My colleague Tom Popomaronis wrote recently about how Shark Tank star, investor, and Dallas Mavericks owner Mark Cuban regrets passing on the chance to invest in The Boqus Company, which cuts out the middlemen in the consumer flower industry.
That got me thinking: I wonder if Cuban regrets not running for president? I wonder what else he regrets, besides missing a not-exactly-well-known investment opportunity?
It turns out there's a lot of reporting and analysis out there about what Cuban regrets in life. Here are seven of the most interesting, ranked in order of how relatable they are to the rest of us.
1. Not forcing an NBA player to change his Twitter avatar
This is the least relatable regret I found. I can't think of many occasions when most of would ask anyone to change their Twitter avatar--much less regret not doing so later.
Context: In 2015, Cuban worked out a handshake deal with one of the stars of the Los Angeles Clippers, DeAndre Jordan, to come to the Mavericks on a four-year, $80 million deal. A few days later, Jordan backed out of the deal and instead re-signed with the Clippers.
"I think the only thing I would have done differently is make [Jordan] change his Twitter profile picture right off the bat," Cuban told ESPN afterward. "I think by having it just stay the way that it was, it gave him an out. He hadn't fully committed. Having him change his social media profiles right then was something I thought about and I thought, 'Nah, that's not an issue. Let's not bring that up.' But it happens. You move on. Next."
2. Not becoming an early investor in Uber
This regret, which Cuban articulated in 2014, is partially relatable and partially not relatable: Most of us would likely regret not investing early in Uber if we'd had the chance--but we'd be unlikely to have had the chance.
Cuban, however, had invested in Uber CEO Travis Kalanick's previous, unsuccessful company, Red Swoosh.
"I turned down--well I had a chance to invest in Uber and didn't," Cuban told Fox Business Network. "Probably my biggest mistake investing, but Travis is a grinder. He works hard he's smart and he's aggressive and when you're aggressive sometimes you know, you tend to be a little heavy handed."
3. Not investing in this shrimp burger company.
I think this one is more relatable simply because most of us would be more likely to have a shot at investing early in a strange company like this, than in a future unicorn like Uber.
Six years ago, an entrepreneur called Shawn Davis--also known as Chief Big Shake--was on Shark Tank, pitching his blend of gourmet shrimp burgers to the sharks. Cuban and the rest of his fellow investors all passed--but then Davis's business took off. Cuban later said on Good Morning America that he regretted missing out on this opportunity
"He had these shrimp sandwiches, and one of the things in business [is] you have to try to stick to what you know--and I don't know shrimp sandwiches from hot dogs," Cuban said, "but I like the guy. He was a great entrepreneur, he had a great idea. He had the heart behind it. And I passed. And now he went from $200,000 sales a year ago to over $6 million."
4. Undervaluing a star--and losing him.
Steve Nash was a All-Star point guard who played for Cuban's Dallas Mavericks from 1998 to 2004, when he became a free agent. Nash wanted to stay in Dallas, but he got a better offer from the Phoenix Suns, and Cuban declined to match it.
After he switched teams, Nash played even better--and was twice named the NBA's most valuable player.
"We thought his body would break down and it certainly didn't. So bad advice, bad across the board," Cuban told the Fort Worth Star-Telegram's Dwayne Price (and prompting a string of "Cuban's Biggest Regret" stories across the media.)
I think we've all failed to recognize other people's potential and importance at times. I think this regret and the next one are probably nearly equally relatable.
5. Undervaluing a key employee--and letting him leave.
Okay, this one was unexpected. Cuban told a Dallas radio show that his biggest regret came in 2012--allowing Don Kalkstein, who was the Mavericks team psychologist, leave the team in 2005--reportedly at the behest of then-coach Avery Johnson.
Kalkstein left and went to work for the Boston Red Sox, and he earned a World Series ring with the team in 2007.
"Seriously. I think if I hadn't done that we win a championship with Avery," Cuban told the radio show, adding, "We've had years where we've had great teams and my inability to solve that problem or in the case of not having Doc there, hurt us, so literally that was the biggest mistake I made."
6. Speaking without choosing his words.
This one is highly relatable, right? We all put our feet in our mouths at some points.
A few years ago, at an Inc. conference, in the midst of the controversy over racist comments by the then-owner of the Los Angeles Clippers, Cuban admitted to his own internalized prejudice, saying:
"I know I'm prejudiced, and I know I'm bigoted in a lot of different ways. If I see a black kid in a hoodie on my side of the street, I'll move to the other side of the street. If I see a white guy with a shaved head and tattoos, I'll move back to the other side of the street. None of us have pure thoughts; we all live in glass houses."
Cuban's words sparked a lot of controversy. He later said he regretted them--not because he didn't think he should have admitted the point, but because it "wasn't considerate to the Trayvon Martin family, who I've met. Because of the whole hoodie thing. So I probably could have phrased it differently, but my point, I'll stand behind it then and I'll stand behind it today."
7. Not working hard enough.
This one has to be the most relatable of all the regrets we can find Mark Cuban articulating over the years. And, he acknowledged it in an interview with Inc.:
"I think my regrets have come from not quite putting in enough effort, which has kind of motivated me for the next time. My regrets come from kicking myself in the ass for saying, 'Okay, there was an extra hour in the day you could have used. There was this time when you decided to sit and eat dinner, and catch a breather and catch your breath, instead of keep on going. To me you have to grind to be successful, and my regrets have come from maybe I didn't grind hard enough. Or maybe there's somebody out there outworking me. That's just not acceptable."
Then again--who knows? In another interview last year, Cuban said he didn't have any regrets at all.
Bonus: His biggest fear
Here's a bonus insight, because I think you can often learn more about what motivates people by examining their fears, rather than their regrets. In Cuban's case, it's the fear that as a result of growing up with far more money than he did, his kids could "grow up to be entitled jerks."
He talked about it in a 2015 interview with a Dallas television station.
"It is the scariest thing in my life, ever. After their health, there's nothing scarier. My wife and I talk about it all the time," Cuban said.