Contrary to conventional wisdom, KP's most successful portfolio companies (like Rippling and Glean) overwhelmingly hire for potential, not past titles. 38 of the top 40 executive roles are filled by individuals reporting to the CEO for the first time, emphasizing adaptability and growth over a long resume.

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.

Second-time founders (“Act II teams”) possess a unique advantage. They can solve the same core problem but with complete clarity from the start, knowing the edge cases and organizational structure required. This allows them to leverage modern technology while avoiding the mistakes of their first venture, as seen with the founders of Workday and Affirm.

The ideal founder archetype starts with deep technical expertise and product sense. They then develop exceptional business and commercial acumen over time, a rarer and more powerful combination than a non-technical founder learning the product.

Lacking deep category knowledge fosters the naivety and ambition required for groundbreaking startups. This "beginner's mind" avoids preconceived limitations and allows for truly novel approaches, unlike the incrementalism that experience can sometimes breed. It is a gift, not a curse.

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.

Lacking a traditional resume forces young founders to constantly learn, as they have no preconceived notions of how things 'should' be done. This contrasts with experienced leaders who might wrongly assume their past success provides a playbook for a new market or company stage.

Rapid startup success stories are misleading. A company's quick victory is almost always the result of its founder's decade-long journey of grinding, learning, and failing. The compounding effect of skills, credibility, and network building is the true engine behind the breakthrough moment.

Many iconic founders, like Southwest's Herb Kelleher, were beginners in their industries. This lack of experience was an advantage, freeing them from established dogmas and allowing them to approach problems with a fresh perspective. They built unconventional models that incumbents dismissed or couldn't replicate.