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

Denne episoden er hentet fra en åpen RSS-feed og er ikke publisert av Podme. Den kan derfor inneholde annonser.

Episoder(31)

How to redesign an $800M-a-year software giant for the AI era - Dan Rogers [Asana]

Today on BILLIONS, I'm sitting down with Dan Rogers, CEO of Asana, to discuss AI agents, the future of SaaS, and what comes after the chatbot.Dan took over an established software business with around...

29 Sep 37min

From 100 sales meetings a week to $600M ARR - Carles Reina [ElevenLabs]

Today on BILLIONS, I'm sitting down with Carles Reina, the first investor and fourth employee at ElevenLabs, to unpack the AI bubble, the rise of Chinese models, and Europe's fight to stay in the race...

15 Sep 50min

Why the "SaaS is dead" narrative is completely wrong - Aaron Levie [box]

Today on BILLIONS, I'm sitting down with Aaron Levie, the co-founder and CEO of Box, who has rapidly transitioned his enterprise platform from a pure SaaS model into a cutting-edge playground for auto...

9 Jul 34min

Why focus on only ONE product built a $1B super-brand (on just $6,000) - Pete Maldonado [Chomps]

Today on BILLIONS, I'm sitting down with Pete Maldonado, the visionary who took $6,000, one failed food venture behind him, and zero institutional backing and built a dominant food empire that's appro...

2 Jul 52min

The man who built a bank for people banks don't want - Jason Wilk [Dave]

On this episode of BILLIONS, I'm sitting down with Jason Wilk, four-time founder and CEO of Dave, the neobank built to take on the predatory overdraft fees that quietly bleed billions a year from the ...

25 Jun 47min

Why the world’s biggest tech companies may never IPO again - Peter Singlehurst [Baillie Gifford]

On this episode of BILLIONS, I'm sitting down with Peter Singlehurst, who built the private companies team from scratch at legendary investment firm Baillie Gifford, deploying billions into more than ...

18 Jun 58min

Why high valuations are secretly killing tech unicorns — Martino Cadoni [Deepl]

On this episode of BILLIONS, I'm sitting down with elite finance operator Martino Cadoni, current CFO of DeepL (one of Europe's leading AI companies) and the veteran strategist behind one of Central E...

12 Jun 58min

How a $75 sneaker bot became a $300M/Month financial engine - Steven Schwartz [Whop]

Is traditional international banking officially obsolete?On this episode of BILLIONS, I'm sitting down with Steven Schwartz, co-founder of Whop, the internet marketplace that is quietly constructing a...

4 Jun 53min