Success brings knowledge, but it also creates a bias against trying unconventional ideas. Early-stage entrepreneurs are "too dumb to know it was dumb," allowing them to take random shots with high upside. Experienced founders often filter these out, potentially missing breakthroughs, fun, and valuable memories.

The most significant founder mistakes often arise from abandoning one's own judgment to do what is conventionally expected. Jason Fried notes that these errors feel worse because you aren't just failing, you're failing while trying to be someone else, which undermines the core identity of your company.

Undiversified founders can't afford a VC's portfolio mindset. Instead of pursuing ideas that *could* work, they must adopt strategies that would be *weird if they didn't work*. This shifts focus from optimizing for a chance of success to minimizing the chance of absolute failure.

While capital and talent are necessary, the key differentiator of innovation hubs like Silicon Valley is the cultural mindset. The acceptance of failure as a learning experience, rather than a permanent mark of shame, encourages the high-risk experimentation necessary for breakthroughs.

Disagreeing with Peter Thiel, Josh Wolf argues that studying people who made willful mistakes is more valuable than studying success stories. Analyzing failures provides a clear catalog of what to avoid, offering a more practical and robust learning framework based on inversion.

Founders who succeed by randomly trying ideas rather than using a systematic process don't learn repeatable skills. This lucky break can be detrimental, as it validates a flawed strategy and prevents the founder from learning the principles needed for consistent, future success.

In school or corporate jobs, the 'rules for success' are provided. Founders enter a world with no such rubric and often fail because they don't consciously develop their own theory of how the world works, instead defaulting to shallow, unexamined beliefs about what founders 'should' do.

Companies like Instagram that succeed early become risk-averse because they lack experience in navigating failure. In contrast, enduring early struggles builds resilience and a willingness to experiment, which is critical for long-term innovation.

Contrary to the popular trope, you learn far more from success than from failure. It's more informative to see how things are done right than to analyze what went wrong. To accelerate your career, you should prioritize joining a winning team to observe and internalize successful patterns.