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Lou Williams’ Journey From 6th Man to Music CEO | Brick By Brick

After authoring an NBA career for the record books, Lou Williams is preparing to pivot and indulge his other longtime love: music.

Lou Williams is not scared of retirement.

“I’m embracing it,” the three-time Sixth Man of the Year tells Boardroom. “I speak so freely about it because I don’t know when I’ll retire. I have the freedom to make that decision, whether it’s this year, next year, or if I want to keep going and my children say they still enjoy coming to the games and watching me compete. It’s not a lack of talent. I’m just mentally in a space where I’m ready to give my energy to something else.”

In his second season with the Atlanta Hawks — his first full campaign after an emotional trade from the Los Angeles Clippers last March that tempted him to retire on the spot — Williams has happily shifted into the veteran role of mentor for the NBA’s next generation, including his All-Star teammate Trae Young. He is committed to paying forward what Allen Iverson did for him as a 17-year-old selected out of South Gwinnett High School in the second round of the 2005 NBA draft by the Philadelphia 76ers.

“Everything comes full circle,” said Williams, whose high-level longevity was further solidified by breaking the NBA all-time record for most career appearances off the bench this week.

In all likelihood, he will finish his unprecedented playing career in his hometown Atlanta with the team that “had the opportunity to draft me and decided to pass on me” 17 years ago. Whenever that final bow comes, he’s at peace.

“A lot of times, [retirement] would scare you because you don’t have a backup plan,” he said. “You don’t have anything to look forward to. I got so many different things to look forward to.”

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Away from the court, Williams is already pouring everything he has learned — about business, about leadership, about relationships — into indie music label Winners United, which he runs as CEO alongside partners Paul Williams and multi-Platinum engineer KY Engineerin’ (born Finis White).

Winners United is home to burgeoning Atlanta singer-songwriter Landstrip Chip and viral hip-hop sensation Akeem Ali, who was an opening act for a portion of Jack Harlow’s 2021 sold-out Creme De La Creme Tour.

Music was never Williams’ backup plan, but it is definitely his second act.

Lou Will’s Musical Roots

Music and basketball are tied for bragging rights as Williams’ first love.

12 years younger than his sister and 10 years younger than his brother, Williams’ musical palette was influenced early by their favorite artists. He recalls weekends at the house soundtracked by such legends as Boyz II Men, TLC, and UGK.

“It made me more mature as a person because I hung around teenagers,” he explained. “Listening to the music that they were listening to, [or] going to proms and dances with my sister and brother because they couldn’t go unless they took me.”

These formative experiences opened the floodgates for obsession. Williams studied everything about the music industry, down to how his favorite artists — Lil Wayne is his unquestioned No. 1 of all time, it should be noted — handled their projects’ rollout campaigns, developing a keen understanding that Winners United now benefits from.

Once Williams became a teenager himself, he essentially blinked and was drafted by the Sixers. His passion for music never waned, but from 17 to 20 years old, he locked in completely on basketball and finding his footing as a boy in a league of men. He knew that “basketball was gonna be the vehicle to bring all of these other things to the table.”

Basketball wasn’t a chore, though. He achieved one of his childhood dreams and was determined to become a great hooper. It didn’t hurt that his first mentor was Iverson, whom he still considers his “big brother.” A.I. was (and forever will be) a cultural icon because of the example he set for athletes refusing to be contained to any particular box. In other words, the now-Hall of Fame guard was never going to sacrifice his freedom to express the dimensions of his humanity.

Williams took note then, and reflects now on what stuck with him from that time:

“He’s the reason that I have the confidence that I have to be an undersized scoring guard and to have that confidence to do different things outside of the realm of basketball and be comfortable in my skin with the criticism that comes. … It’s getting more and more progressive now, with people just accepting athletes to do things outside of a field or a court or a baseball diamond. We’re all starting to be more expressive in our clothing. We’re all starting to be more expressive in our personalities. One thing I look back on, I just wish people were more open to listening to the music and trying to catch a vibe with athletes that were artists at the same time like they do now.”

Still in Philadelphia come 2011, Williams found another crucial mentor: Meek Mill. The two-time Grammy nominee invited him to be a featured artist on his single “I Want it All.” Meek and Williams “recorded a ton of music,” and at that time, were in the studio every day. “

We have close to 30, 40 songs together,” Williams teased.

Throughout his career — six different teams, five different cities —Williams has recorded hundreds of unreleased songs based on his eye-popping experiences. He traces his confidence to spread his wings as an artist back to Meek, whose early approval validated him in believing that he could (and should) be taken seriously in the music industry.

But first, he needed to embrace his position in the basketball world.

The Sixth Man: ‘I Made it Cool’

At first, Williams took being considered for Sixth Man of the Year “as a slight.”

“I didn’t even understand what a Sixth Man was,” he said. “I would hear the term, and I was like, ‘What the hell does that mean?!’ I never understood it. I never embodied it — until I lost my first one. When James Harden beat me [in 2011-12], once I had that first experience of losing an award in the NBA, I was like, OK, I want that; now, it’s personal. That was the moment I embraced it and tried to make myself the best Sixth Man of the Year that there ever was.”

Well, objectively, mission accomplished: Williams and Jamal Crawford are tied for the most Sixth Man honors in league history. But Williams took it one step further than the history books. With his LOUWILLVILLE alter ego, which has since blossomed into a full-blown lifestyle brand much bigger than him, Williams takes pride in making the role of sixth man cool.

“I don’t think a lot of young hoopers really wanted that position or really saw it as something that could be their own or could be successful — could be a pathway to making more money, a pathway to getting further along in their careers,” he said. “Jamal and I have been finalists to be All-Stars in this league. We’ve averaged 20 points a game in this league. We’ve been leading scorers on our teams. We’ve done the things that a lot of superstars do night in and night out. We showed young hoopers that you can do this job, still have the perks, and still be considered a household name. You can still be legendary in this game. That’s the difference between Jamal and I, as far as that goes, was I just embraced it and turned it into a lifestyle.”

Williams’ first Sixth Man Award came with the Toronto Raptors in 2014-15. (He won the other two back-to-back during his Clippers tenure, in 2018 and ’19). With it, he became the first Raptor to earn any NBA award since 1999. Williams’ campaign for the honor was endorsed by Drake, an official Raptors ambassador and Toronto’s unofficial No. 1 fanboy, with his If You’re Reading This It’s Too Late track “6 Man”:

“Boomin’ out in South Gwinnett like Lou Will / 6 Man like Lou Will,” Drake, the 6 God, spits in the first verse. “Two girls and they get along like I’m (Lou) / Like I’m Lou Will, I just got the new deal.”

Those bars have endured as Williams’ favorite out of the countless times he has been name-dropped in songs because it gave him his “soundtrack” for one of the more memorable times of his life.

But it is this timeless line from Drake’s 2010 classic “Thank Me Now” that more closely resembles his next chapter:

“I swear sports and music are so synonymous / ‘Cause we want to be them, and they want to be us.”

“It’s the truth!” Williams confirmed. “I think athletes and entertainers, we flourish on our respective stages. You’ll go to a concert, and you’re like, ‘Damn, that’s one person up there. Everybody’s here for that one person.’ And then you flip it to sports, it’s nonstop action. You’re always doing something to impress the crowd. It’s so positive because you’ve got very small kids up to old people, and so, in sports, it’s a little more universal than entertainment. We both just have a thirst for the different ways we can entertain people.”

With Winners United, Williams won’t settle for anything less than an eternal, universal impact.

The Future of Winners United

Williams isn’t scared of soon retiring from the only game he’s ever known because he believes wholeheartedly that he is just beginning to etch his overall legacy.

Williams, an accomplished NBA veteran with over 15,000 career points to his name, still hustles like the 17-year-old kid out of South Gwinnett.

That was never more evident than with “Big Tuh,” his single featuring 2 Chainz and Lil Wayne that dropped last summer.

Over a year prior to its release, Williams recorded “Big Tuh” by himself one night. While driving home at 3 a.m. and listening to the track in the car, he immediately knew the song was something to be proud of. But it could be better.

“You slick gotta get on this for me,” he texted 2 Chainz, half-joking and half-serious but mostly just wanting his friend to listen and be proud of him. Much to Williams’ surprise, 2 Chainz knocked out a verse the next day, and Williams marinated on the song for another three weeks.

“And then I randomly was like, ‘Lil Wayne will make this song something completely different than what I’m expecting it to be,” he said. “It was already dope with just Chainz and me, but I was like, I just want to shoot for the stars. Wayne has done songs with Dame [Lillard]. He’s done songs with other athletes. I was like, ‘I’m gonna shoot my shot!’”

One month after Williams reached out to Weezy’s management, he received a text back “out of the blue” asking for the beat because the five-time Grammy winner was on his way to a studio session.

“[Wayne] sent me a 24-bar verse,” Williams said. “Chainz and I only did eights. That was major love. And he didn’t charge me! I definitely wasn’t expecting it to come to fruition.”

That shoot-for-the-stars mentality isn’t exclusive to “Big Tuh,” as Williams meticulously builds Winners United into a desirable destination, under the LOUWILLVILLE umbrella. He’s able to dream big because he has laid the foundation to support it.

“In my career, I’ve been afforded the opportunity to own all of my logos. Own all of my trademarks. Own all the names associated with me,” he said. “I had that opportunity because I don’t think a lot of people found value in it. So, for me to have the opportunity to have all of these things under my ownership umbrella and to build it to a place where it has value and people want to be associated with it, that’s special and meaningful to me.”

Williams wants Winners United to conjure “good music, good feelings, good vibes.”

He can’t wait to discover other diverse artists who “can cover multiple genres of music” and expose Winners United “to different lanes of people, different waves of fans all over the world, instead of just being stuck in one box.”

And to that point, he empowers Akeem Ali and Landstrip Chip to be just as bold as he was in sending those texts to 2 Chainz and Wayne — to express themselves as unapologetically as Iverson long ago taught him.

Underlined on Williams’ big-picture plan for Winners United is to afford his artists the same autonomy and opportunities he fought to earn for himself and his family.

“I’m a strong believer in your foundation having integrity — how you want to be known,” he said. “You don’t want to be viewed as the label that the artist hates, [and] they go on Twitter and Instagram and they lash out against their record label because you’re not seeing eye to eye. I am also an artist, I am also an athlete, who’s dealt with the business side of things that could have been better for me. I sympathize with those experiences.

“For you to be successful — for you to have a long imprint in something — I think you gotta do good business and you gotta do right by your people.”

And with that, it is clear that even as Lou Will evolves into a powerful label CEO — and maybe even star rapper — he will always possess the team-first qualities of the ultimate sixth man.

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