Sequoia secured an investment in Citadel Securities after 2.5 years of persistence. The key was framing their value around building technology businesses—an area where Citadel's Ken Griffin wanted help—rather than trying to compete on market-making knowledge.

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Trying to win a competitive Series A against a firm like Sequoia is nearly impossible for a smaller fund. Top firms leverage an overwhelming arsenal of social proof, including board seats at the world's most valuable companies and references from iconic founders, creating an insurmountable competitive moat.

To write a billion-dollar check, a firm needs "dogmatic conviction." Thrive Capital achieves this through extremely long diligence and relationship-building periods, often spanning years. This deep familiarity, like their 10-year relationship with Stripe before a major investment, is the foundation for making huge, concentrated bets.

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.

When raising capital, the ability to articulate a clear and compelling narrative is as crucial as the underlying financial model. An operator with exceptional storytelling skills can successfully secure funding, potentially even winning out over a competitor with a marginally better deal but weaker communication.

Series A is a brutal competition where top-tier firms have an insurmountable advantage. Their brand and network are so powerful that if a smaller fund wins a competitive Series A deal against them, it’s a strong negative signal that the top firms passed for a reason.

Competing to be a founder's "first call" is a crowded, zero-sum game. A more effective strategy is to be the "second call"—the specialist a founder turns to for a specific, difficult problem after consulting their lead investor. This positioning is more scalable, collaborative, and allows for differentiated value-add.

Sequoia makes consensus investment decisions, viewing each deal as "our investment." This is only possible through a culture of high trust and "front stabbing"—brutally honest, direct debate about a deal's merits. This prevents passive aggression and ensures collective ownership.

Ken Griffin warns startups against direct, head-on competition with industry giants, stating, "you're going to lose." To succeed, you must find an asymmetrical advantage—operating "under the radar" or solving niche problems incumbents ignore. Citadel initially did this by hiring unconventional quantitative talent.

To build immediate trust and demonstrate value, QED partners engage with founders by simulating a board-level conversation from the first meeting. This "pretend I'm your investor" approach showcases their expertise and builds rapport, proving their founder-friendliness rather than just promising it.

Sequoia Won Citadel Deal By Pitching Tech Expertise, Not Finance Knowledge | RiffOn