BILLIONS – Details, episodes & analysis

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 Games

Today on BILLIONS, I’m sitting down with Harry Stebbings — the guy who turned a microphone in his bedroom into a $400 million venture fund.

He started The Twenty Minute VC as a teenager, and it became the place where the smartest founders of unicorns, and the world’s best investors all lined up to talk.

In this episode, Harry opens up about the deals he missed, the unicorns he caught early like Linktree and Tripledot, and how he turned content into capital.

If you’ve ever wondered how storytelling can build an empire, this is the playbook.

TIMELINE :

00:00:00 - 00:03:36 : Turning content into deal flow: The 20VC playbook
00:03:36 - 00:06:26 : From obsession to insight: How Harry predicted the future of VC
00:06:26 - 00:09:03 : Why most VCs suck at content—and how to stand out
00:09:03 - 00:12:48 : $400M facepalms: Inside Harry’s biggest investment regrets
00:12:48 - 00:17:35 : What separates great founders from everyone else
00:17:35 - 00:27:50 : Building the fund: Raising $8M from a podcast mic to $400M
00:27:50 - 00:36:22 : The underrated VC weapon: High-impact content as revenue driver
00:36:22 - 00:44:52 : Going public vs staying private: Who really wins?
00:44:52 - 00:58:52 : Charisma, crisis, and credibility: The raw truth about founder DNA
00:58:52 - 01:04:23 : Bullish on Europe: Beating Silicon Valley at its own game

REFERENCES :

- Peter Thiel

- Michael Moritz

- Alex Bouaziz (Deel)

- Christina Cacioppo (Vanta)

- Peter Fenton

- Daniel Ek

- Nick Storonsky 

- Marc Benioff

- Guy Kawasaki

- Steve Ballmer

- Thibault Elziere 

- Torsten Reil

- Mati Staniszewski

- 20VC

- Project Europe

- a16z

Today on BILLIONS, I’m sitting down with Nicolas Dessaigne — the engineer who bet everything on one idea, built Algolia into a multi-billion-dollar global search platform… and then did something almost no founder ever does:

he walked away.

Nicolas went from obsessing over one company for a decade… to shaping hundreds of startups every year as a General Partner at Y Combinator, the most influential accelerator on the planet.

In this episode, we will talk about why he left Algolia, how founders should think about liquidity, what really happens inside YC, and why the next wave of AI will be bigger — and stranger — than anyone expects.

If you’ve ever wondered what happens when a unicorn founder switches sides and becomes the one choosing the next unicorns… this conversation will change the way you think about ambition, ego, and the future of startups.

TIMELINE :

00:00:00 - 00:06:39: Why I walked away from my billion-dollar company

00:06:39 - 00:11:46: The brutal truth about founder liquidity and secondary sales

00:11:46 - 00:17:35: Inside YC's investment strategy and partner dynamics

00:17:35 - 00:22:31: How to spot the next unicorn founders before anyone else

00:22:31 - 00:28:02: The AI company revolution happening right now

00:28:02 - 00:34:50: Why your kids will outperform you with AI superpowers

00:34:50 - 00:40:47: Robotics and the future of physical AI agents

00:40:47 - 00:46:09: The model wars - who's really winning the AI race

00:46:09 - 00:51:04: Why Google shocked everyone and OpenAI's real advantage

00:51:04 - 00:54:44: The counterintuitive way to find billion-dollar startup ideas

REFERENCES :

- Bryan Onel, Oneleet founder 

- François Chollet, ARC Prize founder

- Yann LeCun

- Y Combinator

Most marketers dream of having Gong’s billion dollar brand. But few realize that behind every courageous campaign, there’s an even more courageous marketer. In today’s episode of BILLIONS I have the pleasure to interview Udi Ledegor, chief evangelist and former CMO at Gong.

I’ve known Udi for a few years now, and not only I’ve always been super impressed by how Gong’s brand is so unique but also by how great of a piano player Udi is!

Udi thanks a lot for joining me today!

Timeline :

00:00:00 - 00:01:00 : How gong became a billion-dollar brand (before the revenue)

00:01:00 - 00:04:38 : Punching above your weight: gong’s billboard strategy playbook

00:04:38 - 00:07:26 : The viral formula: what makes content spread like fire

00:07:26 - 00:11:26 : Gong labs content series: 1.5 people, zero excuses, maximum impact

00:11:26 - 00:14:20 : Why content > distribution: rethinking roi the gong way

00:14:20 - 00:17:19 : Turning content into pipeline: metrics, gating, and reciprocity

00:17:19 - 00:21:44 : From free to unstoppable: scaling organic marketing and thought leadership

00:21:44 - 00:27:04 : Super bowl ad on a startup budget: the story behind gong’s boldest move

00:27:04 - 00:35:21 : Going enterprise: how gong landed fortune 10 clients (and what changed)

00:35:21 - 00:49:38 : Retention, equity, and billion-dollar thinking as a non-founder exec

References :

• Courageous Marketing: The B2B Marketer's Playbook for Career Success by Udi Ledergor
• Kyle Lacy - CMO at Docebo
• Moneyball: The Art of Winning an Unfair Game by Michael Lew
• Crossing the Chasm by Geoffrey Moore - Classic business book about bridging early adopters to early majority
• Made to Stick by Dan Heath and Keith Heath - About principles of viral content and what makes things memorable
• The Tipping Point: How Little Things Can Make a Big Difference by Malcolm Gladwell - About what becomes a trend and viral phenomena
• Influence, New and Expanded: The Essential Guide to the Psychology of Influence and Persuasion in Everyday Life by Robert Cialdini - Psychology book about persuasion, specifically reciprocity effect

Today on BILLIONS, I’m sitting down with Arthur Waller, one of the sharpest French founders of his generation.

He sold his first company to Booking.com in his twenties — and instead of retiring, he came back to build Pennylane, a fintech that turned accountants from enemies into growth partners and became one of europe fastest-growing unicorn.

In this episode, we will discuss how six co-founders actually share power, what founders get wrong about fundraising terms and dilution, and what Arthur thinks about secondaries, freedom, and building a company that lasts twenty years.

If you want to understand what it really takes to scale, cash-out without selling out, and keep your ambition alive after success - then this episode is for you!

TIMELINE :

00:00:00 - 00:03:37 : First exit to Booking.com at 25 - the $80M deal structure

00:03:37 - 00:08:08 : Why the earn-out worked and 3.5 years at Booking

00:08:08 - 00:13:58 : Coming back stronger - choosing accounting as the next battlefield

00:13:58 - 00:18:12 : Seven co-founders sharing power and equity splits

00:18:12 - 00:24:01 : Fundraising strategy - diluting less than 10% early rounds

00:24:01 - 00:30:34 : Making accountants allies instead of enemies

00:30:34 - 00:36:08 : European expansion vs US market strategy

00:36:08 - 00:41:56 : Secondary transactions - $30M for employees, $70M for founders

00:41:56 - 00:46:38 : Staying private vs going public - the Stripe model

00:46:38 - 00:48:43 : The one advice for young founders

REFERENCES :

- Booking.com 

- Felix Blossier

- Tancrède Besnard 

- Alexandre Roquoplo

- Charles-Philippe Letellier

- Brian Halligan

- Partech

- PayFit

- Alan

- Qonto

- Indy

- QuickBooks

- NetSuite

- Salesloft

- Outreach

- Sequoia Capital

- Carta

- Cegid

- Shine

- Stripe

- Revolut

- Andreessen Horowitz (a16z)

Today on BILLIONS, I'm sitting down with Stan Massueras - the guy who's scaled companies to billion-dollar valuations not once, but multiple times.

He was one of Facebook's first European sales hires in 2008, then helped Twitter expand across the continent and after that, he spent six years scaling Intercom to unicorn status.

Now he's doing it all over again at ElevenLabs, the voice AI company that went from zero to $6B+ in under three years.

In this episode, we'll dig into what it actually looks like to scale sales, how selling AI is fundamentally different from selling SaaS, and what Stan had to unlearn from the typocal Saas playbook to succeed at ElevenLabs.

If you want to understand what it takes to repeatedly win at the billion-dollar level - and what breaks inside companies growing this fast - this episode is for you.

Stan thanks for being here today!

TIMELINE :

00:00:00 - 00:01:17 : From Facebook to ElevenLabs: Meet the billion-dollar scaler  

00:01:17 - 00:05:21 : Why selling software in Europe breaks the US playbook  

00:05:21 - 00:10:10 : The AI sales revolution: Killing the SaaS sales hierarchy  

00:10:10 - 00:13:56 : No middle management, no titles: How ElevenLabs runs flat and fast  

00:13:56 - 00:18:34 : Inside ElevenLabs’ $300M ARR sprint: Remote, lean, relentless  

00:18:34 - 00:22:47 : Mastering two motions: creative tools vs enterprise AI  

00:22:47 - 00:26:39 : Expanding from voiceovers to luxury AI agents  

00:26:39 - 00:30:54 : Taking updates seriously: enterprise upsell strategy and product marketing  

00:30:54 - 00:34:22 : Deepfake fears & Hollywood deals: AI voice ethics in action  

00:34:22 - 00:40:45 : Billion-dollar impact: AI accessibility, ALS, and global translation  

00:40:45 - 00:54:44 : Career regrets, recruiting lessons, and the real rocket-ship mindset 

REFERENCES :

- Sheryl Sandberg 

- Jason Fried - (Basecamp) 

- Carlos Reina 

- Guillaume Kabane

- Dave Gerhardt

- Arthur Waller (PennyLane)

- Harry Stebbings (20VC)

- Matthew McConaughey

- Bruce Springsteen

- Mark Zuckerberg 

- Skyblog (Note: Mostly inactive now; legacy site)

- Lemlist

- Deel

- Salesforce

- Oracle

- Canva

- Figma

- Zendesk

- Lovabl

- Synthesia

- HeyGen

- Coinbase

- Sales Navigator (LinkedIn)

- Y Combinator

- Station F

- SaasStock

Today on BILLIONS, I’m sitting down with Noah Kagan — the guy who got fired from Facebook before it was worth a trillion… and turned that loss into the biggest comeback story in online business.

He went from losing a fortune on paper to building AppSumo, a $100 million-a-year bootstrapped empire - all without raising a single dollar of VC money.

Noah, thanks a lot for being here!

TIMELINE

00:00:00 - 00:02:10 : The trillion-dollar miss at Facebook

00:02:10 - 00:06:43 : Leadership lessons from Mark Zuckerberg's billion-dollar rejection

00:06:43 - 00:12:13 : The lifetime deal dilemma destroying software value

00:12:13 - 00:19:40 : Why most entrepreneurs never take action

00:19:40 - 00:26:49 : Building discipline through small daily choices

00:26:49 - 00:33:10 : The scary reality of AppSumo's uncertain future

00:33:10 - 00:42:09 : Community quality crisis in the AI era

00:42:09 - 00:48:58 : Testing new models before it's too late

00:48:58 - 00:57:07 : Hiring secrets for bootstrap businesses

00:57:07 - 01:04:29 : Finding contentment beyond the billion-dollar dream

REFERENCES

- Mark Zuckerberg 

- Peter Thiel 

- Marc Andreessen

- Sean Parker

- Dustin Moskovitz

- Soleio 

- Bill Gates 

- Steve Jobs 

- Moody

- Christine Rogers

- Jesse Mecham – 

- Ayman Al-Abdullah

- Reid Hoffman

- Million Dollar Weekend by Noah Kagan

- AppSumo  

- TidyCal  

- Airbnb   

- Asana  

- Lemlist   

- Reclaim

- Bolt

- Hostinger

- Emergent

- Pika  

- YNAB

- Vercel

- Tabby  

- YC

Today on BILLIONS, I'm sitting down with Cornelius Schmahl — a college dropout who keeps finding his way into billion-dollar outcomes.

At 23, Uber sent him to markets nobody wanted. South Africa. Uganda. Ghana. No playbook. Figure it out or fail.

By 27, he was running Uber Russia. One problem: Yandex was winning.He helped engineer a 3.7 billion dollar merger — then walked away from operating entirely. Started writing angel checks. Lime. Liquid Death. BillionToOne.Climeworks. Four bets. Four unicorns.

What does this guy see that everybody else misses?

Cornelius thanks a lot for being on BILLIONS.

TIMELINE :

00:00:00 - 00:03:58: From college dropout to Uber's unwanted markets

00:03:58 - 00:09:02: The brutal reality of launching Uber in hostile territories

00:09:02 - 00:16:06: Engineering violent price cuts and discovering the utilization game

00:16:06 - 00:25:47: The Russia war - infiltrating Yandex and burning millions strategically

00:25:47 - 00:32:35: The $3.7 billion merger and why timing beat fundamentals

00:32:35 - 00:44:26: Angel investing reality check - why unicorns on paper don't pay bills

00:44:26 - 00:52:28: The three-step framework that creates billion-dollar companies

00:52:28 - 00:58:52: From billionaire dreams to therapy - the consciousness shift

00:58:52 - 01:01:48: Marc Benioff email scandal and building leverage through controversy

Today on BILLIONS, I'm sitting down with Ross Andrew Paquette, the CEO who broke every Silicon Valley rule: he bought OUT his investors before buidling a 1.7 billion dollar empire. He founded Maropost in 2011, and by 2016, it ranked #7 on the PROFIT 500 as one of Canada's fastest-growing companies.Ross, thanks a lot for being here!

TIMELINE :

00:00:00 - 00:01:12 : From lifestyle business to a $1.7 billion empire

00:01:12 - 00:03:32 : The 75% ebitda secret and why growth at all costs is a trap

00:03:32 - 00:05:37 : Founder mode and signing clients every single day

00:05:37 - 00:08:18 : Why "experienced" executives fail and the return to young and hungry teams

00:08:18 - 00:12:14 : The $37 million wire transfer to buy out investors

00:12:14 - 00:16:18 : Why advisory boards beat professional investor boards every time

00:16:18 - 00:26:48 : The contrarian ipo strategy for australia and canada

00:26:48 - 00:33:08 : Why you should never take vc money if you want to keep your drive

00:33:08 - 00:51:56 : The brutal reality of m&a and culture integration

00:51:56 - 01:00:48 : Two metrics that actually matter: revenue and profit

REFERENCES :

- Adam Robinson 

- Larry Ellison 

- Patrick Campbell 

- Elephant & Highland Europe 

- Summit, Insight, TA 

- Shopify Plus

- Atlassian 

- Oracle 

- Attentive & Klaviyo .

- Groq 

- Neto & Retail Express - Australian companies acquired by Maropost 

- Findify - Swedish search/merchandising company acquired by Maropost

- ProfitWell & Baremetrics

- Stripe

Today on BILLIONS, I'm sitting down with Antoine Le Nel the guy who spent 7 years scaling Candy Crush into one of the most addictive products ever created... then walked away to go kill traditional banking.

At King, he helped turn a mobile game into a machine that prints billions. When Activision bought them for $5.9 billion, he could've stayed forever.

Instead, he joined Revolut in 2021 — right as most fintech were collapsing. Three years later? $75 billion valuation. $4 billion in revenue. 65 million customers.

His secret? Ignoring everything Silicon Valley preaches about growth.

Antoine, thanks for being here!

TIMELINE :

00:00:00 - 00:01:07 : Scaling Candy Crush to a $5.9 billion exit

00:01:07 - 00:03:38 : How to avoid the "one-hit wonder" trap in gaming

00:03:38 - 00:06:54 : The Facebook hack that reached 70% of global users for free

00:06:54 - 00:10:35 : Activision's acquisition and the reality of pre-ipo stock options

00:10:35 - 00:16:59 : Why Revolut prioritizes unit economics over venture capital hype

00:16:59 - 00:21:00 : Decoding the exponential LTV curve that defies banking logic

00:21:00 - 00:30:13 : Charging for the card: A masterclass in buying user engagement

00:30:13 - 00:46:01 : Killing the middleman: Revolut's secret to autonomous, lean teams

00:46:01 - 00:54:08 : From ROI to F1: Building a generational brand with Audi

00:54:08 - 01:00:53 : The uncomfortable truth about brand value and engineering mindsets

REFERENCES:

- ⁠Mark Zuckerberg⁠ 

- Nik Storonsky

- Patrick Collison

- King Digital Entertainment 

- Activision Blizzard 

- Stripe 

- Booking.com 

- Primavera Sound 

- Como football team

- Audi F1

- Drive to Survive

- Revolut Business