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 worst feeling for an investor is not missing a successful deal they didn't understand, but investing against their own judgment in a company that ultimately fails. This emotional cost of violating one's own conviction outweighs the FOMO of passing on a hot deal.

Entrepreneurs often get burned by a failed investment (like a bad ad agency) and become hesitant to invest in that area again. This is a cognitive trap. The first loss was the money spent; the second, more significant loss is the opportunity cost of not trying again with a better strategy.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

Bessemer Venture Partners publicly lists massive companies it passed on to foster a learning culture. This highlights their philosophy that the opportunity cost of missing a transformative company (a crime of omission) is far more damaging than investing in one that fails (a crime of commission).

While focus is critical for entrepreneurs, being too rigid can lead to missing out on emerging asset classes. The host expresses regret for not pursuing Industrial Outdoor Storage (IOS) in its early days because his team was too focused on their existing industrial niche, illustrating the difficult balance between discipline and opportunism.

Hesitating to start a project for fear of wasting time and money is a paradox. The most significant waste is the opportunity cost of inaction—staying on the sidelines while revenue and experience are left on the table.

A founder's retrospective analysis often reveals that delayed decisions were the correct ones, and the only regret is not acting sooner. Recognizing this pattern—that you rarely regret moving too fast—can serve as a powerful heuristic to trust your gut and accelerate decision-making, as inaction is often the biggest risk.

Beyond analyzing losing positions (errors of commission), the speaker emphasizes studying mistakes of omission—high-quality businesses he understood but failed to invest in. This reflective practice helps identify flaws in process, time management, or conviction, which can be more instructive for future success than reviewing simple losses.