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Chris Gandy is the Founder of Midwest Legacy Group, a boutique concierge insurance group for executives, professional athletes, physicians, business owners, and entrepreneurs.

Chris has spent the last two decades helping individuals reach their most important financial goals. His firm focuses on unique tax reduction strategies, retirement income optimization, generational wealth, and more.

Chris is a former pro-basketball player. He played for the University of Illinois, where he was co-captain before playing professionally for the Chicago Bulls, San Antonio Spurs, and France. He’s been featured in numerous magazines such as Crain’s Chicago, GQ, Black Enterprise, African American Career Worlds.

Chris has served on multiple boards including the Chicago Concussion Coalition, The Urban League, and he is currently serving as board member of the National Association of Insurance and Financial Advisors, and the National Committee for Diversity Inclusion Task Force where he is the youngest member serving on the national board.

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Here’s a glimpse of what you’ll learn:

  • How playing sports helped shape Chris Gandy’s attitude towards competition and financial success
  • What Chris had to do to play basketball at the highest level after they told him he couldn’t play
  • Chris talks about the financial junk drawers people have and what’s in it
  • Why athletes in the NBA and NFL struggle to manage their finances and end up going bankrupt within five years of retirement
  • The top five issues executives have while managing their finances
  • Chris discusses some sacrifices people can make to ensure a financially-secure future despite early retirement
  • Chris shares a few things you need to know if you’re working with African Americans
  • Chris shares his favorite NBA stories

In this episode…

The high income or revenue of an athlete, a professional, an executive, or an entrepreneur appears to come suddenly within just a few years. Earning so much in such a short period of time creates a new problem for these individuals, and one of them concerns how they will manage their money. Of course, they would want to maintain a good quality of life even after retirement, the question is, how can they do that?

Chris Gandy says that the first thing they have to do is to clear out the junk in their financial junk drawers. Doing so will help them to better understand why they have issues managing their finances and learn how to grow and preserve their assets.

On this episode of Inspired Insider, Dr. Jeremy Weisz interviews Midwest Legacy Group Founder and former pro-basketball player, Chris Gandy, about the financial know-hows that athletes, professionals, executives, entrepreneurs, and other high-income earners need to be aware of. They will be discussing some of the major issues that high-income earners have managing their finances, how they can properly plan for their retirement, and how Chris helps them take control and build legacies. Stay tuned.

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Episode Transcript

Jeremy Weisz

Dr. Jeremy Weisz here, Founder of where I talk with inspirational entrepreneurs leaders. I am super excited about today’s guest Chris Gandy of Midwest Legacy Group. I will introduce to you to him in a second. Check out other episodes of the podcast I Pat Williams. Pat Williams if you don’t know brought the Orlando Magic to Orlando he went door to door selling season tickets so he could bring the team there. He was playing an integral part of me history helping draft Charles Barkley Shaq Don Yaeger also an 11 time New York Times bestseller has some amazing books about athletes coaches, John Wooden, Walter Payton, Michael Jordan, you’ll see why this relates to today’s interview in a second. But before I do, this episode is brought to you by Ries25, which I co-founded my business partner John Corcoran, we help businesses give to and connect to their dream 100 partnerships and relationships in general, because we help you run your podcast and you know, Chris, for me, the number one thing in my life is relationships. I’m always looking at a way to give to my relationships. And podcasting has been amazing to profile some of my favorite people that I admire, like you and other business leaders on my podcast and shout out to the world that people should be checking out when you’re talking about what you’re doing. So if you thought about starting a podcast, go to we’ve been doing it since 2008 and helping many many companies all over the United States in world. Today’s guest Chris Gandy is founder of Midwest Legacy Group and Chris has spent the lesean an amazing background in history. He spent the last two decades helping individuals reach their most important financial goals. In 1989, Chris started his own financial services practice and since then has traveled the US working with athletes, key executives, and minorities and his firm focuses on unique tax reduction strategies, retirement income optimization, generational wealth and so much more. He actually his background he played at the University of Illinois fighting align a basketball team where he was co captain. After college, Chris played professionally for the Chicago Bulls, San Antonio Spurs, and in France, and he’s been featured in numerous magazines, Crain’s Chicago, GQ, Black Enterprise, African American Career Worlds, and he serves on multiple boards as well. I don’t know how you have time for all this. Chris Chicago Concussion Coalition, The Urban League, and he serves on the National Association of Insurance and Financial Advisors, National Committee for Diversity Inclusion Task Force as the youngest one serving on the national board. Chris, thanks for joining me.

Chris Gandy

Thank you for having me, Doc. I appreciate it. I appreciate the opportunity to to share these wonderful ideas, you know, fantastic history and, and hopefully a couple key nuggets that people take away from our dialogue today. And hopefully they implement in us to be more efficient in where they’re trying to go and and what they’re trying to accomplish.

Jeremy Weisz

Yeah. And I there’s so much I want to ask you, we will talk about some of the major issues that executives have and how you help executives and even how to take advantage during COVID and protect your assets. And I love we before we hit record, you were telling me the 10 things you didn’t know if you’re working with someone who’s African American, and I think that is really important in general and in the reception you got from talking about those things has been amazing. But I want to start early on your career because what has shaped you and is sports. And because you I love when you talk about sports isn’t is a basically a reference analogy for so many things in leadership in business. When you were growing up, Chris, what did you want to be when you grew up? Did you knew you want to be a basketball player?

Chris Gandy

Uh, no, actually, it’s interesting if you rewind the tape a little bit. I was when I was growing up, I actually was a was a track kid. So I played, I ran track and had opportunity to do well at that I was a was the 800 800 relay guy was a 400 relay guy ran a 400 stretch and then also did high jumps. So I was good. I didn’t want to do much more than that. And then I found the love for baseball, baseball was always one of those things. We were young, we would sit around Big League Chew and always wanted to be like, you know, Andre Dawson, right? You remember that name? Right? So we want to be like an Andre Andre Dawson type of guy. Right. And we would we would go out and play stickball right when people used to do that and play wiffle ball until the dark until it got dark and your mother would say something like don’t let it Don’t let the streetlights catch you coming home. Right? So had a fantastic youth growing up. Just quite frankly, being a kid. And then someone said one day they said hey, you should you should consider playing basketball. You know, your uncles play basketball. You know, my uncle played basketball actually in college, he went on to play Juco basketball and then went on to play at a small d one school or D two school. My uncle’s played. My other uncle played football, my other uncle so so from a fairly athletic family, again, can walk and chew gum at the same time. So it just led me down the path of saying, hey, let’s play basketball. But the first time I played basketball, I said never off of basketball again. So why but because people told me I couldn’t do it, you’ll never be able to do it just because you’re tall started this, this addiction that I would say that I have towards competition. And that is if someone tells me I can’t do something I say to them with there’s a 1% chance, if there’s a point 1% chance of us being able to accomplish it, I want to take that 1.1% chance. And and that’s kind of how we operate is is we don’t believe in anything’s impossible. But we believe in everything’s possible. And everything’s probable giving the right mindset given the right obstacles ahead of us and given the right opportunity to succeed at it. And we try to instill that in our clients, even if they’re starting late. With planning, retirement planning late, they have people on the team, they’ve been doing this for 2025 years. Many times we’ll encounter clients that have what I call the the financial junk drawer, which is everybody has a junk drawer at home. If you dealt then you don’t live here in the United States, or you just moved right to junk drawers where you put everything and you say, okay, when I get to it, you know, I’ll go through that drawer and I’ll clean it up. That financial junk drawer is where we help people organize, and organizing people’s actions and intent so we can ultimately align ourselves to be more efficient and effective. And that’s what I believe sports has allowed for us to do is allow people to build game plans, the true X’s and O’s, of how to to win on a regular basis versus just win once or win twice or have a good year have a bad year or be uncertain about the outcome of the game. We got one chance to play this game and we want to win on a regular basis.