Money, sports, and women — a powerful combo. In this episode of Financial Feminist, Tori Dunlap chats with Annie Bailey, Chief Operating Officer and Equity Partner, RISE Sports Advisors and former lacrosse star about the changing world of women in sports and finance. They break down how female athletes can score big both on and off the field. From the transformative impact of NIL (name, image, likeness) deals, and the persistent gender disparities in sports compensation, to long-term financial goals — Annie shares pro tips on managing money, building a brand, and securing your future. Whether you’re a sports fan, aspiring athlete, or just looking to level up your finances, this episode is a must-listen.
Key takeaways:
- NIL (Name/Image/Likeness): A game changer for women athletes: The NIL era is leveling the playing field for female athletes. By turning their name, image, and likeness into cash, women can now earn through endorsements and sponsorships and build financial empires while still in school.
- Money matters: financial literacy for athletes: Annie stresses the importance of financial literacy for athletes, noting that many athletes, including professionals, often lack basic budgeting skills and financial management knowledge. One shocking statistic she shared is that 78% of professional athletes are broke within 3 years of retirement. The role of financial advisors and wealth managers, like those at RISE, is crucial in educating athletes about taxes, investments, and budgeting to prevent financial mismanagement and ensure long-term financial stability.
- Closing the pay gap: Women athletes are crushing it on the court, field, and track, but their paychecks aren’t matching their performance. Despite increasing viewership and popularity of women’s sports, female athletes, like Caitlin Clark, still face significant pay gaps compared to their male counterparts. The conversation calls for continued efforts to close this gap and ensure equitable compensation for female athletes.
- Build your brand: Your personal brand is your most valuable asset. Building a strong personal brand can open up numerous opportunities for endorsements and career transitions. By using your platform to connect with fans, inspire others, and network, you create opportunities that will lead to a lasting impact beyond their sports careers.
- Encourage female leadership: Annie encourages women to take risks, invest in themselves, and pursue entrepreneurship. Both Tori and Annie emphasize the importance of women recognizing their worth, seeking education, and not being afraid to make mistakes as they build their careers.
Notable quotes
“They live by the gross and die by the net.”
“Say yes to the next thing. It doesn’t have to be your forever thing. It can lead you to wherever you’re supposed to go.”
“When you surround yourself with a supportive community who are on the same path as you, you’re going to go exponentially further, no matter how disciplined you are if you’re on your own.”
Episode at-a-glance:
≫ 02:13 Annie’s background and career
≫ 02:23 Understanding NIL and its impact
≫ 11:09 Challenges and opportunities in NIL
≫ 17:23 Financial education for athletes
≫ 25:00 The pay gap in women’s sports
≫ 26:51 The impact of NIL on female athletes
≫ 30:15 Financial challenges for retired athletes
≫ 32:13 Preparing athletes for life after sports
≫ 36:58 The Caitlin Clark effect
≫ 42:08 Encouraging women in entrepreneurship
≫ 45:00 Mentorship and community impact
Annie’s Links:
Website: https://www.rise-advisors.com/
Instagram: https://www.instagram.com/rise_advisors/
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Meet Annie
Annie Bailey has a passion for developing relationships and creatively fostering marketing and entrepreneurial opportunities, Annie thrives to find success for those she represents. As a 2017 graduate of the University of Colorado at Boulder with a BA in Broadcast Journalism and Communications, Annie brings her dedication, work-ethic, and tenacity from the Division 1 lacrosse field to each project she collaborates on. Annie has a passion to help each RISE clients create a successful and sustainable athlete enterprise.
Transcript:
Annie Bailey:
I think as women too, we are trained from the society around us that we should take care of everyone else and not ourselves. So what can I do to make sure you’re comfortable, even if that’s sacrificing my own comfort, we have to completely rewire our thought process around that.
Tori Dunlap:
Hi, financial feminist, welcome to the show. I am thrilled to see you. Thank you as always for being here. If you’re an oldie buddy goodie, welcome back and if you’re new here. Hi, my name is Tori. I fight the patriarchy by making you rich. We have a podcast. We have a New York Times best-selling book. We have tons of free resources online, and we have over 5 million social media followers. Today on the show is going to be a great guest, but first we got to talk about women in sports because really that’s what we’re talking about on today’s show. Yes, the Caitlin Clark effect is real. But let’s talk about the incredible women who have been at this for decades who have paved the way, especially black and brown women. Everything from Billie Jean King to Serena Williams to the World Cup Women’s soccer team demanding equitable pay.
This is such an incredible time for women’s sports because of not just incredible players right now, but incredible women who have been at this for a very long time. This is my direct plea, Sue Bird, Megan Rapinoe, please come on the show. I’m a Seattle girly. I have my together shirt. I’m not wearing it today, but everyone watches women’s sports. I have it. I love you both. We would love to have you. I would absolutely die. Also, Abby Wambach who just followed me on Instagram, also hello. Megan Sue, come on the show. Thank you. We’d love to have you. Okay, Annie Bailey, today’s yes. Let’s talk about her. Annie Bailey has a passion for developing relationships and creatively fostering, marketing and entrepreneurial opportunities. Annie thrives to find success for those she represents. As a 2017 graduate of the University of Colorado at Boulder with a BA in broadcast journalism and communications, Annie brings her dedication, work ethic, and tenacity from the division one lacrosse team to each project she collaborates on.
Annie has a passion to help each rise client create a successful and sustainable athlete enterprise. So what does Annie do? She’s managing a lot of the finances of your favorite athletes and of people who are rising in the athletic space. So you might be thinking, what does NIL have to do with me if I’m not a collegiate athlete? I think more than ever, with the way the world is changing so fast and how much personal branding has become a part of our careers, it’s really important to talk about the importance of protecting your name and how to make sure that you’re the one profiting from it and not somebody else.
So we talked about how Annie got into wealth management and what it is and isn’t, how Annie and her team work with athletes and individuals on building a financial legacy. How the change in NIL rules is helping women across the sports world and how NIL relates to you even if you are an athlete. We also talked about the Caitlin Clark effect. We talked about women, especially in sports and still the pay inequities that we’re seeing between male and female athletics. So without further ado, let’s go ahead and get into it. But first a word from our sponsors. I love the very, I don’t know, European, it’s like for those not on YouTube. It is a what, a horse. Where are you at? I’m trying to figure out. It’s like portrait of a guy riding a horse, somebody training the horse. I don’t know. Tell me more.
Annie Bailey:
Yeah. So well, I’m in my husband’s office, so it’s very manly, which is-
Tori Dunlap:
Very masculine.
Annie Bailey:
Unfortunate, but my family owns race horses, so that was actually my-
Tori Dunlap:
That’s so cool.
Annie Bailey:
Yeah, so that was my grandpa’s and when he passed away, I snagged the painting and hung it up in here.
Tori Dunlap:
It’s technically illegal, but we would go, there’s Emerald Downs here near Seattle in Auburn, Washington, and starting at seven, I would bet on them, and then tell my mom what I wanted to do. So that was a whole science. It was a female jockey. Yes, I’m betting. Gray horse, I always bet on the gray horse, which is not what you’re supposed to do. Then my mom and I’s logic is if they pooped, they’d be later. So that’s what we bet on.
Annie Bailey:
Those are good. That’s very logical. I know a lot of people who only bet on the grays and female jockey, always got to cheer for the fellow ladies. So yeah.
Tori Dunlap:
It ended up working out all right. Then I got worse as I made it more serious. As I started getting older, I got worse off. The joke was always like ten-year-old me would bet more or not bet more, but would make more than my dad who would do these super complicated bets. So it was very funny.
Annie Bailey:
Oh yeah, yeah. The more you know, the harder it is because you overthink everything. It’s all luck anyways.
Tori Dunlap:
Totally. We’re so thrilled to have you. We love asking people what their first money memory is. When is the first time you remember thinking about money?
Annie Bailey:
Yeah, so I don’t have a specific like, oh, I remember thinking about money here, but I do know growing up money was always prevalent. I come from, on both sides of my family, maternal and paternal side, family businesses. So on my father’s side, my brother is actually fifth generation right now, taking over our family business, and my grandfather is the one who expanded it and instilled just a lot of the growth and hard work that came from that.
Then on my maternal side, my grandpa grew up in an incredibly poor household, dirt floors, shoes with holes in them, no souls in his shoes. He actually hitchhiked to work and eventually purchased the business that he hitchhiked to and now still runs it, and it’s turned into an incredibly successful business. So from the time I can remember the value of hard work and appreciating the team around you and just knowing the value of a dollar has always been kind of intrinsically in me. You’re only as good as those you surround yourself with. So got to have a good team and take care of that team and make sure that they know that they’re valued and appreciated and all of that good stuff.
Tori Dunlap:
You played lacrosse in college. You have a lot of experience as a student athlete, navigating the world financially. What brought you then into the world of wealth management?
Annie Bailey:
Yeah, it’s kind of a strange story. I never had a passion for what I wanted to do after school. I knew that sports were really all I knew. I didn’t know if I was going to be a sports broadcaster or some way, I wanted them to still be in my life after I graduated. My boss, and he’s now my business partner, let me intern directly for him as his executive assistant when I was in college.
He owned a training company for college athletes, high school athletes, a lot of professional athletes, and saw the broken system of how many professional athletes go broke within two or three years of being retired or even when they’re playing, they’re actively broke as they’re playing and just how broken that whole culture is. So he started RISE, which is where I currently work, and the whole mission is just to educate, connect, and empower these athletes to take care of their money, be able to speak in a business setting, know what to do with their money, how to invest it, where to invest it. So that’s how I fell into it and it’s become totally my passion at this point.
Tori Dunlap:
For the civilian listening, what is a wealth manager and what do you do on a daily basis for clients?
Annie Bailey:
Yes. So a wealth manager would be like financial planning and portfolio management. At RISE, we actually are a multifamily office, so we do a little bit more than just wealth planning. That is a big part of what we do. We have a whole division dedicated to budgeting, investing, all that stuff. But the big piece of what we do is just education, making sure that athletes can speak on their own two feet, serve on boards. Like I said, we have a wealth management division, but we also work with a lot of other financial investment firms, Goldman Sachs, Stifel, places like that, that take care of the money. We just help advise on the best way to handle their money, where to put it, and if they’re cautious, if they’re conservative, if they’re risky, however they want to handle that.
Tori Dunlap:
The biggest question that I want to dive into that I think is really interesting for athletics, for the kind of student athlete to professional pipeline is NIL, name, image, and likeness. It’s so interesting about how much has changed in the last couple years. Can we first define what it is and then talk about how it might relate to not only athletes but other professions as well?
Annie Bailey:
Yes. So in 2021 is when it officially changed. NIL is basically just a student athlete can benefit from the use of their name, image, and likeness. So previous or prior to 2021, a school was just the sole person benefiting off of that. They were the only ones making money, and it was illegal for a student to see any of that. Now, they can be sponsored, they can get paid, they can have marketing deals, and they can participate in that success that the school also gets to participate in when they have a star athlete like that.
Tori Dunlap:
Yeah, I mean, I think the biggest transition I’ve seen is you have student athletes who are also influencers or spokespeople who can profit off of sales of their jerseys. Prior to this, prior to a couple of years ago, you couldn’t do any of that. To your point, it was basically your name, image, and likeness was owned by the school unless you went pro beyond that.
Annie Bailey:
Yes, and I think there are, which we can get into. There are some issues that come into just the amount of money that the athletes are able to make at this point, but it’s a great opportunity.
Tori Dunlap:
Yeah, let’s talk about that.
Annie Bailey:
Well, yeah, I think, I don’t know if you have any specific questions or if you want me to just jump into what I see, but-
Tori Dunlap:
Well, I think about the benefits of like, and this is one of my questions for you, is it’s like name, image and likeness in theory puts a lot of the power back in the individual’s hands, but I imagine there’s also cons to that too.
Annie Bailey:
Yes. I think the biggest thing that we see, and we don’t work with a ton of NIL clients because fiscally, they have to be a huge moneymaker for it to make sense to work with us. But when we do, the biggest piece that we want to do is educate them. You are making oftentimes six figures or close to it, you now have to pay taxes. You are getting taxed on that, which a lot of them have no idea the amount that the government takes for taxes. Are you investing it? Are you budgeting it? Just all of the issues that go into giving a 17, 18-year-old kid a lot of money.
I think that’s our biggest goal is to educate them on how to handle all of that success that they’re seeing. I do think too, an issue I could see happening as well is these huge schools, Ohio State or the big, big time Alabama, the schools like that are going to just start getting bigger and bigger and bigger because they’re able to pay the athletes more. The smaller schools that still get really good athletes, I think are going to get pushed to the wayside because they can’t compete with that type of NIL payout that a lot of the big schools can.
Tori Dunlap:
Right, because almost like you’re not just getting an athletic scholarship, you’re getting the platform of one of these bigger schools. So it’s like it’s a marketing move now. It’s not just about college or it’s not just about even college athletics. It’s about, yeah, how do I want to position myself? It’s a lot easier to position yourself at Bama than it is at random school no one’s ever heard of.
Annie Bailey:
Exactly, exactly. Just the gap is just going to continue getting wider. I mean, it was always there just because of the platform those big schools gave you to try and make it to the professional athletic, but I just think those smaller schools may get eaten alive in the long run.
Tori Dunlap:
Well, I’m thinking a lot about the benefit this has had for female athletes specifically. I’m thinking about a lot of gymnasts, I think LSU gymnasts right now are killing it on social media, and they’re some of the most, I put in quotes, but profitable players or athletes for themselves, that would not have happened a couple years ago.
Annie Bailey:
Yeah, and I think gymnastics is so interesting because that’s not typically a sport that you would think is a big moneymaker, but it has turned into, I mean, people always enjoy watching gymnastics in the Olympics and things like that, but coming from someone who played a sport that wasn’t a moneymaking sport, I don’t see, unless you were the star player on the team, that it would’ve really affected me at all as someone who was not the star player on the team. I think if NIL was around when I was in college, it wouldn’t have impacted my life. But you’re seeing some of these underground sports come alive and a lot more attention is being brought to them, which is amazing.
Tori Dunlap:
I think highlighting a lot of female athletes too in a way that, again, it was largely football and football is usually played by men. So was I think in that way, it gives a little bit of democratization to female athletes or to these kind of sports that you’re talking about that don’t usually get the spotlight.
Annie Bailey:
Yeah, I mean, look at what happened in basketball this year, the Women’s NCAA [inaudible 00:14:33]. Yeah. I mean, it’s so amazing to see that the ticket sales for the Women’s NCAA Tournament blew the men’s out of the water. It was honestly more fun to watch.
Tori Dunlap:
It was way more fun to watch. Oh, God, yes.
Annie Bailey:
Yeah.
Tori Dunlap:
No, that was my other big thing I want to talk about is the Caitlin Clark effect and everything going on. It makes me teary. I’m even crying as we even talk about it because it just makes me so happy. But we’ll get there in a second. Yeah. Any other downsides of NIL that you can think about? Because I think we’ve talked a lot about, yeah, okay. Putting money back in the athlete’s hands, which I think is important. Okay. The rise of female athletes, some getting their dues, but to your point of like, okay, it might not change, it’ll change some people’s lives, but they were probably set up for success already because yeah, if you play at a smaller school or you’re not the star athlete, you’re exactly right. Are you getting influencer deals? Probably not. Are you getting Jersey sales? Probably not.
Annie Bailey:
I mean, I think overall it’s a great thing and it’s giving athletes the ability to make money where money is due. It was never right that they couldn’t participate in the massive success that universities were having. I just think that there’s a lot of responsibility that comes with receiving that amount of money, and that’s what makes me nervous. As someone who is in the field and is working to educate and make sure those issues don’t happen, that’s my goal, is to bridge the gap between, okay, you have this money, now what do we do with that money? Make sure you don’t just continue this broken system of spending it all.
Tori Dunlap:
Yeah, that’s one thing I would love to hear more from you, because I think about this a lot, is folks who do end up making it big. We hear about the NBA specifically a lot because it’s a lot of folks of color who didn’t grow up with a lot and then suddenly are making 12 million plus, 50 million, crazy contracts. Something that breaks my heart is them not having the education, them not having the resources. It’s very difficult psychologically to go from basically nothing to being a multi, multi, multi multi-millionaire overnight. I just see so many athletes, and we’ve seen this time and time again, have nothing to show for it. They work so hard, they get these scholarships, they end up going pro, but then all of their millions of dollars, they end up squandering on basically stupid shit because they don’t know any better. So that is something that I know you’re actively trying, the whole mission of your work is trying to actively combat. So talk to me about that cycle of, yeah, okay, your brain on poverty, and then suddenly you’re making crazy amounts of money.
Annie Bailey:
Well, you would be surprised at the number of athletes that we come across that have never once had a budget of any sort. One of the sayings that my boss always says is they live by the gross and die by the net because they see what the line of their contract says that they’ll get paid, and then it’s just cut in half almost by the time taxes get taken out and all the money they spend and all of that. So that’s one of the first things that we do is make sure they have a solid understanding of the budget of absolutely everything they’re going to be spending, even down to a fun money category if they want to go out to the club and buy section or whatever they want to do to spend that money.
We’re not saying that they can’t have fun. It’s just let’s allocate how you’re going to spend that so that we don’t go overboard in that situation. But it’s education. It’s getting strategy sessions on what their goals are, what they want to do, who are the biggest people in their lives that we need to make sure are either taken care of or we want to help educate them, connect them, help them get jobs. That’s our whole mission is just making sure people are empowered to go be able to do it on their own, and they’re not relying on the contracts that transparently may not be there tomorrow if they get hurt or anything could happen, especially in the NFL, nothing is guaranteed.
Tori Dunlap:
Well, and I want to highlight for everybody listening, probably not a lot of professional athletes listening, but this is-
Annie Bailey:
Maybe.
Tori Dunlap:
This is your money too. This is the same thing, especially as a business owner. I don’t make NBA levels of money, but I make pretty decent money, and we just paid the largest tax bill of my entire life and my entire business, and it was a lot. To your point of I think a lot of people, business owners especially, but anybody making money, you see the dollar amount. You see the salary, okay, I’m getting paid 70K a year. Great. No, you’re not. It’s not 70K a year. You have taxes, you have fees, and then if you’re a business owner, right, to your point, okay, let’s say you do play in the NBA, you’re paying a publicist, you’re paying for your team of people, actors, same thing, right?
You’re paying for hair and makeup, you’re paying for a security guard, you’re paying for your limo ride to and from the Met Gala. There’s a lot of things that you are paying for before you’ve even touched your money, expenses, taxes, et cetera. I think it’s so important for everybody listening. You might not be an athlete, you might not be an actor, you might not be making 50 million a year, but you have to think about when you’re pricing yourself, when you’re negotiating for things, it’s not just that number to your point. It’s not just the gross. It’s the net too.
Annie Bailey:
Yeah, and I think the biggest thing with that is just planning, actually sitting down and thinking through-
Tori Dunlap:
And knowing your numbers.
Annie Bailey:
Yes, exactly. So many people choose just not to look at that stuff, and that’s fine for some people, but if you actually want to become an entrepreneur and build wealth and save money and put it to work, you have to plan for the worst and just be ready for the worst to happen, because chances are something bad, something is not going to go your way.
Tori Dunlap:
To anybody listening who does have this, like, okay, I’m not making a lot of money to what we call lifestyle creep where you suddenly do make a lot more money. I think to your point, I think the steps there are knowing your numbers, planning, I would advocate for, everybody needs to check in on their money. We call it the ostrich effect in my book, where you’re burying their head in the sand. You don’t look, you act like your problems don’t exist. That is temporarily easier because you don’t have to deal with it, but it is not the solution in the long run. So yeah, I think, again, I’m trying to tie it back because most of us aren’t all star athletes.
Annie Bailey:
Exactly.
Tori Dunlap:
But a lot of these stories are stories that we see in everyday life, which is like, oh, I did negotiate 20K more on my salary. I want you to have something to show for that. Oh, I am a business owner now, and I’m thinking about pricing myself. I need to price myself accordingly knowing that I’m going to have to pay a thousand dollars client. I’m not getting a thousand dollars in my account. I got $300 worth of expenses and another 300 worth of taxes, and that’s only 400 bucks. So yeah, there’s a lot to, I think, take away.
Annie Bailey:
Sometimes too, you have to pay a little bit upfront and that’s really going to pay off in the long run.
Tori Dunlap:
Yeah, talk to me about that.
Annie Bailey:
You have sticker shock sometimes of, wow, I have to pay all of these people to take care of all of this money that I have. Again, whether you’re a professional athlete or you’re someone like you and me who’s just trying to save our money and build generational wealth the best we can, it’s sometimes worth it to pay the financial advisor, pay someone like RISE, pay someone to do your taxes so you know they’re being done the right way and you’re not going to have to pay in the long run or for hair and makeup if you’re an actor, is someone going to be able to do a better job and then you’re going to be able to land a bigger role? Sometimes it’s worth it to make that upfront expense and then it’ll pay off down the road.
Tori Dunlap:
Yeah, I think investing in yourself is something that we’ve talked about on this show, but that we are socially conditioned as women to not do, because again, it feels more risky. I think, and I’m painting with broad strokes, but we also have the data to support this, that men are more likely to say, yeah, okay, couple thousand dollars to go take a course or to go do, to your point, okay, work with this person. Yeah, it’s an upfront investment, but I’m hoping it’ll pay off. Women are more risk-adverse in regards to that. So I think that’s really interesting, especially when you’re working at that level. When you’re an athlete, there’s so much to think about of your image and your whole brand and what just kind of the vibes you’re trying to give off are cultivated.
Annie Bailey:
I think as women too, we are trained from the society around us that we should take care of everyone else and not ourselves, so what can I do to make sure you’re comfortable, even if that’s sacrificing my own comfort? We have to completely rewire our thought process around that. I know you as obviously the financial feminist, that’s a huge thing for you is making sure women understand their worth and their power and that’s huge for me too, as a woman in sports and as a mom and a wife, and just, I’m trying to stand up strong for women.
Tori Dunlap:
That transitions us perfectly into we’re having this fun moment that isn’t a moment because it’s been building for years, and it’s not just Caitlin Clark, but I feel like we’re in this perfect storm of like, okay, women’s soccer for the past, what 20 years has been so dominant in the United States. We have, yes, Caitlin Clark, but we have Angel Reese, and we have all of these, Cam, and all of these women who are playing such incredible basketball. I’m a huge Kate Martin fan, by the way. I feel like she’s underrated, the [inaudible 00:24:42]. I fucking love Kate Martin.
I think with Caitlin specifically, we have arguably the best female athlete in her sport, at least right now, coming out of college. Number one draft pick in the WNBA, she’s making 75 thousand dollars a year. She’s making 75K a year. So first of all, what the fuck? Second of all, what can we do to bridge the gap? I think we’re already starting to see this. I hear the conversation a lot, which is like, well, when the WNBA starts selling out stadiums and start being broadcast, then we’ll pay people better. I’m like, well, that’s fucking happening.
Annie Bailey:
It is happening.
Tori Dunlap:
So when will the pay reflect that too? Also, you should get paid equally regardless, but talk to me about this whole perfect storm of this moment that isn’t a moment because we hope it stays, but also we’re still not seeing the equity yet.
Annie Bailey:
Well, it’s crazy. I mean, it’s absolutely insane, especially if you look at, NBA players are paid. I mean, their contracts are absolutely insane.
Tori Dunlap:
Ludicrous.
Annie Bailey:
As someone who’s not personally an NBA fan, I much prefer college basketball. I just think, personal preference, I don’t love the NBA, but WNBA, you don’t even see televised most of the time. I never would have turned to an ESPN has a WNBA game on. They probably have cornhole or some other men’s sport that no one even talks about playing because no one would tune in. So I hope now that they’re seeing these beast women athletes who deserve every second of the spotlight, the men are getting that they’re able to pay them. I transparently don’t know what goes into the difference between like an NBA salary and a WNBA salary, but I would think it has to do with viewership, which is up. So you have to at some see that they’re getting the same exact viewership that men are getting at this point and pay them what they’re deserved. But the NIL helps with that too. Going back to that quickly, at least Caitlin Clark and Angel Reese are being paid on these State Farm deals, big time commercials and they’re at least seeing a paycheck that they deserve.
Tori Dunlap:
Yeah, I think that that is, again, one of the pros of NIL is we are seeing, again, a little more democratization where again, you have, and this has been forever, right? We’ve had incredible, I’m from Seattle, Sue Bird, we’ve had Sue Bird, we’ve had Kelsey Plum, we’ve had all of these women who are doing really incredible things in the sport but have not gotten their due. I think it’s back to the quote of, you have to be what three times as five times as good as any mediocre man in order to get the credit. So I think we’re seeing that with Caitlin is she’s so dominant and people are finally starting to pay attention. I think the NIL is helping with the legitimacy maybe, and also with her getting the money she’s due. But again, at the end of the day, her salary for the sport she’s playing is still less than a hundred thousand dollars a year compared to a bench warmer in the NBA is, you know, what? 2 million a year, maybe.
Annie Bailey:
Millions. Yeah.
Tori Dunlap:
Right.
Annie Bailey:
Millions. It’s crazy. But I do think NIL gave Caitlin the platform to be seen because you started seeing commercials of Caitlin Clark and seeing social media ads of Caitlin Clark, and then people were like, oh, who’s this girl from Iowa that’s insane at basketball? Let me watch her. Then now-
Tori Dunlap:
Little girls in her jersey, and she gets paid for that now, right?
Annie Bailey:
Yes. So now that she’s in the WNBA, I think that’s giving a lot of awareness to the low salaries and just the huge disparity between the men and women in the sport. So hopefully something changes sooner rather than later.
Tori Dunlap:
Another thing I think about a lot, and I’ve said it on this show before, and she actually just followed us on Instagram, and I had a conniption, Abby Wambach.
Annie Bailey:
Wow. That’s huge. That’s awesome.
Tori Dunlap:
[inaudible 00:28:58]. It literally happened right before I went on Good Morning America, and I was like shitting my pants in the green room. I was so sick because I love her.
Annie Bailey:
That’s a big day. That’s a big day.
Tori Dunlap:
It was a big day. It was a big day. But yeah, so she and her wife, Glennon host a great podcast, but her background, she played professional women’s soccer and is arguably the greatest of all time, at least greatest top three. She infamously has this video that went viral that she talks about. She won the same award that Peyton Manning and Kobe Bryant won. Yet she talks about how she was going into a very different retirement.
She was not only getting paid, of course, millions and millions and millions of dollars less than Kobe and Peyton, but she was at the top of her sport, the height of her game, and she was exiting and retiring with no brand deals, with no Budweiser, what is it? Peyton Manning’s doing, like Bud Light commercials, right? No shoe sponsorships, none of that. So she literally said, I don’t know how I’m making rent next week, and yet I’m getting the same award as these two men, rightfully so who are getting this award, but I am entering a very different retirement. So can we talk about even the athletes who do make a lot of money but then stop working? They either retire, to your point, they get injured and they’re no longer able to play, what happens to them then?
Annie Bailey:
Right. Well, and that’s where you see the huge percentage of professional athletes that unfortunately go broke. I think the percentage is 78% of professional athletes are broke within three years of retirement. That’s insane. That’s absolutely insane. So I think one of our huge focuses at RISE is put your money to work while you have the spotlight and while you can and you have the sustainable income. So that, a lot of our goals for our clients is to live solely off of not their game check. Fully put your game check into a really great investment into something that it’s going to start working for you so that you can live off of just that income that’s sustaining itself and growing without ever having to touch it. I think a lot of people don’t know to do that or just don’t have the people around them to educate them to do that. Or as a woman in sports, you may not have enough income to do that. Hopefully now with brand deals or with higher salaries, you can, so that you’re not living paycheck to paycheck just to make ends meet.
Tori Dunlap:
Well, and what happens too, maybe even from a psychological level, what happens when you stop playing your sport? I’ve spoken with many athletes on the show who like, okay, you’re making your money, you got your Nike sponsorship, but also your identity is runner, gymnast, basketball player. What happens when you have to, maybe if you don’t have enough money, go out and get a normal job, a civilian job, what is that transition like?
Annie Bailey:
Yes. I mean, sports is all, a lot of these athletes know. So again, I keep referencing what I do at RISE, but that’s just, I mean, this is our whole focus is making sure-
Tori Dunlap:
That’s why you’re here. No, [inaudible 00:32:21].
Annie Bailey:
Yeah. Making sure you’re set up for success. So we really try hard to pull out, what are your passions outside of football or basketball or baseball, whatever it is that you’re playing, so that we can slowly start, you’re still focusing on what you need to focus on, but let’s start pulling out those interests. Is it real estate? Do you want to be a real estate investor? Do you want to do that when you’re done? Are you super interested in community impact? Can we set up a 501(c)(3) for you that is going to employ your family member and give you something to focus on? Do you want to be a serial entrepreneur? Do you want to be a sports broadcaster? That’s a huge, huge thing that we start slowly pulling on the second we sign someone so that they aren’t set up to fail when the sport comes to an end, because it’s a huge issue.
Tori Dunlap:
I think, again, using the Abby Wambach example is the perfect template for this. I think that not just with the sponsorships and everything, or women go into, women athletes, you might not get the sportscaster offers. You might not get the Nike sponsorships for life. You might not get the notoriety. I think a lot about, we had my friend who’s a rugby player who’s a professional rugby player in the Olympics, and most of the time you’re actually paying to be in the Olympics, and you only make money if you medal. That’s something that I wish more people knew and talked about. Michael Phelps is one of the only people, maybe like a Katie Ledecky or Simone Biles. They’re the people who are making money, but a curler or a rugby player is not making the same money.
Annie Bailey:
Exactly.
Tori Dunlap:
So I think it’s not just about money, it’s also about opportunities and reputation. Again, the best player, arguably the best women’s soccer player to ever live didn’t have all of those opportunities set up because women’s sports was just not recognized in the same way that men’s were.
Annie Bailey:
I think make those connections while you can, when you have even the smallest of a spotlight on you, go network and use your name, image, and likeness, use that while you can so that after you’re done playing, you can still go back and reference those connections that you made and start tapping in on, okay, now do you have any opportunities that I could either learn from you, shadow you, intern with you, have a career opportunity, any of those things, because the spotlight’s not going to stay on you forever. It’s even smaller, unfortunately, as a woman. So you got to play on it while you can.
Tori Dunlap:
What can the industry do to change other than of course, giving women their due, but a lot of individual things that we can do of, yeah, networking, of making sure that you have a team around you. But most of this really that we’re talking about is it’s like the industry not respecting the contribution of women athletes or the industry giving MBA MLB stars 20 million a year, but not teaching them how to manage it.
Annie Bailey:
I think it’s a little bit of all the things you just said. I think it’s pushing the education onto the players, not making it a nerdy thing. If you want to go to the educational seminar that not many athletes are going to choose to go to because their peers aren’t going to it, somehow we have to bridge the gap of making education fun and showing them how we can break the system to better themselves. You’re not trying to throw this education on them for any other purpose than helping themselves. Then I think too, when it comes to women in sports or the less popular sports that don’t get the spotlight, it’s providing those same opportunities to them, giving them a spotlight, giving them a chance. Because as we’re seeing with Caitlin Clark, she’s just as good as the men, and she’s getting more recognition, so let’s treat her the same as we do the counterpart. Then I think we’ll start seeing changes in the long run.
Tori Dunlap:
I would say arguably better than most men playing right now. So yeah, yeah.
Annie Bailey:
Agreed. Agreed.
Tori Dunlap:
I don’t know if you saw this post, it’s been going around. It’s been making its way around Instagram, but it was like a tweet, I think, and it was the teacher, like a PE teacher who said that one of her boys who was in class before he shot the ball up said, Caitlin Clark, as opposed to Kobe Bryant. [inaudible 00:37:20]. Kobe. Right. Right. As opposed to Lebron James, it was Caitlin Clark. She was just like, oh, we’re in a different time now.
Annie Bailey:
That makes me happy, though.
Tori Dunlap:
Especially little boys.
Annie Bailey:
Heck, yeah. Heck, yeah.
Tori Dunlap:
I just fucking love it, it makes me cry. I have to keep moving, but it’s going to make me cry. I just think it’s so fucking cool. Again, it’s like we’re talking about Caitlin Clark, and I always want to acknowledge we’re here because of the women who came before her. We’re here because of not just the women in basketball, but all of the women who have been doing this sort of work and advocating for equal pay and all of that. So it’s just been really cool to see.
Annie Bailey:
Yeah, I mean, think back to when you and I were growing up. The only female athletes I can think of are Mia Hamm, which, kudos to her because she was in Gatorade commercials, so she was a badass, well before her time. Then Lisa Leslie, those are the only two huge names that even really come to mind. That’s so sad because there was so many more amazing women playing sports that just never got a chance.
Tori Dunlap:
For me, I grew up in a very golf heavy family, so like Annika Sorenstam, Lorena Ochoa. But the only reason I know those women is because my parents took me to LPGA events. That’s the only reason, it was not really, it was some televised, but of course, the LPGA is only televised on golf channel. It is not televised on CBS. The Masters is televised on CBS. LPGA is not. So, yeah, and I think that was the other cool thing again about the popularity of Caitlin Clark, Angel Reese, all of that crew of women this year or past year technically is we were seeing their games not on ESPN2. We were seeing them on ESPN or Primetime ABC. I could not believe that. It was so cool.
Annie Bailey:
I mean, it’s honestly, it’s a breath of fresh air because it’s just, you only have men’s sports that were on before this, and I think the championship for the women was at a way better time than the men was at this year. I know that that’s-
Tori Dunlap:
And it was viewed, way more viewership, way more attendance.
Annie Bailey:
Yes. As it should have been. I know we already said that, but it was way more entertaining than the men’s tournament was this year.
Tori Dunlap:
Yeah. So my question, and again, I’m fan girling at this point because I just fucking love it, and it feels just so good. How do we continue this momentum? Because the biggest fear I have is we have this incredible moment that we’ve been working towards forever, and we have know Sue Bird and Rapinoe who are out here trying to make this not just a moment, but what I’m scared about is it’s like, okay, it was this little uptick, but then it’s going to go back to where we started before. So how do we as viewers, how do we as entrepreneurs, how do we as professionals continue the momentum?
Annie Bailey:
You just have to keep the conversation going, and we have to start looking at the next generation now, who is still in college or just coming into college and has the potential to be the next Caitlin Clark. Let’s keep looking at Caitlin Clark, but let’s give these new kids the opportunity to go meet Caitlin Clark or have the same stage now that she has to keep the conversation going, because you have to just keep the interest up. We as females, and we as people in the sports industry, have to keep that momentum going, keep sharing, keep talking about it, keep giving women the do praise that they are deserved at this point. So I think it’s just everyone has to make a conscious effort to break the norm of only focusing on men’s sports.
Tori Dunlap:
Yeah. Well, as someone who’s managing the wealth and the assets of athletes, are you seeing kind of like a Caitlin Clark effect in that regard? Are you seeing a rising tide, lifts all ships where, okay, we might see definitive, a definitive increase in how much women are making because of it?
Annie Bailey:
It’s hard to say. I mean, I’m not in those conversations or in the room. It looks like it’s trending that way. I hope that it is. But I would say at this point, from my perspective, it’s still too early to know if it’s going to keep up or, I would hope it’s at least going to go up a little bit. I don’t know how long it’s going to take to get to the level that the men are making, but-
Tori Dunlap:
Oh yeah, we’re years out from that, if not decades.
Annie Bailey:
But progress is progress, so baby steps to get there.
Tori Dunlap:
One of the tiebacks I’ve tried to make is like, okay, you’re not a professional athlete, but maybe you’re an entrepreneur and you’re making money. For me, entrepreneurship was the biggest thing that I did to become a millionaire, to be able to grow my own wealth. So as an athlete turned entrepreneur for you, do you have any suggestions for people considering bridging that gap, becoming an entrepreneur?
Annie Bailey:
I think it’s just not being afraid to try different things. As an entrepreneur, you are doing so many different tasks and juggling so many different things, and I think there’s going to be things you hate. There’s going to be things that you love, but if you’re trying to bridge that gap of finding that, don’t be afraid to strike out a couple times. I thought I wanted to be a physical therapist. I thought I wanted to be a sports broadcaster. I hated a lot of different things before I found what I liked. So I think it’s educating yourself, having a grind, a work ethic.
To be an entrepreneur, you cannot be afraid to get your hands dirty and be in the weeds with everyone else doing the dirty work that you don’t always want to do. I think it’s always continuing to educate yourself, never thinking you’re the smartest person in the room. Always seeking out further knowledge of an expert that knows better than you, because eventually you could be an expert in that space, but just never think that you’re the smartest in the room is huge. That’s something I always take with me when I am in a room full of smart people.
Tori Dunlap:
I think echoing that too, you will never know all of the answers to the questions, and you’ll never know all of the questions either in advance. I think women are great planners, right? We’re very strategic. We’re good at project management. So before embarking on entrepreneurship, we feel like we need all of the answers to all the questions. Again, we don’t even know what the questions are. You will figure it out. You have to get started only through experience where you start to understand what the answers are to the questions. If I was looking in 2016 when I first started this thing at all of the questions I was going to have, I would be immediately overwhelmed, but I didn’t even know what to ask three years later. You learn that by doing.
Annie Bailey:
Experience is the best teacher, and also, you cannot be afraid of making mistakes because that’s the fastest way you’re going to learn, and you’re not going to want to make the same mistake twice or three times, but you are going to mistakes. Again, when I started with RISE, I’ve been a part of the team for eight years now, and I just got named partner and COO, but I started as an intern, and then I was a client relations specialist who had no clue what I was doing, but I asked the questions and I came to work every day, and I was not afraid to work hard and do things that I didn’t necessarily want to do, but that’s the only way that you’re going to grow and get to where you eventually want to be.
Tori Dunlap:
Can you tell me a story of when you helped someone feel closer to their purpose or their passions through their work?
Annie Bailey:
I think there’s two sides of it. Professionally and personally. Personally, I have recently found that I enjoy being a mentor and meeting with people who don’t quite know what they want to do with their life, because that was me not very long ago. So just grabbing a coffee with someone who’s in high school or in college and helping them understand it’s okay to feel the way you feel. It’s okay to not necessarily enjoy anything at this point, just you got to keep trying new things and not give up and know that you will find something. So that’s been really cool. I’ve met with a couple kids who just have been lost and I felt lost at one time. So just helping them get to where they want to go. Then professionally, a lot of what we do, like I talked about, is the community impact and helping them find their goals and what they want to focus on off the field.
One of our clients, Jessie Bates, he is really passionate about single moms and giving back to single moms, and he grew up in a single mom household, and that’s his whole vision and purpose off the field, and we’ve helped him create this. It’s called the JB3 Single Moms Fund, and just have brought it to life. Our first year was in 2019, and then this past year was, I think our fourth year. We took a year off for COVID. But helping him bring that passion to life and affect and impact other single moms and their kids and educate them and give them resources and help them just find their way has been my absolute favorite thing to watch, because it’s amazing to watch someone flourish.
Tori Dunlap:
Thinking holistically, I love that about, again, you’re not just an athlete, but what else are you passionate about? What else can we do to support what you’re trying to do? Especially if you’re in the NFL, if you’re in the, you have a platform and you can use that platform to advocate for issues that are important to you and advocate for causes that are important to you.
Annie Bailey:
Yes, yes, absolutely. The football or the sport gives you the platform to speak about way more important topics, and it’s not always a great thing, but people are way more willing to listen to you if you have that spotlight as an athlete. That’s just the way it is. So we might as well figure out how to use that for a good thing.
Tori Dunlap:
It was so great talking to you. Where can people find out more about you and your work?
Annie Bailey:
Yeah, I mean, on Instagram RISE, Advisors, you can follow me personally, Annie Morches Bailey. We also have our website or symposium that we always post a lot of information about, that’s just to educate people, educate the masses. So definitely check out our social medias, our LinkedIn. We’re always posting on there.
Tori Dunlap:
Cool. Thank you for your work. I appreciate it.
Annie Bailey:
Yes. No, it was great chatting with you. I’m so honored to meet you and just have a conversation with you. So thank you.
Tori Dunlap:
Thank you so much to Annie for joining us. You can follow her work over at RISE_Advisors on Instagram, and we appreciate this conversation. If you want more conversation about women in sports, it’s something that I’m personally passionate about and want to talk more about. So please tell me if you want more, because we’ll do more and probably if you don’t say yes, we’re going to do it anyway. Thank you so much for being here. We appreciate you. As always, you can subscribe, you can turn on auto downloads. That’s the easiest way to support the show. The show is entirely free for you, but expensive for us, so we appreciate your support in those very specific but very easy ways. You can also share this episode with someone who you think would love it. Thanks as always for being here. We’ll catch you back here soon. Okay, bye.
Thank you for listening to Financial Feminist Her First 100K podcast. Financial Feminist is hosted by me, Tori Dunlap, produced by Kristen Fields and Tamisha Grant. Research by Sarah Sciortino, audio and video engineering by Alyssa Midcalf, marketing and operations by Karina Patel and Amanda Leffew. Special thanks to our team at Her First 100K, Kailyn Sprinkle, Masha Bakhmetyeva, Taylor Chou, Sasha Bonnar, Rae Wong, Elizabeth McCumber, Claire Kurronen, Daryl Ann Ingram, and Meghan Walker. Promotional Graphics by Mary Stratton, photography by Sarah Wolfe and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First 100K community for supporting the show. For more information about Financial Feminist Her First 100K, our guests and episode show notes, visit Financialfeministpodcast.com. If you’re confused about your personal finances and you’re wondering where to start, go to herfirst100k.com/ quiz for a free personalized money plan.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over five million women negotiate salaries, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of over 2.1 million on Instagram and 2.4 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
