Ten years ago, at age 20, LeBron James left a successful agent who had negotiated more than $150 million in deals for him so he and three friends with no experience could run his business.
The move was instantly panned. Social media was in its infancy -- James didn't have a Facebook page at the time -- yet he was widely chided for being naive and foolhardy.
But James has always had a talent for being able to take in a wider perspective and think for the longer term, even when many around him do not. It's the same skill that allows him to see two passes ahead on the floor or the driving lane no one else notices. Which is how James arrived at last Monday, when he and Nike announced his signing of a lifetime contract.
The deal, worth hundreds of millions on top of the hundreds of millions that Nike has already paid him in their 13-plus years together, was negotiated over the course of months, but it has really been under construction for years. When James signed his last Nike deal, in 2010, it included provisions to protect him. So when Kevin Durant signed a 10-year deal with Nike last summer for a reported $300 million after a bidding war with Under Armour, James knew he was going to be in position for a historic deal.
The timing, like so many of his cross-court bounce passes, was impeccable. Nike is having one of the best financial years in its history, is the best-performing stock of the year on Dow Jones and has astronomical growth projections.
James, however, doesn't intend for this to be his biggest business move. If he is going to eventually be a billionaire with this latest deal, James surely wants a bigger prize -- perhaps to someday join his idol Michael Jordan as an NBA owner.
That is something he has talked about. But just when you think you can see James' plan, understand he has probably envisioned something more expansive.
For years now, his visions have gone beyond basketball. Why not an NFL owner? Majority owner of a Premier League team? Head of his own Hollywood production and talent firm? What about running for public office? James and his team have shown they don't operate within established parameters.
He's past the point of picking up a large paycheck for putting his name or face on a product. As James slowly became obsessed with the bigger picture and started thinking in terms of 10 figures and not eight or nine, he realized he wanted to rise above someone who endorses brands. He wanted to own the brands. If he was associated with it, he wanted equity in it.
It's why he recently left McDonald's to become an investor in an upstart pizza chain, and why he has cut back on commercials -- to the point where Blake Griffin and James Harden have appeared in more over the past few years.
Harden is getting paid for pitching Taco Bell; LeBron is trying to make his money from owning a franchise like Taco Bell.
The other big-business announcement James made last week was a $15.8 million investment in Uninterrupted, a social-media platform he and his partners created last year that allows direct interaction between athletes and fans. (James, Ronda Rousey, Carmelo Anthony and Rob Gronkowski are among the athletes who have already participated.)
The investment and idea were heralded in the financial and Hollywood press as forward-thinking. The irony, of course, is that James is using the same principles he did with "The Decision" back in 2010, when he and his team wondered why they should give something of such value -- i.e., access to him and his thoughts -- away for free on Twitter or at a news conference. "The Decision" didn't work, but it was an example of him pushing for ownership, thinking bigger. And it led directly to the concept for Uninterrupted, which he now is in position to profit from.
There have been other stumbles along the way. He has invested in companies and watched them fizzle. He has made high-profile partnerships that haven't worked out as expected, such as one with Microsoft. But he has never stopped looking to expand on opportunities or create new concepts.
When a fledgling headphones company called Beats came to him in 2008 looking for marketing help, James put an equity stake ahead of a bigger check. He didn't make a commercial for Beats until years later, but he gave pairs of the headphones to his Team USA teammates. Sure enough, images of the product at the Beijing Olympics helped launch the brand. Beats, of course, later sold for $3.2 billion to Apple, and James participated in the sale to the tune of tens of millions.
His production company, SpringHill Entertainment, currently has deals for shows with Starz, Disney, Showtime and NBC, and a development deal with Warner Bros. And while portraying himself in "Trainwreck" opened the door in Hollywood for more acting roles, he's more interested in owning a piece of a blockbuster.
There's also the deal struck last summer with the University of Akron and Chase Bank. James will do promotion for the university and Chase will get to link itself to him. In return, potentially thousands of students from his Akron-based "I Promise" program will be guaranteed four-year scholarships. James could've just done a straight deal with the university, but instead he and his foundation looked for a way they could extend the partnership.
If you come to James with an offer, it is now routine business for him to find a way to step back and increase the scale. And if he can't, he probably won't do it.
Next year, James is expected to have the highest salary in the NBA for the first time in his 13-year career. He knew this in 2014, which is why he became the first megastar player to take a one-year contract (with a one-year player option) in the midst of his prime, and why he did the same this past summer, positioning himself to cash in on the upcoming salary-cap spike.
But James is already thinking beyond next season. A year before signing with the Cavs in 2014, James' friend, Chris Paul, was elected president of the players' union. James later joined him, becoming vice president in February 2015. Now the duo is in control of how the next collective bargaining sessions will go in 2017, when the NBPA is expected to opt out of the current deal.
The pair's plans for those talks, as of now, remain secret. But you can assume James has put plenty of thought into them -- and not just about the contract he can sign in 2017, one that could be the largest in NBA history.
Yes, James has a season to play and a huge challenge trying to get the Cavs back to the NBA Finals. The Golden State Warriors appear to be one of the strongest adversaries he has seen in his career. Maybe he'll figure them out, maybe he won't.
Along the way, many may compare him to a contemporary like Stephen Curry, an outgoing great like Kobe Bryant or a legend like Jordan. But James has long considered such talk trite. He's in the middle of an entirely different conversation.