Tiny

Andrew Wilkinson started his career doing what most entrepreneurs do—starting businesses from scratch. He launched a web design agency called MetaLab that immediately found product-market fit, giving him the confidence to try his hand at seemingly obvious opportunities. He started a pizzeria, a designer cat furniture business, an online DJ school, a skin cream business. He lost money on nearly all of them, sometimes spectacularly. After years of this grind—starting around 10-15 businesses with a high failure rate—he found himself exhausted, asking what he actually wanted his career to be. The answer was clear: this wasn't it.

Wilkinson picked up a biography of Warren Buffett and realized he'd been going about it all wrong. Buffett doesn't wake up at 4am stressed about operations. He sits quietly, reads, and makes maybe one or two big investment decisions a year. He owns 260 businesses across Berkshire Hathaway but operates with total calm. Wilkinson realized: why start businesses when you can *buy* them? Why deal with the 90% failure rate of startups when you can acquire businesses that are already generating revenue, already have customers, already have management teams?

So he founded Tiny—a holding company modeled on Berkshire Hathaway. The core thesis: find profitable, sustainable businesses with defensible moats, buy them, leave the management alone, and hold them forever.

Tiny's acquisition strategy is counterintuitive. Wilkinson looks for businesses that already work—that have network effects (like Letterboxd, a social network for film lovers), strong brand loyalty (like Aeropress coffee makers), or deep user bases (like Serato DJ software). When Tiny acquires a company, almost nothing changes. If there's an existing CEO, Tiny doesn't interfere. If the founder wants to leave, Tiny brings in a professional CEO. But the product, the strategy, the team—all stay the same.

This patience is the opposite of venture capital's growth-at-all-costs mentality. Wilkinson's thesis: the best businesses don't need to burn millions to work. They grow naturally when they're good. A business with real moat—whether brand, network effects, or switching costs—will compound quietly for decades.

Tiny now owns over 40 companies generating nearly $300 million in annual revenue, all bootstrapped (no VC). The portfolio includes: - **Dribbble**: Design community - **Letterboxd**: Social network for film lovers - **Serato**: Professional DJ software - **Aeropress**: Coffee maker company - Plus businesses in niche markets: form-filling software for government benefits, pest control software, pressure-washing agencies

Many of these acquired businesses are deliberately "boring"—they solve unglamorous problems for niche audiences. A government form-filling software makes $30M/year. A pest control software business quietly generates millions. These aren't the companies founders tweet about, but they're the ones that actually print money.

Tiny represents a massive shift in how Wilkinson thinks about business. Rather than the exhaustion of starting, the stress of raising money, the pressure to scale at all costs, he's built a machine that quietly acquires great businesses and lets them compound. At various points, his net worth exceeded $1 billion—not through a single unicorn exit, but through patient, disciplined acquisition and holding.

Wilkinson is now exploring how AI can automate even more of his work and life. He's built AI agents in Lindy.ai that manage his email (filtering, prioritizing, drafting responses), schedule his calendar, organize his meetings, and track contacts. What used to require a full-time assistant now runs automatically for $200/month. He uses Claude and ChatGPT to understand new business models instantly. He builds web apps in Replit with AI. The message is clear: the future of running a holding company—and arguably, any business—is leveraging AI to eliminate friction and let good businesses compound without distraction.