On a postgame team flight back to Chicago in 2021, Thaddeus Young and a few of his Bulls teammates were playing booray, a gambling card game. During a break, Bulls star guard Zach LaVine noticed Young combing through a document on his laptop. It was a business deck for digital sports brand Overtime.

LaVine was curious and wanted to know more about the Gen Z media company, so Young told him about the value proposition of the brand that garners more than 100 million social media followers. LaVine wanted in. Young later connected LaVine with Overtime president Zack Weiner.

The rest is history; the former teammates, along with ex-Bulls forward Garrett Temple, are all now on the cap table at Overtime, which is tracking to cross $100 million in revenue this year.

“Who’s not going to let an NBA basketball player [invest] in a basketball company,” Young said about Overtime, which calls more than 6% of active NBA players investors. “You want as many stars as you can to be around it.”

Young, who just finished his 17th season in the NBA, has been one of the catalysts for the culture change in the NBA as more players are conversing about deal flow and sharing investment opportunities, rather than boasting about their new sports car purchase or fancy summer home. The latter won’t ever stop, of course, but for many teams, especially ones led by veteran players who have earned multiple contracts, it’s now normal to discuss their venture and equity matters.

NBA players no longer merely associate themselves with businessmen. They are businessmen.

It’s a realization today’s ballers are having after watching stars of the past score big off the court, from Kobe Bryant’s lucrative Bodyarmor investment ($400 million exit) to LeBron James’ ownership stake in SpringHill Company (valued at $725 million in 2021). These walking enterprises not only want to grow their own wealth but more often want the rest of the NBA’s closely knit brotherhood to also be successful.

“It’s been pretty drastic as to what guys are comfortable and open to talking about in the locker room,” New Orleans Pelicans forward Larry Nance Jr. said in an interview. “Before I could go to a vet and ask him what he does, but it wasn’t openly discussed. Now we talk about it on the plane, on the bus or in the locker room. There’s no time where it’s inappropriate.”

One of the contributing factors is the shared relationships players have with trusted agents and financial advisors who are introducing and providing guidance on deal opportunities. Nance Jr. and Indiana Pacers guard TJ McConnell, for example, have the same agent in Mark Bartelstein. Nance Jr. and McConnell have become not only friends but also business partners. Last year, McConnell, an avid soccer fan, tipped Nance Jr. about an opportunity to invest in upstart English Premier League club Leeds United, which is owned by 49ers Enterprises. The two partners posed together after a game three months ago, did the ‘Leeds salutes’ and the club posted the moment on its Instagram feed. It’s been a noteworthy investment for Nance Jr., who says it likely wouldn’t have happened without McConnell.

Due to non-disclosure agreements, there are some deals Nance Jr. must keep close to the vest, namely those related to European soccer. But inside the Pelicans locker room, it’s never short of financial literacy conversations. The former first round draft pick says it’s not uncommon for him to speak with Herb Jones, Jordan Hawkins or Trey Murphy about franchising or the importance of patience during growth. In a different corner of the locker room, Nance Jr. and savvy investor teammate CJ McCollum pass pitch decks and investment opportunities back and forth like a basketball on the court.

“We present different things to each other,” Nance Jr. said. “It’s definitely a part of our relationship, and I’ve learned a lot from him in that aspect.”

Nance Jr. says that even when business-related chatter in the locker room digresses to materialist buys, it’s not always about depreciating assets. It can quickly turn to vintage watches, rare artwork and other items that can provide a financial return. “The conversations are a lot more about the preservation of wealth,” he said of the changes in conversations among NBA players.

NBA teams with younger players are less likely to be discussing investment strategy or ways to diversify their portfolio. After all, many of them are enjoying the fruits of their labor for the first time without much thought on how to multiply their assets off the court. Often those locker room conversations are more about brand building or connecting with their fans through video games and esports platforms. But that hasn’t stopped some business curious players on fresh-faced teams from getting into deals. Orlando Magic forward Wendell Carter Jr., who was drafted to that veteran-led Bulls team in 2018, is another example of this.

A couple months ago after a team practice, Magic guard Admiral Schofield approached Carter about a real estate play which would allow him to earn a piece of the revenue generation of a new medical-related facility in Portland. It’s an opportunity for Carter to join other NBA players who are considering the proposal.

He’s planning on working alongside Schofield as both a teammate and business partner. This also goes for another fellow teammate in Magic guard Gary Harris, who is having ongoing conversations with Carter about investing in a marijuana dispensary chain based in Arizona.

“That’s the name of the game right now,” Carter said. “Guys are more hands-on now. You hear the horror stories of back in the day of [players] giving all their financial decisions and access to someone else, which [led] to stories of people stealing money and things like that. That’s a part of it. Guys are not only more hands on but want to find more ways to make money.”

The conversations between NBA players extend beyond their physical shared spaces. It’s not uncommon for multiple players to be connected in deal flow text message group chats where various opportunities are being discussed. It’s on the players though to still be selective and diligent about their investments. While there’s a growing trend of more players being involved and communicating their strategies, there remain numerous deals from startups to more mature brands that never materialize and leave players in the negative. That’s why strong recommendations are still golden around the league.

“I’m just grateful that as a league, whether you’re doing it in the locker room or not, guys are wanting to learn more,” Carter said. “It’s only going up. I see these teams being owned by the players at some point. That would change the whole game.”

The rise of NIL only makes players entering the NBA more comfortable navigating the various pitches that come their way, especially since they’re screening deals earlier alongside their financial teams that were created in high school and college. Already in business mode, it’s becoming normal for rookies to arrive to the league as millionaires, an occurrence that will have a ripple effect with knowledgeable and financially astute newbies around to groom the next generation. It’s just the beginning of this culture change as many veteran players have yet to see exits on deals that take five to seven years to realize.

“We’re only in the third inning,” longtime athlete financial advisor and Atlanta Falcons limited partner Rashaun Williams said in an interview.

The NBA is in a good place, with the new media rights deal expected to be worth about $76 billion over 11 years. With more expendable cash for the players, it’s only natural this additional capital will be deployed in various avenues such as early-stage venture capital, while at the same time the players continue to train themselves to be more self-sufficient entrepreneurs and CEOs of their own multimillion-dollar brands.

Drafted in 2007, Young has noticed the culture change firsthand. NBA players are no longer waiting until the twilight years of their careers to take a seat at the boardroom table. It’s all about now.

“At the end of the day, we have a short window to make as much money as we can.”