How the next generation of billion-dollar investors think - Jonathan Userovici

Billions • January 16, 2026 • Solo Episode

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Today on BILLIONS , I’m sitting down with one of Europe’s youngest General Partners — Jonathan Userovici from Headline , a global venture firm that spots the next billion-dollar companies before anyone else. Jonathan’s already backed some of Europe’s fastest-growing unicorns and he’s quietly redefining what it means to invest with both data and instinct . In this episode, I want to talk about the behind-the-scenes of fundraising, how he spots future billion-dollar founders, and where the biggest opportunities in AI are. And of course, we’ll talk cash — secondaries, cap tables, and the real economics behind staying hungry once you’re rich on paper. If you’ve ever wondered how the next generation of billion-dollar investors think — this episode is your blueprint. Jonathan, thanks a lot for joining! TIMELINE : 00:00:00 - 00:01:09 : The rise and fall of unicorns 00:01:09 - 00:03:42 : Backing founders who build long-term compounders 00:03:42 - 00:08:48 : Speed of iteration: The ultimate founder advantage 00:08:48 - 00:12:46 : Unicorn playbook: 00:12:46 - 00:20:35 : Deal flow secrets: Scoring, signals, and global sourcing with AI 00:20:35 - 00:26:34 : Headline’s global roadmap strategy and industry watchlist 00:26:34 - 00:34:08 : The true trillion-dollar AI opportunity 00:34:08 - 00:42:20 : Secondaries, incentives, and cash: De-risking without losing hunger 00:42:20 - 00:49:12 : VC exits, liquidation prefs, and cap table traps to avoid 00:49:12 - 00:55:40 : Valuation games in the AI world REFERENCES : - Arthur Mensch - Loïc Soubeyrand - Daniel Nathan - Christian Miele - Arthur Waller - Mistral AI - Black Forest Labs - Bioptimus - Harvey - Legora - Lovable - Grok - Swile - Pennylane - Homa Game s

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