Sam and Shaan break down Andrew Wilkinson’s journey from a $250K web design agency in 2006 to a publicly traded holding company (Tiny) valued near a billion dollars. Key lessons: the arbitrage of Canadian wages and Silicon Valley prices, the power of not raising VC, the Buffett buy-and-hold playbook, and how to tell a story when you announce an acquisition. Plus Shaan’s $25K missed investment in ApplyBoard that became a $3B unicorn, and the strategy of surrounding yourself with young, hungry people.
Speakers: Sam Parr (host), Shaan Puri (host)
Andrew Wilkinson’s Origin: $250K Agency to Billion-Dollar Holding Company [00:00:00]
Sam: Our friend Andrew Wilkinson — Tiny is going public. He owns roughly 71% of the shares, and it’s going public at nearly a billion-dollar valuation. That’s about $700–800 million that Andrew will have, all starting from a bootstrapped agency.
Shaan: To be precise: Canadian dollars. CAD. But close enough.
Sam: So the story. 2006. Andrew was 19. He started a web design agency called MetaLab. His big early client was Stuart Butterfield — who eventually built Slack. Andrew’s team helped design it, more than logos but including logos. Web interfacing. Year one: $250,000 in revenue with a 50% profit margin.
By 2012 — year six — he’s at $3 million in revenue, growing about 30% per year. By 2020 he’s at roughly $20 million. By 2023, around $40–50 million.
Here’s why the agency worked so well: he’s based in Victoria, British Columbia — basically the Boise of Canada. He’s paying Canadian wages. But he’s charging Silicon Valley prices to companies like Slack. The margin is fat. He takes those profits and starts launching companies.
Shaan: It doesn’t work at first. He launches a little software company — I think it was called Flow, an Asana competitor. It doesn’t pan out. He goes: screw this, what if I just buy a company? He reads Warren Buffett, becomes a Buffett guy, and starts buying businesses.
Sam: He buys a couple that do okay. Then he buys the crown jewel: Dribbble.
The Crown Jewels: MetaLab and Dribbble [00:10:00]
Sam: Dribbble is basically GitHub for designers. Designers post portfolios, share work, get discovered by employers. The founders were great designers but not particularly business-savvy — lots of traffic, not much revenue. Andrew probably bought it for $5–10 million. Now, if I had to guess, it’s worth $200 million or more and doing many tens of millions in revenue.
Shaan: I invested in Tiny recently when it was private, so I know more of the numbers — but I don’t know what’s public. What I can say is: MetaLab is the cash flow engine. It’s probably doing $40–50 million revenue with $20 million in profit. That’s what funds all the acquisitions. And Dribbble has become one of the major value drivers.
Then they also had WeCommerce — a Shopify app roll-up that they originally took public via SPAC. So you have three crown jewels: MetaLab, Dribbble, WeCommerce. The rest of the portfolio is rounding errors by comparison, but they’re real businesses.
What Andrew Did Differently [00:18:00]
Shaan: Several things Andrew did that are worth naming.
He didn’t raise money for MetaLab. As soon as you raise VC, your cap table is one of the few things you can’t reverse. He used his own profits to invest in other things. VC would have said: no, reinvest that into making MetaLab bigger.
He built where he lived. Location arbitrage — Canadian wages, Silicon Valley prices. That gap is a little smaller now, but it still exists. My friends building businesses right now with Indian talent are getting great products at a fraction of U.S. prices.
He did the Buffett one-pager. He read that Buffett would meet a company, understand it, and write a one-page term sheet. If Buffett can buy a billion-dollar company with a one-pager, Andrew figured he should be able to buy a $3 million company with a one-pager. No complicated lawyer process.
He branded it publicly. Every other private equity player has a website that says two lines: “We acquire software companies.” Andrew built a sexy brand out of it. Wrote publicly about what he was doing. That deal flow found him.
Sam: And he tells stories. There’s a blog post he wrote when they acquired Dribbble that everyone should read. Most acquisition announcements are soulless:
“We are so pleased to announce… they built a really nice business and we’re happy to be stewards… we’re really looking forward to the future…”
Here’s how Andrew opened his:
“When I first started MetaLab, Dan Cedarholm was my hero. Bulletproof Web Design was the first book I read. I used to reverse-engineer his stylesheets. I drove my front-end developers nuts trying to implement every one-pixel detail I learned from him.”
That’s it. One paragraph. You’re in. And then he explains that he kept emailing them every month — “my moxie finally paid off” — until they agreed to talk. He told the story like a person, not a press release.
The 13-Year-Old Scout Who Found ApplyBoard [00:28:00]
Shaan: I want to tell you about a $25,000 mistake that cost me tens of millions of dollars.
Back in 2015, I met a 13-year-old kid named Saroosh. He used to come hang out in our app’s Silicon Valley chat room after school every day. We were like: “Kid, go try to have a social life, not sit in these chat rooms.” He was like: “I want to come work with you guys.” We’re like: “You’re in middle school.”
So I said: here’s what you can do. Every week, send me a company you think is interesting. Just write why you think I should invest. I gave him this homework assignment expecting he’d do it once and quit.
First company he sends me, I ignore. Second company:
“Uncle Shaan, here’s the second company I want to introduce: ApplyBoard. They help international students find the right university and apply on their behalf. They have 11 schools contracted to pay them a commission for every student that signs up. 14 more schools in the funnel. Over 1,500 students signed up. 160,000 Facebook likes. All with $10 in paid marketing. Customer acquisition cost is a few dollars. LTV is $1,000. Sustainable growth. P.S. — If you have feedback on the company I’d love to hear it. I’m trying to correct my shots so one day I could hit the bullseye for you.”
This kid is 13. I said: “You know what, this is actually pretty good. I’ll take the meeting.”
The Meeting and the Mistake [00:35:00]
Shaan: The founder, Martin, comes to my office. Absolutely charming — had that Israeli founder energy, just dripping with sauce.
Here’s the business: colleges in the U.S. have surge pricing for international students. A domestic student might pay $25K at a state school; an international student pays $50–75K for the same thing. And they don’t always know the landscape — they can’t always differentiate between University of San Francisco and Columbia. So a lot of schools take advantage. International students make up a disproportionate amount of their revenue.
ApplyBoard goes to schools and says: we’ll send you a student, give us $3,000. The school says yes. Martin says to me: “I haven’t really talked to anybody else yet.” I said: “Brother, I’m in.” He said: “You’re the first guy in Silicon Valley. You’re my champion.”
Then he starts pitching other investors. They say no for various reasons. With each no, my conviction starts to waver. But I’d said I was in.
When the round closes, I’m supposed to write a $25K check. At the time, that was basically my entire savings. And I start overthinking it. I didn’t back out explicitly — but I stopped replying to emails. He followed up a few times. I just… didn’t respond.
Sam: Bro.
Shaan: Fast forward five years. I get an email from Saroosh:
“Hey, remember this? ApplyBoard’s a unicorn now.”
Three billion dollars.
Sam: What’s the lesson?
Shaan: A few. First: if you say you’re going to do something, do it. That’s just basic.
Second: you don’t need the full check size. I should have said: “I don’t have the bankroll to place 20 angel bets, which is what you need to make angel investing work. But I can do $5K at the same valuation.” Or I should have gone to somebody with money and said: “I found this deal, it’s good, write the check and give me some carry.” That’s what I did later with Lambda School and it worked.
The real mistake was: good opportunity, small obstacle, and I let the obstacle feel bigger than the opportunity.
Hire Young, Hungry People Into Your Orbit [00:45:00]
Shaan: The Saroosh story became a core strategy for me: have 3–5 young, hungry, naive people somewhere in my orbit. Give them an excuse to be around — a homework assignment, a Slack channel, some small project.
You have to throw away 60% of what they say. But 40% is pure signal — things a 22-year-old sees that you can’t see anymore because you’re too comfortable. Their excitement is contagious. Their desperation is clarifying.
I’ve got a few examples of where this played out:
Michael — the kid who made TikTok clips of our podcast in his dorm room. Got 10 million views. I offered him $5K and told him to do it full time. He built it into a company, sold it to Morning Brew. He’s 22 and he’s off to the races.
Saroosh — the 13-year-old scout. Built his own wealth in crypto. Doing great.
Ishan — the intern who edited video. Took his $100K savings, found a delisted stock nobody wanted, bought it at 10 cents on the dollar. It ran to a few million dollars. There are articles about him in the Australian press.
Steve Bartlett — hired him when he was 20. Had this ridiculous swag, wore rings, said words I didn’t know. His tweets went viral. Built a social media agency, took it public, created a massively popular podcast, became a Shark Tank judge in the UK.
Sam: You need to refresh your young bloods.
Shaan: They’re all 24 or 25 now and rich. Time for a new batch.
The Scalabrini Standard [00:55:00]
Sam: Have you heard of the Scallenge?
Shaan: Tell me.
Sam: Brian Scalabrine played for the Celtics. Redhead, six-nine, okay player. Called himself the White Mamba. After he retired, he started playing rec leagues at the YMCA and scoring 60 points a game. People online started chirping: “You suck. I could beat you.” He said: “Wait — I might suck compared to Derrick Rose, but I don’t suck compared to any of you.”
So he started doing a tour. Went to the hoodest basketball courts, the best YMCAs around the country. Challenged anyone who thought they could beat him. Destroyed them. Did it 10-0. He said to one kid who thought he could hang:
“Let’s get something straight. I’m closer to LeBron than you are to me.”
Shaan: That is the greatest line I’ve ever heard. There are levels to greatness. The gap between you and a pro is much smaller than the gap between a pro and an elite. Never forget what level you’re actually at.