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The Evolution of Chasing a Passion

We talked with Gail about:

  • "Sending the elevator down" to help lift up the next generation
  • How our mental health affects how or if we invest
  • Why everyone needs a board of directors for their lives

About Gail Perry-Mason:

Gail Perry-Mason’s prowess as the senior director of investments at Oppenheimer is just a fraction of the deep investment she makes in her community. Inspired by her own journey, Gail’s true passion includes investing in today’s youth and cultivating a community around them to elevate their financial footing. Through exposure and development, Gail teaches young people how to make money work for them. She shares tips about time management and finding a work-life balance that may inspire others to start making moves toward their next big dream. 


Featured Resources 

Full Audio Transcript

Lauren Hong: 

All right. Well, Gail, I am so excited to have you on the show today. I was just reviewing just your background and resume and it's so extensive and impressive. Your career went from receptionist to senior director—talk about hustling—and then you have been a speaker for government agencies, religious groups, nonprofits, youth organizations, universities, and the list goes on and on. And then you have this really rich experience working with the youth investment club. And then Money Matters for financial literacy. And I'm so excited to dive into that. I mean, not only for the work and the knowledge you have within your day-to-day, but then you've been able to really cultivate a unique voice for youth and for families around financial literacy. So I'd love to just start there and let's maybe start with a little bit of your background and your story and then we can get a little bit more into the financial literacy side and how you've really been able to create a voice and show your passion through that. But I'll turn it over to you. Let's hear a little bit more about your background. 

Gail Perry-Mason:

Thank you for this opportunity and thank you for just being so awesome and just letting me tell my story and letting others tell their story. We need people like you in the financial service industry who do podcasts and tell our story because everybody looks at the financial industry and thinks they're just stuffy and this and that. No, you give a voice to everyone. So I thank you from my heart to your heart that we are doing this. So anyway, I started out, and I don't know if you want me to bring this up, but I was adopted in Detroit and all this stuff, foster care, missed growing up, and got adopted by an older family that never knew anything about the financial industry. 

They just said, Gail, have a joint account with Jesus at the credit union that only you and Jesus know about. And I was like, okay, that's all I knew. It was just to have an account at the credit union. I grew up in a strict household but then I went away to college and I ended up having a child in my second year of college. So I was broke of course like most people. And then I ended up having to send my resume out everywhere and I was like, oh my God. I sent my resume out and a brokerage firm called me and I was like, oh wait a minute, <laugh> this is divine order: I'm broke—brokerage firm. I had no clue about the stock market at all. 

So I didn't even know what a brokerage firm did. But anyway, I became a receptionist and as you can already tell, I love to talk to people and meet people. So I was a receptionist and everybody was coming in the front door. Nobody looked like me. And what I mean by look like me, the gender was all males. This was in the ‘80s, all males and nobody was African-American. So I was like, oh wait a minute. And it was gnarly. So one time this woman came in and was just so nice to me. She had just got divorced and I got divorced also. And I was like, wait a minute, you got divorced. 

I'm thinking, okay. And she says, well, why are you here? She said I'm coming to invest my money from my divorce settlement. And I’m thinking the only thing I got from my divorce settlement, matter of fact, was overdraft protection on my line of credit. Yeah. So I got nothing; I had no settlement at all. Just goodbye. So anyway, so says I'm gonna have a million dollars. I'm thinking you got a million dollars. Like, well basically who did you marry? But anyway, that's a whole other story. So I said, wait, what are you gonna do with this money? I need to talk to you. I need to know what are you gonna do? She had small children. I said, how are you gonna make it? What are you gonna do? 

She said, I don't wanna work. I wanna raise my children and I'm gonna live off the dividends. And I'm thinking, okay, I'm gonna learn everything that's going on. So I always say success leaves clues. So I look at what she was doing and living off the dividends. So that's why I became a secretary. I said can I get promoted to a secretary please? And they allowed me to do that. And then actually going to people's accounting, okay, dividends, you're doing this, you're investing. I'm like, I have to teach people, this is how life is supposed to be. We're supposed to work for our money and money is just a tool and then we make it work for us. So I say, oh, let me figure out how to do this and how I'm gonna teach people. The only way I'm gonna do that is to get a license. 

So I asked them, could I get licensed? And they were like, yo, no, no, no, no, no, you cannot get licensed. Actually what was told to me, this was back in the ‘80s, you're African-American or you're Black and you're a single mom; the answer is no. You cannot become an investment advisor. Well I worked for some rookies, that's what they called 'em back in the day. And I worked for some other established investment advisors. So I was the secretary for them or sales assistant. So one of 'em left their books on the table one day. Lauren, lemme tell you what I did. There was a copy machine; I picked up my son from daycare, came back to the office, and Xeroxed the Series 7 study guide. I studied every morning. Oh wow. And it was a sales assistant who sat next to me because nobody would actually allow me to do it. 

So the sales assistant—this is why women stick together—she and her husband paid for me to take the test. So anyway, I ended up getting sponsored; my job said they'll never pay for me, never send me to training. Anyway, so fast forward, I took the test, passed the test, and then they took bets. I'll never pass it, but I became a licensed secretary. But I started putting on seminars when I was a licensed secretary after hours. And I called a guy named John Rogers from Aerial Capital and everybody knows who he is. Him and Melody Hobson called them to Detroit and said, hey, come on the seminar with me. And Melody was an intern at the time. So fast forward, I ended up opening up over 100 accounts at night, people investing and all. 

So I ended up coming in saying, hey, I got 100 accounts. They said okay but we don't want these little accounts. And I'm thinking, I just start crying. And they said but you know what? You can try to be a broker. We're gonna give you 90 days. If you don't make it as an investment advisor and hit these numbers, we want you to slide back over to another chair with wheels on it <laugh> and just go back to being secretary. Well anyway, I just slid over and just started teaching people and that's why I do what I do, Lauren. And that's when I became an investment advisor. So I would never change anything, any obstacle or any way in my path. But when I have changed, I wanna change for other people. And that's why I do what I do, Lauren, I send the elevator back down to the next generation. 

I don't want anyone to say no and deny people the opportunity I was denied. Even though I still made it in the industry, it was a different track that I was on. But I want people to actually have the training, be invited in to become an investment advisor and to teach people. So if I have a seat at the table, turning 60 this year, I look back and say, wow, I have 60 women who I have mentored who are now in the investment industry. Whether they're women and several African-Americans—over 20—who are in the investment industry. And the thing is to send the elevator back down and then they rise higher than me, which means they're doing better than I am in the industry. That is the reason why I'm here. And that is why I love and what brings me joy is that once a seed was planted, I learned we have to reach back and we have to teach others. We have to let them have a seat at the table with us. And that's why I love what I do. And that's why now I start with teaching children and our youth. 


Oh my gosh. Incredible. 


That's what I do Lauren. And that's my backstory. 


That’s a great story—how you found your way to where you are but then have been able to, like you said, bring up the next generation. I'd love to hear more about that. So is that mostly through the Money Matters program or for the youth initiatives you're involved with? Tell me more about what that consulting looks like and really what that mentorship looks like. 


Yeah, one day I was reading the Wall Street Journal and this was in 1996. Because I always read about successful people. I always say success leaves clues and we have to case out the situation, which means copy and steal everything <laugh>. I started casing early. So I ended up watching how somebody did a rich kids camp but in this rich kids camp you had to have so many millions in assets, which mostly the African-American community did not have at that time back in the ‘80s and ‘90s. And so I said, wait a minute, I gotta figure this out. How am I gonna do this in Detroit? So I did this: they had to bring $50 and have $10,000 in assets to send your kid there. Then your child had to have $10,000 to invest. I said, I'm gonna do it here in Detroit and I'm gonna make this work. 

So of course I put up my own money and I haven't had a vacation since 1996. I take off a week every year and I take a few hundred youth, I call them young investors. I divide 'em up like small cap, mid-cap, and large cap; small cap is elementary school, mid-cap is middle school, high school is large cap. And they graduate each year. So as they get older in different schools I ended up having them learn everything about how to invest. But the first thing I teach 'em is don't ever love anything. They can't love you back; money cannot love you back. But we teach them how to make money work for them. And I actually give them a pillowcase. And they actually write on the pillowcase how their money is gonna work for them while they're sleeping. 

So they have to actually do their vision board on a pillowcase or I have this one plate they have to write on. How are they gonna serve the world and make money also? So we have all these analogies so it's mostly an experience. So what I do is give our young people the experience of going to meet Warren Buffett, going to the Berkshire shareholders' meeting. So I take them actually to learn to vote. So they learn if you own stock you can vote. So I have young people who own Berkshire, who own all these companies, who actually go to the shareholders' meetings and then they have to set up their own personal board of directors, whether it's somebody who mentors, an accountant, a banker, a credit union, whatever you wanna call it. 

But then also in the last few years because of COVID, I incorporated mental health into everything. So I'm not talking about stocks individually but my kids will take stocks where DoorDash versus Uber Eats cause they eat out all the time. I can't believe these kids. So they do tug of war the very first day. So large cap versus mid-cap or mid-cap versus whatever. So they actually learn the strategy of the market and the strategy of when to hold on, when to let go, do your research, talk about your strategy, how you're gonna hold on or how you're gonna let go and not get burnt. But also when I incorporated mental health it comes to the same thing with anxiety, with depression, with hate, with forgiveness, you've gotta know when to hold on and let go. 

So I actually have change agents because everybody needs a change agent on their board. And that's actually to talk about mental health. So I have a lot of psychologists come out to talk, since a lot of reasons we don't invest is because of self-esteem, not knowing different things. And with my camp too, a lot of the young people, some come from affluent families and some come from foster care or some come from inner city Detroit who've never even gone outside the city limits. So I end up taking everybody and they all learn how to spell the word opportunity. And the word opportunity is the word unity. All of these young people come together and start their own business, set up their own personal board of directors. And we don't have enough time to talk about the success stories about them starting their own business. 

And now one young man, you're talking about 60 something million later, has his own staff in LA. I mean just the businesses that they have started. Even now we have a lot of young people who have clothing lines and everything, or they're in the financial services industry and they have their own venture capital funds. Now they're doing everything. I mean, I'm like, look at these kids having their own hedge fund and they actually start their own portfolio in the money camp. I say our youth are like Kodak film—they need exposure and development. We have to expose them to the world of finance. That's the main thing. And then we have to not only expose them—we can't just turn the TV on and expose them—we have to develop them with experience. 

For our young people, hands-on experience is everything. But the main thing we teach them too is gratitude. Once you learn something, you always write people letters. Like I do, I do gratitude notes. I do 10 a day. I will write John Richards or Melody Hopson, Warren Buffet or whoever or you know, the CEO of Ellevest, Sally, all of them. I write them a letter and just say, I'm proud of you. I don't ask them for anything. I just want people to know I'm proud of them. So the power of the pen is still so important. So they end each day writing a gratitude note to someone. So we teach 'em everything—how to sit at the table, for men how to hold the chair for a lady, and what fork to use, what knife to use. Because we have a board meeting on the last day. 

So it's from A to Z, whether it's fencing, lessons on how to stand up straight or it's how to sit down and how to eat pizza with a knife and a fork and what knife to use, what fork to use. So we teach them everything and how to start a business and how to budget is so important too. So I know I'm talking a lot Lauren, but I'm loving it. You probably have another question. That's my money camp. And it's my passion and Lauren, you know, for a living, as you already know, I work in the investment industry, but for life I invest in others and that brings me the biggest dividends and the biggest joy. I may not have the big portfolios like probably a lot of people listening to this podcast, but my portfolio of youth, oh it's tremendous. And their dividends are they will live on forever. That is what I want basically as my building wealth legacy. 


Amazing. I feel like there's a lot of people in this space and they wanna be able to give back and do the kinds of things you're doing but you found a space for it and you've made time for it. And how have you gone about doing that while managing to climb the ladders with your day-to-day as well? What was it? Have you been doing this at night, on the weekends? How have you been so successful in both realms? Both from a passion side plus having a family and all these other aspects of life? 


Well, Lauren, I will say, and I know you know it's difficult having a family and trying to balance it. When my kids were younger, every one of them had to go through the money camp. Every single one of them had to work the money camp. And they're still, to this day, they'll take their vacation and come back and help me along with about 50 others. They will take their vacation time. So normally I never take a day off is one thing. I work seven days a week. My clients become my friends, they're my friends and my family and they actually come and help me teach the kids, whether they're business owners or whatever they come. So I use an all-inclusive, holistic approach to my strategy of balancing life where I include everybody. It’s like, hey, you like kids, you wanna give back, come on and help me. 

Help me with this passion, this mission. And then even a lot of my clients want to send their kids to the camp. So everybody gets involved. So it's kind of like all around a wraparound but balancing it, lemme tell you about balancing it, I have to start every single day. I literally start every single day on my knees because it is a strategy to do the right thing for my clients and have time for them, and then I have to write down, matter of fact, you probably see this right behind me right now. Okay, I gotta call this person, I gotta do this, gotta do this. And I do that every single morning. 

And then I try to balance and I take an hour out of each day, okay, let me follow up on money camp. This is what I'll give to money camp, give the rest to that. And then leading up to it I'll take a few days off and try to get it all organized. So I now have my own board of directors I've made up to say, hey, hey, I need help with this. I need help. And I think everybody, even our clients, I tell my clients to have their own personal board of directors that we can call on people because you need that life coach. You need that mental health coach. You need that physical coach, that somebody who helps you to stay healthy. And then I also have a meeting with my sons. I call them sunshine Sundays, and say, hey, okay, what can you do this year? 

How can you help me with the money camp? You know, what can you do? And it becomes a family affair. And what I mean by family affair, I have so many young people I call my sons and daughters and they all come over on Sundays too, and we work together. I love cooking. So I cook for everyone and then I end up, okay, let's do this, let's get this together. So it is difficult to balance sometimes but I do my best to balance and I keep a calendar and I just try to do what I can for everyone. And that's when it comes down to speaking and everything else too, Lauren. It's difficult but it can be done. 


I mean, it sounds like it truly takes a village. It sounds like you've been able to cultivate your community, both at work, personal, et cetera, to be able to pull everyone together. And then over time, how have you really been able to amplify the voice and the value here? It's like identifying the youth and creating those opportunities. People are aware of this program, this opportunity. What have you done to be able to plant those seeds and pull that together? 


So what I've done absolutely is I plant seeds in different neighborhoods in Detroit with the youth. We actually go to different neighborhoods; this is how we cultivate families to really bring change. We plant a financial garden and we lead kindness rocks all throughout the year. Oh wow. So this is what I do. So many. Yes. So we planted gardens at homeless shelters everywhere. It's just so amazing. I love to plant a financial garden and have the youth go over and water it because to have anything you have to pour into it. 

I do have a village that actually plants a garden, that actually gives back and helps me. And so that's the number one thing we all do together. But the way I find my children, I will go and speak at different high schools in the city of Detroit or outside of the city of Detroit. I will also go to foster care homes. I also sleep outside with the homeless once a year. And I find a lot of homeless youth and they need this. And my one major success story I found when she was 16, she was sleeping in her car, her name is Courtney. And she was sleeping in her car. She thinks of me as her god mom. I call her my daughter and I followed her all the way through college. 

And when Courtney was sleeping in a car, I said, hey, I got you. I'm gonna make sure I work with the organization called National Association of Securities Professionals. We give scholarships every year. I said, I'll make sure you get a scholarship every year. I work with them and chair the scholarship bond and all of that. So I said, hey, we wanna make sure our youth can go to college because sometimes they just need the opportunity. I wanna make sure they're not poor. Poor means passed over opportunity repeatedly. She was in the system, foster care, she was passed over once we got her the resources she needed. She went to Harvard, she went to Eastern Michigan. She has her own organization called the Phoenix Center. She gives back, she's a Rockefeller. She gets money from the Rockefeller Foundation. 

I mean, you name it, she's killing it. Courtney's just doing great. I'm so proud of her. So I will find them; I don't care whether they have a home. And the thing is, when I was born, this is why I do this, and I'll tell you this, Lauren, when I was born and I was left at the hospital, I was labeled special needs. They said I'll never be able to walk, never be able to talk my entire life. Because my mother just walked away and left me at the hospital. So I was just a ward of the state. So they labeled me. And then one time this doctor came over when I was adopted at the age of four, and said, you know what? She's not walking, she's not talking. You know what, hold her, hug her, and love her. 

Give her love. So this 80-year-old woman loved me. She was in her 80s, and she said I'll take that responsibility. And she loved me and I never shut up Lauren. But the thing is, I needed love. So when people label our young people as, oh, they're homeless, they're this, they're that. No, I think love heals. And that's what everybody in my money camp will tell you. I always tell 'em, love means obstacles vanished effortlessly. And we have to get over these obstacles because the only way we're gonna do it is love. But of course everybody says, okay, how many assets under management do you have? My thing is, how many young people, those are my assets under management, those are the greatest assets I could ever have in my entire life. And they're under my management and they're bigger than the assets I have where I work. And that's what really matters. Oh my gosh. So, and wait, Lauren, I'm getting emotional.


I can feel it on this side too. It's such a beautiful story and I'm so thankful for the opportunity to be able to hear it, despite geography, distance or anything like that. I mean, you can feel the impact of what you've done and also just how it's come together and touched so many people's lives. And also just like the legacy of that. I mean, it's not just seeds we've planted yesterday or a year ago but years ago, all that time and effort and cultivating to where it is today to these kinds of stories is just amazing. I'm sure so many people look to you and are so amazed. 

It's absolutely beautiful what you've been able to do. And I'm, like I said, grateful to hear it firsthand. So I know I want to make sure to include resources for those who want to get involved but are there any other thoughts you would share to anyone who wants to be able to get involved or be able to give back to our youth or our community? And like just first steps of where would you start, because it can be an undertaking and then also cultivating all the resources and energy but what would be advice to someone who wants to get involved? 


You know, try your local Junior Achievement. We partner with Junior Achievement and they have a stock market contest and of course my children always win, my young investors. But even if you just mentor one person, and I'll encourage everyone in the financial services industry, the lending business, the banking business, whatever, bank on our youth, lend them your time. Invest in them no matter what job title you have. I just think we're more than our job title. Our job title is a servant leader. If we made it to the C-suite, that means we need to have compassion and caring. And that C-suite, we need more of that. So if you made it to that suite, it's time to bring others in that suite with you and give them a seat at the table. 

And then don't look down; the only time we should look down on somebody is when we're helping somebody up. That's the only time. And I think we just can't look down on others. That is just my biggest thing. I think it'll make the world a better place. And the financial services industry, it's the center of our world, but we can bring so much change in this industry. And that's what we're doing this year. We're doing this sport of investing. So I'm adding sports into it. So this year we're doing financial football, everything. Ballers and basketball, we're doing it all. 


Oh my gosh. So amazing. I know, and like you were saying earlier, you're going to send that elevator back down again, right, to bring people up. So yes, I just appreciate all the work you've done, appreciate you sharing your story, and it's so impressive. I've got goosebumps. 


It’s really beautiful and I have tears. I'm like, oh my God, I talk about my babies. Like I said, I don't have enough time to talk about all the stories, but they're more than amazing. All my young investors. So I just want them to leave the door open for them and send the elevator back down. So thank you, Lauren, for this opportunity and thank you for everything you're doing. We all need you on our board of directors; what we need is a Lauren. Thank you. 


We all need each other. Like you said, it takes a village. And thank you again for all the work you're doing.