Early ventures that failed weren't seen as setbacks but as low-cost learning opportunities. This perspective, framed by his grandfather's high-risk business, eliminated fear and built foundational skills with minimal downside, making eventual success more likely.

During due diligence, it's crucial to look beyond returns. Top allocators analyze a manager's decision-making process, not just the outcome. They penalize managers who were “right for the wrong reasons” (luck) and give credit to those who were “wrong for the right reasons” (good process, bad luck).

When studying failed money management firms, WCM found that founders were unwilling to discuss their mistakes. The most valuable, unfiltered lessons about what truly went wrong came from conducting deep diligence with former employees of those organizations.

When making early-stage investments, avoid the common pitfall of betting on just a great idea or just a great founder. A successful investment requires deep belief in both. Every time the speaker has invested with only one of the two criteria met, they have lost money. The mandate must be 'two for two.'

Students often believe their target industry is too crowded. Bravo counters this, recalling how a top PE head told him the industry was 'taken' in 1997. He argues the next generation can build bigger firms by ignoring such cyclical pessimism and focusing on execution.

During his final offer dinner with Carl Thoma, Orlando Bravo asked for carried interest. Thoma was so put off by the request that he almost withdrew the offer, teaching Bravo a crucial lesson about earning your place before making demands.

A crucial, yet unquantifiable, component of alpha is avoiding catastrophic losses. Jeff Aronson points to spending years analyzing companies his firm ultimately passed on. While this discipline doesn't appear as a positive return on a performance sheet, the act of rigorously saying "no" is a real, though invisible, driver of long-term success.

After early failures, Orlando Bravo pioneered software buyouts. This was a contrarian move, as the prevailing view was that these companies were either too old or too risky. This niche focus on making unprofitable software businesses viable became the foundation of his firm's success.

Orlando Bravo didn't get a return offer from his internship. Instead of giving up, he sent 500 resumes and cold-called firms, landing his pivotal role just two weeks before graduating. It shows that persistence, not a linear path, is key to breaking into competitive fields.