Andrew Wilkinson, founder of Tiny (publicly traded holding company), joins Sam and Shaan to discuss his Twitter paid subscription experiment, what it’s really like hanging out with billionaires on a $100M yacht, and how Metalab became a massively profitable agency. They also dig into the “one plus one equals 100” compounding advantage framework, interesting businesses like No Story Lost and Maui Nui venison, the mechanics of Hampton’s community business, and how Andrew thinks about dividends, personal spending, and the Profit First methodology.
Speakers: Sam Parr (host), Shaan Puri (host), Andrew Wilkinson (guest, founder of Tiny)
Introduction and Episode Setup [00:00:00]
Shaan: All right, what’s going on everyone. We have Andrew Wilkinson on the pod today. Andrew’s one of our great friends. He runs this company called Tiny, which is publicly traded in Canada. It’s a holding company that owns about 40 different companies. I think it’s publicly traded at around an $800 million market cap, does about $150 million a year in revenue. So he’s got really good insight.
Shaan: We talked to him about a few interesting things. One thing that sounds kind of not that cool but actually is cool is he hung out with a few folks worth like 10 or 20 billion dollars recently and talked about what it’s like in that sphere. We talked about Metalab, his agency that he started, which provided all the profits to start Tiny and how it makes something like 20 million dollars a year in profit — we asked how the hell does it make so much money. We also asked which agency he would start now. We asked him about his new Twitter experiment — why would somebody worth all this money run a Twitter experiment that makes 10 or 20 grand a month? And then we asked him about dividends. When you take dividends from a company, what do you actually do with them, where do you invest them, how much do you pay yourself? He got really transparent about that.
Shaan: So check it out. This is Andrew Wilkinson. It’s Shaan and Sam. If you guys like it, subscribe on YouTube, subscribe on Spotify, wherever you listen to podcasts. See you soon.
Opening Banter: Hair, Health, and Ozempic [00:01:30]
Sam: Before you got on, we were making fun of the badger — he looks like Kevin McAllister’s mom in Home Alone. He looks like he just took up rollerblading in the 90s.
Andrew: You’re saying I look like Catherine O’Hara?
Sam: Look at her character in Home Alone — she had this massive wave. It was cool. You’re like a bully in a movie.
Shaan: I think you look good. I think it’s cool.
Sam: She was hot. It’s all right.
Andrew: Well, welcome back. There’s no podcast on Earth where you’ll be welcomed with open insults like My First Million.
Sam: This is great. You guys want to roast me for another 10 minutes?
Andrew: Yeah. I was supposed to come on like three weeks ago and then I got strep throat. Dude, I haven’t been that sick in years. I was on death’s door. I ended up taking like three different antibiotics. I’m glad to be alive.
Sam: You’re on a health kick now. You’ve been lifting weights.
Andrew: Yeah, I’m doing a muscle gain competition with a bunch of friends. That’s been really fun.
Shaan: I’m perpetually eight weeks away from having exactly the body I want. The problem is the clock restarts every time DoorDash or Taco Bell happens.
Sam: Have you tried just doing ozempic? I have so many friends taking that and they’re suddenly ripped.
Andrew: It just doesn’t do it for me.
Shaan: Shaan’s very anti that kind of thing. Are you an anti-vaccine guy?
Andrew: No, but I do think the COVID vaccine was not a vaccine, because I was like — wait a minute, you still get it? You still spread it?
Sam: All right, well that doesn’t sound like science to me. You’re anti-putting-stuff-in-your-body.
Andrew: I don’t drink caffeine. I take some supplements — protein powder, whatever. But I try not to be dependent on anything. And the weight loss thing — I’m already married, I’ve got two kids, I don’t really care to lose weight aside from conquering my own mind and doing something I wanted to do. If I took ozempic, it wouldn’t be satisfying the way it will be when I just do it myself.
Shaan: I’ve always told myself that at some point in my life I want to look like Wolverine, even if it’s just for one week and then it’s over and unsustainable. I just want to get there. I want to have the photo.
Andrew: You should do the Jesse Itzler / Living with a SEAL thing. I feel like that’s in play for you.
Shaan: That sounds so freaking miserable.
Sam: That was the David Goggins thing. Did you read that?
Andrew: Just remember you guys had him on — you’ve got to read that book. It’s called Living with a SEAL. He writes it almost like a diary, so it’s not a long book with a bunch of flowery language. It’s very simple. What’s great is the perspective — you’re reading it not from David Goggins telling you that you’re soft, but from a guy who was kind of soft getting yelled at by David Goggins. So you’re secondhand receiving the info.
Sam: Have you guys seen the cover? It looks like the cover of Ernest Goes to Camp.
Shaan: Very outdated.
Sam: We’ve got Jesse coming on the pod soon, and I was thinking about it, Shaan — we’ve asked the question of who has the ideal life. He’s up there. He’s kind of nailed it.
Jesse Itzler as a Life Template [00:05:30]
Shaan: What does Jesse do exactly?
Sam: He just does these experiments. He went and lived with monks, did the Navy SEAL thing. But before that — I think he initially made a little money having a rap group and writing jingles for the New York Knicks. That was his career. Then he created Marquis Jets with his buddy and sold that to NetJets, which Buffett owns. Then he married Sara Blakely, the founder of Spanx — she’s a billionaire. He also got into Zico coconut water early and helped sell it to Coke. He basically goes from passion to passion and has had pretty good results. He owns a part of an NBA team. He’s like, “I’m into fitness,” so he creates a running club.
Sam: He reminds me a little bit of you, Andrew. You experiment. You get into something and it almost looks silly from the outside, but there’s something in you that’s identified an opportunity. Right now with Jesse it’s like he loves pickles and there’s no great pickle company, so he’s scouring the Earth to find the best pickle company to buy.
Andrew: I think it’s really cool. We talked about this before — Nick Gray, any of these people who build their life around the thing they actually love doing. So many of us were like “I want to get rich, I want to build a big business” and you get into doing something but don’t actually love a lot of the tasks. If you can build a business where your job is to meet interesting people, or be a podcaster, or do these crazy life experiments — that’s awesome. But it’s a double-edged sword. I’ve made that mistake where I’ll get into a hobby, turn it into a business, and it takes the joy out of it. You’ve got to find that right spot in between.
Andrew’s Twitter Paid Subscription Experiment [00:09:00]
Shaan: That’s why I didn’t want to do the Twitter thing. You’re doing Twitter subscribers — you’ve got a community now. I think it’s actually kind of a business. Six figures a year in revenue. Are you enjoying it?
Andrew: Yeah. Let me explain. I have about 240,000 Twitter followers. I’ve never monetized it. I just tweet every day — literally in the shower or on the toilet, I think of something and tweet it. That’s always been my life on Twitter. I’ve met tons of interesting people from it.
Andrew: But the issue is — and I know you guys have this problem too — you get endless reach-outs constantly. For a while I had open DMs and it was overwhelming. I was getting like 100 DMs from random people pitching me on crypto scams. But every 25 people, there’d be some incredible 22-year-old with an amazing cash flow business they wanted to sell me, or they needed money, something like that. So I had an incentive to go through it and I would spend 30 minutes a day triaging them and kind of hating my life.
Andrew: When I saw this subscription feature, I was like — okay, this is actually a filter. Twitter lets you have gated tweets. You can say anyone who pays to subscribe gets these extra tweets. So I said, okay: if someone will spend $29 — basically the cost to buy me lunch — they can DM me. I’ll respond. I used it as a filter. But then it surprised me when I started doing the math.
Andrew: I said I’d do an AMA once a month, video, and made a Telegram group. I said I won’t even respond to the Telegram group — you got the AMA and my tweets, that’s it. But when you do the math: I have about 550 paying subscribers today, growing pretty consistently. That’s about $16K of MRR — about $200K a year. Basically pure profit. I probably spend an hour or two a month doing the AMA or whatever.
Andrew: And if you look at the conversion math — a one percent conversion rate on 240,000 people is 2,400 subscribers. That’s like $800,000 of recurring revenue. If I get two and a half percent, that’s $2 million. If I do five percent, that’s $4 million. And if you think about what you’d pay for a business that makes you that much money a year — this is like $5-15 million of value. So I’m looking at it going: this is great. I’m getting dinguses filtered out, I’m making money, and I’m actually getting deal flow. I’ve literally hired two or three people from this group. I go to the group and say, “Hey, I need a CEO for this business” or “I want to buy a business like this.” So it’s been awesome.
Sam: Do you pay to follow Andrew?
Shaan: No. I can just text him.
Sam: I will. I’m in the Dingus group apparently.
Shaan: I paid literally to figure out why the hell Andrew was doing this, and then my mind started going with conspiracies. I texted Andrew and asked if I could share my theory.
Andrew: Go for it.
Shaan: Okay. So I sent Andrew a voice note. I said: you’re way too rich to be doing this, so there’s got to be another reason. Why would Andrew start using all the paid features of X, these subscriber experiments, speaking so glowingly about how great it is, saying he’s discovering his true fans? This doesn’t add up. It’s too much work for too little money for this guy. And then I was like — I know what he’s doing. I’ve seen Andrew do moves like this where he throws his weight around to meet the cool people he wants to hang out with. And who really wants cool, interesting people like Andrew using all the paid Twitter features to build a small business and would love that they’re telling the world how great it is? Elon freaking Musk. So I thought: Andrew is using this feature on blast, he’s the most legit guy doing it with a unique use case, he’s got a big following, he’s going to be the gold star example. He’s going to get a follow. He might get a DM. He might get invited. Andrew’s going to end up friends with Elon Musk from this whole thing.
Sam: Is that true?
Andrew: No. I mean, I’ve invested in SpaceX quite a while ago and I have tons of friends who know Elon. Honestly, I don’t know what I would say to the guy. I feel like he’s a super genius engineer — super kind of Asperger’s guy. There are a lot of people I’d love to meet. I’d love to be at a dinner table with Elon, but I don’t know what I would say to him. It’s like meeting Thomas Edison. How am I interesting to this guy? He likes boring businesses.
Sam: Who would you most want to meet?
Andrew: I really want to meet Larry Ellison. I’ve been trying for probably two years. I went to Lanai — he owns the entire island of Lanai, it’s insane, all the businesses, all the hotels, all the real estate — and while I was there I was trying to find a mutual connection. He kept driving by me in this orange Corvette. The guy just rips around Lanai. And I just couldn’t get the meeting.
Status Games and Billionaire Social Dynamics [00:16:00]
Sam: It’s so funny. From the outside, Andrew, you’re in your mid or late 30s, very successful, company worth roughly a billion dollars, publicly traded, and you still can’t meet some people.
Andrew: I claim I want to look like Wolverine but instead I look like the mom from Home Alone, and we still can’t get it done. It’s insane.
Shaan: I went down to LA and did a bunch of pod interviews and some meetings that I didn’t record. Just wanted to meet people and see what they’re like. One person — I can’t say who — was showing me around their house. Famous, successful person in LA. They were telling me about trying to get their kid into a school. This is a person who’s rich and famous, who can get almost anything they want. But there are these schools in LA, private schools that are basically Harvard for kindergarten — they reject everybody. And they got rejected. He said something really insightful. He goes, “I couldn’t tell you — that morning I felt something I hadn’t felt in seven years. Rejection. Nobody had told me no in seven years.”
Shaan: And I was like, wow. So to your Larry Ellison point — I think it’s actually great that you have certain things that didn’t work out, certain rejections. When we were in LA meeting maybe 20 people that week, a very common thread was that people were out of touch with rejection. Either they weren’t trying enough new things and were just in their comfort zone, or everybody around them said yes — even to their bad ideas. You could see firsthand how that’s not a great thing.
Sam: Has success helped you with women? Or do they mostly not give a sh*t?
Andrew: I haven’t really been single for very long. It’s definitely helped, but ultimately it comes down to status in whatever room you’re in. If you’re in a club, you know who the man is — it’s the DJ, the guy making less than the bartender and getting paid in drinks. That’s who everyone wants. So if I’m at a business conference and people know who I am, yeah, maybe that helps. But day to day, you’re way better off being like an Instagram influencer — something that girls actually care about.
Sam: How do you play the status game in those mixed social settings? I have to be vague about this, but somebody I know went to someone’s house — a billionaire who’s also famous — who entertains a bunch of people in the summers. All the other guests are also rich and famous. And the person I know was a regular person, nobody famous, and they felt very intimidated to the point where they were like, “I’m just going to go eat in my room.” They were talking themselves out of engaging. How do you deal with that social anxiety when you’re in your own head about the status of the people in the room?
Andrew: I’ve just realized that everybody wants to talk about themselves. It’s the Dale Carnegie thing — find out what someone likes to talk about and talk to them about that, keep asking questions. If I make them feel good, if they get to talk about the thing they’re interested in, they will leave that experience thinking of me as a very positive person, regardless of status.
Shaan: There’s a famous story where this young guy is hanging out with a rich, powerful guy, and the young guy just asks questions for 90 of the 100 minutes. At the last 10 minutes the rich guy finally asks him just a little bit, and the rich guy leaves the conversation being like, “That was the best conversation I’ve ever had, that person is great.” And the other guy is like, “Dude, I barely said anything.”
Andrew: That literally happens to Ben — my business partner — all the time. He’ll come back from a meeting and I’m like, “How’d it go?” He’s like, “Great.” He’s like, “I literally didn’t tell him anything. I didn’t say anything, he didn’t really ask me too much. I just asked him questions about things I was interested in.” At the end, the guy stood up and was like, “Man, this is one of the best conversations I’ve ever had, I really like you.” And I’m like — you did it again. He’s the walking version of that book. You leave and you know nothing about him. He didn’t ask any questions. But I think it’s great if the person is really fascinating.
Andrew: The status stuff though — where I get annoyed. So about 13 years ago I was at a conference. My business is making a couple million bucks a year in profit, pretty successful. I sit down next to this VC. He’s very disinterested. He says, “What does your startup do?” I say, “Well, I don’t have a startup. I have a business and it’s profitable.” He literally goes, “Oh, a lifestyle business” — and turns his back. Just turns completely away and starts talking to the guy next to him. I remember who it is. There will one day be a comeuppance moment.
The $100M Yacht Story [00:23:00]
Andrew: And then the other thing that happened recently — so I was on this yacht. I’ll tell you about that.
Sam: Do it now.
Andrew: Okay. So I got invited on a $100 million-plus yacht, which I was really excited about. Just always been curious about it — this bizarre thing you really don’t get to see very often. I thought I’d love it. But I actually found it incredibly odd. It’s something I feel like is very desirable because others desire it, and we all have this idea of it, but in reality I just don’t get it. You spend this insane amount of money to be isolated in a floating hotel away from everyone.
Sam: What was the net worth of the guy who owned it?
Andrew: To have a $100M yacht you’re worth like $5-20 billion plus. Very, very wealthy. I won’t say who, but someone who’s a subscriber of yours on Twitter.
Sam: Oh, exactly.
Andrew: You know like — have you ever been on a really nice RV? One of those bus RVs where you’re like “I can’t believe this has a shower, I can’t believe it has a king-sized bed.” But at the end of the day it’s still an RV. The king-sized bed is not as nice as being in a hotel. I felt like that was the rich person equivalent. Everything on this boat is amazing, but it’s not as nice as staying at a Four Seasons, and it costs a hundred times more. This thing costs $10-20 million a year to maintain.
Sam: No way. Really?
Andrew: Thirty staff for 10 guests. Just this whole boat for 10 people.
Andrew: Anyway, while I’m on this yacht there’s this guy who runs a publicly traded company. I’m doing my thing, asking questions, chatting with everyone. He’s kind of the serious guy, very unimpressed by me. He goes, “Oh so what’s your business?” I say, “I’ve got a holding company.” He goes, “Is it public?” I say yes. He goes, “How big?” I go, “Trading at around $800 million today.” He goes, “Oh okay.” His is like $10 billion. He’s like, “Oh, lifestyle business.” Haunting me.
Sam: Exactly that same feeling again.
Andrew: Right? And it’s like I still get that same irritating feeling. I’m just opting out. I can’t deal with this game.
Shaan: That’s the weird thing with the status game — there’s no end. I was talking to a multi-billionaire once and he goes, “Oh my god, Laurene Powell Jobs is so f***ing rich — she’s worth like $20 billion.” And I looked at him and I’m like, “What can you not do that she can?” And he kind of goes glassy-eyed and says, “Super yacht. I can’t do a super yacht yet.” That is the most pathetic, insane thing. But you’re falling into that trap, as am I, as Shaan probably is. You’re not a billionaire but I’m sure someone looks at what you have and goes, “Why would you want more?” And in your head you’re like, of course I want more. And you’re angry at yourself for wanting it.
Andrew: It’s never enough.
Sam: It’s like leaving a party and you move to the next room and they put you back at the kids table. I just keep ending up at the kids table no matter what level I get to.
Shaan: We were at a basketball event and Ben has this thing — like facial recognition software — he recognized the minority owner of an NBA team standing alone. So we walk over to introduce ourselves. Hey, what’s going on. The guy turns — he’s got two AirPods in. We say the first line. He looks at us like, “Are you going to leave or is there more?” There’s more, okay. Then he takes out his phone and slides the volume slider down halfway. He’s still got them in. He just temporarily gave us some airspace.
Shaan: Ben actually knows this guy, so we’re asking him about his business. But this guy — if there was a cologne called “Leave Me the F*** Alone,” he would have been spraying it all over us. We walk away. Next day, someone snaps a picture of him on Instagram and he’s smiling so bright. I texted our friend who was with us like, “Oh look, that’s him — right after our interaction was over.” I always wonder what the moment was where I did that to somebody. I never want to become that.
How Does Metalab Make So Much Money? [00:31:00]
Sam: I want to ask you something. Shaan put this here. How the f*** does Metalab make so much money? It’s astounding. Your services division — I think Metalab alone does something like $60-70 million a year with really healthy margins. That’s a very big agency.
Andrew: Agencies can be incredibly profitable and incredibly hard. When you do it for almost 20 years and you have a niche — with Metalab, those numbers you’re seeing are the blended collection of I think six or seven different agencies. Anyone can go look at the filings. But for the group — they can be incredibly profitable if you find a really good niche.
Andrew: The nice thing with Metalab is that we basically owned product design and building MVPs for startups since 2007. We worked at it for a really long time. When you have that reputation, people pay up to get you. There’s really not that many people that do it well and have the capabilities we do. So you can charge a premium and have really healthy margins. That goes up and down depending on what’s going on in the market, depending on how hard it is to hire a designer or developer.
Andrew: The problem with an agency is that it’s the most variable business in the world. They produce a lot of cash flow, but for the last 20 years we’ve been aggressively diversifying away from agencies. And the agencies have just been the Little Engine That Could — they kept on growing and growing. We didn’t ever expect Metalab to get to the scale it’s at.
Sam: Simple question — how many salespeople does Metalab have? People whose core job is to bring in new accounts.
Andrew: They don’t do a lot of outbound. It’s mostly inbound demand. That’s another reason why the agencies have been profitable — we focused on reputation and organic. A lot of big agencies have much lower margins because they have to have a whole bunch of people out there cold calling and selling. We don’t have that problem to the same degree. People come to us. The sales team is maybe six or seven people. The whole company is about 150 or so.
Shaan: You’ve had a bunch of agencies — Metalab for product design, a no-code agency, a content agency. Metalab seems to be the biggest winner by far. Is it because you started at the right time? Because you were there as the founder sweating it? Because that niche is just better?
Andrew: So here’s what happened. Metalab was the Golden Goose that provided all the cash flow we used to build Tiny and buy all the other businesses. Honestly, we were saying we don’t want more agencies — we’re happy to own that one, we’ll hold it forever, but it’s not where we want to focus.
Andrew: Metalab was getting to the point where they could only do projects for $500,000 and up. So we had tons of leads coming in that we had nowhere to send. We were just saying no. And so we went out, acquired a small agency in Spain, spun up 80/20. We basically said, “Look, we’ve got a sawmill. All this sawdust is coming out — we should be forming it into wood pellets and selling it.” So we created a constellation of smaller agencies to service the leads from the bigger one. And then those agencies have kind of moved out of the house — they’re not as reliant on Metalab leads anymore.
Andrew: Most of those we started for $25K or bought for up to $500K. The biggest ones today do $2-3 million of EBITDA. We’ve had some really good wins.
One Plus One Equals 100 [00:38:00]
Andrew: You guys had Syed on. What did you think?
Sam: Loved it. Great.
Andrew: And there’s so much about the way he thinks — we’ve read all the same books. But what he did with WP Beginner, where he’s got this huge source of traffic, all these users wanting to be told what plugins to use, and then he goes and buys those plugins that have a customer acquisition problem — they built a great product, they’re built by a developer who doesn’t know how to market it. When you put those two things together, you’re basically buying this business on historical earnings but you know you can 10x it tomorrow.
Andrew: That kind of reminds me of what we’ve done in the agency space. We had 100 leads coming in every month that we couldn’t serve. We spun up all these agencies to make money from that demand. I love that model.
Sam: That’s the one plus one equals 100 framework you talk about?
Andrew: Yeah. Basically the idea is: if you have an unfair advantage, use it. For Syed, he has WP Beginner with tons of people asking “what WordPress plugins should I use?” — and he can buy those plugins cheaply and he knows he can boost them. It’s like a guaranteed return. Or, imagine if you own an airport with 10,000 people in the lobby every day. A hot dog stand is not a good business. But if you put a hot dog stand in the middle of an airport, I can guarantee you’re going to sell a lot of hot dogs.
Shaan: There’s a story after the Syed episode where I started reading about Warren Buffett — I’d known nothing about him before. I started texting Andrew, “Oh I get why you did this, this sounds awesome.” There’s this story from the late ’60s when Buffett is maybe 35 and he goes to a movie theater and he’s like, “Boy it would be nice to own a little bit of all these ticket sales — this seems like a wonderful business.” And then he’s like, “There’s this company called Disney that’s doing this. They even have a theme park.” So literally he and Charlie go to the theme park to figure it out. They talk to the attendants at the rides: how many people come through? That’s how they’re doing their research. And he ends up buying five percent of Disney for about $4 million.
Shaan: There’s another story — somebody said Warren Buffett was supposed to be this wonderkind investor and I saw him walking around New York pacing and counting his paces. And he’s like, “Oh, we’re going to invest in some real estate deal and I wanted to figure out how many paces make up this square block so I can guess the foot traffic going in.” He would actually test these things in real life. He would look at the financials and then go verify in the real world.
Sam: Or there’s a story of him literally knocking on Geico’s door — “Hey, can someone talk to me about this company? Tell me what you guys do, because the financials look great.” Pretty funny how hands-on he was.
Andrew: Buffett is business abstracted to the ultimate degree. This guy has 90 or 100 companies, 375,000 employees, and sits on his ass reading in Omaha every single day. I look at that and go: how do I do that? And I don’t know that sitting on your ass reading all day is what you want to do necessarily, but how do you take enough of Buffett’s approach to have freedom to spend your time however you want?
Sam: I heard people say that so I started reading — like, Thriller novels — and I was like, “I’m just like Buffett.” Then I read his biography and it’s like, oh, he’s reading annual reports all day. That’s not what I thought.
Andrew: When Chris and I started Tiny, maybe eight or nine years ago, we were reading all the Buffett books. We’re like, “Okay, we’re just going to read annual reports all day.” We printed out all these annual reports. I think we lasted about four hours. It’s so boring. These guys, all they want to do is read. Charlie Munger just reads all day. Buffett said 500 pages a day.
Sam: That’s a book a day.
Andrew: And when I went and looked at the actual filings I didn’t even know what these words meant.
Cool Business: No Story Lost [00:47:00]
Andrew: All right, let’s do some cool businesses. Have you guys heard of StoryWorth?
Sam: Yeah. Big fan of it.
Andrew: Super smart. Started by this guy Nick Baum — he and I worked out of the same office when he was starting it. I was one of his first customers. He’s living it up on Maui right now. Basically, you buy it for about $99 for your parents or grandparents, and all it does is send a drip campaign of questions — “Tell me about your childhood,” “What was a moment where you struggled in a job,” “Who was your first boss?” — things you’ve always been curious about your family. At the end of the year it compiles everything into a book you can print and share.
Andrew: I thought it was amazing. Spent $200 buying it for my parents. Of course they fill it out for three weeks and then stop. My dad said, “Well, it’s a lot of writing.” So I was a little annoyed.
Andrew: But then I met this guy locally here in Vancouver who has a business called No Story Lost. It’s like the VIP version of StoryWorth. You schedule three Zooms, just talk to these people, and they have biographers who interview your parents or siblings and actually write a proper biography. I’m about to get a professionally written book about my dad’s life and I’m so excited. My dad was so much happier because he just had to talk, and my dad loves to talk. It’s like $2,000 versus $200.
Sam: Do you know how big that business is?
Andrew: I don’t think it’s very big. I actually invested $25K in it on basically no questions asked. I think it’s doing maybe a million or something. Their big problem is customer acquisition. One plus one equals a hundred — here I am talking about it, maybe I blow this up.
Sam: I think Nick makes a ton of money off StoryWorth because it’s automated. You basically build it once and then just market it. Whereas with No Story Lost you have to actually have a writer work with every single person. Much harder business model. But as a customer, awesome idea.
Shaan: These are the businesses that AI is going to really help with margins. An AI biographer is a really good use case for LLMs — asking questions designed to poke and prod, taking responses and asking follow-ups, transcribing all the audio. You could cut the writer’s work down by 50-80 percent.
Sam: Did you guys see Scribe Media? My friend Tucker Max started it — you’d talk to someone for a few sessions, pay $30-50K, and they’d write a business book for you. Mostly for people who want it to generate paid speaking and consulting gigs. I thought it was doing great and then all of a sudden out of nowhere it went bankrupt. There were even petitions from the writer contractors revolting.
Sam: They owe Shaan a book, right? You paid tens of thousands and just kind of bailed?
Shaan: I paid, I was like — yeah, I want to write a book, these people help you write a book, I’m a guy with more ideas than time. You have the book idea, you hop on the phone, they flush it out, they draft it in your voice and you edit. I was like, great. But then we started Milk Road, I was so busy, I paused it. And we have like five friends who all bought books and paused them for various reasons.
Andrew: I can say this because they tweeted it — Enduring Ventures, Xavier and Sieva, they bought it.
Sam: I’d heard about that but wasn’t sure if it was going to happen.
Andrew: For a company to go bankrupt that quickly, without any obvious signs, something must have been going on.
Andrew: I actually tried Scribe years ago. I think it’s great if you want to write a corporate handbook to hand out to employees — a cheesy business book. But if you actually want to write something really serious and legit, it’s a bit hard. I know David Goggins is their hit. But how do you guarantee quality at scale? You’d have to move up market.
Sam: I’ve been waiting for you to mention your book, Andrew. I wasn’t sure if it was public.
Shaan: Sean, you should read his first chapter. I read the whole thing. Normally when people ask me to read something I’m like, I don’t want to. But I started reading his and I was like, okay, I’m actually into this. It’s pretty good.
Andrew: Thanks, dude. I just sent my publisher my rough draft. It’s still in the phase where I’m embarrassed by it. But I know that’s the important step. I think it’ll come out in 2024. What’s my motivation? Kind of to muddle through lessons that I haven’t read in other books — around business and stuff. It’s the story of building Tiny, but also about this thing we were talking about earlier: how everybody wants more, how it’s never enough, how people are always trying to upgrade or play the status game, and how that usually comes from childhood trauma or something else. For me it’s been about pulling that string for myself. A bit of personal exploration. I’ve really enjoyed it.
Cool Business: Maui Nui Venison [00:59:00]
Andrew: So this one is really interesting. I thought it was super goofy when I first heard about it. Me and my girlfriend were visiting Maui and Huberman said, “Oh you should meet this guy Jake who runs Maui Nui.” So this guy picks me up in this ramshackle truck — looks like a Navy SEAL, super jacked. He drives us into this huge ranch and starts telling me about the business.
Andrew: Basically, there are these deer called axis deer from Asia. Some Hawaiian royalty brought them to Hawaii to hunt about 150 years ago. Because they had no natural predators, they’re an invasive species — they’re like rats, everywhere. They actually destroy the ecosystem. So the government literally flies helicopters and machine-guns them down. That’s the current solution.
Andrew: Jake was like, this is great meat. A lot of native Hawaiians hunt it and it’s super healthy and delicious. But the FDA won’t let you sell deer meat commercially. So he basically spent the last seven years getting FDA approval to hunt and sell this meat. That’s this really interesting moat in the business — it’s going to take someone else seven to ten years to compete.
Andrew: What they do is have professional hunters go out with sniper rifles in the middle of the night and shoot these deer in the head. The FDA requires a headshot specifically. So imagine: you’re a deer, you get to live this awesome life, you’re eating organic food, running all over Hawaii. And then one day in your sleep — boom, you’re dead. I was like, okay, this is fascinating.
Andrew: Huberman, Tim Ferriss, Attia — they all invested. And what’s crazy about the meat is that not only is it the most ethical meat you could possibly have, they’ve tested it and it has crazy micro-nutrient content. A piece of salmon is like 14% protein. This is 20% protein. Beef is like 9%. Good for the environment, animals live natural lives, then one day: headshot, done. If you’re not eating meat for ethical reasons or health reasons, this is like an incredible business. They’re doing I think $10-20 million a year in pepperoni sticks and stuff.
Sam: Did you invest?
Andrew: I did. Can you tell?
Sam: Your sales pitches are good. Okay, how did you have these same deer on your ranch in Texas?
Andrew: I don’t know anything about animals or hunting, but out on my farm you can only hunt normal deer for two or three months out of the year. But we have this thing called axis deer. I don’t know if axis deer is like a category of animal or what.
Andrew: They’re basically deer with spots. Sometimes they have tall ears. They’re called axis deer and they’re all over Texas. I don’t know if it’s the exact same species.
Sam: I love how this random guy in Hawaii just told this fascinating story about Hawaiian royalty and you’re like, “Yeah, I got ‘em, guys. They’re rats that are everywhere.”
Sam: I’m ordering some of this beef. I’ve gotten a little soft over the last two weeks — had a little injury, didn’t work out, been eating too much ice cream. For the next 30 days Shaan, you should join me. I’m only going to eat meats and plants.
Shaan: “Planted animals.” That’s good. I like the way you branded that.
Sam: Plants and animals. For the next 30 days. I gotta get my act together.
Andrew: I think it’s super complicated. They can charge a premium because I think they’re the only ones FDA-approved to sell it. They have the story, the brand, the investors. But it’s a hard business. These guys are basically going on hikes in the middle of the night, sniping deer, then shoulder-carrying them back to the truck. Then there’s this whole facility to process them.
Sam: Isn’t the problem that the bigger it gets, the worse it gets?
Andrew: When I talked to Jake about scaling, he was like, “Look, there’s a lot of Hawaiian islands, there’s a lot of deer.”
Sam: Honestly, I think you’re right that there’s something here. But I also think this is a little bit of a “Larry Ellison investment.” This is what rich people do — as you make money you start investing in things that are interesting to you. You start investing in dinner party conversations. I can’t have my whole portfolio in healthcare SaaS, even if that’s where the most money is made. I need to invest in things that are interesting to me, cool people I want to hang out with, businesses worth talking about in life. There’s a positive EV to that. You just gotta keep the check small and do a bunch of them.
Andrew: I would say you’re wrong about the ceiling, though. Think about Athletic Greens. Somebody comes to you and says, “Hey there’s these guys, it’s like a vitamin but it’s powder.” You’re like, that’s the stupidest thing I’ve ever heard. What makes AG1 amazing is they spent the last 15 years building relationships with all the most influential health people in the world. Tim Ferriss, Huberman, all these people — who not only buy ads but also own equity. A million competitors can come out but in your brain AG1 is the winner because that’s what you’ve heard and all the people you respect do it.
Sam: That’s different though. Vitamins were a thing. Green smoothies — people understood “I should eat my vegetables.” I don’t know how many people are like, “The protein content on my salmon is too low, I need to eat axis deer.”
Shaan: There’s a huge audience for people who go, “I want ethically sourced meat.” That’s why I don’t buy a lot of beef — I don’t like how they kill cows.
Sam: You turned me on to that, Shaan.
Shaan: I think anybody who says “ethically sourced meat” — look, if we’re being honest, it’s still killing things for our enjoyment. There’s a much further point on the spectrum that you go if you choose to. I’m a bit of a hypocrite on this in that I do eat meat. But at least I don’t lie to myself and say I’m doing something great morally by killing them the nicest way. It’s like driving an electric car — it’s better than a gas car, but you’re still producing toxic chemicals from the batteries. Just a little bit better.
Andrew: I do think in 100 years we’ll look back at eating meat and be a little shocked.
Shaan: 100%.
Shaan: Would you, for example — for Thanksgiving, did I tell you we killed our own turkey?
Sam: No! How was that?
Shaan: So — would you do it if that’s what we were doing?
Sam: Would I be excited? No. Would I do it? Sure. I’m not anti the whole experience. But I also want to say — turkey is massively overrated. It sucks. And killing it and eating it did not taste good at all. The Butterball turkeys taste way better.
Hampton: What’s Hard About Community Businesses [01:17:00]
Andrew: I was curious — Sam, I’ve said this privately, but Hampton is the business I’ve thought about starting for 10 years. I joined something called Entrepreneurs’ Organization about 15 years ago and was like, this is a very good business. Every member pays $5,000 and there’s all these local chapters that self-organize. These guys must be making an absolute killing. You have total lock-in because once you like your forum group, people don’t want to leave. They pay their $5K a year, go to events. And for years I’ve been like, someone needs to start the new EO. And you have. What are the things about Hampton that are hard to run or that surprised you?
Sam: The thing about Hampton is — in terms of the physics behind it — this is going to be a massive company. There’s very little outside forces that are going to ruin it. But the number one thing that sucks, and the thing that 100% could ruin it, is if you start letting in too many people too quickly. You cannot scale it crazy fast. You can scale it fast, but not like software — you’re not just throwing bodies at it. We have to be super thoughtful about who we let in and why.
Sam: Another thing is the feedback loop is fairly short. People in Hampton have monthly meetings and annual or twice-yearly retreats. So we don’t get feedback that quickly. I can’t just have an MVP of a retreat because someone’s flying across the country — it has to be good right away. That’s stressful. There’s no iterating. If you screwed up a Shopify store, you can just refund and fix it. With community, once you screw it up, I don’t think you can fix it. So it feels high-stakes all the time. That’s why we’re trying to be meticulous about growing slowly.
Andrew: I think you’re right. The thing that made me leave EO was the chapter head let in a couple of people I really didn’t like. Sketchy people, businesses that gave me bad vibes. And that caused me to dread going to some events. That was the thing that made me leave and start my own forums. I now have four forums I manage myself. And you really have to be thoughtful about who you let in. And the hardest part — I’ve run a lot of forums over the last 15 years — is that if there’s someone who’s toxic, the cancer has to be cut out. But that is an incredibly awkward conversation.
Andrew: The other thing is these businesses last a really long time. Do you know Vistage? I think they sold recently for like $1.5 billion, already doing half a billion in revenue. EO, YPO, Vistage — all were either started in the ’50s or ’60s. The cool thing is if you nail it right, you can have it for 50 or 100 years. Zero technological disruption. AI will have zero impact. That’s why I’m really fascinated by these types of companies.
Sam: How does it feel to be sitting on a winner? Did you feel this same way with The Hustle?
Sam: With The Hustle, I felt like I’m not sure if the math shows this will work — we were still learning. With Hampton I’m like, no, it’s 100% gonna work. The only thing that screws it up is us. That’s why I say there’s no physics stopping this from working perfectly.
Andrew: You also have an unfair advantage. Once you started talking about Hampton publicly, it became so unfair. You have free customer acquisition — going on podcasts, talking about it, your brand value as a person being associated with it. That’s one plus one equals 100. Right now you’ve had five, six, seven thousand people apply, which makes customer acquisition easy.
Andrew: But you look at On Deck — they had that same advantage and totally screwed it up. Treated it like a tech company, weren’t thoughtful enough, tried to scale too fast.
Sam: They raised Venture, too. Why would you raise Venture? This is a business that pays for itself. You have a negative cash conversion cycle — people pre-pay you for services delivered over a year. It’s an insane setup.
Sam: I think it could be like a billion-dollar company. I don’t think we’ll ever sell it. Feels good.
Andrew: Tiny if you ever decide to sell it, or if you ever want to take money off the table — hopefully it’ll be big enough and we’ll be buying you.
Sam: You know, when people have asked to invest I’m like no — this is my Metalab baby. This could be what I love. I don’t ever want to sell it. It might make a ton of profit and we can use that profit to buy stuff that supplements it. I don’t want to take money because I don’t want to feel guilty about the return.
Shaan: I’m gonna be on a helicopter and it’ll land on Sam’s yacht and then I’ll get there and he’ll be like, “Oh what’s your market cap?” and I’ll be like “$5 billion” and he’ll be like, “Oh, Hampton’s $25 billion. That’s cute.”
Sam: I remember when we hit five — those come-up moments are the best. I haven’t talked about Hampton publicly too much because this is the first time where I’m like, I’m just going to shut up and keep going. Because it’s working nicely. I think it’s actually quite hard to replicate. You have to have an audience. It was quite hard to get the early customers. But yeah, it feels good.
Andrew: You’re reading the right book. Reading the Buffett stuff and moats. People think investing is numbers — there’s a little bit of that, there’s napkin math. But at the end of the day it’s assessing the competitive advantage. You have such a crazy advantage in terms of customer acquisition and customer lifetime.
Andrew: And the logistical challenge — imagine 10,000 members doing all these retreats, that’s basically a retreat a day. Quite challenging. But I don’t think you have to scale up headcount massively. What EO does is outsource everything. They have chapters, all the members pay dues, there’s a chapter head managing it, and when they have retreats one person from the forum is responsible. They just self-organize. That might be the better model.
Sam: Yeah, we want to do a massive conference — all of Hampton with insane speakers — I’m just trying to figure out the logistics.
Profit First and Dividends [01:35:00]
Sam: Andrew, what is this Profit First methodology? You love this book.
Andrew: Yeah. One of the CEOs — actually the CEO of Beam — sent me this book. I love the idea. Basically, there’s this concept of if you eat your food on a smaller plate, you eat less. Same principle in business.
Andrew: Let’s say you earn $100 in your business and you want a 50% profit margin. The day the $100 comes in, you take $50 and put it in a separate bank account you can’t see. That’s it. You and your team are left with $50 to run the business. You adjust the number and figure out what’s sustainable.
Andrew: What I learned running my digital businesses was that we had businesses with 90% net profit margins. If you had looked at that business and said “this kind of business should have 20% profit margins,” we easily could have run it that way. But because Chris and I were incentivized — we owned the whole business — we paid a lot of attention to the P&L and what was possible. We tried to run it at maximum profit. This methodology basically allows you to achieve the same thing psychologically. You’re budgeting for 50% profit and saying, “Figure it out.”
Sam: Does this cause issues with your CEOs?
Andrew: We don’t do this ourselves. This is something we’ve sent to all our CEOs as like, “Hey, this is really interesting, might be worth trying.” I think it works better for small businesses. I know a lot of people who tell me they have an agency but can’t figure out how to hit their target margins. I tell them: rip the Band-Aid. If you want 30% margins, take $30 of every $100 that comes in and move it to another bank.
Sam: That’s what you told me to do and I’ve not been comfortable with it yet.
Andrew: Sam and I have had legit screaming matches about this. My whole thing is you don’t want to leave excess cash burning a hole in the CEO’s pockets or making them complacent. If you own a business with a payroll of $500K a month, a lot of people will leave like $20 million in that business. I think that just lets the CEO feel relaxed. I like them to basically have one to two months of cash. I want them paying attention to the P&L.
Sam: But you’re spending cash that you haven’t earned yet sometimes.
Andrew: If they hit a snag and need more for payroll or R&D, they just say “Hey, send me some of that back.” But for Tiny, the holding company above is the bank. We basically say, keep your money with us and if you hit a snag we’ll send it down in 12 hours.
Sam: For Hampton, for example — someone pays $10K for a year of service, so you have all this cash sitting in the bank. But you have new members constantly streaming in, very predictable cash flow.
Andrew: From my perspective I would just say, all right, what’s your expected margin, take that and dividend it out immediately. The goal is creating a feeling of always paying attention to the bank account, always paying attention to the balance sheet and P&L. When you have a year of cash sitting there, your CEO will naturally be like “Oh we could do a super conference and spend $10 million on it” or “It’s okay we didn’t do great this month because we’ve got all this money in the bank.” Psychologically, you want everyone eating from a smaller plate.
Shaan: And when you say “dividend out” — what percentage is Andrew Wilkinson actually taking home to buy houses and cars versus reinvesting?
Andrew: It’s different now that we’re public. What I used to do is I owned 80% of Beam, so I’d get 80% of those dividends. Those would go to my personal holding company and I’d buy stocks or invest. My general framework though is I want to spend 5% of what I earn at most. Whatever that number is — if you’re earning $10 million a year, $500K a year is just living, doing whatever. And everything else should get invested.
Shaan: So you live on 5% of your income and the rest goes to Tiny or your holding company. Was it always 5%?
Andrew: When I was earning a million a year, I wasn’t spending $50K. I was spending more, maybe 20-30% back then. But over time it came down to about 5% or less, probably for the last 10 years.
Andrew: One thing I see that a lot of people do wrong — they don’t let themselves live it up. They own this amazing cash-flowing business and don’t let themselves buy the beautiful house or the great car. So they end up going, “I’ve got to sell my company, I’ve got to have an exit.” And I’ve had friends where it’s like, dude — the exit was right in your bank account. You could have just dividended the money out to yourself and not had this really stressful experience with private equity. So I’m a big advocate of living a nice life. Don’t go crazy and buy Fabergé eggs. But buy a nice car and a nice house and invest everything else.
Shaan: What percentage of your income do you spend?
Sam: I don’t even think about it in those terms. My income has 10x’d and my spending has 2x’d, so as long as that ratio stays about right, I’m fine.
Shaan: In my 20s I was making like $120-160K for a bunch of years. Living in San Francisco, paying California taxes, I was probably spending the bulk of it — maybe saving 20-30%.
Shaan: Tim Ferriss said something on a podcast I really liked: “Unless something’s going to make a ton of money, give it away for free.” I think that’s a great rule in business and content. It’s partly why I don’t like your Twitter experiment, though I understand the reasons. The same goes for personal finance — either something needs to make a lot of money or save a lot of money, or I’m giving it zero mental budget. Otherwise I’m just using mental energy on too many things. For most of my 20s I was just thinking: how do I make way more money? Not how do I go from 20% to 30% savings rate. That paid off, because once you do it, you’re so glad.
Andrew: Ramit Sethi has a great book called I Will Teach You to Be Rich and he talks about this. People obsess over, “Oh I used to spend $6 on a Frappuccino but now I just buy black coffee and save $3.” You’re so much better off focusing on the macro — your mortgage, the big expenses — and then focusing on making way more money to the point where it really doesn’t matter. Don’t focus on $3 problems like a cup of coffee. Focus on $30,000 problems like getting a raise.
Sam: I notice this with hiring too. I’ll be negotiating a $5-10K salary difference and I’m like — okay, that’s about $800 a month gross, net to them after taxes is like $500 a month difference. Not nothing, but consider: the percentage of their concern around that gap versus whether they’re really thinking about how to use this opportunity to make 10 times more money in the future. What are the terms on their stock options? How are they struck? What’s the valuation? Is it reasonable? What does great performance look like, and what’s that worth to the employer? Can I structure an incentive where if I knock it out of the park I can make three times my salary this year?
Sam: Of 100 people, at least 20 should be asking themselves those questions more often. Before I met any business people, I just thought you go get a job after college. I didn’t think there were other options. And once I saw people doing business and having more fun and making more money, I was like — okay, I guess I could go do that. More people should hear the question: How do I make three times more in half the time? How do I have twice the fun on the same salary? There are just better questions you can ask yourself.
Buyer: Negotiation as a Service [01:55:00]
Andrew: I really miss this one business we started called Buyer — it was negotiation as a service. Amazing idea. Amazing guy running it, Kimia. We ended up selling it to Ramp.
Sam: Yeah, that was an awesome idea.
Andrew: I didn’t really want to sell it but for Kimia it was his first big exit, so it made a lot of sense. But I really missed that business. You know, when I’m buying a car or doing a big renovation or whatever, I still want that service. So I’ll put this out to the audience: someone needs to restart that business — negotiation as a service.
Shaan: That’s a great Nick Huber business.
Andrew: Are you going to make money on the Ramp stock?
Sam: We didn’t take stock. We just took cash, because within Tiny we knew we could get a good return.
Closing [01:57:00]
Shaan: Dude, these are the best podcasts. We’re just hanging out.
Sam: I wonder if the listener prefers these where it’s just loose.
Shaan: I like those better personally.
Sam: That was super fun, guys. If you like it, say so in the YouTube comments. If you don’t — well, you’re probably already gone by now. Thank you.