Illustration by Matthew Billington
Andrew Wilkinson is leaning over a hearty chicken salad, telling me all about his ADHD medication. It has been, in a way, his salvation.
Wilkinson was diagnosed with ADHD in 2025 and suddenly everything made sense. His life up until that point had been marked by a relentless anxiety that felt like a high-octane fire in the skull. He tried to outrun it by chasing more: more wealth, more businesses, more connections. It was never enough.
“There was a lot of anxiety there around money and wanting to make a lot of it so I could make my family happy and make the anxiety in my head go away. I went crazy and did [all] this to the nth degree, and I was still miserable,” he says.
Forget happiness. Money, it turns out, can’t even buy level-headedness. But suddenly, there were the meds.
“When I medicated, I was like, ‘Oh my god, I don't feel that itch anymore,’” he says. “I don't feel that anxiety.”
We’re sitting at Caffe Fantastico in Victoria’s Quadra Village on a gorgeous August afternoon. It’s been a month since news broke that Tiny, Wilkinson’s holding company, is planning to sell Letterboxd, the popular film-tracking social media site, of which Tiny owns 60%. The platform is valued at US$300 million and could earn Tiny — and Wilkinson — a “hefty sum.”
The sun is gleaming off whatever product he’s applied to his hair to hold his coif in place, and his personal items are assembled in a pile next to his elbow: iPhone, Apple Watch (he’s also sporting a Steve McQueen Rolex Explorer on his wrist), keycard, and a half-empty packet of XyliMelts, the small, adhesive mints that dissolve slowly over time, which he uses to combat dry mouth from his medication.
I wasn’t sure what to expect of Wilkinson leading into this interview. He inhabits a peculiar space in online notoriety: you’ve either never heard of him, you confuse him for the former leader of the B.C. Liberal Party with the same name, or you follow most, if not all, of his prolific missives on whatever online realm he inhabits these days.
Or maybe you’ve worked for him, as I did for a time, at Overstory Media Group, Wilkinson’s troubled news startup. I never interacted with Wilkinson, who was more like a mythic being we heard from now and then via cryptic tweets that could have been about our company if we squinted.
I met him only once, briefly, in the green room of Vancouver’s Vogue Theatre as he was about to go on stage to speak in front of 1,200 people. I didn’t think he’d remember me, and he confirms as much.
It's tempting to form an opinion based on those things alone, along with the fact that he fervently promotes himself online as an unabashed Rich Guy at a time of growing wealth disparity.
But Wilkinson is easy to talk to. He’s charming in a way that could be dialled up for the benefit of the person writing a 2,000-word profile on him, but could also be the secret to his success. He might be a person with 1,000 times my net worth, but, like me, he's a divorced dad with two kids who loves film and pickleball — though he built a court on his property.
He's both down to earth and out of touch in a way that the super wealthy tend to be.
I ask him what he makes of the notion that people have never heard of him. Does he have trouble breaking through to the general public, or is it simply the nature of online bubbles?
“It must be a bubble thing,” he says. “People have recognized me on the streets of L.A.”
Wilkinson was raised in Shaughnessy, the “poor kid” in Vancouver’s wealthiest neighbourhood, which he describes as a “weird mind fuck.” His father owned an architecture firm, which, given the volatility of that industry, was in perpetual financial distress. The Wilkinson household was rife with money stress as a result, and Wilkinson soaked all that tension up.
“I would go to my friends' houses, and I'd see their dads seemingly relaxed, living in big houses and driving nice cars. I was going like, ‘What's going on here?’ My dad's working so hard and he's so stressed out. There's something not fair about this,” he says.
“There's this great Francis Ford Coppola line: ‘The story of the father is embedded in the son.’ So I was like, OK, I'm going to be successful in business. I want to be a rich dad.”
By 2020, Wilkinson had developed a reputation as a kind of tech-investor wunderkind, initially by starting the boutique design agency Metalab, which he launched in 2004, and then with Tiny, a holding company that he and co-founder Chris Sparling modelled to be Berkshire Hathaway 2.0.
He’d also become known, whether it was true or not, as a billionaire — a title he wrestled with, but ultimately embraced, publishing a memoir in 2024 called, Never Enough: From Barista to Billionaire.
“There were times where I'm like, ‘Fuck yeah, I was objectively a billionaire.’ Then there were other times where I was like, ‘Yeah, you people are fudging it,’” he says.
By 2024, Wilkinson’s carefully curated image was decimated in a trifecta of humiliating blunders. First, there was Overstory, which was positioned as a solution to preserve local journalism, but ended in mass layoffs and intense public criticism instead.
Then, Tiny went public — a disaster that wiped out roughly 90% of the company's value in the following two years, and resulted in Wilkinson and Sparling stepping down as co-CEOs in June 2024. The fallout also erased a considerable amount of Wilkinson’s net worth just as his book was being launched, which opened him up to further criticism.
“I've been utterly humbled in that regard,” he says.
“[My net worth] has never actually been something that I stressed about. It was more the shame of saying the word ‘billionaire’, and now that I'm not, it made me an easy target.”
There are two Tinys — or three if you count the charitable Tiny Foundation — Tiny Ltd., the public company, and the private Tiny Fund, of which Tiny Ltd. is a 20.24% limited partner. Together, they own or have a stake in 21 companies across the globe, including Metalab; AeroPress, the popular, single-serve coffee maker; and Serato, the DJ software company, which Tiny bought 66% of last year.
The crown jewel, though, is arguably the film-review social network Letterboxd, in which Tiny invested $60 million for its 60% stake back in 2023. That deal earned Wilkinson and Tiny a profile in the New York Times, which painted the company as a new frontier of private equity firm, and Wilkinson its cowboy-in-chief.
Since then, Letterboxd has nearly tripled its users to 30 million.
“It’s my favourite type of investment,” Wilkinson says. “It’s something I'm passionate about, and I don't have to change or mess with the business at all. From the moment we bought it, we haven't told them what to do.”
Variety reported that Netflix was in early talks to buy Letterboxd, with Sony Pictures and Skydance allegedly also in the mix. The day the story broke, Tiny's stock spiked roughly 19% in a single session. Deadline later reported that the New York Times and A24 put in second-round bids for the platform.
But Wilkinson says the reports were merely rumours. “People can say whatever they want,” he says, “but we haven't said anything about that. We just say no comment. It's like how the FBI won't confirm or deny anything.”
Despite his understandable reticence on a potential Letterboxd sale, Wilkinson’s not exactly known for his shyness. He became a prodigious Twitter user through the COVID-19 pandemic, posting constantly about any thought or nugget of wisdom that entered his fire-addled brain: the merits of being hated (“I want you to read my tweets and seethe”), the details of his daily habits (he’s really into reading business biographies), and the potential for AI to help raise his kids (“Just watched my 5-year-old son chat with ChatGPT advanced voice mode for over 45 minutes. I think it’s going to be revolutionary.”).
Wilkinson leaned into his new rich-guy influencer status, appearing on numerous business and wealth-oriented podcasts, like My First Million and Chris Williamson’s Modern Wisdom. He published his memoir and launched his own (currently inactive) podcast, also called Never Enough. He says this has been an essential customer acquisition tool for Tiny –– “a magnet for good things,” he wrote on X.
“Andrew's a natural loudmouth,” Sparling says. “If this was 200 years ago, he'd be on some wooden pedestal shouting his thoughts.”
What’s true online is also true in business. Sparling says Wilkinson has a fondness for the “swoop and poop” — or what is otherwise called seagull leadership — where he’ll reach out to some mid-level accountant or designer, who’s never spoken to him previously, with an idea or critique with little to no context provided.
One former general manager at a Tiny-held company, who requested anonymity, recalls winding down with a cocktail on a Friday night and getting a “How’s it going?” text from Wilkinson, responding with a mini-investor update in iMessage form (his preferred communication medium), and getting no acknowledgment, not even a thumbs up.
“He doesn't think he's grilling them. He’s thinking, ‘Why can't I just ask this question?’ But people who had a full day of work now have to explain something not necessarily productive — all because Andrew had a fleeting thought,” Sparling says.
“But there's a superpower in someone coming in with limited information and a lot of gusto, and who's also willing to be told they're wrong.”
Sparling met Wilkinson in 2009, when he was working as a financial adviser at TD. Wilkinson wandered in to apply for a credit card and they bonded over Volkswagen GTIs as Sparling filled out the card application.
“On the spot Andrew said, ‘Hey, you seem pretty smart. I need help with finance. Do you want to be my CFO?’" says Sparling.
They’ve been more or less inseparable ever since — Wilkinson “the gas” and Sparling “the brakes,” Sparling says. Together, they grew Metalab into one of the most sought-after boutique design agencies in North America, developing initial UIs for Slack, Coinbase, and Uber.
They founded Tiny in 2014 with the idea of being a founder-led private equity firm, where they’d invest in, or buy up, a business and let the experts run the show. Wilkinson developed a knack for pouncing on opportunities during this time, relying on instinct.
“Andrew's best quality is that he's ready to shoot before he aims. It's blown up in our faces plenty of times, but it's worked more often than not,” Sparling says.
In April 2023, Tiny went public via reverse takeover, merging into WeCommerce — which they’d renamed Tiny Ltd. — with Wilkinson and Sparling listed as co-CEOs. The stock crashed, wounded by the company’s thin margins and heavy debt.
The following year, Wilkinson and Sparling stepped down as co-CEOs to co-chairman roles. Later that week, Wilkinson filed to sell 1.7% of his shares and the stock dropped 16% that day, erasing roughly $80 million in market cap. Wilkinson’s ownership has since drifted from 64% to 51%.
Today, Sparling says the underlying business has been doing “better than ever,” with several of the companies generating “significant cash.” As of last October, they moved up to the Toronto Stock Exchange from the Venture exchange they were first listed on. As of Tiny’s Q2 2026 filings, trailing revenue over the last 12 months is $209 million, up 9%, and trailing recurring revenue is up roughly 60%. Trailing adjusted EBITDA, meanwhile, is almost $40 million. This doesn’t include the public company’s stake in Tiny Fund.
Sparling notes that these are the best numbers Tiny has had since the company listed. “But stories are hard to rewrite.”
Was going public a mistake? “Definitely,” says Sparling. “I thought it would give us more tools for bigger mergers and acquisitions, and it's done the opposite. At this point, it's more of a handicap.”
He says the decentralized structure is Tiny’s strength, with CEOs operating with complete freedom. Most of the time, for most of the companies, it works well.
“The reason I chose Tiny in the first place is they've been very much about letting companies do things their own way, and not getting too involved in interfering with what the founders or the management team are good at. So that's been really great,” says AJ Wilderland, co-founder of Serato.
He says the negotiations between the two companies almost went sideways several times because Serato’s investment bankers were advising that Tiny wasn’t operating the way other private equity firms do. But for Wilderland, that was exactly why he wanted to work with them.
“The difference between founder-run companies and equity-run companies is that founders often make decisions where short-term gains aren't the main deciding factor. You're thinking 20 years out, not five,” he says.
“I think it helps that [Wilkinson] is a tech founder himself. When I've talked with them, I've found people who think, in many ways, the way I do. So I can talk to the CEO about the plan, or if I want to have a real blue-sky conversation, I can talk to Andrew. It feels good to be working with like-minded people.”
Wilderland’s experience is the polar opposite to how his critics talk about him, especially online.
Leland Roach, who runs The Value Road newsletter on Substack, published a 2024 post titled “Tiny Ltd: A Collection of Lousy Internet Companies,” in which he describes Wilkinson as “distracted by the attention of podcasts, Twitter, book tours.” He also called out the fact that Wilkinson had been charging $10,000 to take one-hour calls with whoever was willing to pay. “I feel like all of these are distractions to running a public entity,” Roach wrote.
“It's hard not to take that personally when so much of your identity is being the co-founder of the thing,” Sparling says.
These days, with fire in his head kept mostly to a low flame thanks to the meds, Wilkinson is focused less on crazed empire building and more on tinkering with AI — building software, solving problems in the business, and developing automations.
He has no deliverables in the organization, he says. His job is to tell its story and fill the funnel.
“What was valuable about [the public humiliations] was realizing that something quote-unquote terrible could happen, and I could wake up the next morning, still go to the same coffee shop, still see my close friends, and life went on,” he says.
This level-headed outlook is due, in part, to the ADHD diagnosis. It’s helped redefine his entire worldview, in fact. No longer wild with anxiety. No longer pressing to start “a gazillion businesses.” No longer tweeting his days away.
He’s learned, in other words, how to chill.
“I've been doing my business for about 21 years now, and I'd say for the first 15 years, I was like, ‘Oh my God, I want to meet all the world's most successful people, because they must know something I don't. They must be living this amazing life,’” he says.
“What I realized is that these decabillionaires, or people who run these massive businesses — it's such a brutal thing to do that you kind of have to have a personality disorder to do it,” he says. “That's not me. I would never want to do that. That's really miserable.”
