Tiny (Tiny Capital)

Andrew Wilkinson didn't set out to build a holding company. He started as a designer and founded Metalab, a design agency that eventually became the proving ground for the operational principles that would define Tiny Capital. The agency's profitability came from an unconventional advantage: charging San Francisco-level rates while operating remotely from Victoria, Canada, where overhead was significantly lower. This margin structure gave Wilkinson the capital and confidence to start investing in other businesses.

Tiny's model emerged from Wilkinson's belief that company building is repeatable—not at the startup phase, which he calls "black magic," but at the growth phase. He and his partner Chris began acquiring companies and immediately applied a systematic approach: they sourced experienced CEOs through their network, preferring people who had already succeeded in similar roles. As Wilkinson explains, "when someone's done something a million times, they know exactly what to do and you really don't have to oversee them that much." The firm identified universal growth levers across diverse businesses: pricing strategy optimization, SEO, copywriting, conversion optimization, email marketing, renegotiating vendor contracts, and identifying proven revenue streams from other businesses.

Tiny's deal flow came largely from cold outreach and referrals from within their network of existing CEOs. Wilkinson credits the firm's credibility to his prior success at Metalab, where he built reputation through strategic public positioning—famously publishing an open letter to Tony Hsieh of Zappos critiquing their website design, which generated significant attention and led to enterprise clients. This pattern of doing high-quality work and finding creative ways to share it publicly became Tiny's acquisition strategy as well.

Wilkinson's most instructive failure was a restaurant he opened in Victoria with business partner Chris and friend Rajiv. Despite being successful tech entrepreneurs, they vastly underestimated the difficulty of brick-and-mortar operations. The margins were razor-thin (1-5% net), scaling was capital-intensive and labor-heavy, and retaining committed staff was nearly impossible. "Real businesses—what I mean by real is brick and mortar grinded out businesses—are incredibly difficult," he reflected. The restaurant ultimately failed, but it reinforced his conviction that software and internet businesses, which scale infinitely with minimal incremental cost, were far more advantageous.

Tiny's success came from applying Charlie Munger's mental models—frameworks like incentive-caused bias and availability bias—to identify and fix problems in acquired companies. Wilkinson discovered businesses with millions of email subscribers who never sent emails, pricing that hadn't been optimized in years, and contracts that hadn't been renegotiated in five-plus years. Each discovery became a lever for growth.

Tiny has grown to own approximately ten software companies. Wilkinson and Chris funded acquisitions primarily with their own capital generated from Metalab, though they've brought external capital partners into larger deals without charging fees or carry. As of the time of this interview, they were in the process of raising a fund, anticipating that the economic environment would create more acquisition opportunities than they could tackle alone. Wilkinson emphasizes that the key to scaling from one business to twenty-plus is mastering delegation: trusting good people, aligning on strategy, and aligning incentives so that when the business wins, managers win too. His philosophy now centers on freedom, family, and using capital as a tool to protect his lifestyle rather than chase endless growth.