Episodes

Have you ever put something on a roadmap knowing, deep down, it probably was not going to happen on that date? In this episode, Karl talks with Janna Bastow about the uncomfortable truth behind most roadmaps and the moment she realized they were quietly training teams to overpromise. Janna shares the story of building her first roadmap tool and the surprising pattern that emerged when almost every product manager came back asking to “just move everything over by a month.” It was not a tooling p...

What happens when the people building your product do not work for your company, and still feel deep ownership over every decision? In this episode, Karl talks with Reese Gifford about the lived reality of building products in open source, where community passion can be both your greatest strength and your hardest constraint. Reese shares what it was like stepping into Mozilla, falling in love with the mission, and then navigating the very human tension between keeping Firefox open and free whi...

What if being a great product manager had less to do with sounding smart and more to do with getting your hands dirty? In this episode, Karl talks with Ali Rakhimov about a product career that started far away from tech titles, roadmaps, or polished decks. Ali shares how he quite literally tripped into product work while trying to solve real problems in K–12 schools, like watching student cash disappear at the front office and deciding someone had to fix it. No role, no playbook, just curiosity...

What if your path into product management started behind a coffee counter, in the middle of a global pandemic? In this episode, Karl talks with Flora Taagen about a journey into product management that looks nothing like a straight line. Flora shares how she went from studying computer science to serving coffee during COVID, where suddenly “making coffee” also meant rethinking safety, budgets, and how a small business survives when the rules change every week. That experience, it turns out, tra...

What if you were already doing product work years before you ever heard the job title? In this episode, Karl talks with Adil Hussain about a path into product management that started with a teenage side project and quietly grew into a career. Adil shares how, at just 14, he and a co‑founder were building websites, talking to users, and figuring out what people actually needed, without realizing they were doing product work at all. It wasn’t until much later, sitting in a tiny meeting room with ...