buy them. You could do this for other verticals, or you could just do this in other cities. If these guys are only in New York and LA, why not Beverly Hills, Brooklyn, Texas? You could run it quarterly or twice a year and still make it work. It’s like your own little farmer’s market, a flea market that you get to stock and run.
Shaan: Do you know Kingsford Charcoal? You know it — the blue bag, most popular charcoal. Do you know how it was created?
Sam: I think it’s a byproduct of something else?
Shaan: Exactly. Ford — when they were making cars, they had all these furnaces making metal. They took the leftover char and compacted it really tight. That’s how charcoal came to be. It’s a byproduct business. I love byproduct stuff. It’s kissing cousins with the sharing economy. And this is one of those.
Sam: That’s awesome. Their website is really challenging to use, which I think is actually a good sign — because I can’t really tell if they sell online or if it’s mostly in-person.
One thing I do hate whenever I go to New York: seeing people wait in line to buy Supreme clothing. Just put the gun in my mouth, man. I’m never waiting in line and spending my valuable time to purchase a thousand-dollar thing that should cost a fraction of that. The only thing worse is bottle service at a club — guys paying seven thousand dollars for a table and a thousand dollars per bottle they could walk across the street and buy for forty bucks. You walk through the chump line.
Whenever I see that stuff it makes me want to throw away everything and go live off the land.
HostShare and the Vacation Rental Swap Network [00:16:00]
Sam: Here’s an idea you’re gonna like more. HostShare. I got a DM from a guy named Michael Fisk. He shows me this thing called hostshare.com. Here’s the situation: you have a short-term rental, right?
Shaan: Yeah, a property.
Sam: Shout it out so people can go.
Shaan: marathonranch.com — Marathon Ranch. Sam comes by, has dinner with you, gives you a massage. It’s fantastic.
Sam: So you don’t have 100% occupancy. You have some nights unused. 60% occupancy is profitable — so you’ve got roughly 40% unused nights. What are you doing with those nights? Michael Fisk has an answer: trade your unused nights with other hosts who have unused nights. You stay for free there, they stay for free at your place.
I think this is a really smart idea. How many hosts are on Airbnb?
Shaan: Four million.
Sam: So you have a market of four million hosts you could make an inter-host network for. If you’re a host, you get to travel for free.
Shaan: How do you normalize the values across properties?
Sam: They calculate how many shared nights you’d give in exchange for 21 days of travel per year. Higher-value properties share fewer nights, lower-value share more. So if your average night is $500, you’d share approximately 15 nights per year. If you’re at $100, you’d share 45 nights. Everyone gets the same minimum amount of travel.
Shaan: So what’s your property per night right now?
Sam: $700.
Shaan: So they’d basically say: make your place open for 12 days a year and in exchange you get 21 days free booking in the network. Would you take that deal?
Sam: Yeah. In fact, I do. There’s a thing called live Kindred — K-I-N-D-R-E-D — and I’ve used it where someone stays at my home when I’m not there and I get credits for the marketplace. I’m gonna go to Taos, New Mexico — I have like eight credits because someone stayed at my house for eight nights. So I can go stay somewhere else for free.
My dream situation is to find another couple with similar style, lives in New York, wants to be in Austin, and we just swap. I haven’t found a good solution for a direct six-months-for-six-months swap. But Kindred is close — I actually use it.
Shaan: I didn’t know something like this existed. Do you give up your space? Is it free?
Sam: You put your space in the network, and there’s some type of service fee. Frankly, I don’t think it’s a good business. I don’t understand how they make money. When I signed up I was like, I’m getting a lot of value and not spending a lot — I don’t know how you guys are doing this. That’s a VC subsidy right now. Andreessen Horowitz money. I’m trying to use my credits quickly because I don’t know if they’re going to stay in business.
Shaan: That’s hilarious.
Sam: So yeah, I like these types of businesses. HostShare — I think I basically just created it. If you could pull it off, it’s a pretty amazing model. Hard to monetize. I think you have to charge a flat membership — $500 or $1,000 a year to be in the network. Pay only if you use more than five nights or something. Make it a fair trade. Get a subscription going.
There are similar things for luxury rentals — I think it’s called Avanta? You pay like $5K a year and get access to boutique hotels. There’s also this company called the nerd wallet of England — actually it’s called Money Supermarket — started by a guy named Simon. He started a blog comparing mortgage rates and taking affiliate fees. Built it up, took it public, sold his shares 20 years later. Now he owns this thing called Simon’s Resorts — he bought like 50 really nice homes around the world and you can use them when he’s not there. I love these businesses. Just buy all this stuff and share it with everyone.
AI Santa: Sam’s Christmas Deepfake Experiment [00:25:30]
Sam: I think I’m gonna do a little random experiment this Christmas season. A deepfake Santa. You’ll be able to come to the site, pay $35, type in your message — “Hey, wish my daughter Jessica Merry Christmas, tell her great job with the soccer thing, be nice to her brother” — and it’ll create a video of Santa saying this to your kid.
I want to try this thing Replit has where you can buy developer cycles. You put up a bounty — “I want somebody to build me this deepfake Santa, it’s got to do A, B, and C” — and people will just build it for you. It’s kind of like 99designs. You put up the dollars, people compete, you pick the winner.
Shaan: So you’re gonna pull an Emerson Spartz — you’re gonna do the money grab.
Sam: No! I’m gonna bring the joy of Christmas — the belief in magic — to millions of kids around the world. What are you doing for the children this year, Shaan?
Shaan: Sam is doing the Justin Bieber pitch: “We had a problem. We wanted to bring joy to children. What better way than a deepfake Santa? A world full of war and divisiveness — joy is all we have left. Magic. And how do you get people to believe in magic? Technology.”
Sam: We’re going to create a fake cartoon about a fake person, charge real money, and it’s going to be a fantastic result. Are you really going to do this?
Sam: Yeah, because I really want to try the bounty thing. What’s the URL going to be?
Shaan: SantasReal.org. Give it a dot-org. Let’s make all of our businesses dot-org.
Sam: For a long time I wanted to make my businesses dot-net so people would think I’ve been around for a long time. But dot-org is way better.
Shaan: Dot-org is way better than that stupid XYZ crypto stuff. Dot-AI, dot-IO — I’m not into it. We are a for-profit dot-org. It’s fantastic.
Sam: Is that what dot-org means? I think you have to be a nonprofit for dot-org.
Shaan: I’ve always been firmly in the dot-com camp, but I’m ready to get my dot-org on for the rest of my life. That’s like — backstage at a conference, someone used the “P word.”
Sam: Philanthropy. Don’t say that around me. Don’t flex on me with philanthropy, bro.
Shaan: So instead of philanthropy, it’s dot-orgs. wilkinson.org — go ahead and email me there.
Vice Goes Bankrupt: The Shane Smith Story [00:30:00]
Shaan: I want to talk about Vice. Vice.com is about to declare bankruptcy — cue the Michael Scott clip where he just walks out and declares bankruptcy.
The reason I want to talk about them is not because of Vice but because of the story of the founder, Shane Smith. If you’re under 26, Vice probably means nothing to you. They’ve very quickly lost relevancy.
So Vice originally was a punk rock magazine based out of Montreal — three Canadian guys. One of them is Gavin McInnes, who you may know as the founder of the Proud Boys. Shane Smith was the other. They got a grant from the government that let them launch this magazine. It started as a skateboarding punk rock magazine — they’d write amazing articles like Vice’s Guide to Drugs. They’d use all kinds of provocative language. It was like, I want to be in your face — that was the whole vibe. Old school covers like a tab of LSD on a hot chick’s tongue.
Sam: I don’t remember seeing Vice magazine. Was it a zine?
Shaan: There’s a difference. A zine is the punk rock version. A magazine could be like GQ.
Sam: So you’ve never seen these but it started as hardcore punk rock — articles about doing drugs, having sex, just rock and roll.
Shaan: Yeah. And it started getting picked up. They started the company in ‘94, but in ‘99 they moved to New York and that’s where things changed — right when the internet was just getting started.
Sam: You’re looking at magazine covers.
Shaan: Yeah. You said “rock and roll” and I was thinking about influential people. Musicians were influential people and they did this stuff. The tongue with the LSD. Versus now what’s “influential” — someone entering a cold plunge, someone meditating.
Shaan: So the internet starts coming around in the late ’90s. They raise about $2 million and move to New York. They create the website. Originally it was a free magazine they’d hand out and make money off ads — just the three of them writing articles. They’d have fake authors, people who weren’t real. Entertainment, so fine.
They start growing and take off. And they’d invented what we now call branded content or advertorials. Their whole shtick was: we’re gonna make awesome content, get the eyeballs of Millennials — back then Millennials were the elusive, hard-to-reach audience — and we’re gonna reach them and make the best content and just plaster your logo on it. This was pre-Facebook, so performance advertising wasn’t much of a thing. That’s how you advertised.
Eventually they blow up. And the important part isn’t just that they blew up — it’s the antics along the way.
They raised money from Rupert Murdoch, from Viacom. Eventually they were valued at $6 billion. Today they’re nothing, but they still make $600 million a year in revenue. I want to talk about some of the crazy stuff the founder did, and how their business model actually works.
Sam: Have you ever heard of Shane Smith?
Shaan: Never.
Sam: If you Google him, you’ll see pictures of this guy who almost looks like a punk rock Santa Claus — bigger guy, sleeve tattoos, shirtless, smoking a cigar. He looks a little bit like the number two guy in Billions. Like that guy, if that guy had a tattoo around his nipple.
Shaan: He’s crazy. Vice became respected because they’d do all this wild stuff — but it was Shane, the CEO, actually doing it. He’d go to Liberia during the Civil War, just bring a camera, get dropped in, figure it out. In 2013 he traveled to North Korea because he organized a basketball game between the Harlem Globetrotters and the North Korean national team. And eventually Dennis Rodman going to North Korea — that was for a Vice documentary.
They’d post these free documentaries on their site and then YouTube, get lots of views, put an Intel logo on it. That’s how they made money.
He was known for walking around the Vice office — which I’ve been to, and it’s as magnificent as you’d think, the coolest of the cool — he’d walk around shirtless and just say crazy stuff.
One time when he hired a CEO named Nancy he said, “We’re the modern-day Bonnie and Clyde and we’re here to take all your money.”
There was another time, early on, when Intuit came to the office to hear a pitch. Twenty-four hours before the meeting, he built a glass conference room so it looked legit and you could see your employees. Then he went and hired a bunch of actors, got tons of friends to come work in the office, to make it look like they were important. He always said things like, “We want them to think we’re rich. We’re gonna act as if.” They got a $25 million deal from it and it worked.
Sam: There was another time — in a 2003 Vice documentary about themselves — he tells this story about getting arrested in Bangkok when they started the company. A few years later someone asked him about it and he goes, “I made it all up. We needed a story for how the company started and I heard the story from someone else, so I just took it and made it mine.”
Shaan: He spent $380,000 at dinner in Vegas. A reporter asks, “Did you really spend $300,000 for dinner?” He goes, “No, it was $380,000 plus tip. And it was barely dinner — it was mostly wine.”
He even told crazier stories. This is a quote from the Financial Times: “I would be at the party, get wasted, take coke, have sex with girls in the bathroom, and afterwards mail my advertisers drugs because I knew if I sent them drugs in the mail they’d keep buying ads with us.” He admits all this stuff.
Sam: Where did we go wrong? Was it when we mailed customers drugs, or when I did drugs during the day working shirtless?
Shaan: He tells a story about him and his co-founders and people who were going to buy ads, and he says they were like mobsters who accidentally clanked shovels together while burying a body. Someone asked him about the physicality of it all and he goes, “Yeah but it’s just like two mafia guys and our shovels accidentally clank while we’re preparing the body.”
This guy is a showman. Total showman. Of course it didn’t work out well for the company — but it worked out for him. Google “Shane Smith house.” There’s an amazing article from 2018: “Shane Smith’s Living Large.” He purchased a $30 million mansion in LA, recently sold it for $50 million. He came out on top.
He spent 15 to 20 years doing his thing right before the tide changed. Vice was the opposite of woke — and then right before that change happened, he got his money, got out, hired a CEO, and bounced. His story is super fascinating.
Sam: I’ve never heard of him. I knew Vice started as a zine or magazine.
Shaan: What’s your main takeaway? You’re a media guy, you’re a bit of a wild man — what’s your take?
Vice Takeaways: Media Business Lessons [00:46:00]
Sam: I have a bunch of takeaways. First let me tell you how the business model works, because that’s part of it.
A lot of people don’t realize how they make money. They still make $600 million a year in revenue but they’re wildly unprofitable. I consider them like a mortgage-backed security for media. Remember 2008 — banks would buy tens of thousands of mortgages in one tranche, and it turned out 4,000 of the 10,000 were garbage. That’s exactly what Vice does.
They got famous because they only had 20 or 30 million monthly visits to vice.com — which isn’t a ton for hundreds of millions in revenue. What they did was partner with omgfacts.com, distractify.com, all these clickbait websites, roll them up, call them part of the Vice Network. They’d tell Intel and other big advertisers: “We reach all millennials, we have 100, 200 million monthly uniques to our network.” In reality it was on garbage sites. Once that came out it was frowned upon.
The other way they made money was an agency called Virtue — Vice and Virtue, pretty clever. Their whole company was basically a creative agency. They’d make content for Snapchat, Facebook, eventually HBO, and get paid a service fee. One big agency.
Sam: Takeaway one: if you’re going to be a company that makes money from multiple streams of revenue, you gotta nail one first. They didn’t even nail one stream. They had five other things that added up to a lot, but not one of them worked well enough to be profitable.
Takeaway two: they always said they’re going to be the next Disney. Shane once said, “We’re worth $10 billion right now but conservatively I think we’ll be worth $40 or $50 billion in a couple of years.” That couple of years would have been like 2020. Never worked out. He goes, “We’re going to be just like Disney except with cocaine.” Why didn’t it work? Because nobody loves them. If you’re gonna build the next Disney, people gotta love you. People love Mickey Mouse. They don’t really love Vice. If you’re going to be a media company you have to have something people love.
Sam: The third thing: if you’re going to be in the news business, that’s really hard because you have to stay relevant. You want something people grow into, not out of. A Wall Street Journal, a New York Times, The Economist, Financial Times — as you get older you aspire to read it, like it, understand it, brag about it. Whereas Vice — once you’re no longer 28, reading about this stuff isn’t exactly cool anymore. I’ve always thought about this with Barstool Sports. Dave Portnoy is getting older and some of these antics are going to start looking more pathetic than cool. You either stay with the schtick and start looking like a clown as you age, or you gotta sell, get out, change your life. It’s very hard to let go because without the craziness you wouldn’t have gotten to this level of success in the first place. And you can get addicted to the character, the fame, the money that comes with acting a certain way. You’re being rewarded, rewarded, rewarded — and then you’re 57. You’re Vince McMahon now, or Hugh Hefner.
Sam: The fourth thing — and this is a compliment. You texted me right before you went to speak at that conference. What did you say?
Shaan: “About to drop some showmanship on these guys.”
Sam: And that is totally true, and that is what he did. Showmanship. Even though it seems like he conned a lot of people, he kind of got the last laugh. And had it worked out it would have been a lot cooler, but the showmanship totally worked.
There are so many crazy stories about this guy. His employees would say, “When I’m with Shane I feel like I’m going to war, and I’ll go to any war with him.” Johnny Knoxville did an interview and said, “He’s the greatest leader you could ever have — also the greatest drinking buddy.”
He has all these amazing one-liners. Have you ever heard me say, “The best way to circumvent someone’s BS detector is to not BS”? I stole that from him.
There’s a story about him with Rupert Murdoch — they’re walking together, Rupert Murdoch is like the guy from Succession, the mean old man, and Shane sits down and goes: “You don’t have millennials. But I do. I have everything you don’t have.” Just totally swings above his weight and says it to this billionaire. I think it’s really fascinating to learn from this guy.
Shaan: Good segment. Good job.
Emerson Spartz: The Viral Content Engineer [00:55:00]
Sam: Actually, I have a spin-off of that. You mentioned a company — OMG Facts. Do you know who started OMG Facts?
Shaan: I do. I forget his name but he’s an oddball, right?
Sam: Emerson Spartz. I met Emerson maybe ten years ago. He was building OMG Facts and a network called Dose Media. He’s a genius.
Shaan: He is. I met him too and I was like, wow, this guy is super smart. I think if he’d applied himself to other areas he would have done some absolutely amazing things and everybody would know his name.
Sam: So let me tell you a couple things about Emerson Spartz. When he was 12 years old he built a website called Muggle Net. I’m a Harry Potter guy and I was on Muggle Net all the time. It was the number one Harry Potter fan site in the world — tons of traffic. At the time Harry Potter was like Justin Bieber-level famous. In between the books, people wanted a place to discuss, post theories, write fan fiction, debate what should have happened. Millions and millions of visitors.
When he’s 18 he publishes a best-selling book called — I think it’s called Harry Potter Should Have Died — controversial views from the number one fan site. You could already see this guy’s got the sauce. He’s got the showmanship.
Shaan: Where did you meet him?
Sam: I don’t even remember, man. I remember being on a video call with him and I think his girlfriend at the time. They were creating Dose Media. I go, “So what is it?” He goes, “We’re gonna make really viral content.” They had OMG Facts and four or five other websites — one for science facts, one for funny stuff, one for pop culture and TV show references.
In my mind at the time I was like, going viral is just lightning striking. You can’t really try to do it. He goes, “No, no.” He had built a four-part system.
“We’re a different type of technology company,” he said. “We have 18 engineers and four writers and we reach millions of people a month.” I was like, what do the engineers do?
“All the viral content in the world starts in one of three places first: Reddit, Imgur, or 4chan. Before it hits Instagram, before it hits Facebook, before it hits Twitter, it gets popular there first. So we built a detector that finds stuff getting hot on those platforms first. Then the writer writes a summary. Then we built an A/B tester that creates multiple headlines and different frames of the same story and tests them really quickly. We’d pay to get it in front of like 5,000 to 10,000 people, find the winning angle. Then we post the winner and distribute it to our audience.”
So you could engineer a higher degree of virality in every piece of content. Find the best stuff. Package it quickly. Remix it with the automated A/B tester. Juice up the headlines and images. Spray it out, get data feedback on which of 15 variations is the winner. Post the winner.
Sam: I was like, dude, this is amazing. Over the next few years I watched him build it up and his traffic kept going up and up. The problem was flyby traffic — the lowest common denominator of the internet, very dependent on social networks. And then Facebook manually went in and unplugged the viral engines for these companies. Like 10 companies died in that transition.
Shaan: Did I tell you about my partner at Hampton — Joe? He had a company called Little Things, the same type of thing — a clickbait content website. He started it in New York, had multiple floors of an office building, and it was killing it. They were at $100 million in revenue. He had a deal. They went through due diligence. Two weeks before the money was supposed to go through — that Facebook change you just referred to? It happened to Little Things. At the time, Little Things was the most trafficked website from Facebook in the world. The deal was about to close, I think for $100 and something million. He was going to walk away with $50 million after taxes. Two weeks before the money was supposed to go through, that changed happened. He lost the deal, and only a couple months later they had to shut down the company. All because they built everything on top of Facebook.
Sam: That’s a Mike Tyson gut punch.
Shaan: A bird’s gotta fly, a fish gotta swim, and deals fall through.
Sam: That’s too common. So what happened to Emerson? Here’s his bio now: “AI, history, complex systems, Bitcoin.” His goal: “I’m going to die number one on the leaderboard of people who changed the world.”
What he’s doing is something called Nonlinear. It’s a company funding people working on AI safety — making sure AI is safe. They incubate existential-risk nonprofits by connecting founders with ideas, funding, and mentorship.
Shaan: What’s x-risk?
Sam: Ben says existential risk is the risk that something could end the world.
Shaan: So he’s gonna save the planet. And his website is a dot-org. Noble mission dot-org type of guy.
Sam: When I read about him I was like, why are you doing this dose media thing? You seem like a genius, you’re absolutely wasting it. He’s a 10-out-of-10 entrepreneur going at a 4-out-of-10 opportunity. That’s how I felt when I met him. This is now 10 plus years later. I haven’t spoken to this guy. You mentioned OMG Facts and in my mind I’m like, that guy’s smart, I should follow up — because he left such an impression. He was really, really clever, really smart, and also surprisingly wholesome. Everybody I know in viral media is kind of a certain kind of person. He wasn’t that. Really soft-spoken, really nice guy.
TrueMed: The FSA Startup Sam Regrets Not Investing In [01:05:00]
Shaan: When I was in Austin a friend of mine was hanging out with Justin Mares, who’s been on the pod before. He said something I thought was a great quote. He goes, “It doesn’t matter how you make your first nut. You just gotta make your first nut. But after you do that, you want to work on a noble mission.” He was like, “Do whatever you have to do to make that first few million dollars where you’re financially free and you can work on whatever the hell you want. But then don’t go chase the second nut. Go after something that’s a noble mission. Go after something that’s awesome.”
Very few people actually do that.
Sam: Isn’t he doing like an FSA spending store? That seems like the most opportunistic thing.
Shaan: The way he pitched it was pretty awesome. He said, “Obesity in America is an epidemic. 60% of people are overweight. We want to make you eat healthier by making it easier to acquire this type of food and healthcare — and we’re doing it via…” that’s where the pitch came in.
His site is called TrueMed. It says: “Food is medicine. Exercise is medicine. Sleep is medicine. We don’t mean this in a theoretical sense — food, exercise, and sleep are all scientifically proven to prevent or alleviate physical and mental illness. In short, these are medicine.”
TrueMed is a payment integration that enables qualified customers to use pre-tax HSA and FSA funds to purchase health-promoting products and services from their favorite merchants. Soon available at checkout for merchants who sell healthy food, supplements, exercise equipment, and other health and wellness products.
Shaan: This is such a good idea, by the way. This is a phenomenal idea. This is a 10 out of 10 opportunity. Why haven’t I invested in this?
Sam: I didn’t invest because I was just saying no to everything and I deeply regret it. This is the best way to pitch a business — you paint this dreary picture. “Did you know that if you add up all the terrorist attacks, all the gun deaths, all the car accidents, it would only be a tenth of the people who die from obesity.” This is the outcome if we continue on this path. And the way we happen to be trying to solve it is X, Y, and Z. And I’m like, that’s a great pitch.
Shaan: I am so jealous I’m not invested in this. I’m messaging him right now.
Sam: All right, that’s the pod. We’re out of here.