In a bull market, it's hard to tell if a GP is skilled or just lucky. A downturn reveals their true discipline regarding valuations, capital deployment speed, and how they support founders through down rounds, providing LPs with robust underwriting data.

The most successful venture investors share two key traits: they originate investments from a first-principles or contrarian standpoint, and they possess the conviction to concentrate significant capital into their winning portfolio companies as they emerge.

Fundrise secured stakes in top companies like Anthropic and Anduril during the 2022-2023 downturn by buying from distressed funds or filling rounds when other LPs got scared. Moments of maximum fear are when the best, otherwise inaccessible, assets become available.

In venture capital, the greatest danger isn't investing at high valuations during a boom; it's ceasing to invest during a bust. The psychological pressure to stop when markets are negative is immense, but the best VCs maintain a disciplined, mechanical pace of investment to ensure they are active at the bottom.

While investing last in a round is less risky, Outside VC's Ethan Austin favors being the first investor. This 'first believer' position allows the firm to have a more significant impact on the company's direction and development, which he finds more rewarding.

Kyle York of York IE passed on Adhawk despite loving the founder because of a recent bad experience in the ad tech industry. The founder later pivoted the company into a SaaS platform for the flooring industry (Broadloom) and achieved a great exit, demonstrating that strong founders can escape challenging markets.

Large, contrarian investments feel like career risk to partners in a traditional VC firm, leading to bureaucracy and diluted conviction. Founder-led firms with small, centralized decision-making teams can operate with more decisiveness, enabling them to make the bold, potentially firm-defining bets that consensus-driven partnerships would avoid.

The venture capital business requires consistent investment, not sprinting and pausing based on market conditions. A common mistake is for VCs to stop investing during downturns. For companies with 50-100x growth potential, overpaying slightly on entry price is irrelevant, as the key is capturing the outlier returns, not timing the market.

With efficient discovery from accelerators like YC, the main opportunity for smaller VCs is to invest when a promising company stumbles or its re-acceleration is non-obvious. These "glitches in the matrix," where progress is non-linear, are moments where mega-funds might look away, creating an opening.