An Intense Pursuit of a Wife, Wealth & Wisdom Rewarded with Charley Donaldson

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 main drivers for Charley’s success, he tells me, is making sure he didn’t peak in high school.

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. Lotta laughs. Please enjoy!

Questions asked:

Did you know coming into 9^th grade that you’d be competing with the quarterbacks of other junior highs (Truitt, Watkins, Cook)?
What were your prospects of starting?
Did you feel a sense of unfairness when you got to 9^th grade and you’re competing with guys that were older than you?
Did you have any opportunities to play beyond high school?
How does a kid decide to become a pole vaulter?
Were you recruited by many schools to be their pole vaulter?
What makes you paranoid [as an entrepreneur]? What does it lead you to do? How does [paranoia] manifest?
Why do you think it’s common for athletes to be entrepreneurs?
Can you talk about where the idea for CaringBand came from?
What’s considered high-net-worth vs. ultra high-net-worth?
When did you realize that you were going to seek outside investors [for CaringBand]?
Are there mistakes from other entrepreneurial endeavors that you were able to correct for this [CaringBand] concept?
How important is social media marketing?
How did you decide to go with Kickstarter?
Who’s your ideal customer [for CaringBand]?
Do you think it’s male / female differences that led you to a struggle with your wife?
Do you think transferring schools helped you to gain connections?
What were the conversations like in your house when you decided to become a full-time entrepreneur?
What is your overarching investing strategy?
Do you invest in any individual stocks?
What’s the biggest mistake you’ve ever made, investment-wise?
Do you teach your kids about money & investing?
Were you conscious about not coddling your kids and exposing them to the negative aspects of life?
Do you have to put reins on yourself sometimes from getting too excited/involved as a parent?
Have you ever felt an obligation to learn Bitcoin because of your clients?

Fun questions:

Is not wanting something as good as having it?
Did you have a high school sweetheart?
Social media – net positive or net negative for society?
When is the first time you logged on to the Internet and what did you do?
What is something you’ve learned from your kids that you share the most with people?
If somebody dropped $1 million in your lap tomorrow, what would you do with it?
If somebody gave you $100,000 tomorrow and forced you to invest in 3 companies: Apple, Amazon, and Tesla – how would you allocate those funds?
Same dollar amount, but you’re forced to allocate $100,000 toward gold or Bitcoin – how do you divide that up?
Do you have a favorite book?
Do you have a favorite podcast?
Who’s the best quarterback ever?
Overrated/Underrated: Maria Bartiromo, Jim Cramer, Mark Cuban, Randy Yost, DeShaun Watson, Bill O’Brien, Aaron Rogers