BILLIONS

Today on BILLIONS, I’m sitting down with Arvind Jain, founder and CEO of Glean. Before Glean, Arvind spent years at Google working on search, then co-founded Rubrik, which became a multi-billion-dollar public company. Instead of retiring, he started again from scratch. Today, Glean has crossed $300M ARR and was last valued at $7.2B. And Arvind has some very strong views on where AI is going next....

Today on BILLIONS, I’m sitting down with Daniel Chait, co-founder and CEO of Greenhouse, the hiring platform used by more than 7,000 companies. Daniel has spent more than 27 years as an entrepreneur and built Greenhouse from an idea VCs initially dismissed into a $100M+ ARR company. Now, hiring is being disrupted again. Candidates are using AI to apply to more jobs and make every resume look bette...

Today on BILLIONS, I’m sitting down with Kieran Flanagan, SVP of Agentic GTM & Systems at HubSpot. Kieran spent 10 years helping build one of the most copied growth engines in SaaS, left to become CMO of Zapier, and then came back to HubSpot to help rebuild its entire go-to-market playbook around AI. And they had no choice but to rethink it. In just one year, HubSpot lost 140 million visits —...

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 $800 million in revenue. His next challenge: turning a platform built for human collaboration into an operating system for teams of humans and AI agents. A model can generate an answer. But who...

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. Carles helped build ElevenLabs' go-to-market engine on the road to over $600 million in annual recurring revenue . As the founder of Baobab Ventures , he also sees the other side of t...

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 autonomous AI agents. Aaron has a masterclass view of the data infrastructure that legacy tech giants wish they controlled. In this conversation, we pull back the curtain on the high-stakes battle for...

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 approaching $1 billion in revenue this year. Pete and his co-founder Rashid bet everything on a category the entire industry assumed was dead: the gas-station meat stick. For nearly ten years they...

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 Americans who can least afford them. Jason's story is one of the wildest comebacks in fintech. After going public via SPAC in January 2022, Dave hit a $5 billion valuation, then the macro turn...

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 100 of the most important private companies on the planet. Peter operates on a timeline that makes typical venture capitalists look shortsighted. From backing Tesla in 2013 at a $3B market cap to ente...

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 sc...

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...

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 d...

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 Britis...

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 bu...

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...

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...

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...

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...

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 $...

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 "Sa...

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...

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 m...

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...

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...

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 —...