Binary to Billions - Season 2 Episode 2 with YouMon Tsang, Founder and CEO of ChurnZero.

When ChatGPT launched in November 2022, YouMon Tsang's first reaction was "oh no." He thought he'd started the wrong company, at the wrong time, with the wrong people, and was ready to hand the keys back to his investors. Then he spent the holidays asking one question: if AI's only goal was to kill ChurnZero, what would it take?

In this episode of Binary to Billions, Rob Scott sits down with YouMon Tsang, founder and CEO of ChurnZero, the customer success platform he built after noticing that the teams responsible for keeping customers had the worst technology in the entire go-to-market stack.

ChurnZero is YouMon's fourth company. Before it came Milk Truck, an award-winning product killed by a new business model; Biz360, an early SaaS company that launched straight into the dot-com crash and 9/11; and Engine140, acquired by Vocus. He talks openly about losing confidence in himself, bringing in two professional CEOs who didn't work out, and the lessons from multiple exits.

He also has a clear view on what AI means for customer success teams, and a warning for anyone still skeptical about it.

"I ask my founders every month: do we deserve to exist?"

In this episode:
→ Why he's a great employee and a bad employee, and why that makes a founder
→ The business model shift that beat his favourite product
→ Why the winners in B2B are almost never the pioneers
→ What selling a company actually feels like
→ Why AI will mean fewer CSMs managing much bigger books of business
→ The mistakes he sees first-time founders make again and again

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Connect with Rob Scott on LinkedIn: linkedin.com/in/iamrobscott

Find out more about ChurnZero: churnzero.com

Binary to Billions is back for Season 2!

In this episode of Binary to Billions, Rob Scott sits down with Melissa Solis, CEO of Inbenta, the AI company she bought just three months before ChatGPT changed everything.

Meliassa's father left when she was seven and took everything: the furniture, the car, and every dollar in the bank. Thirty years later, she started a company with her brother and $300 from her purse, and sold it for a reported $610 million.

Melissa grew up with no electricity, on food stamps, and struggling with undiagnosed dyslexia. She talks openly about the moments that shaped her: watching her mother fight to keep the family afloat, surviving a federal investigation that nearly ended her company, losing her sister to addiction, and making 14 of her employees millionaires when she sold.

She also has a blunt theory about why so many AI projects are failing, and a warning about what AI means for the millions of people, mostly women, working in call centres.

"Money does not make you anything. Money is a mirror, and it simply shows who you are."

In this episode:
→ Why she bootstrapped instead of raising money
→ The eight-hour testimony that cleared her company's name
→ What really made it all worth $610M
→ Why "deflection" is failing customers, and what AI should do instead
→ The reckoning coming for companies that rushed into AI
→ How to stay valuable when your job gets automated

Stream Binary to Billions on your favourite platform: Apple Podcasts or Spotify.

Stay inspired, Rob

David’s story starts with a discarded 486 computer his dad brought home from work. Where most people saw junk, he saw possibility. While teaching himself to code, David discovered something that still drives him today: with software, you can take an idea in your head and make it real within hours.

In his early 20s, he co-founded what became Answers.com - a company that would eventually sell for nearly $900 million. The journey was anything but smooth. He describes running the business like an “internet marketing hedge fund,” living at the mercy of search algorithms - including the time a simple bidding mistake cost $100,000 in minutes.

What ultimately changed the trajectory was a strategic pivot into SaaS. David and his team began acquiring and building subscription software businesses alongside the media engine - slowly transforming the company’s revenue mix. That diversification created the path to a major private equity exit in his early 30s.

And then… he stopped.

For the first time in his life, David took a real break. What he discovered surprised him. He didn’t want retirement. He missed being part of a team. He missed building. He wanted to create something that helped other teams do their best work. That became Capacity, an AI-powered platform designed to automate support across both employee and customer experiences. What began as a Slack bot for internal help desks evolved into a broader AI support platform serving thousands of organizations.

In this episode, David cuts through the AI noise. He breaks down the difference between automation, AI, and generative AI in plain English. He explains why most executives focus too much on models and not enough on data. And he shares why he believes we are entering the “decade of AI agents” - where companies that adapt quickly will compound, and those that hesitate will fall behind.

Share this episode with a founder, operator, or tech leader who’s thinking about scale, platforms, and what AI really means for the future of work.

Subscribe to Binary to Billions for more unfiltered conversations with the builders behind technology’s biggest success stories - where we go beyond the headlines to explore the real human decisions that shape enduring companies.