My First Million Wiki

Andrew Wilkinson

6 min read

Andrew Wilkinson

Andrew Wilkinson became a billionaire by collecting boring internet businesses. Not apps that promise to change the world. Not AI startups racing toward artificial general intelligence. Websites that sell design templates and portfolio hosting for freelancers.

The path from 250,000 in revenue at a 50% profit margin.

That number matters. Not because it made him rich, which it did not, but because it revealed something counterintuitive about business: you can pay yourself extremely well while building, not after.

The Lifestyle-First Heresy

Most founders worship at the altar of delayed gratification. Reinvest everything. Sleep on couches. Eat ramen. The exit will justify the suffering.

Wilkinson took the opposite approach. In the first two or three years of MetaLab, he paid himself 500,000 annually. He bought the lifestyle first and built the empire second.

“I’m very lifestyle focused. I don’t believe in changing the world. I think that’s a ridiculous thing. I think that if you don’t do it, someone else will. I really just want to be happy—wake up every morning and work with interesting people on interesting problems.”

This philosophy became the operating system for Tiny, the holding company he built to acquire internet businesses. Tiny now owns more than 40 companies, went public on the TSX Venture Exchange in 2023, and has crossed the billion-dollar valuation threshold. Wilkinson and co-founder Chris Sparling retained 81% of the shares.

Barnacles and Whales

Wilkinson’s most replicable insight comes from observing where value concentrates in software ecosystems.

He calls it the “Barnacle on the Whale” strategy. Instead of building products that compete for attention in crowded markets, attach to platforms where customers already congregate. Shopify themes. Discord bots. Tools for existing software ecosystems.

The math is simple. A whale platform has millions of users actively searching for solutions. A barnacle product plugs into that demand with zero marketing spend. Tiny’s Shopify theme businesses grew tenfold without advertising because customers were already looking inside the Shopify ecosystem.

This is the opposite of how most entrepreneurs think. They want to build the whale. Wilkinson recognized that barnacles can get very fat while the whale does all the swimming.

Profit First, Everything Else Second

MetaLab generates 20 million in profit. That cash flow engine funds the entire Tiny empire.

The methodology behind this margin is almost aggressively simple. Take a percentage of every dollar that comes in and move it to a separate bank account you cannot see. Run the business on whatever remains.

“Don’t leave too much money in the business. Dividend the money out and keep only a month or two months of cash in the business. If more money is needed, the shareholders can send some money back.”

This inverts conventional wisdom about runway and reserves. Most founders hoard cash for psychological comfort. Wilkinson argues that constraint forces efficiency. When you cannot see the money, you cannot spend it on unnecessary headcount or pet projects.

Lazy Leadership

Wilkinson describes himself as lazy. This requires clarification.

“When people hear me saying that I am lazy, they think I don’t work hard, but that’s not true. I don’t like doing work that I don’t want to do.”

The distinction matters. His laziness manifests as aggressive delegation and systems building. The Tiny operating model requires minimal oversight. Monthly updates cover only financials: profit and loss, balance sheet, key performance indicators. Quarterly SWOT analyses. Some portfolio CEOs go six months without speaking to Wilkinson directly.

This is not absentee ownership. It is a deliberate architectural choice. Build companies that function without you, then spend your time on whatever interests you most.

The Dribbble Arbitrage

The Dribbble acquisition illustrates how Wilkinson thinks about value.

Dribbble was a portfolio site for designers—millions of monthly visitors, minimal monetization. Tiny acquired it for somewhere between 10 million. Now it generates tens of millions annually.

The insight was recognizing undermonetized traffic. Designers visiting Dribbble needed jobs. Companies visiting Dribbble needed designers. The marketplace infrastructure already existed. Someone just had to build the tollbooth.

The Hedonic Treadmill

Wilkinson signed The Giving Pledge, committing to give away the majority of his wealth. He calls himself an “anti-billionaire.”

This is not false modesty. In podcast appearances, he describes the emotional flatness that accompanies wealth accumulation. Despite billion-dollar success, he often feels empty. The creative process itself—building, solving, shipping—provides more satisfaction than the numbers in the bank account.

This observation appears in almost every interview with extremely successful people, yet almost no one believes it until they experience it themselves. The hedonic treadmill keeps moving no matter how fast you run.

Key Frameworks

Barnacle on the Whale: Build products for existing platform ecosystems rather than competing in open markets. Capture demand that already exists.

Profit First: Automatically move profit to an invisible account before paying expenses. Run the business on the remainder.

Lazy Leadership: Build systems that operate without you. Delegate everything you do not want to do. Minimum viable oversight.

Lifestyle-First Building: Pay yourself well from day one. Optimize for happiness and interesting problems, not market domination.

Notable Quotes

On laziness and work ethic:

“When people hear me saying that I am lazy, they think I don’t work hard, but that’s not true. I don’t like doing work that I don’t want to do.”

On life philosophy:

“I’m very lifestyle focused. I don’t believe in changing the world. I think that’s a ridiculous thing. I think that if you don’t do it, someone else will.”

MFM Appearances

Andrew Wilkinson has appeared on My First Million multiple times and co-hosts the annual Milly Awards with Sam Parr and Shaan Puri:

  • Tiny - Wilkinson’s publicly traded holding company
  • MetaLab - Design agency that funds the Tiny empire
  • Dribbble - Designer portfolio platform acquired by Tiny
  • Warren Buffett - Berkshire Hathaway model that inspired Tiny’s structure
  • Shopify - Platform ecosystem where Tiny executes the barnacle strategy
  • The Giving Pledge - Philanthropic commitment Wilkinson has signed
  • Never Enough: From Barista to Billionaire - Wilkinson’s memoir

This article is part of the MFM Wiki, documenting ideas, frameworks, and people discussed on the My First Million podcast.

Graph View

Backlinks