Instead of trying to convince people of the importance of vulnerability, first have them identify their core values. They will naturally conclude that living up to those values (e.g., courage, excellence) requires them to embrace the uncertainty and risk inherent in vulnerability.

To empower teams to act without perfect data, leaders must cultivate psychological safety. This means explicitly framing well-intentioned mistakes as acceptable risks. It encourages reps to trust their instincts and take necessary steps forward in gray areas.

Contrary to popular belief, successful entrepreneurs are not reckless risk-takers. They are experts at systematically eliminating risk. They validate demand before building, structure deals to minimize capital outlay (e.g., leasing planes), and enter markets with weak competition. Their goal is to win with the least possible exposure.

Limited Partners (LPs) value fund managers who are willing to listen and internalize market feedback, even if they ultimately follow their own strategy. This openness is a key positive signal, while a refusal to listen is a major red flag that often appears early in the relationship.

Frame your initial angel investments as a sunk cost, like business school tuition. Instead of optimizing for immediate financial returns, focus on building relationships, acquiring skills, and developing a strong reputation. This long-term mindset reduces pressure and leads to better, unforeseen opportunities down the line.

True growth and access to high-level opportunities come not from feigning knowledge, but from openly admitting ignorance. This vulnerability invites mentorship and opens doors to conversations where real learning occurs, especially in complex fields like investing, which may otherwise seem like a "scam."

Instead of avoiding risk, teams build trust by creating a 'safe danger' zone for manageable risks, like sharing a half-baked idea. This process of successfully navigating small vulnerabilities rewires fear into trust and encourages creative thinking, proving that safety and danger are more like 'dance partners' than opposites.

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.

For short-term mentoring to be impactful, it must be painful. The goal isn't gentle guidance but to make an overlooked opportunity or flaw so painfully obvious that the mentee is jolted into action, partly to prove the mentor wrong. It's 'crash therapy'—uncomfortable but highly effective at driving change.