On this episode of Flight Log, Chris Fitch takes private-equity investor Chihiro Kurokawa thousands of feet up to explore what risk, courage, and self-investment actually look like beyond the boardroom.

Chihiro went from writing insurance claims at Progressive to becoming a Dallas-based investor operating in healthcare and auto dealerships through ZT Corporate. Now he talks openly about the terrifying first steps, the false sense of safety in traditional careers, why “doing nothing” is its own dangerous bet, and how systems and checklists shape both flying and private equity.

And in true Flight Log fashion, Chris hands over the controls mid-conversation — giving Chihiro the airplane and using the moment to illustrate trust, leadership, and why every great investor needs the right “who” long before the “how.”

If you’re an entrepreneur, a W-2 escape artist, or someone wrestling with the fear of doing your first deal, this episode hits you right in the spine.

Buckle up, follow the coastline, and enjoy the ride.

At the end, Chris gives his usual invite:
Want to sit in the left seat and be on the show? DM @chrisdoesdeals on Instagram.

This episode of Flight Log was produced by Martin Brothers Media. Check out @martinbrosmedia on instagram or visit martinbrothers.media for all your aviation media and marketing needs.

In this episode of Flight Log, Chris takes flight with Oscar Rodriguez — an entrepreneur who’s no stranger to risk, resilience, and rebuilding. Together, they talk about that critical first step off the ledge into entrepreneurship, the uncertainty that comes with it, and the gritty persistence it takes to keep climbing when things don’t go according to plan.

It’s a real conversation about what happens after the leap.

Recorded live in the cockpit.
Presented by Martin Brothers Media.

Follow Chris for more at @chrisdoesdeals