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.

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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.