Andrew Wilkinson

Who they are

Andrew Wilkinson is Co-founder & CEO of Tiny — he built MetaLab from scratch in 2006 into a design agency whose clients include Apple, Slack, and Coinbase, then pivoted to acquiring internet businesses, co-owning Dribbble, Letterboxd, and AeroPress.

Person

Andrew went to Oak Bay High School in Victoria and spent a year at Ryerson University before dropping out — the formal education didn't stick, but the builder instinct did. In 2006 he founded MetaLab, a design and development agency that punched well above its size, landing Apple, Google, Disney, Walmart, Slack, and Coinbase as clients. He ran MetaLab as Founder and Chairman while building a second thesis: that great internet businesses could be bought and held rather than flipped. In January 2014 he co-founded Tiny from scratch alongside Chris Sparling, starting with nothing and growing it into a publicly listed Canadian holding company (TSX: TINY.TO) with portfolio companies including Dribbble, Letterboxd, Serato, and AeroPress. He runs the Tiny Foundation, which funds science and journalism. His public writing is active — the through-line across MetaLab and Tiny is buying or building things that compound quietly rather than chasing venture-scale exits.

Company

The freshest development at Tiny is a CEO succession: Austin Singhera was appointed CEO effective May 13, 2026, with the Board taking a more active role in strategic direction and AI-driven efficiency initiatives — Wilkinson remains co-founder but is stepping back from day-to-day leadership. Q1 2026 revenue came in at $51.5M CAD, up 7% year-over-year, with combined unaudited revenue from Tiny Fund at $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, added Spotify and Apple Music integrations, and continued embedding AI capabilities across its portfolio. Letterboxd, Serato, and MediaNet are cited as the company's highest-performing assets. Tiny has set a June 2026 date for its in-person Annual Shareholder Meeting.

Market

Tiny operates as a founder-friendly technology holding company on the TSX, acquiring internet businesses with recurring revenue and durable competitive advantages — a model more akin to Constellation Software than a traditional VC fund. Its portfolio spans creative tools (Dribbble), entertainment discovery (Letterboxd), DJ software (Serato), and coffee equipment (AeroPress), giving it an unusually eclectic mix of consumer and B2B assets. AI-driven efficiency is increasingly central to holding-company operational strategy as portfolio companies integrate AI capabilities across their products.

Network

Chris Sparling is Andrew's co-founder at Tiny — the two built the holding company together from its January 2014 founding. Austin Singhera was appointed CEO of Tiny on May 13, 2026, making him the key operational counterpart now running the business day-to-day.

How they likely show up

  • Long tenure at both MetaLab (founded 2006, still active) and Tiny (founded 2014, still active) → thinks in decade-long arcs, not quarterly cycles.
  • Founded two companies — MetaLab and Tiny — rather than joining others → high agency, prefers to own the structure rather than operate inside someone else's.
  • Tiny's model is acquiring and holding rather than building and selling → values compounding, durable businesses over high-growth exit plays.
  • Active public writing signal → comfortable being visible and opinionated; likely responds well to substantive engagement with his ideas rather than surface-level flattery.
  • Runs the Tiny Foundation (science and journalism funding) alongside a for-profit holding company → willing to run parallel projects when they align with a worldview, not just when they're financially obvious.
  • Stepped back from CEO role while remaining co-founder → Possibly — entering a more principal/capital-allocator mode than operator mode post-succession.

Conversation tips

  • → Come with a specific view on one of the portfolio companies — Letterboxd, Serato, or Dribbble — rather than asking him to explain the holding company model from scratch.
  • → He's a builder-turned-acquirer; ask about the transition, not just the current portfolio — the MetaLab-to-Tiny pivot is a defining arc he'll have thought through carefully.
  • → Reference the CEO succession if it's relevant — it's public and recent (May 2026), and he'll appreciate that you've read the news rather than coming in cold.
  • → He writes actively, so if you've read something specific he's published, say which piece and what you took from it — generic 'I follow your writing' won't land.

Toolbox

Openers

  • Open on the Austin Singhera CEO appointment (May 13, 2026) — it's the most recent public move and signals a real shift in how Andrew is spending his time; asking what he's focused on now that someone else is running day-to-day operations will get a genuine answer.
  • Bring up AeroPress — it's a physical product in a portfolio of software companies, a deliberate outlier that reveals something about his acquisition thesis; asking why it fits tells you a lot about how he thinks.
  • Reference MetaLab's design work on Slack — he built the agency that shipped one of the decade's most influential product interfaces, then walked away from client work to acquire things instead; that transition is the cleanest lens into his current worldview.

Discovery questions

  1. Letterboxd, Serato, and MediaNet are cited as your highest-performing assets — what made those acquisitions work when others in the portfolio haven't hit the same level?
  2. You launched Slab in Q4 2025 in partnership with Alpha Theta — how does a new product launch fit inside a holding company model that's usually about acquiring rather than building?
  3. With Austin Singhera now running Tiny day-to-day, how are you thinking about your own role — more capital allocation, more new deals, or something else entirely?

Avoid

Don't pitch him on a venture-style high-growth opportunity framed around exits or scale — his entire model is built around buying quiet compounders and holding them, so exit-driven framing will signal you haven't understood what he's actually doing.

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Sources

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Generated by briefthecall.com from public web sources on June 5, 2026. Each claim is linked to its source above.

Automatically generated by AI from public sources. May be inaccurate or out of date. Remove or correct this profile →