Michael Phelps has been dismissed before.

Despite retiring as the most decorated Olympian of all time, the 31-year-old swimmer had to overcome the stigma of a DUI before earning his final round of medals.

His biggest challenge, however, still potentially lies ahead. Can Phelps, the supremely talented swimmer, remake himself into Phelps, the savvy businessman?

Many have attempted the transition, yet few have succeeded. Indeed, for every Michael Jordan or Tony Hawk, who build billion-dollar empires with their namesakes, many more make poor investments or simply blow through their fortunes post-retirement. (Think Antoine Walker or Derrick Coleman, to name a few.)

“For me this is my first time really out of the pool and in business world,” Phelps told Yahoo Finance in a rare sit-down interview, prior to an appearance at Intuit’s QuickBooks Connect 2016 conference in San Jose, Calif., last week. “It’s a fun, challenging road being able to switch from competitive swimming to now on land and trying to do that. It’s a new chapter, but it’s something I’m looking forward to. Hopefully, I’ll be able to be good at that.”

Phelps references Michael Jordan’s post-NBA career. Jordan, who retired in 2003, became the first NBA player to become a billionaire, driven by his lucrative Jordan Brand, which generated $2.8 billion in annual revenues for Nike during the company’s fiscal 2016 year. Phelps has his own personal fortune to protect, with a personal net worth hovering around $55 million, according to some estimates, from endorsements such as Under Armour, Omega watches, Sol Republic headphones and a slew of other companies.

More recently, the athlete also loaned his likeness to a character featured in a trailer for Activision Blizzard’s game “Call of Duty: Infinite Warfare.”

“I always like what MJ did: What he did on the court, and then how he transitioned into business,” Phelps explains. “That for me is like now, with the MP [brand]. I have so many things going through my head at all hours of the night.”

That includes expanding the MP brand, a swim gear line launched earlier this year for men and women produced by Aqua Sphere that caters to both casual and professional swimmers. Phelps says he spent nearly a year and a half working closely with Aqua Sphere to design comfortable, Italian-made swimsuits with cutting-edge fabrics that limit water absorption and bonded seams that reduce drag in the water.

Phelps also wants to find a professional swimmer who’s still active competitively to help represent his brand. The big challenge there? Finding the right spokesperson.

“That’s something that we’re talking about now,” Phelps explains. “I wanted to kind of finish my career wearing my own brand and then branch out to potentially having other swimmers who are still competing at a high level represent it.”

“It’s kind of who do I want to represent my brand in the swimming world,” he adds. “I think that brings up another huge question of who is the right first person that we sign to represent MP. I think that’s something that I’ve given a lot of thought to lately.”

Phelps concedes he’d love to court certain athletes for the job, but can’t because NCAA amateurism rules state that college athletes cannot accept money or sponsorships.

On the philanthropic side, Phelps remains dedicated to the Michael Phelps Foundation, which teaches kids water safety. To date, the foundation has helped over 15,000 kids, Phelps says, with plans of being in all 50 states by the end of the year.

Phelps is also exploring the possibility of writing another book.

“We’ve already had a little bit of talk about that and sharing the last chapter in my swimming career, the ending of it, some of the things I was able to overcome and push through,” he explains. “For me, I would love to do it, and I think it would be really good. But I think the hardest part is finding the right author for that book. We’re at the drawing board trying to figure out who would be the best author, narrowing it down to a couple of people who I think would write the best story.”

That story is not all about Olympic glory. When Phelps was arrested for a DUI two years ago, many simply wrote the swimmer off as a troubled has-been — a supreme athlete whose talents in the pool were overwhelmed by personal demons. His Olympic career seemed over.

That proved not to be the case, obviously. Following a transformative stint in rehab, Phelps returned to the water better than ever. “I could barely walk the first three months of training,” he admits. But he wanted to make a comeback.

“My mom wanted me to come back. My coach wanted me to come back,” Phelps says. “But I wasn’t going to come back and fake it like I did in 2012. I had to come back because I truly wanted to come back, because I truly wanted to swim.”

In his final race ever, he led the U.S. swim team to victory in the 400-meter medley relay at the Olympic Aquatics Stadium this August in Rio de Janeiro. Phelps ultimately walked away as the most decorated Olympic athlete of all time: 28 medals in all, 23 of them gold.

“The last two years of my career are probably the happiest I’ve ever been in and out of the water. I’ve been able to have the privilege to have a beautiful baby boy,” says Phelps, who also secretly wed longtime girlfriend Nicole Johnson this June, with a second, more public ceremony this past weekend held in Cabo San Lucas. “After the sort of downfall we had a couple of years ago, I think it just shows you that anything you put your mind to — if you want it bad enough — you can overcome whatever the hell is in your way.”

So if Phelps left behind an Olympic pool-sized legacy as a pro athlete, what does he want to be remembered for out of the water: the aquatic business equivalent of Jordan?

“Being able to see something pay off is really all that matters to me,” Phelps says simply. “The legacy question, that’s whatever you guys decide my legacy is. That’s my legacy.”

Spoken like a good sport.

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JP Mangalindan is a senior correspondent for Yahoo Finance covering the intersection of tech and business. Follow him on Twitter or Facebook.

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