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Damian Lillard’s Boldness Extends to Entrepreneurial Spirit

The Portland superstar has the savvy and stamina to succeed in the business and basketball world.

Chicago Bulls v Portland Trail Blazers Photo by Sam Forencich/NBAE via Getty Images

Damian Lillard might be the most versatile entrepreneur active in the NBA, not only scoring on the court but in music, business and supporting his community.

From humble beginnings in Oakland, California and a relatively under-the-radar four years at Weber State University in Ogden, Utah, the 31-year-old is now one of the world’s biggest names in sports.

Lillard has led the Portland Trail Blazers to the playoffs eight straight years, missing the postseason just once — his rookie season. He earned Rookie of the Year in 2013, six NBA All-Star nods, one All-NBA First Team honor, four All-NBA Second Team selections and an All-NBA Third Team nomination. His array of awards, combined with clutch play, has lured national TV cameras and reporters to the Pacific Northwest.

If anyone wanted further proof of his sporting prowess, Lillard was also recently chosen as one of the 75th best players to ever do it.

Off the court, Lillard is also a force to be reckoned with. Even those unfamiliar with the sport of basketball are still intimately aware of his existence.

How has he done this?

It’s not been sitting around waiting for people to give it to him. Lillard himself has preached hard work has been his avenue to success, consistently using an “against all odds” mantra as ammunition to prove doubters wrong.


Over the years, a few NBA names have dabbled in the music industry, from Ron Artest to Shaquille O’Neal, Iman Shumpert, and Lou Williams.

In most cases, these musical attempts could be considered novelties — NBA players using music as an extracurricular outlet. Lillard, on the other hand, is considered a relevant hip hop artist and rapper, creating four studio albums over the past five years.

Following the release of his fourth album this year, Rolling Stone magazine’s Matt Sullivan posited Lillard as potentially the greatest athlete rapper of all time. He’s collaborated with names including Lil Wayne, Snoop Dogg, Q-Tip, Raphael Saadiq, Blxst, Jeremih and Mozzy earning universal respect. One of his songs, Money Ball, also appeared on the NBA 2K20 soundtrack.

It’s also important to note that compared to professional musicians, Lillard has less time to concentrate on music. He spends roughly eight months every year leading the Trail Blazers through the arduous 82-game NBA season, plus whatever the team achieves during the postseason.

Business and Brands

Lillard is famously signed to the Adidas shoe brand. He ranks as one of the brand’s biggest names, with his own shoe line, fawned over by the basketball watching and playing masses worldwide.

Lillard has also done deals with AT&T, Gatorade, Oakley, McDonald’s, Moda Health, Spalding, Tissot, Hulu and Biofreeze seriously augmenting his $40 million a year contract for playing basketball.

Lillard also participates in more direct entrepreneurial endeavors. Since October 2020, he has been the co-owner of a Toyota dealership in McMinnville, Oregon. He’s infused his own style at the car yard, installing custom Pop-A-Shot games, themed ping pong tables, autographed memorabilia and more.

In June, Forbes named Lillard as one of the world’s 30 highest paid athletes and the 91st highest paid celebrity.


Lillard has accomplished all of the above while raising three young children, two of which are twins, with his new wife Kay’La. He’s also demonstrated passion for the people of Portland and in his hometown of Oakland, California.

Lillard’s name has regularly come up in NBA Cares awards. He finished as finalist for the overall 2020-21 prize. He won the monthly award in November 2018 for his efforts to improve attendance and graduation rates across Portland through his RESPECT program. The program—focusing on Madison, Parkrose and Roosevelt high schools in Portland—encourages young people to show up, work hard and be kind.

In June 2018, Lillard drove a U-Haul to the edge of Irving Park in Northeast Portland, threw open the back of the truck and began handing out sneakers to a crowd of kids. No doubt participants were keen for a new pair of shoes, but they were also plenty excited about meeting Lillard himself.

In his first season with the Blazers, Lillard was named the 2012-13 Maurice Lucas Award recipient. The honor is given to the player who best represents the indomitable spirit of Maurice Lucas through his contributions on the court and in the community.

Even when he’s on the court, Damian Lillard doesn’t forget about his roots. He dons the letter “O” on his jersey, honoring Oakland, Ogden and Oregon.


Damian Lillard is truly inspiring, a model citizen, man and basketball player with the drive and ability to succeed in whatever he applies himself to.

Many have already decided he will not win an NBA championship if he plays out his career in Portland, but those people clearly don’t understand the will of a man destined for greatness, even before a college scout laid eyes on him.

There’s more to Damian Lillard than basketball. He is a bold and determined entrepreneur always looking for another arena to succeed in.