S3E11: From Building Clearbit to Backing Builders – Amit Vasudev on Earl Grey Capital

“Imagine you’re Nike and the best NBA players are like, I don’t really need shoes anymore. That’s exactly what’s happening with venture capital.” The best founders used to say “I have to raise money.” Now they’re saying “I don’t want to raise a dollar.” One engineer with AI tools can replace a team of 20. Companies can iterate to product-market fit in months instead of years.

Which means the middle of venture, those $50-500M funds, is about to have a very bad decade. Too big to write seed checks. Too small to deploy the $100M+ needed for late-stage infrastructure plays.

Amit, Alex, and Matt spent a decade building Clearbit from scratch to a 9-figure exit to HubSpot. Every major B2B company from Stripe to Airtable to Notion used their products early on. Naval Ravikant was one of their angel investors. When they started making their own angel investments, Naval encouraged them to start a fund. So they did.

They’ve deployed across 100+ companies since launching Earl Grey in 2020. Early on it was classic spray-and-pray with $100K checks. It tracked well, but they’d soon feel the flaws of the strategy. Too broad. Not enough ownership. Not enough discipline on valuation.

They’ve since tightened the strategy: bigger checks ($300K-$1M), ownership targets of 1.5-3%, typically the second-biggest check after the lead or helping recruit the lead. Higher concentration with more discipline. They took the data from their early portfolio and iterated like founders building a product.

“Fund size is your fund strategy. When you go after $50M AUM, your sourcing funnel shuts off. You get mediocre deals.”

Identify what’s broken. Ship a new version. Measure. Iterate. Most emerging managers raise their first fund, then immediately start optimizing for fund size and management fees. Amit’s optimizing for what actually generates returns.

The portfolio tells the story. They were early into CrewAI, where Amit convinced the founder João Moura to start the company after Clearbit’s acquisition by HubSpot. They’re consistently in competitive rounds and consistently winning allocation. Not by pitching, by doing the work.

“Don’t talk about it, just do it. Help them think through the company, the product itself, help them find their co-founder or founding team members. We’ve done all of that many times without asking for a thing back.”

The strategy is brutally simple: go early before anyone’s paying attention, add value before asking for allocation, be honest about where you fit on the cap table. They invest in technical founders and second-time founders building in spaces where you need to understand the weeds, where surface-level pattern matching doesn’t work.

“If we’re the only check or we’re the biggest check, there’s actually a problem. You’re not arranging your cap table right. For example, you should have some people who are really good for the brand, some who have time and effort to help you. Know what you’re getting from each investor.”

The pattern across our conversation was that Amit isn’t following a playbook, he’s building one through constant iteration. The early portfolio taught him what doesn’t work. The current strategy is testing what does, and they’re gathering the data points that will inform where they take it next.

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