While unicorns aren’t going public, Barrett plays baseball and basketball with his five-year-old son and takes him to sporting events.
Though Barrett is not a big fan of conference calls, he admitted that the Proust interview is an exception. Let’s see what he has to say to our questions.
What would you otherwise be doing right now?
When I was younger, I’ve always wanted to be an FBI agent. I thought that was the coolest thing ever. But later in life, I’d probably be either teaching finance or doing sports management of some kind.
Your main fault?
I don’t like asking for things. I have a hard time imposing on anyone. Being a business leader, that makes things tough some time. But I would prefer being nice to people.
The quality you most desire in a tweet?
Funny and short tweets with as few hashtags as possible, especially when it comes to politics and business.
Your idea of misery?
On a personal level, doing something that disappoints my son. From the business sense, a calendar packed with conference calls is proper hell.
What do you appreciate the most in your friends?
Trustworthiness, reliability, and kindness. Knowing that they will be there for me when I need them.
Your chief characteristic?
I’m a big believer in transparency and just being who you are.
What skill do you wish you possessed?
Organization. I know others that wake up every morning, have a ten-point checklist, and say I need to get these things done, whereas I tend to go with the flow. It’s very normal for there to be more stickies on my desk at the end of the day than less.
Your most impactful book?
The No Asshole Rule by Robert I. Sutton. Few things in there that just really hit home like you need ten nice people to offset one asshole, and just how damaging even one can be and how important it is, in a small business, to make sure that you don’t have them.
What defines success?
Happiness. Enjoying what you do and surrounding yourself with a great team that’s also happy and fulfilled.
When is confidence lost?
I don’t lose confidence much. I tend to be a really optimistic person. I would just say “F- it, move on” instead of wallowing in lost opportunities.
What’s the biggest problem tech is failing to solve?
My biggest headache everyday is getting my son ready for school. How can tech help me avoid the five minutes of hell trying to get his shoes and socks on every morning.
Editorial note: Answers have been edited for brevity and clarity.