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.
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.
The "Liking-Loving Tendency" causes investors to identify personally with their holdings. They ignore faults, favor associated things, and distort facts to maintain positive feelings. This emotional attachment leads them to rationalize bad news and hold deteriorating assets for too long, destroying capital.
For LPs, the primary benefit of pre-fund co-investments with emerging managers isn't just financial returns. It's a critical diligence tool to observe intangible qualities, such as a sponsor's discipline to abandon a flawed deal, which strongly correlates with long-term success.
Startups in social impact or wellness often receive positive but misleading feedback from VCs. Investors are hesitant to reject these missions outright, so they offer praise while privately declining due to perceived weak business models and a lack of "cutthroat" founders. This creates a "Save the Whales trap" for idealistic entrepreneurs.
Top growth investors deliberately allocate more of their diligence effort to understanding and underwriting massive upside scenarios (10x+ returns) rather than concentrating on mitigating potential downside. The power-law nature of venture returns makes this a rational focus for generating exceptional performance.
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.'
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.
Unlike committees, where partners might "sell" each other on a deal, a single decision-maker model tests true conviction. If a General Partner proceeds with an investment despite negative feedback from the partnership, it demonstrates their unwavering belief, leading to more intellectually honest decisions.
An expert reveals two shocking statistics: 80% of new founders fail their first diligence attempt, and 85% of early-stage investors don't perform confirmatory diligence. This highlights a massive, systemic weakness and inefficiency in the startup ecosystem, creating significant risk on both sides of the table.
The majority of venture capital funds fail to return capital, with a 60% loss-making base rate. This highlights that VC is a power-law-driven asset class. The key to success is not picking consistently good funds, but ensuring access to the tiny fraction of funds that generate extraordinary, outlier returns.