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.

In this conversation, Vlad reflects on his early life growing up in Odessa during the Soviet era, and how emigrating to the United States as a teenager fundamentally reshaped his worldview. He shares what it was like arriving in California with engineering parents, navigating a new culture, and gradually discovering a passion for computers at a time when computer science was anything but fashionable.

Vlad walks through his early career as an engineer in Silicon Valley, before founding his first company, Ring Zero Systems, in the early 1990s. With no venture capital, no safety net, and a small team literally sleeping in the office, Ring Zero bootstrapped its way to becoming a key supplier to the global PC industry - eventually selling the business to Motorola.

That first chapter laid the groundwork for what came next. Vlad and his co-founder began rethinking business communications long before terms like “cloud” or “SaaS” entered the mainstream.

RingCentral was built on a simple but contrarian belief: communication features and workflows belong in the cloud, while delivery should remain flexible - spanning VoIP, mobile, and traditional telephony. This architectural choice helped RingCentral succeed while others faded, and ultimately scale into a global leader.

Vlad makes a bold case that we are entering a new era of communications - one defined by AI-powered conversations rather than simple call routing. He outlines RingCentral’s vision for “RingCentral 3.0,” where AI agents, real-time assistance, and conversational intelligence transform voice into a strategic advantage, rather than a legacy channel. Contrary to popular belief, Vlad argues that AI is driving a renaissance in voice - increasing call volume, improving customer experience, and unlocking new growth for businesses.

Whether you’re a founder building through uncertainty, a product leader navigating platform shifts, or an operator trying to understand what AI actually changes inside enterprise software, this episode offers a rare long-term perspective from someone who has lived through multiple technology cycles.

It’s the story of a builder who started with nothing but conviction, learned to trust first principles over hype, and quietly helped shape how millions of businesses communicate every day.

In this conversation, Craig reflects on his unconventional path from law to venture capital, before being dropped into his first CEO role during the depths of the dot-com crash. Tasked with effectively shutting down a failing VoIP company, he instead rebuilt it from the ground up - cutting costs, reinventing the business model, and ultimately selling the company to Yahoo.

That hard-won experience set the foundation for what came next: founding GrandCentral, the startup that would later become Google Voice. Craig walks through how a small team, a bold product vision, and perfect timing led to an acquisition by Google in just 18 months, and his experience scaling a startup product inside a 20,000-person company.

Craig shares how his frustration with outdated enterprise phone systems led him to reimagine business communications for the cloud with Dialpad, years before remote work became the norm. He explains their long-term vision for a unified communications platform, why small, empowered teams outperform bloated organizations, and how the company quietly got a head start in AI long before it became fashionable.

Craig also makes a bold claim: traditional customer experience, as we know it, is dead. He unpacks why agentic AI will fundamentally reshape CX, and how human-AI collaboration (not full automation) will define the next era of enterprise software.

Whether you’re a founder navigating scale, a product leader building for the enterprise, or an operator trying to separate real AI innovation from hype, this episode delivers first-hand insights from someone who’s been on the frontlines of multiple technology waves.

This is the story of a builder who has repeatedly crossed from one side of the table to the other, learning when to grind, when to refocus, and when to place the next big bet.

Join host Rob Scott as he sits down with Vasili Triant, CEO of UJET and a long-time builder at the intersection of cloud communications, contact centers, and customer experience. From the early days of IP telephony to today’s rapidly converging CX, CRM, and AI landscapes, Vasili’s career offers a front-row seat to multiple technology inflection points.

In this wide-ranging conversation, Vasili reflects on his unconventional path into entrepreneurship, scaling businesses inside fast-growing companies like ShoreTel, and stepping into the CEO role at LiveOps during a period of deep strategic uncertainty. He shares candid lessons on leadership loneliness, culture change, and why splitting LiveOps into two distinct businesses ultimately unlocked long-term value.

The discussion also dives deep into Vasili’s time navigating hyperscalers and enterprise complexity at Cisco, before landing on his journey at UJET - including joining just weeks before global lockdowns in 2020. Vasili unpacks how UJET competes with tech giants, its close partnership with Google, and why he believes much of today’s AI hype is missing the real problems in customer experience.

Whether you’re a founder scaling your first company, a CX leader trying to cut through the AI noise, or an operator thinking about market consolidation and long-term strategy, this episode delivers hard-won insights on timing, focus, and building companies that endure.

This is the story of a leader who has spent decades fixing, building, and repositioning businesses - and who now sees customer experience standing on the brink of its next major transformation.

Join host Rob Scott as he sits down with Michael Walrath, pioneering digital advertising entrepreneur and current CEO of Yext. Their sweeping conversation spans the dot-com boom, the rise of programmatic advertising, and the tectonic shifts reshaping marketing in the AI era. From selling banner ads in the 1990s to building the world’s first at-scale ad exchange, Michael’s story is one of vision, timing, and relentless reinvention.

In this candid chat, Michael reflects on the leadership lessons he’s learnt from scaling startups into global players, navigating post-acquisition bureaucracy at Yahoo, and identifying new market opportunities during moments of economic upheaval. He recounts the founding of Moat to bring transparency to digital advertising, his role in shaping Yext during the mobile revolution, and why he believes today’s fragmented “answer engine” landscape mirrors previous technological turning points.

Whether you’re a founder navigating market disruption, a marketer preparing for the AI-driven future, or simply someone who loves hearing how industries are transformed from the inside, Michael’s journey offers powerful insights into strategy, timing, and adaptability.

This is the story of how one entrepreneur helped shape modern digital advertising, and how he’s charting a course through the next great marketing revolution.

Join host Rob Scott as he sits down with Kirin Sinha,founder of Illuminix - the company behind the perception stack powering the next generation of XR, wearables, and physical AI.

From entering MIT at 16 to building one of the world’s most advanced computer vision startups, Kirin’s journey is a masterclass in intellectual curiosity and fearless innovation. In this far-ranging conversation, she reflects on the transition from academia to entrepreneurship, the early days of developing mobile AR, and the breakout success of Five Nights at Freddy’s AR, which became a viral global phenomenon.

Kirin shares how those early experiments with digital-physical interaction laid the foundation for Illumix’s cutting-edge work with Disney, Six Flags, and MGM - and why she believes contextual computing will redefine how we experience technology. Along the way, she discusses winning against tech giants, raising capital from investors like Lightspeed, Sony, and Mark Cuban, and the new frontier where AI, robotics, and perception meet.

Whether you’re a founder building in deep tech, an investor tracking the rise of physical AI, or simply fascinated by how reality itself is being reimagined, Kirin’s story is one of vision, persistence, and purpose.

This is the story of how one founder is teaching computers to see like humans - and shaping the next era of real-world computing.