Billions How the next generation of billion-dollar investors think - Jonathan Userovici
Jan 16, 2026
Jonathan Userovici, a young General Partner at Headline, discusses his innovative approach to early-stage investing. He reveals how he identifies billion-dollar founders through traits like speed of iteration and strategic thinking. The conversation delves into the unique opportunities within the AI landscape and the importance of balancing quick investments with solid due diligence. Jonathan also breaks down the economics behind secondaries and cap tables, offering insights on maintaining founder motivation while navigating financial complexities.
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Back Founders Aiming For Compounders
- Jonathan Userovici prioritizes founding teams that build long-term compounders rather than chasing quick unicorn status.
- He looks for companies that can scale internationally and reach sustained revenue, not just paper valuations.
Iterate Fast, Learn Faster
- Test and ship constantly; speed of iteration is the key founder advantage according to Jonathan Userovici.
- Iterate on product, hiring, and GTM fast and accept mistakes quickly to learn and double down on winners.
Evaluate Founders Before Fundraise
- Jonathan describes tracking founders months before they fundraise to assess their iteration pace and product velocity.
- He watches how founders change pitches and double down between first interaction and final round.