A16z's decision to add Hollywood agent Michael Ovitz to their board was controversial but genius. It directly led to modeling the firm after Creative Artists Agency (CAA), a novel approach in venture capital. This shows the power of seeking board-level expertise from outside your industry to challenge core assumptions and unlock game-changing strategies.

After a massive failure with their domestic fund, WCM launched an international strategy staffed with an operations person with zero investment experience and a business school dropout. This counterintuitive bet on raw talent and a fresh perspective became the foundation for their turnaround and massive growth.

WCM avoids generic AI use cases. Instead, they've built a "research partner" AI model specifically tuned to codify and diagnose their core concepts of "moat trajectory" and "culture." This allows them to amplify their unique edge by systematically flagging changes across a vast universe of data, rather than just automating simple tasks.

The most effective masterminds consist of people from different industries and business stages. This diversity prevents direct comparison and fosters richer insights. The crucial factor for curation isn't similar resumes but shared values like generosity, honesty, and a willingness to learn. Energy alignment trumps expertise alignment.

Experts often view problems through the narrow lens of their own discipline, a cognitive bias known as the "expertise trap" or Maslow's Law. This limits the tools and perspectives applied, leading to suboptimal solutions. The remedy is intentional collaboration with individuals who possess different functional toolkits.

AI reverses the long-standing trend of professional hyper-specialization. By providing instant access to specialist knowledge (e.g., coding in an unfamiliar language), AI tools empower individuals to operate as effective generalists. This allows small, agile teams to achieve more without hiring a dedicated expert for every function.

In an industry that punishes process evolution, WCM sets the expectation with clients that their investment approach will and should change. They ask clients to hold them accountable for this evolution, reframing change from a risk into a core value proposition of continuous improvement.

Large tech conferences often foster consensus views, leading VCs to chase the same deals. A better strategy is to attend smaller, niche events specific to an industry (e.g., legal tech). This provides an information advantage and helps develop a unique investment perspective away from the herd.

Formally trained experts are often constrained by the fear of reputational damage if they propose "crazy" ideas. An outsider or "hacker" without these credentials has the freedom to ask naive but fundamental questions that can challenge core assumptions and unlock new avenues of thinking.