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The DeSean Jackson Project

He’s not done with football yet, but the Pro Bowl wide receiver isn’t waiting for retirement to plan his next chapter as an investor, entrepreneur, and media figure.

Las Vegas Raiders wide receiver DeSean Jackson knows his standing in the broader football conversation. He’s a three-time Pro Bowler and one of the premier deep threats of his generation, and at 35 years of age, he wants to add to his numbers and achieve even bigger goals.

He wants to overtake Jerry Rice for the most 50-yard touchdown receptions in NFL history; he is only two away with 34. Jackson also wants to keep climbing the all-time receiving yard list — he’s 37th all-time but could pass Chad Johnson as soon as this weekend for 36th.

But Jackson is just as sure of himself off the field, too. Over his career, he’s generated upwards of $100 million in on-field salary and endorsements; combined with a growing portfolio of investments, he’s prepared for a post-playing career that he aims to make every bit as dazzling as his time on the gridiron.

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Family & Friends

Despite his success, Jackson would be the first to tell you that he didn’t do it all himself. He recently spoke with Boardroom about his ventures and visions for the future — and in that discussion, he routinely interrupted himself to give boatloads of credit to various individuals who have shaped who he is today.

It starts with his family. His older brother, Byron, has been by his side since the beginning. So has his adopted brother, Derrick, who works for Boeing and boasts a sharp business mind. His mother, Gayle, has a legal background and was the one, especially at the start, who helped him understand the deals he was signing and everything hidden in the complicated language of his contracts.

She is now president of the DeSean Jackson Foundation, which manages Jackson’s philanthropic ventures — many around fighting pancreatic cancer, which took the life of his father in 2009.

“She doesn’t really trust anybody,” Jackson told Boardroom. “Having a mother that cares and understands money — she worked in a law firm, so she’s very familiar with contracts and numbers.”

Jackson also follows the examples of his NFL friends, like 49ers offensive tackle Trent Williams. Williams is an investor in Dapper Labs, the company behind NBA Top Shot, and also has investments in the real estate market, which is where Jackson himself is most active.

Michael Strahan is another inspiration. The Hall of Famer has successfully transitioned from a wildly successful playing career into the media world; Jackson is aiming to tackle both at once as a player and the host of the “Fade the Booth” podcast.

“Figuring out how to transition over and still make money when you’re not on the football field, that’s genius to me,” he said.

The DeSean Jackson Brand

Age: 35
Home town: Los Angeles, California
Height: 5-foot-10
College: UC Berkeley
NFL Draft: 2008, Round 2, No. 149 overall by the Philadelphia Eagles
Pro Bowls: 3 (2009, ’10, ’13)
All-Pro: 1 (2009 Second Team)

Career on-field earnings: $91 million
Investments: Fanatics, Roll Em Up restaurant, J&D Investment Ventures, $35 million+ in residential and commercial real estate holdings
Instagram followers: 1.4 million
Twitter followers: 891K

Podcast: “Fade the Booth
Charity foundation: DeSean Jackson Foundation

DeSean Jackson’s career NFL earnings by team, via spotrac.com

Let Your Money Work for Itself

Jackson started in residential real estate. He’s bought and sold homes on both coasts, as his playing career has taken him from Philadelphia to Washington to Tampa to Los Angeles before signing in Las Vegas in early November. He says that part of what got him interested in the industry was seeing the money he’s put into his homes — including his $2.2 million Tarzana mansion that went for $200,000 above asking price — go to work and pay off even bigger down the line.

“Once I see my money working for itself, I’m able to pull out from one of the homes I have and go use that money to buy something else,” he said.

As Jackson got a taste of the potential out there on the real estate market, he wanted more. He began investing in multi-family homes, and eventually got into commercial real estate. While he hints at big things ahead, he says he’s not ready to reveal details. Jackson says he is getting close to a $100 million net worth and thinks his commercial will help put him over the top.

All told, he currently has $35 million in real estate investments between residential, multi-family, and commercial endeavors.

He’s already opened three restaurants in California as an investor in taquitos chain Roll Em Up, a business that is preparing to develop more than 400 locations worldwide.

Bumping Your Head

Jackson may have lofty expectations for his long-term earning potential, but is happy with the path he’s taken and would urge other young athletes interested in real estate not to start too big.

“If I knew what I knew coming in, I would have already cracked $100 million,” he said.

Photo by Matt Winkelmeyer/Getty Images

There were times where he trusted the wrong people, Jackson admitted — those who didn’t have his best interest at heart when they said otherwise. As a result, it can really take a while to earn his trust.

Take, for example, business partner Joshua Sanchez, whom he has known since high school. The two of them now own J&D Investment Ventures, a private equity firm that works in technology, real estate, healthcare, and small business. Sanchez has a degree in finance and Jackson is impressed with his track record in the business world. Still, he says it took him years to fully trust his old friend.

“You have to bump your head sometimes,” Jackson said. “With that being said, I’m glad I was able to bump it early on.”

Jackson is a free agent after this season, and has already said that he would like to end his football career in Las Vegas. With more days ahead in the boardroom than on the football field, his thinking has turned more to the long haul. Vegas isn’t far from his home of Los Angeles, and at this point in his career, Jackson is not eager for another move.

He’s content to keep making plays and making money where he is. And just as with his years of burning up the turf, he has every intention of leaving his competitors in the dust.

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About The Author
Russell Steinberg
Russell Steinberg
Russell Steinberg is an editor and writer at Boardroom. He came to the brand in 2021 with a decade of experience in sports journalism, primarily covering college basketball at SB Nation as a writer, reporter, and blog manager. In a previous life, he worked as a social media strategist and copywriter, handling accounts ranging from sports retail to luxury hotels and financial technology. Though he has mastered the subtweet, he kindly requests you @ him next time.