{"id":661779,"date":"2026-10-30T15:04:08","date_gmt":"2026-10-30T15:04:08","guid":{"rendered":"https:\/\/www.newsbeep.com\/il\/661779\/"},"modified":"2026-10-30T15:04:08","modified_gmt":"2026-10-30T15:04:08","slug":"celebrities-and-wealth-series-dqwell-jackson","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/il\/661779\/","title":{"rendered":"Celebrities and Wealth Series: D&#8217;Qwell Jackson"},"content":{"rendered":"<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">For professional athletes, financial success isn\u2019t just about signing big contracts or landing endorsements\u2014it\u2019s about making smart decisions that turn short-term earnings into long-term wealth.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">In this series, I interview athletes and entertainers about how they\u2019ve navigated the financial highs and lows of their careers\u2014learning from the big paydays, the unexpected setbacks and the strategies that helped them build something lasting.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">I recently caught up with former Cleveland Browns and Indianapolis Colts linebacker D\u2019Qwell Jackson, a second-round draft pick who went on to play 11 years in the NFL and earn Pro Bowl honors. Jackson worried every year about losing his starting job, but that caution didn\u2019t always extend to his spending.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">He spoke candidly about how divorce, injuries and career uncertainty reshaped his approach to money, from setting boundaries with family to accepting accountability from his advisors. Today, he\u2019s bringing those lessons about building the right team to his hospitality and networking venture, the Gentleman&#8217;s Suite.<\/p>\n<p data-component=\"related-article\" class=\"RelatedArticle\">Related:<a class=\"RelatedArticle-RelatedContent\" href=\"https:\/\/www.wealthmanagement.com\/high-net-worth\/the-only-way-to-avoid-this-new-tax-burden-don-t-get-married\" target=\"_self\" data-discover=\"true\" rel=\"nofollow noopener\">The Only Way to Avoid This New Tax Burden: Don\u2019t Get Married<\/a><\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">Evan Vladem: You worried every year about getting cut. Did that caution extend to your finances?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">D&#8217;Qwell Jackson: I took advantage of the opportunity, but every year I thought I was going to get cut. No matter how great a season I had, I would ask my agent, \u201cAm I secure for next year?\u201d Anything can happen in this league.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">That approach was purely football: studying and taking care of my body. On the other side, I had no financial literacy.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">My family worked check to check. They didn\u2019t know how much money I was making. In their eyes, I was rich. I could pay for any bill, any house, any car\u2014anything their minds could imagine.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">EV: How did your agent help you manage that pressure?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">DJ: My agent and I created a buffer system because I didn\u2019t know anything about money. I knew how to spend it, but I didn\u2019t know how it worked. He said, \u201cYou may play two years. You may play three years. We need to budget as if you don\u2019t know how long you\u2019re going to play this game.\u201d<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">My money went into a bigger account, and I was only allowed to touch what was allotted to me. I didn\u2019t want a checkbook connected to the big account. I didn\u2019t want that temptation.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">If family or friends asked for a big amount, I could say, \u201cI don\u2019t have it.\u201d If they pressed me, I would tell them to talk to my agent. He created that buffer so I could gain confidence over time. It wasn\u2019t about letting him handle it forever and never learning how to say no.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">EV: What changed as your confidence and spending grew?<\/p>\n<p data-component=\"related-article\" class=\"RelatedArticle\">Related:<a class=\"RelatedArticle-RelatedContent\" href=\"https:\/\/www.wealthmanagement.com\/high-net-worth\/why-family-capital-matters\" target=\"_self\" data-discover=\"true\" rel=\"nofollow noopener\">Why Family Capital Matters<\/a><\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">DJ: Probably around year three, my confidence was skyrocketing. I thought I was invincible. I was playing well, and we were starting to talk about a contract extension. You tell a 25-year-old about millions of dollars\u2014game-changing, life-changing money\u2014and I started getting a little loose with the checkbook.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">At the time, I was also going through a divorce. I had married shortly after entering the league, and I didn\u2019t have a prenup. That took a big bulk of what I had made before the contract extension, on top of the reckless spending.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">Then the general manager who had talked about taking care of me financially got fired. I had a season-ending injury, then another injury. All these plans were unraveling. I thought I was in a secure situation, and suddenly the future was unknown.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">The buffer was there. This was the time when I didn\u2019t listen to them. I was in a rebellious state. I was going through something, and that was my response.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">I was spending on myself, going to clubs. I wasn\u2019t taking private planes or going on big trips. It was little spending that added up quickly. I couldn\u2019t tell you one major purchase other than a chain and a necklace.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">EV: What gave you a second chance?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">DJ: I went to IMG Academy, worked out like crazy and invested in my body. The Browns signed me to a one-year, prove-it deal. I didn\u2019t miss any games the following season, and I signed a game-changing contract.<\/p>\n<p data-component=\"related-article\" class=\"RelatedArticle\">Related:<a class=\"RelatedArticle-RelatedContent\" href=\"https:\/\/www.wealthmanagement.com\/high-net-worth\/your-wealthiest-clients-may-not-have-their-estate-plans-in-order\" target=\"_self\" data-discover=\"true\" rel=\"nofollow noopener\">Your Wealthiest Clients May Not Have Their Estate Plans in Order<\/a><\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">But my life changed because of a relationship. In 2012, I was at a wedding in Turks and Caicos with my girlfriend, who is now my wife. Her best friend\u2019s dad was asking me financial questions, and I had no idea what he was talking about.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">He said, \u201cWhen we get back to D.C., I\u2019m going to set up a meeting. I want you to take it.\u201d That meeting was with the company that represents me now, a family office.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">They asked, \u201cHow do you want to live when you\u2019re done playing? Do you want a boat? Multiple homes? Let us know, and we\u2019re going to work around it.\u201d<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">EV: Do people misunderstand why athletes run into financial trouble?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">DJ: I tell people to imagine gathering 100 individuals between 22 and 25 and giving each of them a half-million dollars to $1.5 million. A lot are going to make similar poor financial decisions.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">The difference in the NFL is that you\u2019re putting your body through a lot of violence, and your career could be over like that. You don\u2019t have the luxury of continuing down a path of poor financial decisions, or you won\u2019t make it back.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">I feel like I had a second chance because I was fortunate enough to play as long as I did. A lot of guys don\u2019t get that second chance.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">EV: How did you learn to set boundaries with family?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">DJ: I wasn\u2019t willing to buy someone a house or a car. I\u2019m here for emergencies. I know things happen, and I\u2019m in a place of privilege. But if someone asks for money, I want the full details. Why are we in this position?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">It\u2019s hard to tell family members no when they sacrificed so much for you. As a parent now, I understand that more every day. It was one of the toughest decisions I had to make.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">Your contracts are out there for everyone to see. You can\u2019t say, \u201cI don\u2019t have it.\u201d They know you have it. But there\u2019s a rhyme and reason. Before I had kids, I would say, \u201cI have to save this for my future family. I\u2019m building something, and I don\u2019t know if I\u2019m ever going to have a job again.\u201d<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">EV: What does accountability look like with your financial team?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">DJ: I\u2019m not afraid to ask anything. I\u2019ve asked, \u201cWhat if I wanted to pull all my money out? Can you get it for me? How do I actually know the money I see on my screen or phone is there?\u201d<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">He\u2019s not afraid to tell me, \u201cYou guys have spent too much. This is the path you\u2019re on.\u201d There\u2019s a mutual partnership and accountability.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">I used to tell young guys, \u201cWhy have a financial advisor if you\u2019re not going to listen to them? Give me the money. I\u2019ll let you spend whatever you want, and I\u2019ll take the fees.\u201d It took growth to get there.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">Now, my advisor has created a portfolio where I don\u2019t feel the urge to jump at outside investments. I send him everything.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">EV: What do you value beyond investment management?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">DJ: Our wills, trusts for our kids, insurance\u2014there\u2019s someone who is the expert in each department. There\u2019s a tax person, and I can have relationships with the insurance companies and brokers we work with.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">I prefer it that way because I\u2019m learning. I don\u2019t want to call one person and just get an answer. I want someone to explain exactly what we\u2019re doing, how it benefits me and why we\u2019re going that route.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">We\u2019ve built trust over the years. To me, that\u2019s the most important thing. I trust that they have our best interests at heart.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">EV: What are you building now?<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">DJ: I created the Gentleman\u2019s Suite, an invite-only networking concept that can operate as a traveling luxury hospitality suite. The first activation was in Martha\u2019s Vineyard, where our family spends time in the summer.<\/p>\n<p class=\"ContentParagraph ContentParagraph_align_left\" data-testid=\"content-paragraph\">There\u2019s food, beverage and entertainment, but that\u2019s the backdrop. I\u2019m creating a locker room outside the locker room where like-minded people can build together, enjoy fellowship and speak freely. There could be business that comes out of it, too. I\u2019ve been a direct product of what it means to have a good team around you. Even when things go sideways, you have people you can count on who hold you accountable in all phases of life. I want to create that with the Gentleman\u2019s Suite.<\/p>\n","protected":false},"excerpt":{"rendered":"For professional athletes, financial success isn\u2019t just about signing big contracts or landing endorsements\u2014it\u2019s about making smart decisions&hellip;\n","protected":false},"author":2,"featured_media":661780,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[14],"tags":[114,268,85,46,266,267],"class_list":["post-661779","post","type-post","status-publish","format-standard","has-post-thumbnail","category-personal-finance","tag-business","tag-finance","tag-il","tag-israel","tag-personal-finance","tag-personalfinance"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/posts\/661779","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/comments?post=661779"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/posts\/661779\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/media\/661780"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/media?parent=661779"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/categories?post=661779"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/tags?post=661779"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}