Applying Conway's Law to venture, a firm's strategy is dictated by its fund size and team structure. A $7B fund must participate in mega-rounds to deploy capital effectively, while a smaller fund like Benchmark is structured to pursue astronomical money-on-money returns from earlier stages, making mega-deals strategically illogical.

Micah Rosenbloom of Founder Collective argues that keeping fund sizes small is a strategic choice. It aligns the firm with founders by making smaller, life-changing exits viable, maintaining founder optionality, and focusing on multiples rather than management fees from a large AUM.

Seed-focused funds have a powerful, non-obvious advantage over multi-stage giants: incentive alignment. A seed fund's goal is to maximize the next round's valuation for the founder. A multi-stage firm, hoping to lead the next round themselves, is implicitly motivated to keep that valuation lower, creating a conflict of interest.

Figma's market initially seemed too small to attract major VC interest or intense competition, giving them space to build a defensible product. Founders can gain a significant advantage by working in overlooked spaces, provided they have genuine passion to sustain them for a decade or more.

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.

This provides a simple but powerful framework for venture investing. For companies in markets with demonstrably huge TAMs (e.g., AI coding), valuation is secondary to backing the winner. For markets with a more uncertain or constrained TAM (e.g., vertical SaaS), traditional valuation discipline and entry price matter significantly.

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.

Conventional venture capital wisdom of 'winner-take-all' may not apply to AI applications. The market is expanding so rapidly that it can sustain multiple, fast-growing, highly valuable companies, each capturing a significant niche. For VCs, this means huge returns don't necessarily require backing a monopoly.

The majority of venture capital funds fail to return capital, with a 60% loss-making base rate. This highlights that VC is a power-law-driven asset class. The key to success is not picking consistently good funds, but ensuring access to the tiny fraction of funds that generate extraordinary, outlier returns.