Success Is Choosing Your Own Game

Andrew Wilkinson built his business empire by avoiding the most competitive markets and focusing on profitable niches where others weren't looking. His approach centers on finding businesses with natural advantages that are difficult to disrupt, rather than competing head-on with venture-backed companies.

The most successful business ideas often come from areas that aren't flashy or exciting. As Wilkinson puts it, "Fish where the fish are," referencing Charlie Munger's advice to find small fishing holes with lots of fish and little competition. This means looking for opportunities in spaces that aren't crowded with competitors, which naturally leads to higher margins and better economics.

For first-time entrepreneurs, Wilkinson recommends starting with simpler businesses that provide immediate positive feedback. He compares this to weight training: "You don't wanna walk into the gym on day one and try and deadlift 300 pounds." His own first success came from a web design agency that was straightforward to operate and immediately profitable, giving him confidence and capital for future ventures.

When evaluating business opportunities, Wilkinson looks for "moats" - sustainable competitive advantages like strong brands or network effects. He's particularly drawn to businesses with passionate communities that create network effects, such as Letterboxd (film enthusiasts) or Serato (DJs). These businesses become more valuable as more people join, making them naturally resistant to competition.

Wilkinson warns against entering markets where others have repeatedly failed, believing you can do better. He lost $10 million trying to compete with Asana in the project management space, learning that "you can't take a brilliant management team and change a bad business model." Instead, he recommends finding businesses in boring niches that solve real problems people will pay for.

On the venture versus bootstrap debate, Wilkinson challenges the notion that bootstrapped businesses can't scale. His company grew to nearly $300 million in revenue without outside funding. The key difference is "the level of tolerance of burning money on fire." If your business doesn't require massive capital to reach profitability, bootstrapping allows you to maintain control while still building substantial value.

For those working with others, Wilkinson emphasizes that "there are no problems, there is only people problems." He's learned to be decisive about removing difficult people, noting that if he ever thinks "should I fire this person," he should do it immediately. He's also found that trying to change people rarely works - it's better to hire someone who already has the skills and mindset you need.

Perhaps most surprisingly, Wilkinson shares that despite his financial success, his happiness came not from wealth but from addressing his underlying anxiety and ADHD through medication. No amount of money solved what "this little tiny yellow pill could do for my mental state," highlighting that external achievements often don't address internal struggles.

This perspective challenges entrepreneurs to consider what game they're actually playing. As Wilkinson reflects on comparing the founder of Things (a small, profitable to-do app) with Asana's founder: "If the goal is the founder has an incredible life, probably has three houses, flies all over the place, does whatever he wants, has recurring revenue, and he gets to work with headphones on building a beautiful piece of software that people love, then I think he's won."

Practical Implications

For founders and ICs, this means:

• Seek opportunities in less competitive spaces where your unique background gives you an advantage
• Start with simpler businesses that provide quick feedback and build confidence
• Evaluate business ideas based on their natural moats and defensibility
• Be realistic about whether you're trying to compete in markets that require massive capital
• Hire for who people already are, not who you hope they'll become
• Define success on your own terms - building a calm, profitable business can be more fulfilling than chasing unicorn status
• Recognize when external achievements won't solve internal challenges