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.
His core message is simple but powerful: speed is the only true competitive advantage for startups - and long-term success comes from stacking skills, not chasing hype.
On a personal level, he shares why he believes in “wholeness” over balance - being fully present wherever you are - whether that’s coaching his son’s basketball team, leading his company, or unplugging for a weekly Sabbath.
Whether you’re a founder building your first company, a leader navigating AI transformation, or someone wondering what success actually feels like on the other side of a nine-figure exit, this conversation delivers perspective you won’t find in a headline.
It’s the story of a Midwest entrepreneur who kept leveling up - from comparison shopping to Q&A, from media to SaaS, from search arbitrage to AI agents - proving that compounding experience beats overnight success.
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.