This one's for you if you've been building something for a few years and you keep measuring it against numbers that never feel like enough. I recorded episode 200 and almost didn't mark the occasion. Before I hit record I went looking for the stats: just about 22,000 downloads, over 100 guests, almost four years of weekly episodes. My first instinct was that it wasn't enough. So I used the episode to look at what's actually changed. The show started as a place to talk about building a life-first business as a parent and an entrepreneur. That goal hasn't moved. Everything about how I'm chasing it has. I went from brand and visibility work to co-founding an AI company, and I still walk my kids to school, which was my definition of success from day one. I also tell the story of a cold guest pitch I'd normally have passed on, the episode it became, and how the momentum from it ended with me on stage at the Ryman in Nashville. The bigger question underneath all of it: what are you measuring, and is it the thing you actually said you wanted?

I don’t sell AI skills. Sometimes, I wish other people would stop selling them. Skills are easy to install, people seem to be buying them and it can feel like you need to make one to keep up. But what if the method inside that downloadable file is the very thing that makes your work valuable? I’ve built more than 60 skills to run processes in my own business. In this episode, I explain why I don’t sell those proprietary processes as skill files, how I’ve found a different role for skills in my customer journey and why the environment where a client uses your tool matters as much as the instructions you wrote. This is a nuanced business decision. Some experts are comfortable sharing their methods, and I welcome that perspective. I want you to consider your own IP, the result you promise and whether a downloadable tool will still serve your client as your field changes.

Every time someone uses an AI tool you built, somebody pays for it. If you sell courses, programs, memberships or templates and you're thinking about putting AI inside them, this episode gives you five questions to answer before you do. After our live AI Product Build Lab, the same pricing questions kept coming up, and we made some big pricing decisions at wAIv that week. I walk through the questions I asked myself, starting with the cost most creators never see: custom GPTs hid it, and a tool people access directly puts it on you. The bigger question for you: if AI is part of what you deliver, have you decided what it costs, or is it just happening?

If you're letting AI write your emails, posts and sales pages and wondering why nothing's landing, this one's for you. Jen Liddy is a messaging diagnostician and former English teacher. She's spent years helping experts find their voice, and she's watched AI change how her clients write. We talk about why you need to know your own voice before you can push back on a robot. We also cover why she stopped building $6,000 messaging guides and the signs that your messaging is the real problem. The bigger question for you: can you say what you want to say before you ask AI to say it for you?

If you run a membership, course or coaching program and want AI to help your clients actually implement, this one's for you. Nadine Nethery, a customer experience and retention strategist, joined me to walk through the AI tools she's built into her membership and workshops. She shared three of them. The first is a survey builder that packages 10 years of her framework. The second powered an interactive workshop that converted 28% of live attendees within 24 hours. The third is a roadmap builder that gets new members committed to a six-month plan on day one. The bigger question for you: where could an AI tool clear the friction that stops your clients from doing the work, and where do you want your own perspective front and centre?

This episode is the practical guide to planning your Custom GPT migration. Your custom GPTs have a deadline. Your IP shouldn't be the thing you give up to meet it. OpenAI is retiring custom GPTs, and enterprise workspaces lose theirs on December 11. If you built GPTs for your clients or your audience, you need a plan, and the most popular option right now asks you to hand over everything inside them.