Uncomplicated: Humans vs. Machines

What does it actually take to build something real in AI — not just wrap a tool and call it a product? Sharon Gillenwater has done it before. Fourteen years building a B2B SaaS company from scratch, bootstrapped, no venture capital, sold for $25 million. Then a private equity firm shut it down without warning. When she called to buy it back, they didn't know the company name, the revenue, or what...

What if the biggest challenge in tech isn’t finding the next AI tool, but knowing how to make sense of the ones you already have? Ghita El Haitmy came to that realization while building Techbible. What started as a platform to help teams discover new software quickly revealed a much deeper issue. Most companies don’t actually understand their own tech stack. They don’t know which tools overlap, wh...

Private-market investing is still running on PDFs, scattered spreadsheets, and manual models, while public markets operate with real-time analytics and platforms like Bloomberg. The gap keeps widening, and AI seems like the obvious fix. But as Olivier and Naunidh explain, most of the real problems in private markets aren’t technical. They’re about trust, workflow, and the quality of the underlying...

Most companies sit on years of hard-earned knowledge — but have no way to turn it into AI that’s private, reliable, and actually useful. In this episode, I’m joined by João Carvalho, a machine learning PhD who spent years at ETH Zurich studying why AI fails, and Wael Abdelmalek, former AWS architect who helped global enterprises turn their expertise into production-ready AI systems....

What if the most important thing you invest in as a founder isn’t money, code, or connections, but belief? When Nomiki Petrolla’s six-week-old daughter was on a ventilator fighting for her life, she walked into her house from the hospital, handed her baby to her husband, and quit her job as head of product at an AI company. That moment changed everything. After 15 years building products for other...

What if the future of recruiting was built on trust, not just tech? After 13 years building engineering teams at Square, Waymo, and Lyft, Danielle McLaughlin walked away from corporate recruiting to start 18C Partners, a boutique agency focused on helping women in tech find roles that match their worth. Now she’s taking that mission to scale with 18C.ai, an AI-powered recruiting platform designed...

What if the future of entrepreneurship isn’t about beating the algorithm — but about embracing the messy, human middle? In this episode, I’m joined by Sam Ogborn: professor, founder, and marketing strategist who left corporate life at Red Bull and Walgreens to experiment online — starting with anonymous whiteboard videos, cringe posts, and therapy-level self-reflection. By being honest about the m...

What happens when the kid they said wouldn't go to college goes on to build products for hundreds of millions of people — and then sets out to fix the $3.8 trillion "understanding problem"? In this episode, I sit down with Trip O'Dell, co-founder and CEO of 5xFive, whose journey from high school teacher on the Pine Ridge Reservation to leading design at Audible and Alexa proves that outliers see w...

What happens when you stop overthinking AI and just start using it? In this episode, I sit down with Sophie Theodorou, founder of Teach2AI, whose approach to everything from leaving the classroom to building a business proves that action trumps analysis every time. Just a few years ago, Sophie was teaching middle school math and science in Winnipeg. Today, she's built a community of 100,000+ and t...

Everyone's losing their minds about AI, but the people actually building with it are just making it up as they go. I'm Carly Jefferson. I've been building startups for over a decade, and I'm bringing you the founders who are writing the rules in real time. No BS, no hype - just honest conversations about what's working, what's breaking, and the big questions we need to have about AI ethics and whe...