Andrew Wilkinson
Andrew Wilkinson Bought the Rich Life. Then He Started Editing It.
The Tiny cofounder has tried the cars, watches and extra houses. His more revealing investments are in time, company and a life he actually wants to live.
The Porsche 911 Turbo was loud, uncomfortable and, Andrew Wilkinson discovered, someone else’s idea of a good time. He sold it. In a 2025 Moneywise interview, the Tiny cofounder also described thinning out his watches and owning a Fender Stratocaster he barely played. Buying the equipment had been considerably easier than becoming the person who would enjoy it.
Wilkinson has made a second public career out of examining that gap. His memoir, Never Enough, arrived in 2024; his personal website now acknowledges divorce alongside business success. The story he tells about getting rich has become a story about deciding what deserves room in his life. He is still an investor, still building, and still based in Victoria, British Columbia.
His early ambition was more practical. After moving from Vancouver to Victoria at 15, he taught himself programming and developed a technology website. In an interview with Bench, he recalled reviewing gadgets, selling advertising and learning how to talk to adults with budgets. When he floated skipping university, his father stopped their old Volvo and warned him about his prospects. Wilkinson tried journalism school in Toronto, left after three months and returned to Victoria.
A data-entry job followed, along with an argument over whether the work could be automated. He quit. Freelance design offered a way to pay the bills, and he learned to present himself as an agency before he had much of one. Looking back, he credited communication and sales as much as his design skills. The teenager interested in computers was also learning how to persuade people.
The business became MetaLab. Tiny’s company history describes an apartment operation, cold emails to startup executives and friends’ photographs standing in for an established team. The archival picture is wonderfully unceremonious: a desk, two computers and a bed close enough to make the commute irrelevant. It is a useful starting point for a man whose later purchases would become podcast material.
Chris Sparling entered the story through a bank visit in 2009. Wilkinson needed financial expertise; Sparling left the bank to join him. Their division of labor grew around opportunity and scrutiny. After years of starting businesses, they turned toward buying them, inspired by Warren Buffett’s approach to ownership. That partnership became Tiny, where Wilkinson is now executive chair. His working life had shifted from designing products to deciding which businesses deserved capital.
The resulting portfolio reaches into surprisingly ordinary pleasures. Tiny’s operations include DJ software business Serato and design businesses MetaLab, Dribbble and Creative Market. Through its interest in Tiny Fund I, it also has exposure to AeroPress and film community Letterboxd. These are investments held through a corporate and fund structure, rather than a list of companies Wilkinson personally owns outright.
His financial position is substantial, but a single fortune estimate would obscure more than it explains. Tiny’s 2026 circular listed 14,995,680 shares under his direct or indirect control, a majority position. It valued those shares at approximately C$86.8 million using the April 15, 2026 closing price. That is a dated valuation of one holding, not his current total net worth. The same filing recorded C$500,000 in director fees for 2025, plus separately reported security services; neither number describes all his personal income.
The company itself is navigating a difficult stretch. For the second quarter of 2026, Tiny reported C$51.6 million in revenue and a C$83 million net loss, largely driven by C$80.7 million in noncash impairments at WeCommerce and Creative Market. Serato and Letterboxd provided brighter spots. Even a portfolio built for patient ownership has to confront businesses that fall short of expectations.
At home, the useful luxuries have become clearer. Wilkinson told Moneywise that multiple properties brought maintenance decisions and that he sold one. A lake house earned its place because it brought together his children and friends. He also valued his waterfront primary home and the convenience of private flying. A yacht charter, by contrast, had left him feeling isolated. The question became what a purchase enabled, rather than what it signaled.
His public account of family life is selective but candid. He identifies his partner as Zoe and says they run Tiny Foundation together. Its funding areas include medical research, journalism and nonprofit capacity. His personal investments sit separately in Folly Partners. Those distinctions matter: the public company, the family’s affairs and the foundation each serve different purposes.
A more recent glimpse of his everyday interests is decidedly less grand than a yacht. Speaking with Every in January 2026, Wilkinson described using AI to build an email tool around his own preferences, after struggling with hundreds of messages a day. He was also experimenting with software for understanding his relationship. He and his girlfriend, he said, laughed together at its observations.
Even his beard had become a project: he told the interviewer that an AI analysis encouraged him to grow it. Software building, which he described as a hobby, was making him excited to get back to work. The old impulse to make something useful had survived the acquisition years. What had changed was his ability to follow an idea without having to organize a whole team around it.
There is a social version of that impulse, too. He founded Interesting People, a gathering in Victoria whose 2026 edition brought together 150 people from fields including music, science, writing and business. Its activities included shared meals, live music and kayaking. Wilkinson traces the idea to feeling dismissed at an early tech conference because he ran a business built around his preferred lifestyle. Years later, he could create a different kind of room.
That makes the most interesting part of his rich life the editing. He can afford to try other people’s definitions of success, discover they fit badly and revise the plan. The next decision is more personal: what to keep, whom to spend time with, and which projects still make him want to begin.