An unbeaten champion with the Bellator and ONE promotions, Askren finally achieved his goal of fighting in the UFC, but he was on the wrong end of a highlight reel knockout by Jorge Masvidal that fight fans love to remind him of.
After retiring from cage-fighting, he took on YouTuber Jake Paul in a boxing match and again was knocked out in embarrassing fashion, but his wrestling background and one of the biggest paydays of his life made the loss a little easier to accept.
"I think if I had been like a golden child who had dealt with no struggle, then losing at the end of my MMA career would have been really devastating," he told Reuters in an interview in conjunction with the launch of his autobiography "Funky".
"But I came from a background where I struggled a lot in the beginning. I struggled and, honestly, a big part of me getting to where I got to was I just love to compete, I love to put it on the line."
Describing himself in the book as average until his late teens, Askren developed an unorthodox wrestling style which, together with his unruly mop of curls, led to the "Funky" nickname and he went on to win two NCAA championships and two Dan Hodge trophies as America's best collegiate wrestler.
He transitioned to MMA, winning his first three professional fights before joining the Bellator promotion where he went on to become welterweight champion.
A move to the UFC never materialised so Askren joined Asia's ONE promotion where he also claimed the welterweight belt, amassing an unbeaten 18-0 record with one no-contest before he finally got a chance in the UFC.
Askren beat former champion Robbie Lawler in his first fight but Masvidal's knee put him out cold after five seconds of their bout - the fastest knockout in UFC history - turning him into a meme and ending his chances of contending for a third belt.
LIGHTER SIDE
"I always tell people, one of the big things is don't tie your ego to your outcome," Askren explained, adding that he can see the lighter side of the knockout now that he has retired and got into coaching.
"It actually has a lot of value, because now kids can't say anything about it. It's like, hey, something bad happens to them - I'm like, dude, something way worse happened to me, right? Stop pouting," he says.
Askren would have preferred a shot at the UFC before age and injuries had taken their toll on his body. By the time he fought Paul in a high-profile boxing match he had had his hip replaced and eventually got KO'd in the first round.
"He (Paul) ended up being kind of good. It's kind of annoying but you know what, you put in your work, you get good", Askren said.
He developed an ability to wind up opponents and fans alike early and maintained it throughout his career, making him one of the most popular and talked about fighters wherever he competed.
Though Akren says he is not financially independent, he is comfortable and at ease with his new life in coaching.
"I would say I get to do everything I want to do in life, meaning when I say yes or no to something I'm not just thinking about how much I'm going to get paid," he added.
