For professional athletes, financial success isn’t just about signing big contracts or landing major endorsements—it’s about making smart financial decisions that turn short-term earnings into long-term wealth.
In this new series, I'll interview athletes and entertainers to explore how they’ve navigated the financial highs and lows of their careers, learning from big paydays, unexpected challenges and the strategies that set them up for lasting success.
To kick things off, I had a conversation with Jacksonville Jaguars defensive lineman Arik Armstead. Raised in a middle-class family where financial literacy wasn’t a major topic of discussion, Armstead has earned over $95 million during his still-ongoing 9-year NFL career. The five-time Walter Payton NFL Man of the Year nominee recently signed a three-year, $43.5 million deal with $28 million guaranteed with the Jaguars, and he is creating an impact far beyond football.
From investing in Silicon Valley venture deals to advocating for educational equity, Armstead has shown that financial success for himself is about more than just making money as an athlete—it’s about making it last and building something even more impactful.
Evan Vladem: When you entered the NFL as a first-round draft pick in 2015, what prepared you for handling that kind of money?
Arik Armstead: To start my career, the money aspect just happened. There was not a lot of preparation in college, studies or through the NFL Draft of what it would be like. I just started working with my financial advisor at the time and started figuring it out. I tried to ask some questions to get educated that way.
EV: What was going through your mind after being drafted 17th overall and signing your first four-year, $9.84 million contract with the San Francisco 49ers?
AA: I was an instant millionaire! My first paycheck was $3 million!
Then, I looked down to the row [on the paycheck] beneath the $3 million, and I saw $1.5 million. I said, ‘Oh Dang! Taxes are real!’
That was the first official check that I received from an employer. I never had an official job in high school or college, so it was a huge blessing for sure. I just realized that a lot of my hard work paid off and life was going to be a little different, but it was not the ultimate ‘everything is going to be perfect now, and I’m set for life.’ It was a huge blessing, but I knew that it was not going to last unless I made some great decisions, continued to work hard and made myself more valuable to my team for my potential earnings in the future.
EV: In 2023, you shared a game check on social media, breaking down how NFL players are paid. What motivated you to do that?
AA: My thinking with that was to educate people on how NFL pay really works. My feeling, which I don’t think is fair, is that how much we make public information with contracts is big news. What is not public is a breakdown of how we are actually paid. We are just like regular people in terms of having a regular job. We have a 401(k), a benefits package and pay taxes. We have all those different [pay deductions] just like any other job, so I thought it would be interesting for people to see what [it looks like from an NFL player’s perspective].
EV: You played nearly a decade in San Francisco—right in the heart of Silicon Valley. What kind of connections did you make in finance, venture capital and tech?
AA: Living in Silicon Valley was great. Living there comes with an environment—knowing that you’re on the cutting edge of innovation and surrounded by companies that will change our world and our country. You’re at the center of capitalism. It was inspiring to be surrounded by it.
Initially, it could be a little intimidating when I was a young player. I would meet people and be in rooms where certain conversations were going on, and I had no idea what anyone was talking about. You kind of feel a little outside of it.
Early in my career, I took some time to learn. Columbia University offered a program just about venture investing. I went there two weekends during my offseason, and I just learned.
Being in that environment at an Ivy League school was pretty special. I took that time and invested in myself and my knowledge to understand the terminology and how venture investing works, along with investing in general.
EV: Who were some of the key people or firms who helped you in the venture space?
AA: Two of my best connections who helped me a lot in the space were a partner at Bessemer Venture Partners in the Bay Area, and I have a great relationship with [rapper, entrepreneur and successful investor], Chamillionaire, who invests a lot in the space too. I’ve known him as a friend for seven years or so. I also joined a fund of his and have been able to learn more about the space from him. He’s someone who has been in entertainment and has transitioned to that space and has had a lot of success. He thinks about it differently, too.
EV: How do you balance the risk when investing in venture capital?
AA: I definitely rely on my advisors as well to build an overall healthy portfolio. I know with venture capital deals, it should be a very small percentage of what you do.
I got some insight from Chamillionaire, which is easily relatable for us as athletes: invest in a venture that you might have spent frivolously or with some money that you don’t mind losing. Chamillionaire used to tell us, take that [money] that you were going to spend at the club or going out or doing whatever you’re going to do that’s here and gone, and try to identify and put it into some companies and see how it does. That was his thought process with it, which was relatable for athletes and entertainers he worked with.
EV: More athletes are trading endorsement deals for equity. Have you taken that approach?
AA: As athletes and people who have an influence on social platforms, we’re a different ‘investor.’ We can provide not only capital but also a platform for a whole host of people. Our brand and name being aligned with the company is more than just a check that we can write.
Even more for myself, every relationship that I enter, I try to think about how I can add value. When I look at a company, if I believe in their mission and the values—then if I think they can provide real impact, whether it's a service or product, I don’t stop it there. I then think about how I can really have an impact through my connections in venture or other people in my network.
EV: Your foundation, the Armstead Academic Project, has done incredible work. How does philanthropy fit into your long-term financial planning?
AA: We not only provide personal donations, but we created a donor-advised fund with our financial advisor to support our philanthropic efforts.
With our foundation, the Armstead Academic Project, we founded it to ensure that students had what they needed to be successful in their education and that their socioeconomic status didn’t determine their outcomes. It is something that we want to make sustainable and long-lasting, making an impact much longer than while I'm just playing. It’s definitely a big part of our overall plan, and it's our responsibility to give back to our community and support the next generation of young people who are our future.
EV: What’s your best advice for young athletes, especially in the face of NIL?
AA: Create a lifestyle that is sustainable—one that you can maintain. Just because you can buy something now doesn’t mean you can afford it long-term. Once you create a certain lifestyle, it’s kind of hard to scale back.
I would rather live like a prince forever than live like a king for a little bit.
Evan Vladem is a financial advisor at Associated Investor Services.
