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Christine Armstrong: AI is Messier Than You're Told

July 13, 2026

AI replacing our colleagues, feeling lonelier than ever despite enforced physical presense at the office. What is going on with the workplace?Caitlin sits down with Christine Armstrong, researcher, author, and founder of Armstrong & Partners, who has spent years doing something refreshingly unfashionable: actually asking people what's happening at work, instead of just theorizing about it. Christine is one of the world's top voices on the future of work, and she goes well beyond boardroom...

Dr. Yoni Freedhoff: There Is No Ideal Weight

June 29, 2026

Diets fail us all the time, and yet we usually blame ourselves. This physician says that neither the blame nor the failure are necessary.In the episode, Caitlin sits down with Dr. Yoni Freedhoff—Canadian physician, obesity expert, and one of the first doctors in his country board-certified in obesity medicine—for a conversation about his book, The Diet Fix. Dr. Freedhoff's book really isn't a diet book at all. Its premise is simple: any diet can work, and the trick is understanding the handfu...

Caitlin & Ben: Milestones & Updates

June 15, 2026

10,000 downloads a month. 11 episodes. 6 months of independence. Caitlin and Ben sit down for a bonus episode to talk about where Simplify has been and where it's going. They bought the show back from Blinkist at the end of last year, set some ambitious goals, and hit all of them. This episode is a chance to catch up, say thank you, and let you in on what's coming next.They get into the ins and outs of funding Simplify and why neither of them is interested in a race to the bottom. There's als...