Leadership in Change with AI - Podcast

Things have changed. The bar used to be produce content, produce content, produce content, and most people didn’t have the time or the persistence to keep going, so just showing up was the whole game. That bar is gone now. Anybody can type a prompt and get ten decent posts before lunch. Which means the thing that actually keeps a reader with you is the part AI can’t fake. David McIlroy has built a...

Travis Rosser co-founded Kajabi , the platform creators have used to sell more than $10 billion in courses, coaching, and knowledge, and he joined me on Substack Live to trace the whole arc. We went from a Shark Lagoon PDF he sold as a kid to a company that put publishing tools in everyone’s hands. Along the way he unpacked why he tells builders to fall in love with their customer’s pain instead o...

Most of us start a business to get our time back, and somehow end up the one person it can’t run without. In this Substack Live I sat down with Cory Blumenfeld , a five-time founder who built a virtual assistant company called BlueMoso , on how to stop being the bottleneck in your own company. We get into why the system usually only exists in the founder’s head, how to hire for the match instead o...

Much of the AI conversation in the business world, for those who have not used AI much, is some version of: kick your feet up, drink the piña colada, watch your revenue shoot up. I’ve seen that promise up close on the fundraising side of the humanitarian work I do, and on a lot of teams AI is the enemy in the room before it’s anything else. Mallory Erickson started exactly where most of her sector...

If you’ve spent any time trying to make sense of where AI is actually going, not the headlines but the structure underneath all of it, you’ve probably run into Gennaro Cuofano ’s work without knowing it was his. He built The Business Engineer (spun off from FourWeekMBA) into a research hub more than 90,000 people follow, and he just launched something new called The AI Supercycle. I wanted to sit...

AI keeps getting better, so why aren’t your results getting better? Bryan Cassady ’s answer: Most people are getting more output, not better work, because they skip the thinking and go straight to the tool. In this Substack Live we get into his Type 3 error (doing the wrong thing, fast), why objectives have to come before any tool, the real $11,000-a-year cost of AI that most leaders never count,...

This one got into the part of AI adoption nobody really wants to talk about. Ryan Deeds runs AI at ALKEME , an insurance company that bought its way from seven agencies to ninety-three in about four years, and his whole argument is that the technology was never the hard part. The hard part is getting fifteen hundred people to actually trust a tool and use it. We talked about the golden path, why e...

I keep running into the same thing when I talk to leaders about AI. They’re excited and they’re exhausted… at the same time . They see how capable the models have gotten, and in the same breath they tell me they’re starting to feel a little obsolete. Curious and anxious, sitting in one person, at the same desk. I wanted to talk to Liz Fosslien and Mollie West Duffy about exactly that, because they...

So this one is about trust, and why it might be the only thing left that AI can’t manufacture for you. I sat down with Dr. Christopher Chou , the CEO of The Christian Post . We got into why people don’t adopt AI when they don’t trust the leaders handing it to them, what it cost his team to stand by a story when the platforms told them to apologize, and the one thing a human brings to the table tha...

TL;DR. So this is the question I keep circling in 2026: if AI can spin up an infinite amount of content from basically nothing, what’s still worth anything? I brought on Michael Schreiber to answer it, because he’s spent years inside the rooms that set the standard, New York Times, HBO, ABC, NBC, and now runs MediaFeed, a content syndication company, plus a local podcast in his New Jersey town. We...

Christopher Chin started out as a coder, one of the jobs you’d think needs the least human communication, and somehow ended up on a TEDx stage teaching people how to speak. This conversation is about how he made that jump, and what he thinks communication actually is once you stop treating it as moving information from one head to another. The frame that I’m still going over is that communication...

Here’s where this conversation started. I keep hearing the same thing from the leaders I coach, and what they’re asking about on the surface is strategy or tools or timing, but the thing underneath it, almost every time, is fear. Here’s where this conversation started. I keep hearing the same thing from the leaders I coach, and what they’re asking about on the surface is strategy or tools or timin...

TL;DR — I just spent 49 minutes on Substack Live with David Allen, the guy who has shaped how I think about my own work for the last 25 years. Getting Things Done turns 25 in 2026, and the question I had walking in was simple: does the framework still hold up in a world full of AI agents? David’s answer was sharper than I expected. AI didn’t really change the underlying principle, it just raised t...

TL;DR — Dan Ariely is one of the most cited behavioral economists alive, the author behind Predictably Irrational and Misbelief , and we spent thirty minutes on Substack Live walking through what AI is actually doing to the way leaders make decisions. The headline isn’t that AI is dumb, it’s that AI is engineered to give us what we want, and what we want is almost never what we need long-term, whi...

TL;DR — Compound With AI is a Substack newsletter teaching 50,000 long-term investors how to compress six hours of stock research into about sixty minutes using AI prompts, Claude skills, and deep research workflows. We sat down on Substack Live this week and unpacked the actual mechanics, the prompt library, the multi-agent setup, the break-my-thesis move, the way he turns deep-research reports i...

TL;DR — AI made content production almost free, which means producing it is no longer what separates the creators who grow from the ones who stall. Trust, voice, and the depth of your actual expertise are. Call it the trust premium. In a Substack Live with Philip Hofmacher , cofounder of Write × Build × Scale, we walked through the litmus test that tells you whether AI is amplifying you or quietly...

TL;DR - LinkedIn locked Melanie Goodman out of the platform she had built a business on for ten years. She got back in, but the 12-week gap taught her something most leaders still refuse to learn: every social platform is rented land. In the AI era, where feeds are flooded with auto-generated content, the leaders who win are the ones who own their audience, sound unmistakably human, and run Linked...

What happens when a 136-year-old Swiss watch brand meets the age of AI? I sat down with Jacque O. , executive at Doxa USA & Caribbean, to talk about one of the hardest questions leaders face right now: how do you stay true to your craft when everyone around you is automating everything? Jacqueline brought 16 years of luxury retail experience and some of the sharpest thinking I’ve heard on balancin...

Thank you Karo (Product with Attitude) , Tina Williams , Jón Sveinsson , and many others for tuning into my live video with Paul the Human ! Join me for my next live video in the app. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit leadershipinchange.com/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit leadershipinchange.com/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit leadershipinchange.com/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit leadershipinchange.com/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit leadershipinchange.com/subscribe

This is a free preview of a paid episode. To hear more, visit leadershipinchange.com A live walkthrough of the full Claude Projects workflow — from NotebookLM research to branded thumbnails. See how I build every newsletter in 12 steps. For content creators and leaders using AI.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit leadershipinchange.com/subscribe