If I was 21 again, this is what I’d do different - Howard Marks

Buying great companies at reasonable prices beats hunting 'cigar-butt' bargains because durable competitive advantages compound over time while low-quality cheap assets often fail to deliver long-term returns.

Acting under extreme uncertainty requires probabilistic thinking and accepting trepidation because when there is no precedent you must weigh outcomes by expected value rather than by confidence.

Letting children make non-harmful choices develops judgment because experiencing outcomes, including mistakes, teaches responsibility and resilience more effectively than parental selection.

Demonstrable restraint, like making a smaller follow-on fund after success, builds credibility because foregoing obvious short-term gain signals integrity and makes investors more willing to commit capital ahead of contrarian opportunities.

Conversational abilities make AI qualitatively different because self-assessment, humor, and personalization let it produce context-sensitive behaviors that defy simple pattern prediction.

Admitting uncertainty reduces catastrophic mistakes because it prevents absolute conviction-driven bets and encourages probabilistic sizing and flexibility.

Raise and commit crisis-focused capital before a downturn because fundraising becomes nearly impossible during panic, and prepositioned funds let you buy assets when prices are most attractive.

Shared values and complementary skills sustain long partnerships because aligned ethics prevent recurring conflict while different but additive abilities create lasting synergy.