About Boardroom

Boardroom is a sports, media and entertainment brand co-founded by Kevin Durant and Rich Kleiman and focused on the intersection of sports and entertainment. Boardroom’s flagship media arm features premium video/audio, editorial, daily and weekly newsletters, showcasing how athletes, executives, musicians and creators are moving the business world forward. Boardroom’s ecosystem encompasses B2B events and experiences (such as its renowned NBA and WNBA All-Star events) as well as ticketed conferences such as Game Plan in partnership with CNBC. Our advisory arm serves to consult and connect athletes, brands and executives with our broader network and initiatives.

Recent film and TV projects also under the Boardroom umbrella include the Academy Award-winning Two Distant Strangers (Netflix), the critically acclaimed scripted series SWAGGER (Apple TV+) and Emmy-nominated documentary NYC Point Gods (Showtime).

Boardroom’s sister company, Boardroom Sports Holdings, features investments in emerging sports teams and leagues, including the Major League Pickleball team, the Brooklyn Aces, NWSL champions Gotham FC, and MLS’ Philadelphia Union.

All Rights Reserved. 2025.

Inside Stephen A. Smith’s Plan to Become the Biggest Name in Sports Media

Before ESPN’s $100 million man starts his next chapter, Boardroom gets a sneak peek at his new home at Disney’s NYC headquarters.

On the second basement level inside the Robert A. Iger Building that houses Disney’s monstrous new New York City headquarters at 7 Hudson Square on Wednesday, Stephen A. Smith had just completed the third ever show from First Take’s new set inside Studio Y. 

He and co-host Molly Qerim sailed through another quintessential episode of the series that’s been sports talk’s top-rated morning show for more than a decade on ESPN. They discussed that night’s NBA Draft with analyst Brian Windhorst, hypothesized about the remote possibility the Denver Nuggets trade superstar center Nikola Jokić with former championship-winning executive Bob Myers, praised new Pittsburgh Steelers quarterback Aaron Rodgers with reporter Kimberly A. Martin, and listed LeBron James and Stephen Curry in Smith’s top five NBA players perhaps solely to embrace debate. The set possessed the aesthetic of a luxury Manhattan high-rise apartment, with a round table in the middle of the room, digital boards used for graphics on either end of the set, and glass panels depicting the Midtown skyline, making it feel like you’re in the penthouse rather than the basement.

Smith was in a positive and reflective mood. He was finally back in his home city after spending all but one week over the last three months on the road. It was also his last day on set before going on a long summer vacation. 

First Take’s move to Hudson Square from its South Street Seaport digs represents Smith’s final adjustment to the new lucrative, expansive future he tirelessly created for himself. Stephen A. carved out space to spread his wings beyond ESPN when he signed a reported five-year, $100 million contract extension with the network, launching a two-hour daily radio show on SiriusXM, expanding his podcast and YouTube channel that accumulated 1.25 million subscribers in two years, and a newfound ability to appear on political shows to bolster the breadth of his growing reach. But he still has a deep appreciation for ESPN and First Take, which helped him become not only the most important person on the network but a multimedia colossus. 

“I know where it started. I know what enabled me to capture those other things,” Smith told Boardroom. “I always pride myself on making sure that I reward the people who reward me, and I owe it to this place to make sure that there’s no dissipation whatsoever in the effort and the commitment that I’ve made throughout the years to get me to this point.”

The 57-year-old’s effort and commitment went into overdrive during the NBA Playoffs, the same way they did over the last several springs, with Smith often pulling double duty with First Take in the morning and basketball studio analysis at night. This, however, will be the last time Smith encounters this particular set of circumstances at ESPN. With the Inside the NBA crew moving over from TNT Sports starting next season, Smith will no longer have those late NBA Countdown assignments.

Inside The NBA is coming here and nobody can be happier for that than me,” Stephen A. continued. “Not just because those guys are great, but it gives me what I believe to be well-earned relief. It’s been a long time. I’ve been covering the NBA for 30 years, so I’m going to get somewhat of a reprieve to some degree in that regard in terms of an inordinate amount of assignments that I’ve had in the past. So, I’m happy about that.”

While Smith said work never fazes him, working without enough sleep can become a real challenge. And with the constant responsibilities he needs to juggle on a daily basis, he can’t afford to have his sleep suffer multiple days in a row, where exhaustion snowballs and productivity and quality of work have the potential to decline.

The reprieve from Countdown hardly means Smith will be awash in free time. It doesn’t seem like his drive, ambition, or work ethic would allow it. His new SiriusXM show airs an hour after First Take wraps, he dedicates a lot of time to his podcast, and he’s still available to jump on SportsCenter or any other show whenever ESPN needs him. His production company, Straight Shooter Media, is a vehicle for Smith to pursue scripted and unscripted content, just in case he wasn’t busy enough.

“The people that are best at those jobs are always pushing themselves, always setting a bar and then trying to leap over that bar,” Mike Foss, ESPN’s senior vice president, sports studio and entertainment, which oversees First Take and all of the network’s studio shows, told Boardroom. “So when I see him outside of First Take, he’s always been prolific. The change or the development is it extends beyond sports now, but he’s always been very, very much out there. I look at it and recognize it as somebody trying to push himself and his boundaries.”

Stay Ahead of the Game, Get Our Newsletters

Subscribe for the biggest stories in the business of sports and entertainment, daily.

People don’t always like it when analysts or personalities try pushing beyond their perceived boundaries. The sheer number of hours Stephen A. is on television opens him up to scrutiny and criticism. When Smith opines on subjects some believe he doesn’t have the “right amount” of expertise on, he’ll be hammered on social media. Sports media watchdog Awful Announcing said his presence was a “net negative” at the NBA Finals, and that he was only at the Draft because “ESPN has to feel like it needs to justify his mammoth salary,” not because he has the requisite knowledge to analyze the picks.

Not unlike a high-profile celebrity or congressman, every move he makes is dissected, from playing solitaire on his phone during the Finals to his interactions with LeBron James, to potential political ambitions, which he denies. Yet Smith deeply understands what his bread and butter is, and that’s First Take.

Smith feels a sense of responsibility in living up to the expectations that come with being the top dog in sports talk. His audience expects to be informed and entertained, he said. That comes with him ensuring that those starring on Stephen A.’s stage exude chemistry and camaraderie. His on-air teammates and family show each other love, but at the same time understand that they have to win in the never-ending ratings game and to be as successful as possible every time he’s in front of the camera.

“A pretty consistent through line for the most successful people that I have ever had the pleasure of being in orbit with is that they are maniacally driven, almost obsessive in the best of ways,” said Foss. “And I don’t think that’s unique to people on television. Michael Jordan, LeBron James, Cristiano Ronaldo, all these guys push themselves to their limit and then figure out how to extend beyond that moment.”

Most successful on-air talent would have been satisfied with a fraction of the shows and projects Smith currently has on his plate. But Stephen A. has been obsessively, maniacally driven to grow in scale, scope, and stature in his pursuit of a media empire. The next half decade of his career is largely set, with the nine-figure ESPN contract, on top of his other income streams, ready to take Smith into his 60s. And while he invests his time and energy into the many hats he wears, Smith makes sure to recognize the people who invested in him, from Jimmy Pitaro all the way up to his workplace’s namesake, Bob Iger.

“I believe in rewarding them by showing them there’s no reason to regret the investment that they’ve made,” he said.

Smith was excited for a vacation where he could go to sleep and wake up whenever he wanted. He was already given leeway to not have to be in New York every time he commanded First Take, with the option of broadcasting from New Jersey, South Florida, Los Angeles, or other locales. When he returns to 7 Hudson Square on a regular basis in the fall, he’ll be ready to properly embrace the new, more secure digs that serve as his home base for the next phase of his career.

“I’ll have a greater appreciation for it come NFL season when I’m back,” Smith said, “because obviously I’ll be fresh, refreshed, ready to roll, and I’ll have an even greater appreciation then than I do of it now.”

What got Smith to this point, where he’s in complete control of what he does and where he does it, is a combination of incredibly hard work and relationship building, both inside and outside of Disney and ESPN. The road for the next five years has now been paved, his present and future secure. And while his body and mind will be shared with other companies, it seems like at Stephen A.’s new playground, his heart and loyalty remain in one place as he looks to prove that making him ESPN’s highest-paid employee and will more than pay for itself over time.

“No matter what I’m doing on my own, no matter what I’ve accomplished or I have established, I’m a proud, proud member of the Walt Disney and the ESPN family,” Smith said, “and I’m going to make sure they know that with the effort that I give every time I show up.”

Read More:

Shlomo Sprung

Shlomo Sprung is a Senior Staff Writer at Boardroom. He has more than a decade of experience in journalism, with past work appearing in Forbes, MLB.com, Awful Announcing, and The Sporting News. He graduated from the Columbia University Graduate School of Journalism in 2011, and his Twitter and Spotify addictions are well under control. Just ask him.

About The Author
Shlomo Sprung
Shlomo Sprung
Shlomo Sprung is a Senior Staff Writer at Boardroom. He has more than a decade of experience in journalism, with past work appearing in Forbes, MLB.com, Awful Announcing, and The Sporting News. He graduated from the Columbia University Graduate School of Journalism in 2011, and his Twitter and Spotify addictions are well under control. Just ask him.