Amit Vasudev / Earl Grey Capital

Amit Vasudev is a Co-Founder of Earl Grey Capital, an early stage fund that’s deployed across 100+ companies since launching in 2020.

Amit’s background is as a founder. He, 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.

Early on it was classic spray-and-pray with $100K checks. It tracked well, but they soon felt the flaws. Too broad. Not enough ownership. Not enough discipline on valuation.

Our conversation gets into how they’ve tightened the strategy: bigger checks with 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.”

The strategy is to go early before anyone’s paying attention, add value before asking for allocation, be honest about where you fit on the cap table. “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.”

Full episode below, or on Spotify / Apple Podcasts