1. Has there been a recent moment (traveling, working with your team, training people on AI, etc.) where you realized you’re entering a completely different chapter than before?

2. Let’s imagine you’re building the fractional CMO model from scratch today, knowing what you know now about AI agents, what would you completely throw out, and why?

3. If a client could only afford you for 3 hours a month instead of 30, what would you insist those 3 hours be spent on, and why?

4. Let’s assume your competitors could copy your AI agents overnight, what would still make your business defensible, and why?

5. If most operational work disappears, what happens to office culture and mentorship, the things that used to happen “in the hallway”?

6. From your perspective, which current job title will feel as outdated in 5 years as "typist" does today, and why?

News & Updates

1. What book(s) or article(s) did you read this past month that stayed with you? What takeaways do you have?

2. What event(s), talks or experiences did you attend this past month that stayed with you? What takeaways do you have?

3. What podcast(s) did you listen to this past month that stayed with you?