Andrew Wilkinson’s Business Playbook: Why Buying Boring Businesses Can Beat Starting the Next Big Thing

Andrew Wilkinson has built a business empire by doing something many entrepreneurs overlook: buying businesses that already work instead of constantly chasing the next big idea.

Through Metalab, his design agency, and Tiny, the company he co-founded to acquire and operate businesses, Wilkinson has helped build a portfolio spanning dozens of companies. His approach offers a revealing lesson about profitability, risk, and what makes a business worth owning.

The Hidden Cost of Starting From Scratch

Wilkinson learned the hard way that entrepreneurial success doesn’t automatically transfer from one business to another.

After building Metalab into a successful agency that worked with companies including YouTube, Uber, and Walmart, he used his profits to launch roughly 10 additional businesses. Many failed, consuming an estimated $10 million to $15 million along the way.

His conclusion? Starting new ventures can be exhausting, expensive, and unpredictable. Buying an established business and improving it might have delivered better results.

That realization helped shape Tiny. Wilkinson and his partner initially invested approximately $4 million to $5 million into the venture, aiming to acquire businesses they could hold and grow over time.

Rather than betting everything on unproven ideas, they began looking for companies with established customers, proven operations, and opportunities for improvement.

Not All Business Models Are Created Equal

Wilkinson’s experience also explains why some seemingly attractive businesses can be surprisingly difficult to operate.

Agencies, for example, can generate substantial profits but often face unpredictable revenue. One major client can bring in millions of dollars in work, only to cut its budget months later, leaving the agency with excess staff and rising costs.

Restaurants present another challenge. They require intensive daily operations, large teams, and countless things to go right, often for relatively thin margins.

Software businesses can be more attractive because recurring subscriptions and high switching costs create dependable revenue. But Wilkinson is increasingly cautious about software companies facing a wave of AI-powered competitors. His preferred businesses have something harder to replicate, such as software deeply integrated with essential hardware or established industry workflows.

The lesson is simple: revenue alone doesn’t make a business attractive. Predictability, defensibility, margins, and the likelihood of success matter just as much.

Build Wealth Through Compounding

Tiny’s strategy focuses on acquiring businesses and holding them for the long term. Wilkinson has described the company as generating approximately $250 million in annual revenue, $65 million in annual recurring revenue, and more than $40 million in EBITDA. Including businesses held through its investment fund, he said the broader portfolio generates more than $300 million in revenue across roughly 30 businesses.

These figures reflect his account of the business, rather than a guarantee of future performance.

The takeaway: Before starting another business from zero, consider whether an existing company could offer a better starting point. A proven business with loyal customers and room to improve may be a stronger investment than the next exciting idea.

Watch the original video: https://www.youtube.com/watch?v=ZOi2DtTVm7o&t=346s