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

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 :

- Harvey

- Legora

- Lovable

- Grok

- Swile

- Pennylane

- Homa Game s

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