Andrew Wilkinson

Who they are

Andrew Wilkinson is Executive Chairman of Tiny Capital — dropped out of Ryerson after one year, went from barista to founding MetaLab in 2006, then built Tiny as a Berkshire-style holding company that owns Dribbble, Letterboxd, AeroPress, and Serato.

Person

Andrew skipped a full university education — one year at Ryerson (2004–2005) after Oak Bay High School — and started his career as a barista before founding MetaLab in 2006, which became one of Canada's top design and development agencies with clients including Slack, Apple, Google, Disney, and Coinbase. MetaLab was the cash engine that let him start Tiny in 2014, originally a two-person operation modeled explicitly on Berkshire Hathaway: buy profitable internet businesses, leave the operators alone, collect the cash flows. He's co-founded Flow (a task management SaaS used by Etsy, Tesla, Adobe, and TED), WeCommerce (a Shopify-focused holding company), Overstory Media Group, and Pixel Union alongside the main Tiny track. The through-line is compounding capital and attention — each company he builds either throws off cash or buys him more optionality. He writes the Never Enough newsletter and blog covering entrepreneurship, business acquisition, wealth-building, and AI, and published a memoir under the same name tracing the barista-to-billionaire arc. He hosts Interesting People, an annual ~150-person mastermind in Victoria, and keeps a personal site at andrew-wilkinson.com; he's appeared on The Knowledge Project, My First Million, Lenny's Newsletter, and Sahil Bloom's VTJ Live.

Company

The most recent development at Tiny is a leadership transition: Austin Singhera was appointed CEO effective May 13, 2026, with the Board increasing its involvement in strategic direction — Wilkinson moves to Executive Chairman. Q1 2026 revenue came in at $51.5M CAD, up 7% year-over-year, with combined unaudited Tiny Fund revenue of $17.8M CAD (USD $12.9M), up from $16.6M in Q1 2025; total assets stood at $464.1M as of March 31, 2026. In Q4 2025, Tiny launched Slab in collaboration with Alpha Theta and added Spotify and Apple Music integrations, while continuing to embed AI capabilities across portfolio products. Tiny's highest-performing assets are Letterboxd, Serato, and MediaNet, all acquired in prior years. The company held its Annual General Meeting in June 2026 and trades on the TSX under the ticker TINY.TO.

Market

Tiny operates as a Canadian technology holding company — a founder-friendly acquirer of profitable internet businesses with recurring revenue, explicitly modeled on the Berkshire Hathaway approach rather than venture-style growth-at-all-costs. There's no direct public-market peer doing the same thing at scale in Canada, though the broader shift toward AI-driven efficiency across SaaS businesses is shaping how Tiny embeds capability into its portfolio. The Tiny Foundation has distributed over $16 million to science, journalism, and child protection services, which is also part of its public identity.

Network

Chris Sparling is Tiny's co-founder and the closest long-term collaborator — he co-founded both MetaLab and Tiny with Wilkinson. Sahil Bloom co-hosted a VTJ Live event with Wilkinson at the Vancouver Playhouse, and Lenny Rachitsky featured him in Lenny's Newsletter on spotting high-margin niches.

Chris Sparling· Co-founder, Tiny and MetaLab
Sahil Bloom· Co-host, VTJ Live event at Vancouver Playhouse
Lenny Rachitsky· Founder, Lenny's Newsletter
Austin Singhera· CEO, Tiny Capital (appointed May 13, 2026)

How they likely show up

Founded MetaLab in 2006 and Tiny in 2014, both still active — long-tenure, long-arc thinking; he's not a serial exiter, he compounds.
Explicit Berkshire Hathaway model from Tiny's founding → prefers acquiring and delegating over building and operating day-to-day; his stated philosophy is 'lazy leadership' through operator autonomy.
Active public writer and speaker (Never Enough newsletter, memoir, Knowledge Project, Lenny's Newsletter) → comfortable being visible and opinionated; he processes ideas publicly, not privately.
Just transitioned from CEO to Executive Chairman at Tiny → likely in a phase of stepping back from operations and thinking more about capital allocation and portfolio strategy.
Runs Interesting People — an invite-only ~150-person annual event he self-hosts in Victoria → high-curation instinct; he invests in relationships deliberately, not passively.
Experimenting with Claude Opus 4.5 for work and life → early adopter of AI tools, willing to rethink personal workflows, not just talking about AI abstractly.

Conversation tips

→ Reference a specific company in the Tiny portfolio — Letterboxd, Serato, AeroPress — and ask about the acquisition thesis; he'll have a crisp answer and you'll signal you've done the work.
→ The Never Enough memoir is fair game as an opener — it's his most public articulation of the barista-to-billionaire arc and he clearly wants that story told.
→ Ask about the CEO transition to Austin Singhera and what Executive Chairman actually means day-to-day for him — it's fresh and he's clearly mid-transition.
→ He thinks in holding company terms, not startup terms — frame questions around capital allocation, recurring revenue, and operator autonomy rather than growth hacks or product roadmaps.
→ Don't treat him as a tech founder who codes; he came up through design and agency work — the creative and aesthetic side of product decisions is genuinely interesting to him.

Toolbox

Openers

Open on the Tiny CEO transition — Austin Singhera took the CEO seat on May 13, 2026, and Wilkinson moved to Executive Chairman; asking what that shift actually changes for how he spends his time is a sharp, timely opener.
Reference the Never Enough memoir directly — he wrote a book about going from barista to building a 30+ brand holding company; it's the clearest signal of what he wants his story to be, and most people haven't actually read it.
Bring up Interesting People, his self-hosted ~150-person annual conference in Victoria — he built it as a curated mastermind and it's running its fourth edition in July 2026; asking about who he selects and why opens the conversation about how he thinks about relationships and networks.

Discovery questions

Letterboxd and Serato are called out as Tiny's highest-performing assets — what made those acquisitions work where others in the portfolio haven't hit the same level?
You've run 75+ businesses by Lenny Rachitsky's count — at what point does the holding company model stop scaling, and what's the constraint you're actually managing against now?
You've been experimenting with Claude Opus 4.5 — how is AI actually changing how you run Tiny, and is it changing how you evaluate acquisition targets?

Avoid

Don't pitch him on venture-style growth metrics or 'scaling fast' framing — his entire model is built on rejecting that approach in favour of profitable, cash-flowing businesses with operator autonomy.

Make it yours