Explore every episode of the podcast BILLIONS
| Title | Pub. Date | Duration | |
|---|---|---|---|
| How the next generation of billion-dollar investors think - Jonathan Userovici [Headline] | 16 Jan 2026 | 00:55:45 | |
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 : 00:01:09 - 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 | |||
| Inside the playbook behind the podcast turned into a $400,000,000 venture fund - Harry Stebbings | 05 Jan 2026 | 01:04:46 | |
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. - Alex Bouaziz (Deel) - 20VC - a16z | |||
| From building a multi-billion dollar company to General Partner at the world’s top startup incubator | 28 Dec 2025 | 00:54:44 | |
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.
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 - François Chollet, ARC Prize founder | |||
| The CMO who built a billion-dollar brand - and what he got in return - Udi Ledergor | 21 Dec 2025 | 00:49:38 | |
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 :
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| From selling his company to Booking.com to building a fintech unicorn! - Arthur Waller [Pennylane] | 23 Jan 2026 | 00:48:43 | |
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
- Partech - PayFit - Alan - Qonto - Indy - NetSuite - Outreach - Carta - Cegid - Shine - Stripe - Revolut | |||
| Growing to billion dollar valuation multiple times with Stan Masueras | 30 Jan 2026 | 00:54:55 | |
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 : - Jason Fried - (Basecamp) - Harry Stebbings (20VC) - Skyblog (Note: Mostly inactive now; legacy site) - Lemlist - Deel - Oracle - Canva - Figma - Zendesk - Lovabl - HeyGen - Coinbase | |||
| From losing $1B to running a $100m per year business - Noah Kagan [AppSumo] | 06 Feb 2026 | 01:04:29 | |
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
- Soleio - Moody - Jesse Mecham – - Million Dollar Weekend by Noah Kagan - AppSumo - TidyCal - Airbnb - Asana - Lemlist - Reclaim - Bolt - Emergent - Pika - YNAB - Vercel - Tabby - YC | |||
| The college dropout who keeps ending up in billion-dollar exits - Cornelius Schmahl | 13 Feb 2026 | 01:01:48 | |
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 | |||
| The CEO who turned down VCs, bought back his company, and built a $1.7B SaaS empire - Ross Andrew Paquette | 20 Feb 2026 | 01:00:48 | |
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
- Oracle - Groq - Neto & Retail Express - Australian companies acquired by Maropost - Findify - Swedish search/merchandising company acquired by Maropost - Stripe | |||
| The growth playbook behind Revolut's $100B+ growth engine - Antoine Le Nel [Revolut] | 27 Feb 2026 | 00:56:55 | |
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: - Stripe - Audi F1 | |||
| The man who helped OpenAI to go from millions to billions in revenue - Zack Kass [Open AI] | 06 Mar 2026 | 00:53:29 | |
Today on BILLIONS, I'm sitting down with the man who had the hardest sales job in Silicon Valley history: Zack Kass. Before ChatGPT was a household name, it was just a research lab. Zack was Head of Go-To-Market. He joined when OpenAI was around a hundred people doing two million in revenue. His job? Sell human-level intelligence to Fortune 500 executives who didn't even know what a token was. He built the playbook for Microsoft. For Coca-Cola. He turned a nonprofit lab into an eighty billion dollar superpower. Then he walked away. Zack, thanks a lot for being here! TIMELINE 00:00:00 - 00:06:34 : Joining OpenAI as the first sales person 00:06:34 - 00:09:47 : The early GPT-3 wrapper ecosystem 00:09:47 - 00:11:03 : Strategy behind ChatGPT's development 00:11:03 - 00:16:45 : The chat interface decision and market response 00:16:45 - 00:21:04 : ChatGPT's explosive growth and company atmosphere 00:21:04 - 00:26:45 : Lessons from viral growth and Microsoft partnership 00:26:45 - 00:30:21 : Scaling challenges and the "bigger boat" moment 00:30:21 - 00:33:44 : Personal burnout and health crisis 00:33:44 - 00:37:29 : AI as humanity's last invention 00:37:29 - 00:45:21 : Technology, inequality, and policy failures 00:45:21 - 00:48:35 : Global AI competition and geopolitics 00:48:35 - 00:50:18 : AI's potential to solve major problems 00:50:18 - 00:54:33 : The next renaissance and education transformation REFERENCES - "The Next Renaissance: AI and the Expansion of Human Potential" by Zach Cass - Lilt - Scale AI - Jasper - Harvey - Waymo - Prenuvo - DeepSeek - OpenAI - RLHF - CRISPR - Jaws | |||
| From selling startups to Google to backing multibillion‑dollar AI winners - Anish Acharya [a16Z] | 12 Mar 2026 | 00:55:21 | |
Today on BILLIONS, I'm sitting down with Anish Acharya. He sold his first company to Google. His second to Credit Karma — then stayed and helped scale their U.S. Card business to nearly a billion dollars in annual revenue. In 2019, Andreessen Horowitz made him a General Partner. Since then, he's led the Series A in Deel, which just hit a $17.3 billion valuation in October 2025. Most VCs have never operated anything. Anish built, scaled, sold, and then learned how to pick. Anish, thanks a lot for being here ! TIMELINE : 00:00:00 - 00:02:30 : Anish Acharya’s entrepreneurial journey 00:02:30 - 00:06:28 : Why 2008 and today are the most exciting times for founders 00:06:28 - 00:11:38 : The AI model competition and Google's comeback 00:11:38 - 00:14:50 : Why the "LLM wrapper" fear is no longer relevant 00:14:50 - 00:20:07 : Multi-model approach and the future of AI applications 00:20:07 - 00:24:01 : Learning from Credit Karma and the importance of winning 00:24:01 - 00:29:14 : Why paternalism kills products and going with human nature 00:29:14 - 00:35:28 : AI's human impact and why it's different from social media 00:35:28 - 00:42:45 : The future of coding, jobs, and why SaaS isn't dead 00:42:45 - 00:55:21 : Investing in Deel, AI companionship, and what it costs to win REFERENCES | |||
| Building Odoo's American war machine - Wilfried Juncker [Odoo] | 19 Mar 2026 | 00:54:29 | |
Today on BILLIONS, I'm sitting down with Wilfried Juncker. He's the Managing Director for Odoo's Americas a Belgian software unicorn that just hit a €8 billion valuation. Under Wilfried's watch, Odoo's Americas operation exploded from 35 people in 2016 to over 950 in America only. In this episode, we're digging into how Wilfried built Odoo's American war machine, what it takes to conquer a new market from scratch, and how he's fighting high SMB churn while scaling at breakneck speed. While SAP and Oracle charge millions for ERP, Odoo's open-source model is democratizing enterprise software and Wilfried built the Americas war machine that's making it happen. Wilfried, thanks a lot for being here! TIMELINE : 00:00:00 - 00:01:05 : Odoo's explosive growth from 70 to 2,000 employees 00:01:05 - 00:02:30 : The early days and Wilfried's journey at Odoo 00:02:30 - 00:05:25 : Entering the US market with channel partners strategy 00:05:25 - 00:09:25 : Open source model and freemium conversion tactics 00:09:25 - 00:14:20 : Building the partner ecosystem and revenue sharing 00:14:20 - 00:18:07 : Scaling partner relationships and management approach 00:18:07 - 00:24:12 : Hiring and retention philosophy - promote from within only 00:24:12 - 00:27:14 : Industry specialization vs size-based team structure 00:27:14 - 00:34:32 : Managing SMB churn while maintaining growth 00:34:32 - 00:42:17 : Demo-first culture and bottom-up sales approach 00:42:17 - 00:48:20 : Resource allocation and offline marketing strategy 00:48:20 - 00:52:27 : Unconventional customer acquisition tactics 00:52:27 - 00:54:29 : Building local ecosystems and final thoughts REFERENCES : - SAP - Sage - Epicor - Infor - HubSpot - GitHub - Lemlist - Clay - Lucia - NPR - NASA | |||
| The 15-day pivot that saved a $1.3B company - Des Traynor [INTERCOM] | 28 Mar 2026 | 00:55:56 | |
Today on BILLIONS, I'm sitting down with Des Traynor, co-founder of Intercom. In 2023, his company was stuck at 10% growth. Customer service teams were shrinking. The old model was dying. So he did something radical: he launched an AI agent priced at $0.99 per resolved conversation. Not per seat. Per outcome. The result? Growth doubled to 25%. $343M in revenue. And a complete reinvention of a $1.3B company in 18 months. TIMELINE : 00:00:00 - 00:01:02 : Des Traynor - Intercom 00:01:02 - 00:05:22 : The $1.3 billion bet on AI : moving 15 days after ChatGPT launched 00:05:22 - 00:09:08 : Why building AI is not building SaaS 00:09:08 - 00:12:51 : The "torture test" for engineering reliability 00:12:51 - 00:20:14 : Developing the "white smoke" moment for product 00:20:14 - 00:25:16 : Defining what "good" looks like in AI 00:25:16 - 00:34:53 : The Blockbuster warning: Adapt or die 00:34:53 - 00:40:27 : Killing hallucinations with actor-critic logic 00:40:27 - 00:48:55 : Outcome-based pricing and the future of CRM 00:48:55 - 00:55:56 : The end of frontline customer service jobs REFERENCES : | |||
| Never wrote a line of code, now a $6.6B unicorn : the vibe coder - Lazar Jovanovic [Lovable] | 02 Apr 2026 | 01:01:01 | |
Lazar Jovanovic is the world's first official "Vibe Coding Engineer." Working at Lovable (the AI startup that hit $100M ARR in just 8 months) Lazar is proving that the future of software engineering isn't about syntax; it's about taste and intent.In this episode, we dive into how Lazar ships production-grade apps for a $6.6B unicorn without writing a single line of manual code. We discuss the "SaaS-pocalypse," why ignorance is a superpower in the AI era, and how you can transition from a traditional role to a Vibe Coder.TIMELINE : 00:00 - Meet the world's first "vibe coding" engineer01:06 - Why "not knowing how to code" is your new superpower04:43 - Is software maintenance dead in the age of AI?09:15 - The Lovable story: hitting $100M ARR in 8 months15:42 - The end of bootstrapping? Vibe coding vs. the old way24:16 - SaaS-pocalypse: the future of software interfaces29:47 - Beyond code: the only metrics that matter for AI products37:01 - Will enterprises ever adopt AI-generated code?44:35 - The "Aladdin & Genie" trick for mastering AI prompts56:05 - How to become a vibe coder (no permission required)REFERENCES : | |||
| $0 to 2 Unicorns: bootstrap vs $250M VC - Jason Cohen [WP Engine] | 09 Apr 2026 | 01:02:17 | |
On this episode of BILLIONS, I’m sitting down with a legendary architect of the SaaS world: Jason Cohen, founder of WP Engine and Smart Bear.Jason has "cracked the code" twice, using two diametrically opposite strategies:The Pure Bootstrap: He built Smart Bear to millions in profit with zero outside funding, eventually leading to a unicorn valuation.The VC War Machine: He raised $250 million from Silver Lake for WP Engine, scaling it to $400M in revenue and 200,000 customers by 2024.This is a masterclass in capital efficiency. Whether you are a solo-founder or a venture-backed CEO, Jason’s framework for building "enduring companies" is the raw truth you won't hear in most boardrooms.TIMELINE : 00:00 - Why AI products almost never work01:20 - Switching from Bootstrapping to $250M VC rounds04:51 - The SaaS-pocalypse: The truth behind HubSpot & legacy decline09:30 - Solving legacy problems with AI-powered search16:17 - Experts vs. Muggles: The three categories of AI products21:55 - Why evergreen insights beat AI hype26:06 - The Power Move: Firing yourself as CEO to save the company34:01 - The "301 Redirect" strategy for management transitions40:48 - Hidden multipliers and the labor of love44:02 - The Raw Truth: Post-exit depression and infinite optionality58:25 - Redefining identity: Leveraging accumulated wisdomREFERENCES : | |||
| $0 to $100M ARR in 3 months: The AI plan to run every company - Ben Cera [CloudKitchens & Polsia] | 16 Apr 2026 | 00:58:19 | |
On this episode of BILLIONS, I’m sitting down with Ben Cera, the man who helped Travis Kalanick (Uber Founder) build CloudKitchens, and who is now building the "God Mode" for startups: Polsia. Polsia is an AI that builds and runs companies autonomously. No employees, no meetings, just 24/7 execution. Ben is currently at a $6M annual run rate with a 30% week-on-week growth and he plans to hit $100M ARR in just 3 months. If you want to understand how AI agents are replacing the traditional SaaS model and how "Product-Market Fit" has become a search problem, this is your masterclass. In this episode, we break down:
TIMELINE : 00:00 "Click a button, get a company": The vision for Polsia 01:12 Building with Travis Kalanick: The CloudKitchens masterclass 04:45 The $100M ARR Plan: How to scale an AI company in 90 days 09:30 Why Product-Market Fit is just a "Search Problem" 15:10 The SaaS-pocalypse: Replacing legacy software with AI agents 22:40 How Polsia finds demand and builds products autonomously 31:15 The Meta Ads Strategy: Scaling from $10/day to millions 38:50 Why "Taste" is the only human skill left in the AI era 45:10 Influencer-led distribution: The new "Billion-dollar" funnel 53:05 Ben’s advice for founders: Stop building for others, build for yourself REFERENCES | |||
| McKinsey's AI leader moved to head a $2B AI workforce - Matthew Fitzpatrick [Invisible] | 28 Apr 2026 | 00:48:39 | |
Is the traditional SaaS model officially dead ? On this episode of BILLIONS, I’m sitting down with Matthew Fitzpatrick, the man Fortune 500 CEOs called when they didn’t know what to do with AI. Matthew walked away from one of the most prestigious roles in tech, leading 1 000 engineers at McKinsey’s QuantumBlack Labs to lead Invisible Technologies. Invisible is the "invisible" engine behind the AI revolution. They don't just build software; they provide the RLHF (Reinforcement Learning from Human Feedback) and the data that trains the models the entire world is building on. With $100M raised at a $2B+ valuation, Matthew is proving that the future isn't in selling tools, but in selling outcomes. In this masterclass, we break down:
TIMELINE : 00:00 The data bottleneck: Why Enterprise AI is currently "stuck" 01:01 Why McKinsey’s AI chief left to lead a $2B unicorn 02:33 The "Four Platforms": How Invisible actually works 05:58 SaaS vs. Outcomes: The pricing model of the future 09:19 Why the "AI Bubble" reality check is coming 15:12 The "Capability Gap" holding back the Fortune 500 22:15 RLHF & Data: Building the workforce behind the major models 31:42 "Process is Code": The new architecture for billion-dollar companies 41:10 Matthew’s advice for founders: Don't just build a "wrapper" 48:20 The future of the "Invisible" empire REFERENCES : | |||
| Creating a $140B market: The secondary market masterclass - Larry Aschebrook [G Squared] | 30 Apr 2026 | 00:56:12 | |
Today on BILLIONS, I'm sitting down with Larry Aschebrook, the guy who invented a market that Wall Street didn't think existed. Larry started personally buying shares in Twitter and Uber on the side and he realized: there are thousands of employees sitting on life-changing paper gains, with zero liquidity, waiting for companies that might never IPO. So in 2011, he quit his safe university job and launched G Squared, a fund to solve that problem. Nobody took him seriously. The secondary market was "taboo." Companies thought selling shares meant you were failing.Today, he manages $5 billion. He turned a $150M Spotify bet into $1 billion. He made $800M on Coursera. And the market he built is now worth $140 billion a year. Larry, welcome to BILLIONS.TIMELINE : 00:00 : The psychology of the secondary market pioneer. 01:13 : Quitting a decade-long career for a "ghost" market. 03:23 : The Hustle: Cold-calling alumni for early Twitter and Uber shares. 05:41 : The $150 million Spotify bet and the $9M personal risk with zero collateral. 11:19 : Data Arbitrage: How Larry knew record labels were secretly buying Spotify. 15:43 : Scaling G Squared: From a $35 million pool to $7 billion AUM. 20:05 : Why DPI (Cash Back) is the only metric that matters, and why paper gains are a lie. 25:09 : The Scars: Learning from the "quick commerce" collapse and other losses. 37:09 : The Future: OpenAI, SpaceX, and the evolution of private liquidity. 53:12 : Advice for Founders: Why you must hire "grinders," not just pedigree. REFERENCES : | |||
| $100M ARR in 7 quarters: inside the $10B AI machine - Reggie Marable [Sierra] | 07 May 2026 | 00:48:09 | |
On this episode of BILLIONS, I’m sitting down with Reggie Marable, the Chief Revenue Officer at Sierra. Reggie’s path wasn't a straight line. He went from being a professional linebacker in the CFL to working in a Sprint call center, and eventually rose to become the Head of Sales for Slack North America. After years at Salesforce, he walked away to join Sierra as employee #23. Founded by Bret Taylor (former Salesforce Co-CEO) and Clay Bavor, Sierra has reached a $10B valuation and is on a path to $100M ARR in just seven quarters. Their secret? A business model that should terrify every legacy SaaS founder: Outcome-Based Pricing. In this masterclass, we break down:
TIMELINE : 00:00 – "If your dreams don't scare you...": The Muhammad Ali mindset. 01:17 – From the CFL to a Sprint call center: Reggie’s raw beginnings. 04:07 – The "fired" moment: How losing his job led to a total reinvention. 05:33 – The Salesforce & Slack era: Mentoring 200+ people and scaling Slack North America. 10:00 – Why Reggie left Slack to become employee #23 at Sierra. 12:23 – Outcome-based pricing: Why the "per seat" model is dying. 16:20 – AI agents in the wild: Real-world results for Cigna, Singtel, and Sonos. 19:00 – The resolution model: Charging for solved problems, not software access. 31:15 – Operational cadence: How a $10B startup manages its weekly rhythm. 35:50 – Hiring strategy: Why "humble and hardworking" beats high-ego sellers. 44:10 – The "diversity" advantage: Building high-performance teams through inclusion. 47:16 – Reggie’s final advice: "Success is a winding road." REFERENCES : | |||
| The fastest revenue engine in SaaS history: $5.4B run rate in 10 Years - Ron Gabrisko [Databricks] | 15 May 2026 | 00:51:34 | |
Is the traditional "per-seat" SaaS model officially obsolete? In 2016, Ron Gabrisko joined a startup with less than $1M in ARR. It was a company of 50 engineers and a product beloved by developers who had never even spoken to a sales rep. Ten years later, Databricks is a $134B giant doing $5.4B in ARR and they are still growing at a staggering 65% year-over-year. No CRO in history has built a revenue engine this fast, from this early a starting point. Ron didn't do it by following the standard Silicon Valley playbook; he did it by pioneering Consumption-Based Pricing and leveraging Open Source as the ultimate top-of-funnel engine. In this masterclass, we break down:
Timeline : 00:00 – The $5.4B Machine: Intro01:20 – Joining Databricks at sub-$1M ARR with 7 PhD founders04:12 – Selling to engineers: hiring "really technical sales folks"06:29 – Killing the SaaS Seat: consumption and the "most basic unit of value"09:22 – Net retention 130%: the multi-product open source strategy14:53 – Planning 65% YoY: the science of forecasting19:03 – Structuring 5,000+ sellers: verticalization and outcome-based selling29:11 – "Don't give your data to us": the data ownership philosophy33:54 – Usage-based vs value-based: why pricing is public on the website | |||
| From Revolut employee #3 to building a £5B energy giant - Alan Chang [Fuse Energy] | 22 May 2026 | 00:58:10 | |
On this episode of BILLIONS, I'm sitting down with Alan Chang, Co-Founder and CEO of Fuse Energy—a tech-driven energy company that has completely shattered the UK market. Alan was employee #3 and Chief Revenue Officer at Revolut. Instead of coasting on fintech success, he and his co-founder Charles took that hyper-growth playbook and weaponized it against traditional utility giants like British Gas and Octopus. In just three years, Fuse has exploded from £2M to £400M in annual revenue, achieving a £5 billion valuation. If you want to know how a lean tech team can buy a wind turbine, acquire a grid operator, and out-execute legacy multi-billion dollar incumbents, this is your blueprint. In this masterclass, we break down:
TIMELINE 00:00 – Leaving Revolut: Moving from a "solved" fintech industry to an unsolved energy crisis. 04:20 – The £1M Full-Stack MVP: Door-knocking for a wind turbine and securing an energy license. 09:33 – The Efficiency War: Why European energy costs are 3x higher than China's. 13:31 – Controlling the Grid: Why Fuse is actively acquiring a grid operator. 17:05 – The Execution Layer: Rejecting complex designs and demanding simplicity. 22:36 – High-Performance Compensation: Why top engineers make 10x more than the bottom tier. 28:50 – VC Term Sheets: Setting absolute founder-control red lines with investors. 36:50 – The Main Job: Why recruiting absolute elite talent takes up the majority of a CEO's day. 43:52 – Product Design: Building beautiful micro-solar and balcony battery products for consumers. 46:05 – Weaponizing AI Internally: Building PR review and error-tracking agents to optimize code. REFERENCES | |||
| Very few growth moats will survive AI - Sandy Diao [Descript] | 28 May 2026 | 00:57:15 | |
On this episode of BILLIONS, I’m sitting down with Sandy Diao, an elite growth operator who has been remarkably right about major market trends long before the rest of the ecosystem. Sandy helped scale products to 200 million users by leading early growth efforts as employee number 30 at Pinterest. She then joined Descript as their first ghost hire, architecting an automated affiliate model that drove 25% of all new users completely self-service. Her thesis is a warning to every modern SaaS operator: the siloed channel specialist is obsolete. In a world flooded by AI-generated content, traditional acquisition paths are collapsing. The future belongs to full-stack, unified operators who realize that trust is the only channel that compounds. In this masterclass, we break down:
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| Why high valuations are secretly killing tech unicorns — Martino Cadoni [Deepl] | 12 Jun 2026 | 00:58:04 | |
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 Europe's biggest banking IPOs.Martino cut his teeth in corporate America's legendary "CFO factory" the grueling General Electric leadership program, working relentless 996 schedules to solve high-stakes financial fires across the globe. From being flown to Budapest on a day's notice to re-evaluate multi-million dollar reserves in two weeks during a currency crisis, to managing capital and balance-sheet strategy as deputy CFO at HSBC, Martino knows exactly what it takes to build institutional readiness.In this masterclass, he pulls back the curtain on private vs. public markets, exposing the lethal structural mistakes tech unicorns make during down rounds and explaining exactly how legacy banking giants accidentally funded their own demise.In this masterclass, we break down:
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| How a $75 sneaker bot became a $300M/Month financial engine - Steven Schwartz [Whop] | 04 Jun 2026 | 00:53:45 | |
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 brand-new financial infrastructure for global creators.What started as a simple $75 sneaker bot sold in Facebook groups has exploded into a massive global network. Today, Whop is a powerhouse where nearly 40,000 people earn over $300 million every single month, and the platform processes nearly $1 million daily in physical product sales alone. Steven breaks down how they partnered with stablecoin giant Tether to unlock open financial networks for unbanked regions across the globe, why they are deliberately driving traditional credit card processing fees to zero, and why 70% of his entire corporate team consists of former founders. In this masterclass, we break down:
TIMELINE 00:00 – The $75 Sneaker Bot: monitoring Nike's Twitter to auto-buy rare drops03:09 – The Pivot: from niche software keys to courses & private communities05:34 – Payments Philosophy: the homeless QR-code project & racing fees to zero08:34 – The Tether Bet: stablecoins & bypassing legacy banks for the unbanked19:32 – "Powered by Whop": the viral loop & the zero-fee ecosystem23:48 – Acquiring for Talent: why 70% of the team are former founders40:04 – From Alabama Construction to $180K/Month: real-world impact42:38 – "Eating Glass": the perseverance to deliver a global mission | |||