BONUS EPISODE: I Sat Down With Mark Ainley in Chicago

Dropping a bonus episode in your feed today for fun. I was in Chicago a few weeks back and sat down with Mark Ainley on the Straight Up Chicago Investor Podcast. I'm actually the first PM industry guest he's had on his show. A few of the topics we hit:(1:09) How PLM came together, and why caring about your audience matters more than a marketing background(3:45) What actually makes a community work (and why it can't be about you)(6:23) The story behind meeting Wolfgang and how Crane went from idea to launch in six months(12:53) What property managers are getting wrong about AI — applying the theory of constraints(16:29) How I structure my week and calendar to actually work on the hard stuff(21:19) The AI disruption nobody in our industry is talking about loudly enough(24:14) Why rapport with owners is going to matter more, not less, in an AI world(27:31) Why I love being a customer of vendors I want to see win(29:22) Why I'm not taking the full month of June off this year — and what that says about the work(34:31) Why I keep going live (even when only 5–10 people are watching)(40:27) How Lazy Leverage came together with John, and what I've learned from doing zero-prep content(48:23) Why newsletters are still the highest-leverage media channel you can buildWe covered a lot of ground: how PLM came together, the conversation our industry isn't having loudly enough about AI, why I'm not taking the full month of June off this year (a first in five years), and plenty in between. Disclaimer: The content of this podcast is for informational purposes only and does not constitute professional advice. I may have consulting agreements with, or financial interests in, companies mentioned in this podcast. Additionally, some of the links included may be affiliate links, meaning I may earn a commission if you purchase through these links. Always perform your own due diligence before making any financial or business decisions.