Athletes with side hustles are nothing new, but not every venture is a roaring success. Sometimes, athletes make headlines for the wrong reasons.
Logan Paul built a global drink empire. Jake Paul turned boxing into YouTube theatre. Travis Kelce became a podcast mogul who somehow picked up Taylor Swift along the way.
And then there are the names who drifted into pure chaos. From Antonio Brown’s failed music label to Johnny Manziel trying everything except staying out of the headlines.
Logan Paul and the PRIME Explosion
Logan Paul turned a YouTube career into one of the wildest business runs in modern sport. PRIME went from an online gimmick to a global drink brand in a matter of months.
Able to leverage his massive star power worldwide, Logan has kids around the globe dragging their parents to the nearest rip-off store to buy a bottle of juice for $10.
UFC and Premier League deals followed before the industry even worked out what the product tasted like.
His WWE run is technically his “sporting” job, but even that acts as marketing for the rest of his empire. If you haven’t spotted the Prime-branded ring mats or the bottles at ringside, maybe you saw Paul frogsplash a life-size bottle of Prime (KSI) at Wrestlemania 41.
I think that’s the wrong person @LoganPaul … #prime #ksi #loganpaul #wwe pic.twitter.com/wNTeiAViXJ
— PRIME NEWS (@primenewsclips) October 17, 2024
If that wasn’t ridiculous enough, Paul revealed he offered Stone Cold Steve Austin $1 million to wear it. Thankfully, Steve has dignity.
Shaq is hilarious… but he knows business
NBA legend Shaquille O’Neal built a business empire so big it borders on absurd. He owns pieces of gyms, car washes, restaurants, tech companies, fast-food chains, and enough real estate to require its own staff room.
No part of his portfolio matches. None of it follows a theme. It’s impossible to reconcile the savvy with the comedy character you often see on TV. Yet it all makes money.
He has investments in Ring, Papa John’s, Google, Five Guys, and Auntie Anne’s. He also fronts insurance adverts, DJ sets at festivals, and any commercial gig that makes him laugh.
And imagine having enough money floating around in your bank that you can buy 155 Five Guys locations. Not because you have a clue what you’re doing – Shaq admitted as much – but because you think the food tastes bad ass!?
He offered a stake to a former McDonald’s manager who had hooked him up with free food during his NBA days and told him to help run the chain. They later sold for a profit.
When side hustles go wrong
For every business empire that works, another athlete launches something that collapses quicker than the Chiefs’ latest NFL title defence.
Antonio Brown has produced a long list of side ventures, most of them brief and often surrounded by noise.
Brown moved into music with his CAB Records imprint and released several viral tracks. His single “Put That Sh*t On” became a widespread TikTok trend, though his music career never settled into a long-term project.
His clothing drops generated attention, too, but fans regularly posted complaints online saying orders hadn’t arrived or were delayed.
The most public breakdown came in arena football. Brown took over the Albany Empire, only for the franchise to be removed from the National Arena League weeks later. The league cited unpaid fees and players said they were waiting on paychecks.
Conor McGregor’s chaos prints money
Not all chaos is created equal. Conor McGregor has spent a decade running through headlines like a whirlwind, but unlike most athletes with side hustles, his version usually ends with another business added to the pile.
Proper No. Twelve turned him from UFC champion into a global whiskey mogul. The brand sold for a reported nine-figure sum, proving his marketing power.
His Forged Irish Stout launched next, alongside his gym chain, his TIDL recovery brand, his McGregor FAST fitness program, and a string of pubs and bars across Ireland.
McGregor understands attention in a way very few athletes do. Even his controversies — court cases, public disagreement, and a constantly shifting UFC timetable — end up feeding his commercial world.
The man can promote a whiskey during fight week, announce a fitness challenge an hour later, and post a pub renovation video before sunrise.
It looks like it makes no sense as a business structure, yet this genius is now worth just shy of $200m.
Johnny Manziel tried everything
If McGregor is the poster boy for chaos bringing success, then Johnny Manziel is the poster boy for, well, just chaos and no success.
He tried nightclubs, party promotions, brand launches, spring-league comebacks, and even a docuseries that ended up focusing more on the chaos than the football.
His brief stint in the CFL ended early. His run in the AAF lasted two games before the league collapsed.
Away from the field, Manziel leaned into nightlife partnerships and promotional appearances. Some were tied to club openings, others to branded events, but none lasted long enough to become steady work.
Even the Netflix documentary built around him underlined the same point. Manziel had access, attention, and opportunity, but no side hustle ever turned into a real business.
NBA stars launch the funniest side hustles
Nate Robinson is a great example. He signed up for a celebrity boxing match, walked into the ring full of confidence, and walked out as a meme. His influencer deals spiked for a week, but that KO clip will live forever.
Dennis Rodman also wandered into the side-hustle wilderness. Befriending Kim Jong-Un had no benefit, but it was funny.
Rodman tried a cryptocurrency project, promoted his own vodka, fronted a brief wrestling comeback, and even launched a clothing line that sold out one day and disappeared the next.
Metta World Peace once tried to balance NBA defence with a rap career, releasing an album, shooting music videos, and even teasing a comedy tour.
Lamar Odom launched his own cannabis line after leaving rehab, promoting it through livestreams and pop-up events that often went viral for reasons he definitely didn’t plan.
