1. What’s something new in your world these days? Anything you’ve seen, heard, or experienced that feels worth talking about?

2. Who was the first person to ask you to sign your book, and what went through your mind when you realised your ideas were now out in the world?

3. What does a healthy network actually look like to you today? Do you remember a time when your network lifted you up or let you down?

4. When you were just starting out, did you feel comfortable surrounding yourself with people more successful than you? Many entrepreneurs struggle with that early sense of “not belonging.” How did you overcome it? Or learn to use it to your advantage?

5. Letting go of control is hard. What was the first thing you actually let go of? The first task, decision, or responsibility you handed off, and what happened next?

6. You talk about how some brokers resist the transition because they fear their team won’t match their own standards. Was there a moment when someone on your team surprised you by exceeding your expectations?

7. What was a moment in your early career where the offer looked incredible on paper but ended up costing you more than it gave?

8. Looking back at the last 12 months, what was the hardest thing you had to unlearn in order to grow? Why?

9. You often talk about business moving in cycles almost like seasons. As you look at 2025 and 2026, what “season” do you personally feel you’re in right now?

News and Update

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

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

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