Suggested questions

1When you think back to your nana taking off to places like Syria and Israel on her own, what’s the earliest memory that made you realize, “Okay… my life is probably going to look a little different”?

2Tunisia at 18 sounds like a sensory overload in the best way—what was the exact moment on that trip where your brain went, “I need more of this kind of world”?

3Early in your career, you kept zig-zagging through roles and countries until something clicked—what did you keep noticing about yourself that made the “normal” travel path feel too small?

4Crooked Compass started as an app with a thousand off-the-beaten-track experiences—what was the first big “this isn’t working the way I thought” realization, and how did it change what you built next?

5Someone challenged you with, “Why aren’t you running your own tours?”—what did you do in the next 48 hours after that conversation, and what scared you most about making it real?

6The Shark Tank deal that went bad is such a brutal trust lesson—what were the warning signs you ignored in the moment, and what do you do differently now when something looks shiny but feels off?

7That International Women’s Day moment—standing up, naming the person you admired, handing over your card—what did it cost you emotionally to do that, and what did you learn about asking for help as a founder?

8During the pandemic you went from momentum to nothing, became a single parent in the middle of it, and still chose to learn to fly—what was happening inside your head that made “I need a cockpit” feel like the sane option?

9You’ve taken people to places many travelers avoid—Chernobyl, North Korea, geopolitically loaded destinations—how do you personally decide where curiosity is worth the discomfort, and where a boundary should stay a boundary?

10Your travelers tend to be wealthy, highly educated, and hungry for the dinner-party story—what have you learned about what people are really buying when they pay for exclusivity: status, meaning, transformation, or something else entirely?