Protect your self-worth by pursuing at least two or three serious interests at the same time. Progress in one domain, like a physical skill, can serve as a psychological safety net when you face setbacks in your primary professional endeavor. This prevents your entire identity from being tied to one volatile variable.

WCM realized their portfolio became too correlated because their research pipeline itself was the root cause, with analysts naturally chasing what was working. To fix this, they built custom company categorization tools to force diversification at the idea generation stage, ensuring a broader set of opportunities is always available.

Advisors for wealthy Asian families face a complex challenge. They must help the founding generation with liquidity events (IPOs or sales) for their traditional businesses, while simultaneously catering to the next generation's vastly different, more global and tech-focused investment appetite (e.g., Mag-7, digital assets).

The key to effective portfolio entrepreneurship isn't random diversification. It's about serving the same customer segment across multiple products. This creates a cohesive ecosystem where each new offering benefits from compounding knowledge and trust, making many things feel like one thing.

True diversification doesn't come from being a generalist, but from achieving undeniable mastery in one specific domain. This deep expertise becomes your leverage—your "in"—to access rooms, build credibility, and then expand horizontally into other ventures like production, investing, and brand partnerships.

Instead of diversifying randomly, a more effective strategy is to expand into adjacent verticals. Leverage your existing, happy clients for introductions into these parallel industries. This approach uses your established credibility and relationships as a bridge to new markets, lowering the barrier to entry.

The tech industry creates first-generation wealth at an unprecedented rate, yet there's a lack of services to help these individuals navigate its complexities. Unlike inherited wealth, they lack pre-built support structures, creating a significant business opportunity to serve this group.

Large enterprise clients are often diversified themselves with multiple departments and divisions. A powerful de-risking strategy is to leverage your existing relationship as a proven vendor to get introductions and sell into these other parts of the organization, effectively diversifying your revenue stream within a single account.

Investor Mark Ein argues against sector-specific focus, viewing his broad portfolio (prop tech, sports, etc.) as a key advantage. It enables him to transfer insights and best practices from one industry to another, uncovering opportunities that specialists might miss.