Speakers: Sam Parr (host), Shaan Puri (host), Andrew Wilkinson (guest, founder of Tiny/MetaLab)
Intro: The Return of Andrew [00:00:00]
Shaan: Andrew, what’s going on? The return of Andrew! We promised that you would come back, and sometimes that’s just something we say — like, “oh, we gotta do this again sometime” — but this was a real one. We’re like, alright, when do you want to do it?
Andrew: Yeah, we had like what — 20 things to get through — and we got through like four. So what do you guys say we also screw around this time and not address half of the topics again, and set it up for a third parter?
Sam: I want to screw one thing first. This kind of — maybe Andrew, you’ll know a little bit about this, but listen, let me tell you guys a story really quick.
Sam’s Twitter Ghostwriting Story: Chris Pronger [00:00:30]
Sam: Andrew, do you know a guy named Chris Pronger?
Andrew: No.
Sam: He is a hockey player. He played in the NHL for like 20 years. He’s from Canada, I think Ontario, and he played for the St. Louis Blues. He’s like the fifth or sixth or seventh highest-paid player of all time. So for some reason he reached out to me on Twitter, and I started talking to him, and we went and got dinner. He wanted to — he’s like, “hey, tell me how this Twitter thing works. It looks cool, should I try this?” I was like, “yeah dude, here’s what we’re gonna do. Tomorrow, call me on Zoom. And the day before you call me, send me five titles of what you think a tweet could be, and we’ll just sit and I’ll just kind of write while you talk — I’ll just find the interesting stuff you’re saying and we’ll go from there.”
And we did it. He tweeted it out, and he went from 20,000 followers to — I think close to 100,000 followers — at this point in 24 hours. The tweet was read by 10 million people and got 30-something thousand likes.
This is the fifth time I’ve done this. I did this with my friend Ramon, and he got on the “How I Built This” podcast because of that. I did it with my friend Val, same thing. I helped do it with my friend Anthony — you guys saw the tweet thread about him living in Africa and eating only meat with the tribe he was staying with?
Anyway, this is crazy. If you just take interesting people — and it’s not like I did any of the work, they were just talking their stories, I just helped them write it — it’s pretty wild how this game works.
Shaan: What were the stories? What did you share?
Sam: Chris’s was easy. Let me tell you one of them because it got picked up by Bro Bible. The Bro Bible headline was: “Ex-NHL Star Chris Pronger Shares Traps That Pro Athletes Fall Into, Including Spending One Million at a Strip Club.”
Shaan: Why did it get so much traffic right away?
Sam: I think because the story got picked up by bigger outlets like Bro Bible, which adds a lot of fuel to the fire. And I retweeted it early on. But I think it’s just — he’s already somewhat famous and cool. I’m not trying to say this to brag because the reality is it’s not that hard. The guy is already a big deal and has an interesting life. If you earn $100 million as a professional athlete, there are only like 100 people who have the insights you have. Those insights are valuable.
Andrew: I wonder what you think the value of what you did for him is. That’s insane. Like, if you went to someone and said, “hey, I’m going to get you 10 million impressions on a tweet” or “I’m going to get you 100,000 followers” — what’s that worth? People pay for that. I’d say it’s like a million-dollar tweet.
Sam: Yeah, but you can’t guarantee that, right? So it’s a hard service to sell.
Shaan: Oh dude, you should do it right here right now. You should say: “I will write tweets for you, but depending on the outcome and the number of followers, you have to pay me a certain amount.” It’s totally variable. That would actually be worth your time.
Logan Paul and Personal Brand Optionality [00:04:00]
Sam: Andrew, right before this I was on a Twitter Spaces with Logan Paul. So you’re only the second most famous person I’ve talked to this morning.
Andrew: Only a little bit more famous. Holy crap, that’s crazy. What’s he doing these days?
Sam: He just launched a marketplace — like a fractional ownership thing. He basically created this thing called Liquid Marketplace. You’ve seen that he’s really into Pokémon cards, like Charizard cards — that’s been his thing over the last few years, these collectibles, either sports cards or Pokémon cards. What he did today was he launched a fractional Rally Road-style marketplace where he put up his Charizard card — he bought it for two million — and you could buy a piece of it rather than the whole thing.
So that’s what he launched today. He was doing a promotional Twitter Spaces, and I just shot my shot, raised my hand, and went and talked to him.
It’s crazy, the moat of a personal brand. Those guys can build 100 businesses off their following. And that Chris Pronger thing — the reason it’s so valuable is he can now start his own business doing whatever he wants: selling shirts, selling NFTs, starting a consulting business, managing money for other hockey players. The optionality is insane.
Obviously the downside is that if you’re Logan Paul, you’re Logan Paul. You’ve ultimately got to be the face.
Shaan: That personal brand thing, Andrew — you kind of got that early on. You built your personal brand back, I think, before a lot of people were doing it. You built it pre-Twitter even, right? Like you had a blog following before Twitter?
Andrew: Yeah, I had a blog and stuff, but honestly I was pretty quiet until COVID. During COVID I was bored and lonely and wanted to talk to people, and going on podcasts was like a way to socialize. Then I realized the power of it — once I started getting 30,000 or 40,000 Twitter followers, I realized that when I talked about a business I was incubating, I had our first thousand customers in a split second. You could literally go bankrupt, lose all your businesses, and reboot in two days with a business idea if you have a Twitter following. Nobody can take that away from you.
Shaan: You were not low-key before Twitter. You were famous before that.
Andrew: Yeah, I mean — I was never on a single major podcast. I was well-known within like the design community, but that was it.
Sam: Before COVID, we had you on the podcast and it was already one of the more popular episodes because you were on it. People already knew your story. The timeline in your head might be a little different than how I perceived it — which was: you were famous when we started the podcast.
Andrew: Yeah, I know, I know. Look, a personal brand does give you doors that open more doors. But the downside is you have to say to yourself, “I’m building my personal brand,” which is one of the lamest statements you could make. If you can live with that, if you can sleep with that at night, it works out. I know it’s hard for me and Sam to do that. That’s kind of why I haven’t started my own podcast or consistently tweeted. I’ll come on here once in a while when I have things to say, but I don’t want to always be on and always tweeting. When I was tweeting consistently, I was driving myself crazy — constantly going like, okay, what’s my big tweet today?
Podcast Milestone: 100K Downloads Per Episode [00:08:00]
Sam: Let me give you guys an update on the pod. I don’t know if I told you this, Shaan. When we first started, I said let’s just get to 100,000 downloads an episode. Shaan, we are now — not consistently for all episodes, but they just told me that a couple of our episodes are now getting over 100,000 downloads.
Shaan: That’s been the north star for a while. Like, what would it mean to “make it” in podcasting? It was: 100,000 downloads per episode. I remember saying that number back when we had maybe just under 10,000 per episode. And it’s been climbing since then.
Sam: It’s kind of crazy that it even happened without us. Like we looked away from it, stopped paying attention to it, and sure enough compounding just worked.
In December — or January — one of the last couple months, we crossed two million downloads per month. The year prior, same time, I think was 500,000. My prediction is we can hit three million by December. No math behind that, but it seems like it could happen.
Andrew: What does Tim Ferriss do per episode?
Shaan: I have to imagine he’s in the 500,000 to million range. I know Bill Simmons or Joe Rogan — I was looking at this once — they’re two of the biggest. I think they were getting like three or four million downloads per episode, consistently in the top five.
Andrew: Think about it — Tim Ferriss has been podcasting for like eight or nine years. You guys might actually be growing faster than Tim Ferriss if you chart it out.
Sam: Well, I’m already over six feet tall so I outgrew him a while back.
Shaan: You are a very dad-joke dad. Alright, let’s do some of these topics.
The Three Paths Debate: Venture vs. Cash Flow vs. Boring Compounding [00:11:00]
Shaan: We were texting about the idea of getting rich fast versus getting rich slow — taking a big swing versus doing something boring. I thought that was on the podcast, but no, that was a text message.
Andrew, can you frame the debate? You had a good take.
Andrew: So I think anyone who’s in the tech world generally reads headlines about people who swung big and won big — like Jeff Bezos. And I always say, for every Jeff Bezos there’s a hundred Jeff Bozos. The guys who tried, who failed — who didn’t raise the convertible debt in 1999 that allowed Amazon to survive, or timed it slightly wrong, or were in the wrong market.
If you think about it: on one hand, startups are like a house. Would you buy a house that had an 80% chance of being worth zero, a 10% chance of making your money back, and a 10% chance of making you rich? Then there’s another house: 80% chance of a solid return, 10% chance of zero, 10% chance of a poor return. Which house do you buy?
When you start a business, you’re saying: I’m going to put 5 to 15 years of my time into this. I’ve chosen the boring house — the 80% chance of a solid return. I’d be curious how you guys think about it.
Sam: I think your idea is right, but your numbers might be wrong. Let me just lay out a scenario — everything I’m saying right now is just made up. Let’s say you want a net worth of $50 million by the time you’re 50. How much profit would you need if you started that business at 30?
I actually did the math on this. If you have $1 million at age 30, and you invest and produce profits of $300K to $500K a year at between 10 to 12 percent, you can have $100 million dollars by 60 with compounding.
Andrew: But there’s a flaw — you’re assuming zero living expenses.
Sam: I’m not really addressing that. The point is the number you need to start with doesn’t need to be that big. A small number can compound into something staggering if you have a long enough time horizon — especially if you’re outperforming 10%, which I think is quite low compared to what you can earn with skills.
Shaan: So back to your $100 million by 60 example — what are you at 50? And at 40? The trick with compounding is it all comes to you at the end. The last two or three cycles is where you make all the money. Backtrack: what do you add at 50 and 40 in that world?
Sam: You basically double every seven years at that pace. So 50 million at 50 — which is sick.
Shaan: Right. That’s actually sick. Okay, here’s the question though. Everyone loves to point at people who are sitting on massive paper gains. Let’s say Sam started a startup and VCs invested at a $5 billion valuation. In reality, Sam’s a billionaire on paper, but he’s not going to realize that until the company IPOs — maybe he takes a small secondary — maybe he has a $10 million or $20 million liquid net worth. And typically the timeline even in a tech startup is 15 years.
My argument is: you can take a big swing with a venture bet, but statistically most venture businesses fail — at least an 80% failure rate. Maybe 5% at most go on to be something at scale.
What I advocate isn’t going uber-conservative, getting a salary, or buying a dry cleaner and working there for the rest of your life. It’s: what’s the middle? What’s the third door?
I look at somebody like Nick Huber, who found a niche and said, “I’m going to buy a bunch of self-storage businesses. These have been around for 100 years. I have a very specific view on how to make them more profitable.” He knows he can earn between 15 and 40% buying those — he does that for the next 10 years, and he’s going to be worth hundreds of millions of dollars.
Sam: I’m actually with you. I did this rant on the podcast that nobody liked, which was: you’re an idiot if you go for the Olympics. Going for the Olympics is a trap that society has tricked you into — giving up your entire life to turn yourself into a human tool that can bobsled at one tenth of a second faster than anybody else. People didn’t like that because everybody loves the Olympics and we’re supposed to honor our athletes.
But basically, venture-backed startups are the same thing. You’re saying: I’m going to swing for this billion-dollar prize that only 0.1% of startups achieve. And if I miss, I get essentially zero. A lot of times the median result is essentially zero — or you’ve underpaid yourself by 50 to 75% of market salary during those seven to ten years you spent trying. And you worked way harder and had a worse lifestyle the whole time.
The venture path is like the Olympics — you sacrifice your lifestyle for a very rare outcome. At least in the Olympics case it’s sort of a trivial piece of metal. At least with startups, if you hit big you do become a billionaire, so that does pay off. But I kind of think the venture path is really only done for ego.
Either you do it because it’s your calling — you stumbled into a business opportunity or a problem, you tried to solve it, and it just so happens the way this looks is going to be a winner-take-all massive business — or you are like, “I want to play the ego Olympics and prove I’m the toughest, smartest entrepreneur in the world.”
And everybody will cheer you on. The media will cheer you on — what’s it to them? The investors will all cheer you on and call you a hero — what’s it to them? They go home at 4 PM to their house in Atherton. They have a portfolio. The entrepreneur is the one who in some ways gets tricked into it.
I say that as somebody who in many ways was tricked into it. Not by anyone’s evil plan — just by the way the game is set up. And now I’ve come to the realization that nimble, small, lightweight businesses that provide a lot of cash flow — or businesses that you just buy instead of trying to start a new genius idea from scratch — is definitely the way to go from a logical, rational perspective.
You can still choose to do the other one because it’s more fun to you, but the logic and reasoning is so far on the side of going for cash flow.
Andrew: And the venture path can all go away so fast. I think the reason it’s not done as often is people are attracted to get rich quick. Nobody wants to get rich slow. The only way people are getting rich right now is in crypto — and those stories are so few and far between.
Even if you’re a billionaire on paper in year two — my argument is you’re not liquid until 10 to 15 years anyway. Liquidity is what matters.
Michael Acton-Smith, Moshi Monsters, and Paper Billions [00:22:00]
Shaan: Have you met Michael Acton-Smith? He’s the co-founder of Calm. Before that he had Moshi Monsters.
Andrew: Yeah, so he created essentially a Pokémon-type phenomenon in the UK. It was this children’s online world — these characters, you’d go in and do this and that. It turned into a brand that they slapped on shampoo and started selling everywhere. He dreamed of having a theme park. He’s a really big dreamer, big thinker — super creative. You wouldn’t have created that kind of phenomenon otherwise.
At one point, one in three kids in the UK were playing it. It was valued at over a billion dollars. He was the man. He looks like Russell Brand — kind of good-looking, free love energy, maximum two buttons on a collared shirt. Just living his best life. He had the persona and the movement to back it up. A Walt Disney type who creates this kind of phenomenon.
And then sure enough, they got ahead of their skis. Third grade came around for those second graders, and they were like, “I don’t care about Moshi Monsters anymore.” Overnight the business starts losing relevancy. As fast as you can climb as a fad phenomenon, that’s as fast as it can unwind.
I don’t know exactly what his net worth was, but the company was worth over a billion dollars — I’m sure he was worth hundreds of millions on paper — but never got to realize it. He had to start back over from scratch as just a guy who went through this roller coaster without the money to show for it.
What makes it even more amazing is that he went on to help seed and co-found Calm, and helped grow it into a multi-billion dollar brand. He’s done it again.
Sam: I had the original agency, and in the early days the agency barely made any money — a couple hundred thousand dollars. I read about the Basecamp guys doing these SaaS products and I was like, “man, I want to make money when I sleep.” So I started taking most of my profits and starting SaaS companies.
I set up a 90/10 — basically taking the majority of profits and investing them in new businesses. I incubated a bunch. Some ended up being worth significant money — I sold one for $7 million that was producing $600K or $700K a year of profit.
I made a lot of bets with that money and ended up compounding into something significant. I kept doing the 80/20, 90/10 strategy of always investing. I started making a lot more money when I went from starting businesses to buying businesses and investing — I started that about seven years ago.
Sam: Hold on, those numbers don’t quite make sense. It sounds like $20 million or $200M net income?
Andrew: No, no. Let’s say Metal Lab’s revenue is a million dollars, we made $500K of profit. I’d take 80% of that $500K and use it to start more businesses. I’d do this on a monthly basis — whatever was left over in the bank that I didn’t need to run the business, I’d go and use it to start yet another business. I’ve been doing that for 15 years, and I think all of our businesses together are worth over a billion dollars now.
Shaan: Do you know how much you were compounding? You took money and either started a business or bought a controlling share in an existing one versus just putting it in real estate or the stock market. How much additional lift do you think you got by doing the extra work of identifying and buying businesses versus a more hands-off strategy?
Andrew: I think if I was passive, I could have gotten 8 to 12% putting it in real estate, stocks, that kind of stuff. By buying businesses, there are a lot of advantages — you can use a little debt because you control the whole business, you can get the bank to give you 20 or 30% which adds a lot of lift on your return, and we were buying businesses anywhere from three to ten times earnings. Then usually within the first two years we’d find ways to double the business. That’s kind of a two-to-five-year payback based on cash, and then the actual value of the business increases over time. The numbers start getting very big very quickly, especially when you’ve done that 20 times.
Shaan: What was the compounded rate?
Andrew: We did the math a couple years ago when we raised a fund — I think it was around 40-something percent. Keep in mind that was at a time when not that many people were doing what we were doing, so it’s gotten more competitive. And those are small deals — it’s easy to compound at high rates when you’re doing small deals. As you do bigger ones, we’ll probably slow down. But it’s not a number I think about. I never was like, “I want to compound at 44%.” I was like, “I just want to make my money back in a reasonably safe way, buy great businesses, and feel good about what I do.”
Shaan: That’s crazy to me, because that’s Munger, you know — the whole Buffett/Munger philosophy is based on compounding over a long period of time. The number one variable is time, and what’s the rate. Even if you drop the rate down to 15 or 10%, it’s still hundreds of millions of dollars. That’s what’s crazy about compounding — you don’t need to outperform massively. You just need to do a little better than everybody else, and if you do as well as everyone else you’re still good.
Which Businesses Last 20-30 Years? [00:33:00]
Sam: Let me ask this: of your businesses, how many do you actually think can last 20, 30, 40 years? And if you can buy any internet-related business right now, what are a handful you’d look for?
Andrew: Think about Accenture — they help people do consulting, strategy, digital transformation. That business will definitely exist for the next 30 years. In the same vein, I think MetaLab and our agency services businesses — we’re really early in every business turning into a tech company. Over the next 20 years, more and more companies will have to build software and go digital, and there’s only so much talent. So I think those are tremendous businesses.
Aeropress is a business I think will exist in 50 years. I don’t see any reason why it wouldn’t — will it have the same competitive advantage? Will it get copycats? Probably. But Kleenex still exists a hundred years later.
I also own restaurants and a bakery, and if people still like their food the way they have for the last 30 years, those will probably exist in 30 years. We do own some businesses that are platform-dependent or technology-dependent where things can change — no way to predict how long they go. But I’ve been surprised how long some of our businesses have persisted and grown.
Shaan: Andrew, I’ll give you the devil’s advocate to the “don’t go for the big home run” strategy: I believe it’s true that a lifestyle business and a moonshot business will both basically take up all of your time. So might as well go big.
I’ve run a restaurant, I’ve started a tech company — in both cases it was on my mind all the time. I was working five or six days a week minimum. A restaurant was going to spit off $150K to $200K of profit off that location. A tech company could be worth $100 million in two years. Those are just different sizes of the prize for the same level of effort.
Also, with a bigger, more ambitious project, you get to be more excited every day. You recruit better people because great talent is excited about it. With my online course business, I know I could do better if I could hire better people — but not everybody wants to come work on that project for a salary I can afford.
Andrew: I’m not advocating for some Tim Ferriss four-hour work week thing. I think Warren Buffett is not a lifestyle business — he has a business he loves to run and does exactly what he wants to do.
Personally, I like incubating businesses, starting new businesses, getting excited about stuff — I just do that off the side of my desk, 20 or 30% of my time. I also like buying great businesses, letting them run, choosing CEOs, doing the Buffett thing. But I need excitement and all the other stuff too.
I’m just saying your odds of success are higher on the boring path. If you go to the gym and you try to lift 800 pounds on day one, you’ll probably fail and it won’t feel very good. But if I give you an 80-pound bench and you lift it, you’re going to feel really good about yourself. I want to jump over the one-foot hurdles. And I think when people start out in tech, do a startup, and it’s brutal — a lot of those people turn around and say, “I’m never doing that again,” when they might have been great entrepreneurs in some other format. It’s just the hardest lift. It’s the Olympics, as you said.
Doing It Wrong Before You Do It Right [00:42:00]
Shaan: Let’s do one of these other topics. Doing it wrong before you do it right — what’s that?
Andrew: People always criticize me because I will hire the wrong person. I’m a big advocate of: if I have an idea and I just want to get moving, I will go hire whoever’s in front of me and say, “let’s go do this.” That doesn’t work great, obviously. But what it does do is it forces you to make it real.
For example, I’ve always loved food and restaurants. I dreamed of starting my own restaurant. I did it — I signed a lease I shouldn’t have, hired the wrong manager, and lost $800K. Total learning experience. But here’s what it did: it forced me into that industry. It made me learn it, made me make a lot of mistakes. Then I found the good people through that. Actually via that failed restaurant, I met the guy next door who ran a very successful restaurant. When his partner wanted to sell, I ended up buying it. And now I own this wonderful restaurant — and I know it’s good because I’ve owned a bad one.
So directionally moving into something — I think people are way too precious with their hiring. They need to just do it and then let people go if it doesn’t work out.
Too many people think they’re measuring twice but cutting once, and they just never cut. They just measure forever.
Shaan: Do you just have to fire people all the time?
Andrew: Not all the time. It’s like 50/50. The pattern I’ve seen — the best thing to do when you’re going into a new industry is look for somebody who’s actually succeeded within it. The problem is that when you’re the rube at the table, when you’re the newbie to the industry, even a fraud looks like a genius. That’s the hard part.
Mailman and Taking Chances on People [00:46:00]
Shaan: You’ve got this new business called Mailman, right? The Gmail plug-in?
Andrew: I’ve had that for a couple years, actually. It makes it so that you only get email a couple times a day — you’re not in your inbox all day. It’s picking up steam.
And yeah, you met a guy on Twitter who you got to run it, right?
Andrew: That same year I tweeted out: “I’ve got this idea for a Gmail plug-in, I need someone to build it, who wants to build it?” This guy Mohit in India messaged me, sent me a great email, said “tell me what you want to do and I’ll have it to you in 48 hours.” He did. Over and over he just kept delivering.
There was another business idea where I did the exact same thing, and that guy just didn’t make any progress. After three months I said it’s not working out and went a different direction. But 50% of the time it works really well. Now we not only have Mailman but we actually started a holding company in India — we’re looking at acquisitions, and he’s managing some of our businesses. It’s been awesome.
Sam: This feeds into this idea of taking chances on people. When I was like 15, I always had this feeling of: someone just needs to give me a chance. I’m a dog to a bone, I just need the opportunity, and no one ever gave it to me. So I had to start my own business.
I’ve had this experience a few times where I’ve taken a crazy chance on someone. Have I told you guys about how I met my business partner Chris?
Shaan: No.
Sam: Maybe two years into business. I’m a bank balance accountant — I don’t do bookkeeping, I don’t understand what’s going on. I would just look at the bank account: if the balance was bigger on day 30 than day 1, I thought I was winning.
One day I go into the bank trying to get a corporate credit card, and the teller says, “you need to go talk to Mr. Sparling, he’ll fill out all the forms for you.” So I go into the back of the bank, get welcomed into this nice office, and Mr. Sparling looks like the son of Mr. Sparling — he’s this little skinny 23-year-old. We start chatting, immediately hit it off. We’re joking around, talking about our days.
After I finished the paperwork I go, “hey, what’s your deal? You want to stay at the bank? What are you doing?” He goes, “well, I’m thinking about getting my accounting designation — I don’t really know.” And I just blurt out: “Do you want to be my CFO?”
He’s taken aback. He’s like, “let’s go get a coffee tomorrow and talk about it.” I convince him to come be my CFO. He has almost no accounting experience — he worked at a bank. On paper he’s the wrong guy to be a CFO. On his first day, I trust him completely — give him my social security number, all my information, banking wires, everything.
Chris is now my business partner of 12 years. He’s responsible for a significant amount of everything good that’s happened in my career. He’s an incredible person.
Now for every story like that, I have someone who was terrible, incompetent — ranging from that to fraudulent. But when you do take a chance on someone, one in ten times it pays off big.
Shaan: I’ve got a good one and a bad one because they both hit yesterday.
The bad one: I took a chance on a person who I still think is a good guy. I met him working out — he trained with my trainer. Nice guy, young, he was an apprentice plumber at the time.
We had an issue with our 3PL for our e-commerce business. We had a theft issue at the warehouse, and the owner was kind of like, “yeah, I don’t know, you can’t prove we stole it.” I got so pissed — I was like, we’re leaving tomorrow. We’re not using this 3PL anymore, we’re going to do our own warehousing.
I didn’t know the first thing about warehousing. But I hastily signed a lease on an 8,000 square foot warehouse and thought — I definitely don’t want to run this warehouse, but the stuff is coming tomorrow. So I’m working out that day, and I’m like, “hey, you want to run a warehouse?” He’s like, “what?” And I was like, “you’re a hard-working blue-collar guy, you want to try this?”
“Well, I’ve never done anything like this.”
“Don’t worry, I’ll take a shot on you. You’re going to make a bunch of mistakes, that’s okay. I understand because you’ve never done this before — I’ve also never done it before. Let’s figure it out together.”
I kind of laid out this vision — maybe he could run our own in-house 3PL, fulfill not just our brand but other brands too. He was super excited about it. In my head I’m already imagining the Hustle Con talk — I always work backwards from: imagine two years from now you’re on stage talking about how you survived chaos. It gets me more excited about the current moment.
It started off good, but a year later, nine months later, balls were being dropped, he wasn’t growing at the rate we wanted. I’m still holding out hope. Then I find out he’s trying to start his own version — kind of on company time, company dime, trying to steal the idea. Look, it’s okay to want to be an entrepreneur, but you do it above board. So that all came to a head yesterday, and I was like, look, this isn’t working. I’ve got to throw that Hustle Con story away — not happening.
And then in the afternoon, I get a call from this guy Johnny — and Johnny’s a kid I hired at age 13 or 14.
He called me one day at the office. “Is this Shaan?” “Yeah, how’d you get this number, who’s this?” “My name is Johnny. I met Pete who works at your office at the dog park. He said I’m in eighth grade and I’m a programmer, and it’s about to be summer, and I just want to hang out around other programmers. I’ve never met one. Can I come hang out at your office this summer?”
I was like, how can I say no to this? So he shows up. First day, we’re in a meeting, and I was like, “we should do this little viral quiz — hey Johnny, can you build a website?” He’s like, “uh, yeah” — he didn’t know how to, but he’s just like, “yeah, I think I could.” I was like, “alright, build this today.” He literally stayed until midnight that night and had a version of it working.
By 10th grade it’s like, Johnny needs to be here full time. He’s the man. He wanted to drop out of high school, and his mom was so worried. I go and meet with his mom. I’m like, “he’s not dropping out — he’s going pro. Like when LeBron James skipped college because he was going pro.” She was like, “okay, if you put it that way.”
And then when we got acquired, he became the youngest Amazon employee during the acquisition. Now he’s — I don’t know, 19 or something — and he’s starting his own thing. Johnny Dallas. He called me yesterday and he’s like, “yeah, it’s going pretty good — we just got a term sheet from” — probably shouldn’t say the firm — “the best VC firm. $38 million post-valuation.”
I was like, have you had puberty yet? What is going on? But I told him: dude, I bet on you. You were my personal angel investment. And now you’re actually doing the thing that I always hoped somebody does — you took the opportunity and ran with it. When it happens it’s so worth it. You’re like: I’ll do this 10 more times even if I whiff nine more times. If there’s another Johnny in there, this is gold.
Andrew: There’s nothing better than when it does work. But it’s so painful when it doesn’t because you’re just going: don’t you see this? That guy could have owned the business with you, done the real estate, all the other stuff.
One question — what were the warning signs that that guy wasn’t going to be the guy?
Shaan: Chris has this thing he calls “gumption.” If you say to them “hey, ball’s in your court” — do they follow up within 24 hours? Do they move the ball forward?
With the warehouse guy: during one of the workouts after we brought him on board, I said “here’s my vision for you — what’s the dream?” He gave me this idea like, “I want to own real estate.” And I was like, “dude, at the moment you have no pathway to real estate. You don’t know anything about real estate.” So I told him: here’s the plan, we’re going to open another warehouse, I want to own real estate, let’s buy it. I’ll give you a piece and you run it. You and I turn this into a business where you’re running your own thing.
And I didn’t hear from him. Three months go by. I meet up with him and he goes, “yeah, I wanted to talk more about that, but I didn’t hear from you — I thought maybe you’d follow up.”
I was like: bro, if somebody gives me a window into a life I want, I’m knock knock knocking. “Hey, about that thing you said — here’s exactly what I’m planning, here’s a spreadsheet, here’s a checklist of what we can do if I hit these goals.” You gotta do the work at that point. The biggest red flag was that he didn’t follow up on that opportunity. It wasn’t that he didn’t want to — he just didn’t know that’s what you’re supposed to do, and it wasn’t his natural inclination.
With Johnny, it’s the opposite. Tell Johnny something — if you give him an inch, he’ll take a mile. He’ll text you at 9 o’clock at night: “hey, check out the website I’m working on.”
Spotting a Winner Early: Safwan and the Hiring Signals [00:59:00]
Shaan: I just found another guy like this, and I’ll tell you the signs that I already know — I’ll bet right now this guy’s going to be a winner.
This guy had emailed me: “Heard you on the pod talk about doing some philanthropy. Here’s a better idea — let’s create a micro-grant where you give out some amount you’re cool with, to people who are going to make things happen. That’s better than charity, it’ll feel better for you.”
He reached out intelligently. He doesn’t pitch his company — which by the way, he was trying to start like an AngelList for grants instead of startups. He gets my attention, and then he follows up like ten times in the next 12 days. “Hey, here’s three ideas for what your grant could be — just send back the number one, two, or three.” Then: “Hey, I saw your tweet about this other thing — remember the grant idea? You should do this instead.”
He kept following up intelligently each time. I was already like: this guy’s a winner.
Long story short, about six months go by. He graduates, takes a job at a hot startup we know of. Then I get an email out of the blue three days ago with the subject line: “I’ve made an irreversible decision.”
Another great sign — his copywriting is good for a 21-year-old. He goes: “I made an irreversible decision. I quit my job yesterday even though it was a great job and they offered me whatever, because I’ve decided I want to come work for you and make XYZ happen.” He’s got a couple other ideas of what he might do, but he puts me at the top of the list. He makes you feel good. Does the flattery thing. Says exactly what he would do. “I have two ideas for how I would make the Milk Road better — let me know if you’re down to hear them and I’ll send them over.”
He baits me. I’m like, yeah of course, send the ideas. And I just reply: “I didn’t honestly care about your ideas. I just want to hire you.” Now he’s working with me and he’s already awesome. We’re on day three. His name is Safwan — Safwan is going to be a winner. Six months from now I’m going to be talking about how amazing this guy is.
Andrew: The problem for me with all this is — I get so much inbound and I’m just not in the mood to figure out who’s legit and who’s not. I don’t want to have to train someone, I don’t want to have to manage someone. Are you guys getting exhausted managing people? Getting worn out talking to people and giving them feedback?
Shaan, I’d love to know how you do this. You’ve alluded a few times to having a team helping you manage channels and look at opportunities.
Managing Inbound: The Ben Wall [01:04:00]
Shaan: Yeah. It’s meant to be a bottomless pit — like, no reply — and then we cherry-pick interesting things and just pull them out dripping wet. We’re like, “maybe we should reply to this.”
Basically my version of your business Chris is Ben. Ben has the keys — he has my email and my Twitter, which are the two biggest forms of inbound. He’s the wall. If you can climb the Ben Wall, you’ve made it. Ben knows what’s interesting and what’s not.
And that’s one of his main things — he gets energy from it, whereas I lose energy doing it. He’s like, “oh yeah, this guy sent me this thing so I checked it out and then I chatted with him.” I’m like, “dude, I would never check it out or chat with him.” He’s like, “yeah, that’s what I like — checking things out, and if it’s cool I like to chat with them.” And I’m like, “you make it sound normal, but I hate doing that.”
He just replies basically as me, sets up the call, and half the time I don’t even show up. They’re like, “is Shaan coming?” and Ben’s like, “nah, it’s just me.” And that’s actually a good counter — if they’re offended by that, it’s probably not going to work. Because I don’t have enough time to dedicate to each individual person. If you’re just trying to meet me, that’s one thing. Versus if you’re trying to advance your cause or your project, you’ll take help from Ben or anybody. You shouldn’t be on your high horse about it.
Sam: Have you ever explored delegating your email?
Andrew: Yeah, I’ve explored it. For some reason I haven’t pounced on it like I should. But probably I should.
Chris and I did it about six months ago — we started using Front. Our assistant reads all the emails first. It goes into her inbox, and she chooses what we need to respond to. A DocuSign goes to the general counsel, a venture deal goes to the rolling fund — I don’t actually see any of it. It’s reduced my email by 70% mentally. Every email you have to even archive is mentally taxing.
Sam: My thing is that after I sold the business, I didn’t have a business — so I couldn’t justify having someone do stuff. Now that I do have things with cash flow coming in, I think yeah, it’s worth justifying.
It must be a huge mess accounting for all your different things.
Shaan: Yeah, you gotta go to the bank and find your CFO.
Andrew: That little thing you said — that’s so true. I always say: hire your favorite vendors and salespeople. Anytime you have an amazing account manager or a banker, I say “hey, if you ever want to switch careers, you’re amazing.”
Same thing with the guy who manages our rolling fund — he works at AngelList. This guy handles such a mess. We’ll send him a deal like, “hey, we’re doing this deal, we don’t know half the terms, we have to sign now and wire the money in three months.” His name is Connor — he’s an absolute magician. You have the same guy, Shaan?
Shaan: Yeah, Connor is so on top of it. We’ll be like, “$100K into this” and he handles everything. I’m just like, this is insane. Connor — I need to basically have him on speed dial as soon as I have enough operational stuff to deal with. This guy handles the messiest, most disorganized situation and just goes, “yep, got it.” Never makes me feel bad about it. Just solves the problem. If he needs something he tells me, and then I give it to him. It’s so nice when you find somebody ultra-competent like that.
It’s four-seasons service — at some hotels they grumble, and at the Four Seasons they say, “yes, we would love to, sir.” Connor is one of those people. My assistant is one of those people.
I’ll give you one more signal: somebody who thinks bigger than you — especially if they’re not in charge of the company. Super rare. Safwan did this. I brought him in to work on the Milk Road NFT project. We’re brainstorming what it could be, and we don’t want to do some throwaway thing, we want it to be really great. It’s like his first or second day. He just goes, “just a thought — right now we think of this as like some cool add-on to the Milk Road, but there’s no reason this shouldn’t be as big as Bored Ape Yacht Club. This could be one of the biggest, best NFT projects around. I just want to say that out loud because I don’t want to limit it.”
And I was just like — if you can make me feel like a little bit small-minded, then you are my favorite employee. I love it. Somebody who breaks those invisible walls around how good or how big or how fast something can be — that’s a winner.
Sam: Shaan, how much more hyped are you about Milk Road than your other things? It seems like this is the most hyped — you’ve found your thing.
Shaan: It does feel good. You’re 33, and it’s taken you 33 years to finally find the thing where you go, “this is what I should be doing.” Ikigai — what you’re good at, what the world wants, what the world’s willing to pay for, and what you’re passionate about. You’ve found that. Whereas before you found things that made money but it was kind of interesting. Then things you were passionate about that didn’t really make money. Now you’re in the center.
Andrew: Yeah, I think that’s true. Maybe the podcast is also a good example of that.
Chris Sparling’s Five Pillars of Happiness [01:14:00]
Shaan: On that note — you have this thing called the five pillars of happiness. What are they?
Andrew: Chris — my business partner — has this one. It’s very simple but I think it’s really powerful. He calls it Sparling’s Five Pillars of Happiness. He counts them out:
One: see family every day. Two: see friends and loved ones multiple times a week. Three: be in nature once a week. Four: new and novel experiences once a month. Five: feel like a man — go with your buddies, go hunting, do sports, whatever makes you feel tough and gritty and ticks that box for your caveman brain. Once a quarter.
It’s a very simple model. We built this little circle where you can rank yourself on it.
Sam: I do this in reverse. I see my family once a quarter and every day I do my caveman stuff.
Shaan: I do think it’s interesting. Do you do any caveman stuff?
Sam: Yeah, for sure. The workout, I play sports, I play basketball, I compete. That’s my version. And sometimes I’ll do manual labor — I’ll just be like, okay, I’m going to assemble this thing that’s been sitting here. It’s not the most manly thing but it’s like — something I don’t really need to do and I’m just going to put my full focus into using my hands and making or building something.
Shaan: It’s so weird — I have a trainer, I do powerlifting. You’re basically paying someone to come to your house to have you simulate doing labor. And it’s amazing — my happiest moment is in the hour after my workout. Even that is caveman brain. You would have been building a log cabin or doing something manly, and now we’re so pathetic that we have to pay other men to simulate it for us in our houses.
Sam: Do you do boxing, Andrew?
Andrew: Yeah, I do that, and BJJ. If you’ve ever done jiu-jitsu, it’s like wrestling — so primal, such a good feeling when you’re done.
Sam: Boxing has been awesome. I love fighting. It’s in a controlled environment, it’s badass.
And then I’m at this ranch now and I’ve been so happy. I’m trying to figure out how to build a fence, and I’m not literally going to build the fence, but having to move stuff and figure out how something’s going to work — where we’re going to put a pool — I’ve found it so much more rewarding than internet stuff.
The problem is internet stuff is also awesome and makes so much more money with so little effort. But I think, Shaan, you’re similar to me in that you’re looking for shortcuts. You want to delegate everything — everything’s DoorDashed, assistant, chef, all that stuff.
Shaan: I did a thing where I had a psychologist do a 360 on me. I heard about it from one of my favorite investors — Mohnish Pabrai did this thing where he hired a psychologist to basically write an operating manual. Here’s what you’re missing, here’s the brutal feedback your friends and family have about you, here’s how you need to improve. I think it was $10,000. He spent like four hours interviewing me, did a whole bunch of testing, then talked to three friends and family members and three people I work with.
I got it back and it was absolutely one of the most brutal experiences of my entire life. Our brains aren’t designed to know what our friends really say about us. But one of the key things he said to me: “It’s almost like all of your friends have come to you and said, ‘Andrew, on Saturday let’s mow the lawn together, and afterwards we’re going to celebrate and have a cold beer — all sit in a circle, sweaty, crack open a Corona.’ And you just say, ‘nah, it’s cool, I got a guy on TaskRabbit, he’s going to do that.’” So you never get the sense of satisfaction of doing the work, and you never get the camaraderie of doing it with anyone.
Andrew: You’re right. That was the feedback and I was like, holy — that’s so true.
Shaan: Except it’s my wife telling me that at all times. One of our biggest fights over the last couple of years was over wheeling the garbage to the street. It would always be like 10 o’clock at night, I’d be in my boxers. I finally found a private garbage service that takes all our recycling — I thought it was awesome. My wife looked at me like I had just failed to defend her in a fight. She gave me that Jada Smith look. She wouldn’t talk to me for weeks.
Andrew: The worst pain is when you hire a cleaning lady and you see her trying to move the heavy trash can. You’re like, “oh no, come on, I got it.”
Shaan: It’s so fascinating to think about how little labor we do compared to someone 75 years ago. If you grew up in a farming family, your parents would think you’re pathetic if you don’t grow your own vegetables. Where do you draw the line? Because I also know people who are wealthy and yet they spend all their time doing miserable tasks they hate — cleaning the cat’s litter box, taking out the garbage, fighting with their wife about it. At some point, delegate that.
Andrew: Dude, you didn’t need to spend the $10K. You could have just asked your cleaning lady. Nobody knows you better.
Shaan: My cleaning lady doesn’t speak English — I text her in Spanish. She doesn’t know anything.
Andrew: At least that’s what you think. She knows where you leave your underwear on the floor, she knows how long that cup sits on your desk before you finally take it to the sink. She knows everything.
Wrapping Up [01:24:00]
Andrew: All right, bros, I gotta bounce — I have someone here.
Shaan: We can wrap it. It won’t be the same without you.
Sam: Ben, what’d you think?
Ben: Making me come on camera on my sick day, but — great stuff. Always a great episode from Andrew. I anticipate this is going to be one of our top-downloaded ones. It usually is.
Sam: Did we cross 100K per episode? What’s our actual average?
Ben: It depends on what window you’re looking at. 30 to 60 days is fine. Most people measure by a 60-day window.
Shaan: Have you guys considered building in public with a graph or something?
Sam: I tweeted out our March numbers — it was 1.5 or 1.6 million, something like that. That includes YouTube, but only people who watch full YouTube videos, not the clips.
Yesterday, Shaan, your video about LaVar Ball got 400,000 views in like 24 hours.
Shaan: On what? YouTube Shorts?
Sam: Dude, you realize what your videos are doing on YouTube right now? YouTube Shorts has like millions and millions of views.
Shaan: It’s got thousands of comments and people just roasting me. It probably has tens of millions of views.
Sam: YouTube is wild — you just get bullied by 14-year-olds.
Shaan: They’re all way better looking, they all wear Vans. There’s nothing good in the comments for us. I’m hairy and ugly and dumb. I was too focused on me to know what they’re saying about you.
Sam: Anyway, for the first time we have multiple YouTube videos with over 200,000 views — actual full videos, not short TikTok-style. In terms of pure podcast, our top downloaded episode is at 70,000 all time. But if you throw on YouTube it crosses 100,000.
Shaan: How much of our growth came from doing all that TikTok stuff? The thing where we were giving money to whoever takes our clips viral?
Sam: Hard to say. That definitely worked, but we were doing other stuff at the same time. Hard to attribute.
Shaan: All right, talk to you all soon.