Charley Donaldson is my guest. He's a long-time friend and serial entrepreneur who has founded or co-founded five companies over the last six years. Today, he spends most of his time at the helm of two early-stage technology startups: CaringBand and DonationScout.

Charley describes himself as a fearless, yet paranoid entrepreneur. He says that he's abandoned the easier road to career & financial success in search of his true calling.

I've known Charlie since we graduated from Cy-Falls High School together in 1998—Charley was our class' quarterback. After high school, he poll vaulted at LSU before transferring to Baylor. One of the things that drives Charley is ensuring he didn't peak in high school (no problem to this point).

In this episode, we recall our time at Cy-Falls. I ask him about his rivalry with Langham Creek star quarterback Joseph Smith. And why Charley ultimately chose track & field over football.

Charley's now a husband, father of three—they live in The Woodlands, TX. We discuss the journey of his startup, CaringBand—from idea to market. Charley says he and his wife created the business after his mother-in-law's successful battle with breast cancer in 2016.

This conversation was fun. Lots of laughs. Please enjoy!