Sam interviews Andrew Wilkinson, the founder of Tiny (formerly MetaLab), who has built a portfolio of 20+ companies including Girlboss, WeCommerce, and a Canadian healthcare startup called Medi-Map. They discuss Andrew’s investment philosophy, his networking approach with billionaires, how he manages email and AMA sessions for charity, his sugar-free bakery concept, and his strategy of paying to be in the right room.
Speakers: Sam Parr (host), Andrew Wilkinson (guest, founder of Tiny)
Introduction: Andrew Wilkinson [00:00:00]
Sam: Today we have Andrew Wilkinson. Andrew started with a design agency called MetaLab, which he grew to about $50 million in revenue out of Canada — very profitable, something like $20-30 million in profit on $50 million in sales. Using that profit, he went and bought a variety of companies. At this point they own like 20 different companies ranging from a bakery to different software businesses. We’re going to talk about what companies he’s buying, why he’s buying them, and his approach to networking with billionaires.
Andrew, how are things going?
Andrew: Not too much, man. Beautiful day here in Victoria.
Sam: I’ve been spending all my time on this podcast trying to make it huge. We’ve got some really cool stuff planned. We did the math — if the last 16 months repeats itself, we’ll be at a million downloads a month by around December. Figuring out how to hack this has been really hard.
Adjusting to Life After the Sale [00:04:00]
Andrew: How does it change for you going from staring at your P&L every month, freaking out about invoices, to suddenly going — I don’t have to do that, I just have to focus on growing the audience?
Sam: It’s pretty great. A lot of people were like, man, you’re only going to work there for a few months and then want to bail. Frankly, I’m having a great time. I think I’m meant to start a company again, and this is my first real job, but it’s been really great. And the obvious thing: I made money for myself, so I can relax a little. If I make a wrong decision, I’m not going to cost people their jobs. The lack of stress is so good.
Andrew: Have you noticed your cortisol levels dropping? I’ve been going from stress to stress for seven or eight years — anytime I’ve sold one company, I’ve been neglecting another for a year and it blows up. I’ve been thinking lately: I gotta de-stress.
Sam: The way I describe it — when I moved to San Francisco, I felt like I’d been living with poor eyesight and I finally put glasses on. After selling, it’s like I put glasses on again and I’m like: oh my god, is this how you feel all the time? You don’t have to worry about X, Y, and Z? What a crazy feeling.
Andrew: It’s so funny — the numbers just get bigger. In 2012 we literally didn’t have enough money for payroll and my business partner lent me money out of his personal account. Now we have enough money to go for years. But there’s still that feeling of 600-700 people relying on me to pay their meal ticket every month. And there’s always people problems. I’m realizing I’m addicted to cortisol and stress.
With COVID, working at a cafe — I’d wake up pounding cortisol, do three or four hours of focused work, then my buddies would show up and we’d go for a walk. Now I’m in a house from 8:30 in the morning until five. I’m realizing that if left on my own devices, I’ll just stress to the nth degree and keep working.
Investment Discussions: Girlboss [00:14:00]
Sam: All right, first investment — Girlboss. You bought Sophia Amoruso’s old company. What is it?
Andrew: Girlboss is like a media company for women. Sophia started it about six years ago — massive following, events, podcasts, a social network. She’d come off Nasty Gal, which was doing $30 million a year in used clothes online, really well, then raised venture money, expanded into retail stores, and it blew up. She said she wanted to bootstrap Girlboss, raise a tiny round, not do venture again. Eventually she did raise venture, built the app, the social network, all the expensive R&D — and then it wasn’t venture-scale.
She sold to Attention Capital in New York. They had all these event contracts, then COVID hit, they couldn’t make the numbers work. They nudged me and said, would you be interested? I said I’ll only buy it if I can buy the assets, not the whole company. They had two million social followers, a huge newsletter, a massive podcast feed. We looked at it and said: what if this company had five employees? Can you run it that way?
Now we have maybe seven or eight. One person doing newsletter, one doing podcast, one doing social. We ran it like a bootstrap business. Sofia was pretty nervous when we bought it. But she’s been really stoked about what we’ve done.
Sam: How many email subscribers?
Andrew: About 250,000. The acquisition price — I can’t share the exact number, but I felt it was a value investment based on the social followers. If you looked at it on a P&L basis it was like, holy crap, this is a mess, they’ve been losing a lot of money.
Sam: What would you be happy with in two years?
Andrew: If we’re wrong about all the big opportunities and only right about base hits — 250,000 newsletter subscribers, can we sell $40-50,000 a month of ads? If we do that, we’ve got a good little business. On the podcast, another good little business. On social, same. It doesn’t need to be huge based on the price we paid. Three million a year in revenue would be an amazing business and a good return. I think it’s a 20-50 million a year business once we do events and the other opportunities. But even the worst case is not losing money.
Investment: Medi-Map [00:28:00]
Sam: Let’s talk about Medi-Map.
Andrew: So in Canada we have socialized healthcare. You can’t just call any doctor and get in — you have to get a referral. There are walk-in clinics all over Canada. A guy came to me five years ago and said: I’m going to build a business where you can go to the website and see the wait times at every single clinic in Canada. I was like, well, who’s going to fill out the wait times? He goes: I’m going to convince the clinic owners they want to be on this site.
I said, this seems insane. Six months later he comes back: I’ve got 25% of all clinics in Canada using this. It turns out every clinic gets 10 phone calls a minute, and all the calls are: what’s the wait time? So the clinic owners went: oh my god, I don’t have to have two medical office assistants. I just need one who punches in the wait time every hour.
Now this business has 86% of all walk-in clinics in Canada. Every single one has the wait time software installed. We’ve been investing in it for five years, it’s been losing money while we build the network. But once you have the network, there’s a lot of interesting things you can do. We’ve started expanding into physiotherapy, naturopaths, massage. We’re also integrating into booking engines. Clinics can pay to promote and get more bookings.
Sam: I’m looking at the site — it says crossroads walk-in clinic, 30-minute wait time, click to join waitlist. How do they make money?
Andrew: Right now the doctor is totally free to use. What we make money on is when you go and say, oh, I want a chiropractor, or I need to find a pharmacy — we do referral agreements with those clinics and pharmacies. We haven’t fully monetized yet. Five or six people work there. It’s a unique database — nowhere else in Canada can you get wait times like this. We’re probably spending almost zero on advertising.
Sam: It’s like an airport business. There’s one airport in the city — if you want to fly, you sit in the lobby for an hour. While you’re there, I’ll try to sell you things. All the stalls are empty right now, but we’re going to start filling them.
Andrew: I made that analogy up. You can steal it.
Sam: I’m guessing you’ve lost about six million dollars on this so far.
Andrew: Yeah, that’s pretty much exactly right.
Sam: I’m doing the math — five or six salaries a month plus hosting, probably $85-95,000 a month for five years. And ZocDoc is your nearest comparable — a multi-billion-dollar company. If they were ever to move international, they’d be a logical acquirer of Medi-Map.
Investment: Braintrust and Crypto [00:42:00]
Andrew: Here’s one that I think has more reasons why it will fail than why it will win: it’s called Tails. But let me actually talk about Braintrust first, which is the most interesting thing I’ve seen in crypto.
Sam: Tell me.
Andrew: So you go to the website and it looks like a really well-designed version of Upwork — hire contractors for design and development. But it says no fees. I was like, how do they have no fees? Upwork charges 5-10% of all projects.
What they do is they have a coin — the Braintrust coin. The project managers on the platform get paid in the coin. All transactions occur in the coin. So as people participate in the network, they get rich in Braintrust coin and they don’t go to Upwork because they’re already rich in Braintrust coin. It creates lock-in and aligns incentives.
Before, it was always labor versus capital. For the first time, it’s all aligned. It’s like if Uber had issued a coin to all their early drivers — as they participate in the network, they get rich, so they don’t go to Lyft. That’s the concept. Very theoretical and early, but it’s obviously the future to me.
The founder is Gabe. He started a lead-gen site for home services, grew it to $30 million a year, cashed out, then started Braintrust about 18 months ago. He’s a very proven entrepreneur.
The Bakery Idea [00:52:00]
Andrew: I own a bakery in Victoria already — my little brother worked there, I know the owner, he wanted to retire, I bought it. But here’s the new idea. A couple months ago I did a paleo diet challenge and I felt amazing — but had crazy carb and sugar cravings. When you’re doing paleo, no grains, no sugar. And the hacks around it — coconut sugar, maple syrup — those all still spike your blood sugar. Sugar is sugar.
So I started researching all the new non-sugar sweeteners. There’s a new generation — allulose, stevia, xylitol — that actually taste really good, don’t cause blood sugar spikes, and are relatively healthy. I contracted a baker and said: make me five or six different things. She made chocolate chip cookies, blueberry walnut cookies — insanely good. I’d give them to friends and say, hey, I baked these, let me know what you think. They’d eat them and say they’re really good. I’d say: there’s no sugar. Doesn’t spike your blood sugar. All healthy ingredients.
I started thinking: everyone wants to be healthy. Given the option, would they choose something higher-end and healthy but that tastes the same or better? I’m calling it Euphoria. Delivery only to start, just as a beta test. Launching on DoorDash in a couple weeks.
Sam: How much is your startup cost?
Andrew: Five to ten grand. Maybe a little more. I hired a designer for a logo, a baker part-time, and a photographer for the photos. That’s it.
Sam: You know what this reminds me of? There’s a guy named David Hauser who started Grasshopper — he sold it for $200 million. He started this thing called Nut Butter now, a peanut butter pouch. The business is so much harder than software, but he’s having so much fun. I think there’s a double-edged sword here — the fun part of entrepreneurship is doing interesting things. But I started a pizza restaurant and lost $800,000. We had an alcoholic manager sleeping in the restaurant, a sketchy landlord — just endless stress. The key is hiring amazing people quickly.
Henry Singleton and Capital Allocation [00:04:00 second half]
Sam: Earlier you mentioned Henry Singleton. What’s his story?
Andrew: The Outsiders — a great book. It’s about 12 CEOs who are “outsiders” — quiet, afraid of the press, usually in locations like Nebraska, not Silicon Valley. They just get pretty good results, consistently, for 50 years. Henry Singleton is basically everyone’s like, Warren Buffett is the greatest investor of all time — I think Singleton might actually have a better record, and almost nobody knows his name.
His whole philosophy: when the market is overvalued and crazy, that’s a great time to issue stock and to sell things. When the market is undervalued, you want to be buying — buying back your own company, investing. Very simple. Not rocket science. But it’s a really important thing to be thinking about right now. It’s a crazy seller’s market. The hardest part is doing nothing.
Sam: How do you sit and chill? I get so antsy.
Andrew: There’s a reason I’m starting a sugar-free bakery. That’s honestly my secret. Before COVID, I’d distract myself with sports, tennis, friends. Now it’s starting businesses — really small ones, hobby businesses, playing with $10-20,000 — which keeps me distracted and happy. I’m still sitting on my hands and building up cash.
WeCommerce and Shopify [00:10:00 second half]
Sam: Tell me about WeCommerce.
Andrew: We met the founder of Shopify when we were running a design agency. He said, hey, we want to launch themes on our platform — we’ll let you sell these themes. We were like, it’s a small Canadian company, nice guys, let’s do it. Shopify grew into a behemoth, we rode the whale and did really well. Actually sold the business in 2013 — didn’t realize how big Shopify would get. Then bought it back in 2019.
Sam: For way more than you sold it for?
Andrew: Five or six times more. We made a big bet that Shopify was going to get a lot bigger. We made a holding company called WeCommerce, started buying and building within the Shopify ecosystem, and took it public in December. Listed on the TSX Venture Exchange. Currently at about $663 million market cap — Canadian.
Email Management and the AMA Charity Hack [00:20:00 second half]
Sam: You told me you’ve fully delegated your email to your assistant for the first time ever. Is it working?
Andrew: It’s working really well. I was getting 200-300 emails a day. I was spending like five hours a day on email. So I set up tech support software, piped my email into it, and my assistant — plus another assistant in the Philippines — basically monitor the email with a set of rules. If someone asks me to sign a document, send it to legal. If someone requests an interview, look at the podcast downloads — if it’s above this threshold, you can schedule it. I made about 10 rules like that. Now I’m getting about 20 emails a day. Just the ones where it’s a friend asking a direct question, or one of our CEOs, or a go/no-go on an investment. Freed up two or three hours a day.
Andrew: The other thing I did — young entrepreneurs would email me saying, can you look at my startup? And I used to write thoughtful responses, but as I got more email I just couldn’t, and I felt really guilty. Now I write them back via template saying: I don’t respond to these by email. What I do is a monthly AMA. If you can afford to donate to charity — just as a way of paying it forward — then Chris and I do a monthly AMA and everyone gets to enjoy the answer.
We’ve donated $58,000 to charity from this — we double whatever the community donates and send it to a local charity. And it saved me two or three hours a month. So it’s like a really great hack.
Sam: Should I copy that?
Andrew: Totally.
Networking with Billionaires [00:32:00 second half]
Sam: You have this interesting philosophy about networking. You’ve had lunches with Bill Ackman, stories about Warren Buffett. What’s your whole thing about networking?
Andrew: I think networking is really fun if you’re an extrovert, and I’m an extreme extrovert. When I feel depressed or sad, I want to be around people.
Starting about 15 years ago, I started seeing interesting people on the internet and thinking: wow, I want to do business with them or become friends with them. I did a couple things.
One: I never eat alone. Pre-COVID, I’d always have lunch with somebody locally, and almost always do at least one call with a random person I’m building a relationship with.
Two: I started paying to be in the right room. I remember telling someone 10 years ago — I wasn’t doing super well, maybe 15-20K a month in revenue — and I paid $10,000 to go to the TED conference. All my friends were like, what are you thinking? When I went to TED, it’s like a secret club. Every single person there is someone interesting. At the very least, they’ve paid a lot of money to be there, so they’re legit. And being in the room means everyone goes: oh, they’re legit too.
I was this twerp with a tiny little business, talking to Al Gore and the founders of Google. Going to TED consistently for three years — probably spending $30K on tickets — I think resulted in $10-20 million in revenue for my various businesses. I’m a big fan of paying to be in the right room.
Three: host events. I try to bring someone interesting to town and invite a bunch of other interesting people. That way, you’re the host. You made this collection of people. You get to meet the speaker. An example: I thought Shane Parrish from Farnam Street was super interesting, so I brought him out to do a speaking event in Victoria. I ended up becoming friends with Shane. Now he’s an investor with us and we’ve done a bunch of deals.
One of the things nobody recognizes is there’s an insane amount of optionality in just knowing great people — both personally, and for business. Being able to call a bunch of amazing people is the ultimate hack.
Andrew: That same thing happened with Bill Ackman. I went into that charity lunch as a kind of diligence thing. I had invested about $5 million in his holding company, Pershing Square Holdings. He’d had a series of challenging investments, the stock had traded way down. I looked at it and said: I can buy a dollar of amazing stock for 65 cents. It was a holding company that owned Lowe’s, Howard Hughes Corp, Chipotle — great blue chip businesses — and you could buy it for 65 cents on the dollar.
I didn’t necessarily think Bill was a genius — I just thought it was a cheap stock. When I saw the charity lunch opportunity, I was like: sweet, I can grill this guy and see if I like him. The upside is he’s just a really smart investor and maybe I can learn something. I didn’t think I’d be doing business with him. It was a pinch-me moment when we ended up investing together.
Sam: What happened to the stock?
Andrew: It tripled. The $5 million went to about $15 million in about six years. And he’s done amazingly well — he had that bet where he invested $25 million and it turned into $2.7 billion.
The Networking Paradox [00:48:00 second half]
Sam: My issue is I don’t really want to talk to people that much. Like, you and I text — other than that, I really only want a small group. But then I feel left out because I see you doing this networking and getting access to all this cool stuff.
Andrew: You have the ultimate hack though — you have this platform. There’s a reason I come on: I have a lot of fun, but also 10,000 people are listening, and a bunch of them are super fascinating and they’re going to email both of us. You just bypassed the problem of networking — you do five boring calls and then one amazing one. With a podcast, you have 10,000 people who learn what you’re about, decide if they like you, and if they opt in, you’ve already pre-sold them. When I get on the phone with someone fresh, I have to tell the whole story. You can just bypass all of that.
Sam: The other day I had this guy Michael Loeb reach out — Synapse, Priceline, he’s a character. He wants to host an event at his house in the Hamptons, the house from the TV show Billions, for 50-100 young entrepreneurs. I’m trying to convince him to make me a co-host.
Andrew: Yeah, I got introduced to him in New York. Chris and I went to his office. He pulls out a printed slide deck — not on a screen, an actual printed slide deck — and goes line by line through it. He had clearly no idea who I am. But I thought it was really charming. He has a shtick, a system. It was interesting because his house is crazy, but then you go to his office and it’s just a random chaotic New York office with shitty chairs.
That guy is crazy interesting. I’m so happy I got to talk to him. I have another meeting coming up and I’m looking forward to it. If I host that dinner or even get to attend, and he lets me invite people — I’m going to invite you, because inviting you is like how I’m going to look legit to this person.