One-on-One with “Hip Hop’s Financial Advisor”

Hello friends! Got a treat for y’all today – an interview with one of my cool wealth manager friends, Rob Wilson. AKA “Hip-Hop’s financial advisor” (which you’ll learn more about here in a second). If you ever needed proof that working with money can be sexy, this is it! As long as you like hip-hop, the NFL, or celebrities in general, haha…

Rob and I connected a couple years back through our online endeavors, but it never occurred to me to actually pick his brain on some of this financial goodness. Particularly with what it’s like to be a financial manager to multi-millionaires. I don’t have plans on quitting my day job anytime soon, but it is nice to know other fun options exist :)

Here’s some background on my man before we begin:

Rob Wilson is a financial advisor at an independent financial and investment advisory firm based in Pittsburgh (a.k.a SixBurgh – The City Of Champions). He received his bachelors degree in Industrial Engineering from the University of Pittsburgh, and his Masters in Business Administration from the Tepper School of Business at Carnegie Mellon University.

In essence, Rob’s a pimp. And he can be found here:

Now on to the interview!

You’ve been (awesomely) dubbed “Hip Hop’s Financial Advisor.” So of course I have to ask – who are some of your celebrity clients?

Great question. During my time as a financial advisor I’ve had the pleasure of working with a number of notable individuals in sports and entertainment.

Two of the biggest recording artists I’ve worked with are rapper Tyga (Lil’ Wayne’s artist from Young Money) and R&B/Rap artist Ryan Leslie. (pics attached). I also work with fellow Carnegie Mellon alum, actor Gaius Charles from Grey’s Anatomy.

In sports, I’ve worked with a number of NFL players, from undrafted free-agents to top-10 draft pics. In fact, I’ve had a client not only play in, but win the Super Bowl for the last 7 years! Here are a few:

  • Jay Alford – NY Giants SB XLII
  • LaMarr Woodley – Pittsburgh Steelers SB XLIII
  • Darnell Dinkins – New Orleans Saints SB XLIV
  • Andrew Quarless – Green Bay Packers SB XLV (damn they beat my Steelers though!)
  • Hakeem Nicks – NY Giants SB XLVI
  • Terrence Cody – Baltimore Ravens XLVII
  • Russell Okung – Seattle Seahawks XLVIII

Is it weird managing someone’s money when they’ve got so much more than you? (At least I presume? ;))

At first, absolutely. When I started out in the financial industry at Smith Barney, they trained me for a few weeks and then gave me a phone, a desk and a list and told me to get to work. Ever though I have an engineering degree from the University of Pittsburgh, worked for Big 4 firm Deloitte Consulting, and had just finished my MBA at Carnegie Mellon, I still had to build up the confidence that even though I was just beginning my wealth building journey, I had the fundamental knowledge and resources to help them with theirs.

Once you start to gain a few clients (I certainly didn’t start working with athletes right away, that took time) and you see the results of your work, it gives you even more confidence. You start to realize that you are kind of like a athletic coach that works with great players. As far as I know, Hank Haney has never won a major championship on the PGA tour. However, he helped Tiger Woods win 6 majors and 31 other tournaments. When you realize how that type of relationship works, you can talk to anyone.

What’s the craziest thing you’ve seen one of them spend their money one? (Definitely do NOT name drop on this one, haha…)

Cars, without a doubt. I’ve seen them buy Bentleys, Lamborghinis, Range Rovers, etc. But it really gets interesting when they start to customize them with rims, sound systems, paint jobs etc. It’s nuts. At the end of the day, though, it’s their money.

What’s the BEST thing you’ve ever seen one of them do with their money?

Listen. It’s hard for a 22 year old who has been told that he’s a “star” all of his life to understand that life in sports and entertainment is typically short lived. You have to plan and be ready for your second act. But the same mentality that makes them the best at what they do (arrogance,fearlessness, bravado), hurts them in other areas of their lives because those aren’t the best qualities in relationships, business, or in general life.

The ones that listen from the start spend wisely, save money and build a portfolio of investments that will create an income stream once their career is over. They’ve bought annuities that will guarantee them income for life. Insurance policies to protect their families.

They’ve also taken the time to learn about business, rather than just throwing money at a venture they have no experience or knowledge of. Franchising is a good way to do this. In fact, I’m working with a recently retired client on opening his first 15 Wingstop franchises. He’s done things the right way.

One of the things I love about you is that you’re always working on ways to connect with your community, especially with the youth. Tell us more about “The Best Kept Secret” show you’ve launched.

Thanks J, I appreciate you saying that. I spend a lot of time speaking to kids, but I never wanted them to become totally fixated on the fact that I work with athletes and entertainers, because it’s very difficult to make it to the top in those fields. I wanted them to know that there are many other options available to them to achieve the success that they desire.

I realized that it’s hard for them to visualize success outside of sports and entertainment, because for some kids, that’s all they see thanks to TV.

I created BKS to expose them to stories of people who are living fabulous lives and have never stepped on a field, court or a stage. When they meet these people or hear their stories, you see the light go off in their minds. “Wow, this person owns a BMW dealership? He looks like me, sounds like me and came from a similar background. If s/he can do it, I can to.” When you see them come to that realization, it’s the best feeling in the world.

I believe that if you show them there’s another way, and give them proof as motivation, they will find their way along that same path.

If you could manage anyone’s money, whose would it be?

Oprah! I’d only need to have one client, and I could learn so much at the same time.

Finish this sentence: The last thing I saved for was ___________.

We’ll I’m currently saving up for expenditures that come along with one of those “big days” in your life. But don’t tell my girlfriend, it’s a surprise. :)

If you weren’t a wealth manager, what would you be doing right now?

I’d probably be a partner at Deloitte. When I started business school, my intention was to augment my engineering degree with business acumen so that I could go back to Deloitte as an unstoppable force with both business savvy and technical skills. When I got there, my perspective changed and I felt like I wanted to do something entrepreneurial.

I wanted a lifestyle where I could do well for my self and do good for others at the same time. Working with and teaching people how to build wealth seemed like a great way to do that. But if for some reason that was taken away, I’d be in the technology space. I’m an engineer at heart, that happens to focus on finance. Now, if only I would have invented What’sApp!

You’re about to launch your 3rd year of March Money Madness. What are you hoping to accomplish with it, and can anyone join?

Yes, I created March Money Madness as a way to use sports to teach people about the stock market and investing. It works just like filling out a bracket for the NCAA College Basketball Tournament, but using stocks instead of basketball teams.

The game between the stocks occurs during one week in the real life stock market. The stock with the highest return during the week wins the game, and so on throughout the tournament until you have a champion. It’s really fun and I’ve gotten tremendous feedback on how much people who know nothing about the market have learned by playing the game.

For anyone that is looking for a structured educational experience while playing the game (weekly recaps, video tutorials, live webinars), they can upgrade to the “Insider” level for only $25. We’ve got a number of schools and programs signed up this year in an effort to increase the financial literacy of their students.

I’m just hoping to educate as many people as possible this year. I believe that the higher the percentage of financially literate people we have in the country, the better the economy will be for everyone.

Have anything else up your sleeve you’d like to share with us today?

Yes, I just launched a new podcast in iTunes called #MoversAndShakers.  It’s an interview show where I interview…wait for it…movers and shakers who are crushing it in business, sports, entertainment etc. It launched in the beginning of January and has already been listened to in more than 30 countries!

I give out a lot of advice but I realized that people also want to hear from people that have put a lot of the principles that I talk about into practice.  This show allows me to show my audience that these wealth building strategies do actually work.

You can find the podcast here:

True or False: Budgeting is sexy?

This is a no brainer. It’s actually the first thing I notice about a woman! :)


BAM! And in case you’re wondering, he does offer his services to the non-super-wealthy too – I asked ;) Here’s exactly what he told me, actually:

“Yes, I can certainly take on new clients.  As a matter of fact, I recently “soft” launched a program for young professionals that need financial advice and guidance, but don’t necessarily have a big portfolio to give to a traditional financial advisor. The program is called Financial Personal Training and you can find it at It’s like having a trainer at your gym, but for your financial health.

I hope that your readers, both baller and non baller, will appreciate the opportunity to work one-on-one with someone who has their best interest in mind and isn’t looking to sell them any products.”

So give him a shout if you’re interested! I make no money off anything, btw – I just like what he’s about. And that he mixes two of my favorite things in life together – rap and cash money, baby!

I hope you’ve enjoyed this as much as I have :) Keep hoarding those dollars!

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  1. Mr Ikonz @ Project Ikonz March 11, 2014 at 5:27 AM

    Having such high profile clients like hip hop artists and sports stars would be rewarding, yet exceptionally difficult! Where most clients will be working for 30 – 40 years and can take time to prepare for their retirement/second act, these guys have hardly any time to prep.

    Great interview!

    1. Rob Wilson March 11, 2014 at 11:04 AM

      It’s definitely difficult at times! The 2008-09 period during the financial crisis was an extremely tough time to be a financial advisor. I’m much wiser having gone through that experience, and it has allowed me to provide better advice.

      1. Mr Ikonz @ Project Ikonz March 12, 2014 at 8:51 AM

        The GFC was tough. Looking back, it didn’t matter how rich your clients were, or how good their throwing arm was, they all lost money.

        You can’t control markets, all you can do as an adviser is make sure a client is diversified and communicate and service the crap out of them!

        Thanks for the reply Rob!

  2. moneystepper March 11, 2014 at 5:41 AM

    Finally, the proof – BUDGETS ARE SEXY!!!

  3. a terrible husband... March 11, 2014 at 6:12 AM

    Nice little niche he’s carved out over there. Who says monetary management had to be all pocket protectors and calculators. Good stuff.

  4. Snarkfinance March 11, 2014 at 7:11 AM

    Sounds like a nice guy who takes an active approach to teaching people about finances. The pro athletes are definitely a nice “selling point”, but its great he still is open to non-wealthy clients (although I wonder how large his team is at this point). I will have to check out his podcast.

    1. Rob Wilson March 11, 2014 at 11:06 AM

      I’ve got a solid team behind me that helps me do all of this. I had to learn very early on that there is no what that I could have the impact that I wanted to have in the world by doing it alone.

      Thanks for reading!

  5. Catina Mount March 11, 2014 at 7:46 AM

    What a rewarding career! My son is CERTAIN he is going to the NBA (and who am I to tell him he’s not…lol) and my biggest fear is the money. Too often we hear stories of how it all got spent. It’s nice to hear of someone out there showing others how to manage it & make a difference.

    1. J. Money March 11, 2014 at 9:17 PM

      And when he DOES make it, you can hook him up with Rob! :)

  6. Dave @ The New York Budget March 11, 2014 at 8:45 AM

    Wow – what an interesting guy! And BKS looks amazing! What a great way to inspire kids. I am all about teaching kids about money and opportunity.

  7. Brian@ Debt Discipline March 11, 2014 at 9:30 AM

    Great interview! The point Rob makes “But the same mentality that makes them the best at what they do (arrogance,fearlessness, bravado), hurts them in other areas of their lives because those aren’t the best qualities in relationships, business, or in general life.” I’m sure this is his biggest challenge is dealing with clients going from make no money to multiple millions over night.

    1. Rob Wilson March 11, 2014 at 11:10 AM


      You’re absolutely right. I once had a client, LITERALLY, go from making $5M per year to 500K per year overnight because of some trouble he got into.

      That’s a very difficult situation to plan for.

  8. John @ Frugal Rules March 11, 2014 at 9:37 AM

    Great interview J! I love how he’s taking everyday things, or things that people enjoy – like sports and using it to educate people about money.

    1. Rob Wilson March 11, 2014 at 11:07 AM

      Thanks John, that is definitely my strategy. I hope it’s working! :)

  9. Becky @ RunFunDone March 11, 2014 at 9:44 AM

    In elementary school, my class participated in a game like March Money Madness! It’s how I first learned about the stock market! Participating classes were each given a certain amount of fake money to “invest” as we liked. My class ended up winning by investing in a company that we knew nothing about, but which one classmate had noticed was steadily increasing in value. I now look back and wonder why my teacher didn’t stop and make us learn about the company we were investing in…but she didn’t!

    1. J. Money March 11, 2014 at 9:28 PM

      Was the company Apple? :)

  10. Cat Alford (@BudgetBlonde) March 11, 2014 at 10:13 AM

    I always find it fascinating to get insight on these things! If I was an athlete or rapper, I’d definitely make sure I had my investments all settled first before buying fancy things!

  11. Rob Wilson March 11, 2014 at 11:01 AM

    Many thanks to J for having me on the blog! It’s great to connect with you all!

  12. Mario Adventuresinfrugal March 11, 2014 at 12:09 PM

    What a great idea to use sports as the bait to get people interested in and talking about personal finance

  13. Jacob March 11, 2014 at 2:37 PM

    Wow, this is awesome. It reminds me of Dave Ramsey’s Wealth coaching, but much more interesting and I love the tie between sports and finances. You really do need to approach finances from a coach’s perspective to find out what motivates people and use that to help them get their money in order.

    I am putting together a financial coaching plan currently and will check out Rob’s stuff for motivation. Seems like he’s doing it right (obviously!). Thanks for sharing the interview J$!

    1. J. Money March 11, 2014 at 9:29 PM

      Glad you got something out of it! Feel free to ping him directly too if you need steering in the right direction – Rob’ a cool guy.

  14. Done by Forty March 12, 2014 at 1:54 AM

    I loved hearing about that program with the youth. What a blessing that day must have been for those kids. And it made me miss Pittsburgh, too! Funny how little things like the blue street signs can make you homesick.

  15. Ryan @ Impersonal Finance March 13, 2014 at 3:31 PM

    That sounds like an incredible way to be able to combine what I think are pretty entertaining industries- those being entertainment and wealth management. I really dig the idea of parlaying an interest in sports to an interest in money. I hadn’t heard of the March Money Madness, but I’m headed there now to check it out. And btw, seriously awesome nickname bro.

  16. Cautioned Observer March 13, 2014 at 6:16 PM

    Just a quick look at the Financial Personal Training website you linked to shows a service with a $497 “setup fee” and a $97 per month fee. If this is geared towards professionals who don’t have a huge portfolio those fees are really bad.

    $25,000 portfolio is 6.6% for the first year, then 4.6% per year after that
    $50,000 portfolio is 3.3% for the first year, then 2.3% per year after that
    $75,000 portfolio is 2.2% for the first year, then 1.5% per year after that

    And this is just the adviser fee that doesn’t take into account any fees for any funds or etf’s.

    That is just way too high. For portfolios that size, online options are a much better option. Come on you shouldn’t be promoting this service to that audience.

    1. Rob Wilson @robwilsontv March 13, 2014 at 8:32 PM

      First off, thanks for checking out the FPT site and I appreciate your feedback. Pricing is something that every entrepreneur has to deal with at one point or another.

      However, I’n not sure if you had the opportunity to read the copy on the page or watch the video, but this particular service has absolutely nothing to do with portfolio management. If someone wants to work with me in that capacity they can do so for 1% annually, period.

      FPT is a coaching program, about working one on one with individuals who need help getting their finances in order before they can even think about investing i.e. cash management, budgeting, credit, starting a business, negotiating a salary improving credit etc. (all things mentioned in detail on the page).

      Often people know what they “should” be doing, but have trouble actually putting those things into practice. This program provides them the tools they need up front and then offers an accountability partner to help them follow through.

      In my experience, if people are going to make REAL change in their lives, they need a lot of information, fast, rather than just working with them on a monthly basis. We jump in, work together intensely for the first month, and then the customer can continue if they choose to.

      I know that most financial advisors won’t work with anyone if they don’t have a portfolio, so I can see how you might get this service confused with the average advisor’s offerings, but this is different.

      In a nutshell, I help people get their $#!t together, so they can begin to build real wealth.

  17. DP Cash October 16, 2014 at 2:13 PM

    Unbelievable that anybody with substantial income or assets would hire a financial advisor with an online infomercial. The hustle out there must be really hard.

  18. Sandra Little August 12, 2017 at 10:55 AM

    I loved everything I read! I also believe in the value of educating our youth! I love that you use ordinary folks to showcase what financial literacy and discipline can achieve.

    While I don’t have celebrity clients, I do have America’s heros. I’m a financial counselor/educator at the largest Marine Corps training installation. I have the privilege of helping our service members and their families with financial matters; doing my best to ensure they are all financially fit and mission ready!

    I would love to have you as our guest speaker! Hope to hear from you!!

    1. J. Money August 14, 2017 at 12:22 PM


      I’ll pass this note over to Rob as it’s a few years old now but he’s still around doing his thing :) I’ll have him reach out to you directly if he’s interested in the speaking part.

      Thanks for stopping by!


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