Backing independent sponsors on a deal-by-deal basis is more than an investment strategy; it is an extended due diligence process. This approach provides deep, real-time insights into a manager's problem-solving skills under pressure, offering transparency that is impossible to achieve before a Fund I commitment.

The memo details how investors rationalize enormous funding rounds for pre-product startups. By focusing on a colossal potential outcome (e.g., a $1 trillion valuation) and assuming even a minuscule probability (e.g., 0.1%), the calculated expected value can justify the investment, compelling participation despite the overwhelming odds of failure.

Thrive's data shows the number of companies reaching $100B+ valuation grew faster last decade than those reaching $10B. This suggests it's a higher-probability bet to identify future mega-winners from an established pool of large companies than to pick breakout unicorns from a much larger, riskier field of thousands.

Top growth investors deliberately allocate more of their diligence effort to understanding and underwriting massive upside scenarios (10x+ returns) rather than concentrating on mitigating potential downside. The power-law nature of venture returns makes this a rational focus for generating exceptional performance.

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.

VCs at the highest level don't just write checks; they fundamentally reset a founder's aspirations. By placing a startup in the lineage of giants like Google and Oracle, they shift the goal from building a big business to creating a generational company.

To win highly sought-after deals, growth investors must build relationships years in advance. This involves providing tangible help with hiring, customer introductions, and strategic advice, effectively acting as an investor long before deploying capital.

Thrive's late-stage philosophy starts with qualitative conviction in the team and product. Quantitative analysis is used to confirm this hypothesis, not generate it. This approach builds resilience against short-term metric fluctuations that cause purely quantitative investors to lose confidence, allowing for bolder, long-term bets.

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.