Being the Buyer You Wish You Had

Andrew Wilkinson's approach to business centers on finding opportunities in overlooked niches where competition is minimal but profit potential remains high. He believes entrepreneurs should "fish where the fish are" but avoid ponds crowded with professional fishermen.

When evaluating business ideas, Andrew looks for areas where your unique background gives you an unfair advantage. The most successful ventures often connect to your personal interests or expertise, but with a strategic pivot toward profitability. For example, rather than managing social media for restaurants with tight budgets, focus on realtors or wealth managers who have larger marketing budgets and higher conversion values.

Andrew cautions against entering highly competitive markets where others have repeatedly failed. His $10 million loss competing with venture-backed Asana taught him that you can't overcome a bad business model with brilliant management. Instead, he recommends starting with simpler businesses that provide immediate positive feedback and gradually building your entrepreneurial muscles.

For bootstrapped businesses, Andrew emphasizes that you don't need venture capital to build something substantial. His company Tiny has grown to nearly $300 million in revenue without outside funding. The key difference between bootstrapped and venture-backed companies isn't potential scale, but tolerance for burning money. If your business doesn't require tens of millions in upfront investment to become profitable, bootstrapping may be the better path.

When buying companies, Andrew looks for businesses with strong moats—either powerful brands or network effects—that are difficult to disrupt. He wants companies that are "so good that it's hard to mess up." His acquisition philosophy is to become the buyer he wished he could have sold to, leaving successful businesses largely alone rather than imposing dramatic changes.

Perhaps most surprisingly, Andrew found that his greatest happiness improvements came not from business success but from addressing his mental health. Despite reaching billionaire status, his anxiety remained constant until he began treating his ADHD and anxiety with medication. This experience taught him that external achievements rarely solve internal struggles, and that addressing the root causes of unhappiness is far more effective than pursuing wealth or status.

Decision Implications

For founders choosing business models:

• Evaluate markets based on competition levels, not just size or growth potential
• Look for areas where your specific background gives you unique insights
• Start with simpler businesses that provide quick feedback loops
• Be wary of entering spaces littered with failed predecessors

For bootstrappers vs. venture seekers:

• Consider if your business truly needs significant upfront capital
• Recognize that bootstrapped businesses can still reach hundreds of millions in revenue
• Focus on businesses with natural growth potential rather than those requiring money to be "lit on fire"

For those acquiring businesses:

• Prioritize companies with strong moats (brands or network effects)
• Maintain what's working rather than imposing dramatic changes
• Look for businesses that are difficult to disrupt and have happy customers and employees

For personal effectiveness:

• Don't assume external success will solve internal struggles
• Consider whether mental health interventions might be more impactful than business achievements
• Recognize when you're making "easy choices" that lead to a harder life