There's a surprising disconnect between the perceived brilliance of individual investors at large, well-known private equity firms and their actual net-to-LP returns, which are often no better than the market median. This violates the assumption that top talent automatically generates outlier results.

A common mistake in venture capital is investing too early based on founder pedigree or gut feel, which is akin to 'shooting in the dark'. A more disciplined private equity approach waits for companies to establish repeatable, business-driven key performance metrics before committing capital, reducing portfolio variance.

Despite median venture capital funds lagging public indexes like the S&P 500 for a quarter-century, capital continues to pour into the asset class. One LP describes this as 'hope over experience,' as investors are lured by the outlier returns of top funds, even though the average dollar invested underperforms.

Most VC funds fail to generate meaningful returns for LPs. Only the top quartile consistently delivers performance that justifies the risk. The asset class as a whole underperforms, challenging the idea that broader retail access would be beneficial.

Unlike venture-backed startups that chase lightning in a bottle (often ending in zero), private equity offers a different path. Operators can buy established, cash-flowing businesses and apply their growth skills in a less risky environment with shorter time horizons and a higher probability of a positive financial outcome.

Scott Galloway actively avoids angel investing, calling it the "worst part of the capital structure." He argues that with only one in seven deals ever providing a return, high dilution risk, and a massive time commitment, it's an inefficient way to deploy capital unless it's for a friend and the money is considered a write-off.

VC outcomes aren't a bell curve; a tiny fraction of investments deliver exponential returns covering all losses. This 'power law' dynamic means VCs must hunt for massive outliers, not just 'good' companies. Thiel only invests in startups with the potential to return his whole fund.

PE deals, especially without a large fund, cannot tolerate zeros. This necessitates a rigorous focus on risk reduction and what could go wrong. This is the opposite of angel investing, where the strategy is to accept many failures in a portfolio to capture the massive upside of the 1-in-10 winner.

For many entrepreneurs, angel investing is a poor use of capital, akin to playing roulette. While it feels like 'paying it forward,' it often results in tying up millions of dollars in illiquid assets with a very low probability of a meaningful return, underperforming simpler investments.