The following article may contain affiliate links or sponsored content. This doesn’t cost you anything, and shopping or using our affiliate partners is a way to support our mission. I will never work with a brand or showcase a product that I don’t personally use or believe in.
Navigating Male Dominitated Industries
Women make up more of the workforce than ever –– but the higher up the ladder your climb, the less women you’re surrounded by.
Some industries have built in boys clubs, and others don’t recognize the lack of diversity in their board rooms, or where they might be pushing women off glass cliffs (see Sallie Krawcheck’s episode for more on this phenomenon). Perhaps no one understand that better than Molly Fletcher, who was once, quite literally, the only female sports agent…for two decades.
Molly joined us to talk about what she learned as a woman working her way up in a male dominated field, how she’s negotiated millions of dollars of deals, and why she believes being the “only woman in the room” is her greatest secret weapon.
The secret to negotiating everything from a job offer to your dental cleaning bill
How Molly utilized her strengths to make herself stand out in her field
What Molly thinks stands out to her when she’s looking for her next client, and how that relates to every job –– not just sports
But I had to shift my mindset in that moment to not say, “Oh my God. This is not going to work. What am I doing? This is a train wreck.” People think that I’m somebody’s girlfriend. Or when I would be out on PGA Tour. Same deal. But I had to tell myself, “You know what? I’m different. I can connect with these guys, I can add value, I can represent at some level their entire family, not just the player themselves,” because they were often male athletes that I was working with. And this is actually a gift.
Hi, Financial Feminist. Welcome back. Welcome back to the show. I’m really excited to see you, as always. Thank you for being here. Thank you for click and play. I know there’s a lot of podcasts to choose from and we appreciate you being here today.
If you have ever been the only woman in a room completely filled with men, I have so many times, then this is going to be a perfect episode for you. If you work in a male dominated field, which let’s be honest, feels like most of them, if you just need a fucking pep talk about showing up and taking space, this is a fucking great episode.
Molly Fletcher is a trailblazer in every sense of the word. Hailed as the female Jerry Maguire by CNN, she’s represented sports’ biggest names and negotiated over $500 million in contracts. Her clients include Hall of Fame pitcher John Smoltz, golfer Matt Kuchar, coach broadcaster Erin Andrews, and basketball championship coaches Tom Izzo and Doc Rivers.
Molly has been featured in ESPN, Fast Company, Forbes, and Sports Illustrated. She’s the author of five books most recently, The Energy Clock. She also flies all over the country doing different speaking engagements.
When she had me on her show, she had literally just gotten back from speaking at the Four Seasons in Hawaii and I was like, “Okay, rich bitch, casual shit.” I fucking love it.
A graduate of Michigan State University, Molly resides in Atlanta with her husband, Fred, and their three daughters.
Molly and I talked about her time as the only female sports agent for two decades. Yes, you heard me right. She was the only sports agent that was a woman for 20 years. Both what it was like to live in work in rooms that were not only predominantly filled with men but where she was often the only woman in the entire room and the only woman in the entire industry.
What made Molly an amazing agent was her ability to negotiate, to feel confident. So of course, we talked about the lessons she learned at the negotiating table that you can apply both in your work and your everyday life. There is so much to gather from this conversation. Molly is incredible. Let’s get into it.
But first, a word from our sponsors.
So you’re in Atlanta, I was just there. On book tour. I was-
Yeah. And then I have family in Decatur-
Oh, no way.
… which is the cutest.
Fun. And, yeah, Decatur’s really a cute area.
It’s so cute. And they’ve been there for years, and so they’re watching all of the transition of the City of Decatur and…
Yeah, it’s grown. Oh, yeah. Oh, yeah. It’s a great…
Atlanta’s been good to me. It’s a great town. I’m glad you’re… Who’s here?
It’s my uncle and aunt. It’s my-
… uncle on my dad’s side. And so yeah, I got to see them and spend a couple days with them and they have this beautiful garden and yeah, it’s lovely. So I love the area. And we were there before it got too hot.
Yeah. Because, dude, it gets smoking here in the summer.
Yeah, I was there for a wedding in June and it was starting to get hot and I was like, “I can’t do this.” I’m Pacific Northwest, I’m like, “82 is peak for me.” That’s great. Anything hotter-
Yeah. And you’re right in Seattle, right?
Is that where you were raised?
I was raised in Tacoma which is about an hour outside of Seattle.
I’m so excited to have you. We love kicking off interviews with money and career experts by asking what your first money memory was. What is the first time you remember thinking about money?
It would probably be when I went to… There was a few occasions, of course, with my mom and dad primarily. But I remember going to the grocery store with my mom… And this is why I’m passionate about the work that you’re doing, by the way.
And so I go to the grocery store with my mom and she’s got a stack of coupons and an envelope that she brings into the store with her and we get up to the register to check out and she starts pulling them all out. Well, 80% of them were expired and I watched her work, this woman checking us out to take these expired coupons even though they really were expired. And that was when I started to see, wow, she was so excited when she’d saved 60 cents or when she clipped the coupon on the way in.
So I always had a sense for the value of a dollar from my parents. When we went to dinner, you got water and we didn’t go out much. But if you did, you got water and you definitely didn’t get a Coke or anything like that.
That was my first experience with money was watching my mom work to save 50 cents or a dollar or whatever using some coupons that maybe weren’t even really usable anymore.
And it’s funny you say, “We just ordered water.” I was just having a conversation with friends last night of I did not grow up in an appetizer family if you went out to eat. I still remember the first time it was when I was 23 and was on my own and I was like, “Oh my God.” I didn’t even look at the appetizer portion of the menu for my entire life.
And then when I had my own money and food was something I love spending my money on, I was like, “Oh my God, do I get to order?” I felt like this is the height of luxury. I get to order an appetizer because yeah, it was like you’re there for the entrée, you drink some water, there’s no appetizer and no dessert unless it’s your birthday. No way.
A hundred percent, a hundred percent.
And you never put one or two things in a washing machine at once and dried it and you never ran a dishwasher if it wasn’t full. You never left the refrigerator open for very long or my dad was barking at us.
We’d take a shower and after two or three minutes, he’d start yelling or he’d just go down and turn the hot water off.
That was what he would do. He would just go down into the basement if my brothers and I… I have twin brothers five years older. And he’d just turn the hot water off. And that was simple. And then you’d want to get out.
So I’m with you, girl. I wasn’t an appetizer family either.
So in our research, we learned that you negotiated your first contract by arranging to teach tennis lessons at this luxury Atlanta apartment complex in exchange for free rent. So tell me about that.
Yeah. Yeah, Tori, that was the beginning and a big help for me.
I moved down to Atlanta from Michigan where I’d played tennis at Michigan State, but I wanted to… And I’d grown up in East Lansing, but I wanted to get in the sports business and Atlanta had the Olympics and the Super Bowl was coming and pro team, sports teams.
So I saved up my money. I saved about 2000 bucks teaching tennis in Lansing, Michigan and then moved to Atlanta. And when I got down to Atlanta, I was able to sleep on the couch of a friend of mine’s apartment until I could figure it out which was great.
But one of the first guys I got on the phone with was a tennis coach that my coach from college had hooked me up with. So the gentleman that I connected with on the phone who was a tennis pro in Atlanta said, “Tennis is a huge deal and people teach tennis at apartment complex.” And he said, “A buddy of mine, he just got engaged. He’s getting married and moving out of the apartment complex where he teaches tennis. That property’s going to need a tennis pro, but they don’t know it yet.” So I was like, “This is amazing.”
So I get my car drive over, the manager was there, and she starts pitching me on an apartment pretty much when I walk in the door. And obviously, the pro hadn’t told her that he was leaving yet. And so as we were chatting, I said, “Well, look, if I played tennis, I taught. I know you have a court here and you have a great pro, which is great, but gosh, if anything changes with him, let me know.” Knowing that this was about to happen. And she said, “Oh, no. He is amazing. We’re good.”
So I hand her my business card, I jump in the car, I’m driving back to my friend’s apartment and I see a pizza place right across the street. Tori, it’s couple hundred yards away. And I think, “Well, that place should be selling pizza to that apartment complex because it’s right there.” It’s really close.
So I pull up, walk into the pizza place, it’s called Pero’s Pizza, right across the street. I said, “Hey, do you sell a lot of pizza to that apartment complex? Because it’s right there. It’s really close, 1100 units, a lot of young people. It kind of feels like you should.” And he said, “A little bit.”
But I don’t think a ton. And I said, “Man, what if you gave me once a month 15 or 20 pizzas for free? I’ll give them to people that come to the tennis clinic, get them excited about Pero’s. If you give me a coupon from Pero’s, I’ll take the coupon, stuff it the newsletter, and we can drive traffic back to Pero’s, everybody wins.”
He was like, “You’ll stuff the coupon in the newsletter?” I go, “Yeah.” He goes, “This is awesome. I love it.” I said, “Well, cool. But Mr. Pero, I don’t have a deal over there yet, but I’m right there, man. So keep it between us.”
So I get my car, I drive back to my friend’s apartment, and as I’m driving, I called my buddy at Wilson’s Sporting Goods who gave me all my tennis gear in college. And I called him and I said, “Hey, man, is there any way you could do me a favor and send me a box of Wilson stuff like goodies, water bottles, keychains, T-shirts, whatever?” He said, “For sure, no problem.”
The next morning, I grabbed my tennis tips. I’d written these tennis tips for a little magazine in Lansing during high school and college years just for experience. And they were probably very poorly written, horribly written, I’m sure.
But I print these tips 115, my box comes in from my buddy at Wilson. I drive back over to the apartment complex, walked in, and the manager was there. I had my box of stuff, my tennis tips on top, and I was like, “Hey, I’m Molly. I came by the other day.” And she goes, “Oh my God. You’re not going to believe this. The pro came in this morning, he’s getting married and moving out. We need a pro.”
You’re like, “Well, I got some stuff and some tips on a [inaudible 00:10:10].”
Yeah, exactly. And I said, “Also some pizzas.”
But those are coming. Those are forthcoming.
So I proceeded to tell her about the Wilson stuff and the tennis tips and then I asked, “How does it work?” And she said, “Well, the rent’s 850. We gave the pro 500 bucks off the rent every month and he’d just write us a check for the difference of 350.”
And then I shared with her about this pizza thing and she couldn’t believe it. And she was like, “Wow.” And I said, “This whole 850, 500 write a check for the difference??” She goes, “Yeah.” I said, “What if we just waived it? It’d be cleaner, it’d be easier.” And she went back and called her boss and came back out and she said, “You’re good to go.”
So I lived in that apartment complex, taught tennis every Tuesday night for free for nine years, which was, Tori, amazing because my first job in Atlanta in sports I was making $24,000 a year. And I had now just removed an enormous piece of my monthly expenses.
So it gave me the opportunity to step into that job where there wasn’t a big base salary and gave me an opportunity to get started because I was able to remove that.
So yeah, I’m a big believer that there’s opportunities to negotiate and ask for what we want all over the place, in areas and in ways that we don’t normally think about that aren’t necessarily traditional, but we can unlock them if we get curious, if we add value, and if we ask for what we want.
Molly, that’s a fucking crazy story. That’s so great.
Well, I’m trying to do takeaways. You’re exactly right. Asking for what you want. I think that that’s the common misconception and I want to talk about this later of like, “Oh, I can’t ask for that. They’ll tell me no.” And I’m like, “Yeah, they might tell you no but you asked.”
We’re also living, of course, in a society though, where when particularly women ask, there is this feeling of, “Oh, they should just be grateful.” So we’re also dealing with society’s perspective on negotiating. So even if we as women come with the greatest negotiation possible, we’ve prepped all of that, we still might be hit with the no or at the worst, “Oh, they should just be grateful and actually I’m going to penalize them.”
But I love that for you, it was just like, “This is super low stakes for me. I don’t have any sort of relationship with this person already. I have this insider info that they’re going to need somebody at some point. And also I’m going to go across the street to the pizza place and be like, ‘All right, let’s see how we can get everybody involved here.” So yeah, that’s so fucking cool.
And what set you on a really amazing path of just… It sounds like you were what? 22, 23 doing this which is crazy.
And I had some odds and in jobs. One of my first jobs was working for the Super Bowl Host Committee and to your point, Tori, I step into this role and I’m super excited because I’m going to be the receptionist at the Super Bowl Host Committee. And my parents were like, “You went to college, you were a student athlete. You’re running down to Atlanta to be a receptionist at what is going to be a job that starts and ends. What are you doing?”
But I met incredible people in that job. But when the head of it looked at me and said, “Now, just so you know, you’re going to meet a lot of incredible people. It’ll be great exposure, it’ll build your resume,” all those kinds of things, he said, “And we’re going to pay you $600 a month.”
And I remember being so excited about the opportunity that I didn’t process the $600 a month. And then I got in my car and I got home and I was processing it and I went, “Wait, certainly he meant a week, right?” And I called my parents and they said, “No, no, no. He knew what he was saying. He probably meant a month.”
But I called him up and I was like, “Hey, I’m really excited about this opportunity, but, listen, man, I got to ask you. You meant $600 a week, right?” And he chuckled and said, “No, I meant $600 a month.”
But to your point, I asked. And no is just feedback. And I think that if we can get more women in the world knowing that when we, to your point, can practice asking in little moments. There’s a stain on a dress at a store that we’re trying to buy, we’re trying to negotiate to grab an extra shot at Starbucks just for fun. The more we can practice in low stakes environments, the better and the more confident we get stepping in and making those ask in the bigger stake environments. Be it career, be it…
And for me, it definitely laid a foundation for me when I stepped into the sports agent space where I was negotiating all day long every day on behalf of my 300 athletes and coaches.
Yeah. I actually want to do a whole solo episode about this. But anytime I see at a hotel, I literally just ask if, “Do you have any complimentary upgrades?” And they’re like, “Oh, let me check.” And I would say 80% of the time they’re like, “Oh, yeah, we got a quarter room,” or “Oh, yeah, we have a suite.”
Now, again, granted all of this, and this is what I want to talk to you about in a bit, is asterisks with I’m a white woman. There’s a lot of privilege in that of just there’s no racist undertones there or sometimes there’s sexist undertones but we still exist in a society where even if again I have a great ask, the perspective or the bias might come in where that person’s like, “No, I’m not going to give you that.” Right?
And again, I can’t speak for a person of color’s experience, but I know it would be different if a black woman walked into that hotel and was like, “Do you have any complimentary upgrades?” I don’t think she would get the same response. So even that, I have to think about of yes, ask for everything and also know that there’s so much outside of your control about whether the yes happens or not.
So my favorite descriptor of you is the female Jerry Maguire. You’ve been described as the female Jerry Maguire and you spent two decades as the only female sports agent. Can you tell us your story of how you became a sports agent and then how you navigated this very male-centric environment? Right? Because if we’re talking about negotiating in a place where men are probably going to hear a yes just
because they’re men, how did you navigate that?
Well, I started at a small agency in Atlanta. We had about four clients at the time, a couple NBA coaches and a baseball player or two. I was brought in to do endorsement deals, marketing deals, go get free dry cleaning for coaches, go take them to appearances, endorsements, speaking engagements, all the… Anything that was possible, if you will, off the field or the court.
And then after the Olympics ended and our head coach of the dream team was a client of ours and after that ended, I remember sitting in my office thinking, “How are we going to grow? Because growth looks like more clients in this situation. And so how am I going to do that?”
And I put a business plan together to go start with baseball. We had one guy, two guys I think at the time, and I knew nothing about really baseball, Tori. I hadn’t grown up going to Tiger’s games or Michigan State baseball games per se.
So I put a plan together and fortunately, the leader of the organization said, “Go for it. If you can figure out how to do this, go for it.” Which I’m so grateful for that he said go.
So I would go down to Georgia Tech, they had a great baseball program at the time and still do. And I would lean on that fence and recruit players.
And so I got a couple first round guys that year, a couple more the next year, those guys would percolate through the minor leagues, into the big leagues. Half of first round guys make it to the bigs.
And then I would go visit them and I would take their buddies to lunch and go see them, take them to dinner, spend time with them, bring them at endorsements, appearances, all of those kinds of things. Added value. There’s not a lot to do with the young guy until he really gets to the big leagues. But that created a platform by which I was in that world building relationships.
And that was how I got into it. And then it grew, Tori. A baseball player later introduced me to a golfer that needed an agent and I started a golf division. We had an NBA coach get fired and the wife called me up and said, “This guy’s driving me insane. He cannot be home all the time. He has got to get a job. Find him a job.” And that was how he started a broadcaster division. We got him on TV calling games. So it evolved over almost 20 years.
So I entered like many of us do. I certainly didn’t swing for the fences out of the gates. I wasn’t going to get A-Rod and Jeter right away.
But to me, what it was about was being who I was, right? When I was leaning on a fence at a baseball game, there was no other women. There was no other women leaning on that fence. The guys had khakis on and golf shirts, chewing tobacco in their lip and clipboards and stopwatches, and I didn’t look anything like them.
And I didn’t want to try to be like them. I really believed that if I could show up as myself and I could connect and add value and make these guys’ world better and I worked equally or more harder than the people that I was competing with, then probably good things would happen. And that was in general my strategy.
And I always had to flip my lens at some level. I believe in these mindset shifts that we have to play at some level on ourselves. I’d be standing behind…
I remember going to see a couple minor league guys in Durham which was a feeder team for the Braves at the time. And I’m standing behind home plate, Tori. The guys are taking batting practice, nobody’s really around. And I’m standing behind the plate. And couple of my guys while BP was going on were turning around and talking to me. And not even guys that weren’t even my clients, but I knew them like Brian McCann and Mark DeRosa and Jeff Francoeur and Jason Marquis, all these guys were turning around and talking to me.
And after the third or fourth guy turned around, the manager walked over to him and goes, “Hey, listen, cut it out. Focus. Quit hitting on that chick.” And my guy, my client at the time looked at him and said, “That’s not just a chick. That’s my agent. So be careful.” And he had my back, which was cool.
But I had to shift my mindset in that moment to not say, “Oh my God. This is not going to work. What am I doing? This is a train wreck.” People think that I’m somebody’s girlfriend or when I would be out on PGA Tour. Same deal. But I had to tell myself, “You know what? I’m different. I can connect with these guys. I can add value. I can represent at some level their entire family, not just the player themselves,” because they were often male athletes that I was working with. And this is actually a gift. This is a good thing.
But I had to shift my story quickly, right? Because if I went down the lane of maybe the things that other players were saying, maybe the things that a manager was saying, a manufacturer’s rep when I was on the range of tour events, I never would’ve made it.
So we have to tell ourselves the right stories I believe in these moments where we find ourselves maybe a little bit different from everybody else.
Molly, I have so many questions for you. Just logistically, so when you are starting out as an agent, this is maybe my naiveté about how this works, but are you in an agency and you are an agent or did you start your own? What did that look like? If you were in your twenties and you’re like, “Okay, I’m going to get these athletes…” I know I’m repped by an agent and I have United Talent is the big agency and then there’s agents in that huge agency. Was that the same thing for you? How did that work?
Yeah, I didn’t own the agency. I worked for an agent. And then what happens, for example, in Major League Baseball, to be certified as an agent, you have to be listed as the player agent. So that didn’t happen for several years until I had a player that was a big league player.
And every sport’s a little bit different. Golf’s a little bit different. But with baseball… So it took probably four or five years before I was an agent per se which really just means that you are the one, it doesn’t just mean, but it means you are the one in the room negotiating their primary contract with the team.
But in so many ways, I was before that on the phone with the players, bringing them deals and appearances, negotiating on behalf of them for smaller things. And then I was also in the room with the players that I had been working closely with the agent that had led our agency at the time. And then as I begin to build my own roster of guys and some gals as well, that was when I was really “officially” in that space as an agent.
I knew you did baseball. No one… Very few people know this about me. I come from a huge golf family. My dad hierarchy of his needs as it’s like my mom and me and our dog and golf. Obsessed.
He grew up in Latrobe. He caddied for Arnold Palmer in the su
mmers. He literally… He was like Caddyshack. He and his brothers, who one of them is in Atlanta… I keep telling them they need to write a book.
They literally caddied for Arnold Palmer when he would come back to the country club. That was their summer job.
And my dad’s… We went to St. Andrews and he is crossed the Swilcan Bridge. He started crying. We are the biggest golf family. I’ve been to the Masters. He’s been I think three times. And so I just love that. Yeah, I didn’t know you did golf too because that’s the sport that I know the most about and it literally is my childhood.
Yeah. Well, I had the pleasure of sharing a stage once with Mr. Palmer. What a treat that was. Yeah, I spoke at Bay Hill which was his tournament. And then he popped into the room and we shared the stage for a little while which was pretty special. That man is unbelievable.
So your dad and brothers… As an agent on Mondays and Tuesdays, I would walk inside the ropes with my players for their practice rounds and got to really experience the way they navigate the club choice-
The pin placement.
… all that stuff. It’s like-
All of that, yeah.
Just like your dad had the opportunity carrying Mr. Palmer’s bag. What an unbelievable gift.
But to your point, I had the opportunity to play Augusta, Tori, and-
The dream. Molly, the dream.
It was really special.
But what was funny given you and your show and all that, at the time, there was no women members-
… the first time I played.
I think it’s what? Condoleezza Rice. And that might be the only woman now I think is-
I think there’s another woman like a CEO.
Yeah. I get there and the member… I needed to change and freshen up and put my golf shoes on and all that. And he’s a wonderful man that took us and he looked at me and he said, “Now there isn’t a women’s locker room yet.” And I was like, “Yeah.” And I was like, “It’s all good, man. I can just pop…” He goes, “No, no, no, no, no. I’ve got you set up in the past champion’s locker room.” And I was like, “Deal. I am in.”
So he walks me through this mahogany door, I open it, and there’s just lockers with every guy that’s ever won the tournament.
Right. In Augusta, there’s a past champion’s locker room where every single past champion has their own locker. It’s engraved. It’s when you win, you get a locker and you also get a parking lot which I discovered recently. You have a separate champion’s parking lot when you drive for the Masters. But oh, that’s so cool.
So it was cool. And it was an example of it’s… Actually, I’m glad you don’t have all this locker room right now because I’m down with picking Mr. Palmer, Tiger, Phil. Pick a locker. It was insane.
So we can always make lemonade out of lemons or however that saying goes.
Well, that’s the perfect transition or even confirmation of you are the only woman doing this. And even the actual places you’re in are not even built for you. I’m the only one doing this. This is really hard. It doesn’t feel like this was built for me. And then you go to a literal sports arena or the Masters and Augusta National is where the Masters which is a golf majors played and you don’t even have a locker room to change into. Is it difficult feeling like you are the only one? Was there pressure around that idea of like, “Wow, I’m the only one doing this?” Tell me about that.
Well… And the good news now is there’s more which is huge. But at the time…
You know what’s interesting, Tori, I’m not sure until probably a decade into it, I spent really any time thinking about that. I wanted to build great relationships with my players so they’d have my back. When things would happen…
I remember going to see one of my golfers actually and we went to his club, the only place that was serving food the day that we were there was the men’s grill and we wanted to eat there and he wanted to eat there. And he had my back. He was like, “This is ridiculous. She’s my agent. We need to have lunch, set a table up for us.” He was kind but he was annoyed, but he had my back.
So for me, it was about building great relationships with my players. So they supported me and respected me and appreciated me and at some level, even their wives.
But then when I started to recognize the uniqueness of it and started to pay attention to that, I thought, “How can I help take other women along with me?” Because what I found was actually being a female was a total and complete secret weapon. It was…
Because in some ways, Tori, what I would do if it was a male athlete which is where at the time, sadly, primarily where the money is, I would often connect with the wives and build great relationships with the wives. And then the wives would come home to their husbands and go, “Dude, you just got traded last year and I had to pick up all the pieces. This is someone who I think can get and take care of not just you and your contracts and do a kickass job but someone who can also look at our entire family through the lens of her work and supporting and serving you and maximizing this window of time.”
And what I knew is it’s a lot easier as a golfer to stand over a putt on a Sunday and drain a putt when your rest of your life is intact.
And so I intentionally built a team around me that helped ensure that we didn’t just maximize every last opportunity that a guy could have as an athlete on the field and off the field or on the course and off t
he course, but that we put people around him to make sure that he could operate like the CEO of his own company and he could have the kind of support he needed to deliver and perform at the highest level which is an enormous amount of visibility, pressure, all those things.
And you need a team to be able to do that. No different than… No CEO does it by themselves. And so I built a little bit of a different approach to it and found that being a woman was an absolute gift.
Yeah. And probably that empathy and the understanding of the whole athlete and not just them on the field or them on the course.
Have you seen Full Swing?
Oh, you haven’t seen Full Swing yet? Do you know about it?
No. What is it?
Oh, it’s this documentary. It’s a eight part documentary on Netflix about golf. And they follow different golfers, they follow…
Oh, I’ve seen some of that on a Delta flight. Yes, I’ve just seen one episode.
But literally it echoes exactly-
Oh, is it amazing?
Oh, it’s so good. But it echoes exactly what you said. They talk about Tony Finau and Tony Finau is a professional golfer and his wife lost her dad and literally, he talked about them going to tournaments with him. He took his entire family. And I believe he’s Samoan. And so he has this really huge family that he would bring along with him. And they talked about the dynamics of that of literally…
And this is the shitty part. Reporters were like, “Do you feel like you’re playing better or worse with your family here?” And it was just really interesting to see. There were certain guys on tour who were just hyper-focused if they have partners or children, they stay at home versus he was bringing his family on tour with him and actually winning. He was doing great.
And so it’s just interesting to think about we are perspective of viewing an athlete of course as a whole person and not just their productivity or what they’re doing on a field. Yeah.
And they’re all different, Tori. Right?
For Tony, that is probably and maybe what works for him. But then there’s other players that are like, “Look, I’m going to go. I’m going to knock it out. I’m going to go to work and I have to focus.” And I think everybody…
I had golfers who traveled with their wife and kids and some that didn’t. And I think they’ve got to look at what works best for them so that they can perform.
But they’re out 30, 32 weeks a year. That’s a lot of time. And so a lot of them want to have their spouse, their partner, their wife, whatever it might be with them.
Yeah. It’s a hard subject to broach but we found in research, not shockingly, that women in male dominated fields are more likely to experience harassment. Is that something, if you’re willing to share, that you’ve either experienced or witnessed?
I have fortunately not.
It’s funny. I remember one time and I will share that. My mom, we have three daughters, and my mom said to me when my daughters were two, two, and three. That’s a whole another story. I had three kids in 12 months, Tori.
I said, “Mom…” I totally idolized my mom. She’s incredible. And I said, “Mom, what do you think is the most important thing for me to instill in these girls, for us to instill in these girls?” And she really didn’t hesitate and goes, “Confidence. Make sure they’re confident, because if they’re confident, Molly, they’re going to be able to navigate lots of different things in life.”
And I think my mom and dad helped do that to me. And so I share that only as a backdrop of gratitude that I had been given that foundation. Because the truth is it made me feel confident enough inside of moments that were maybe a little bit offsetting, and I’ll tell a couple of them, to post somebody up, to have the confidence to walk away.
I remember a guy that I worked with at the Super Bowl Host Committee. I was right fresh into Atlanta and there was a football in the office and we would play catch with it sometimes. And one of the guys, and I think I’d worn a skirt that day, looks at me and goes, “Hey, bend over there, snap me that ball, Molly. Come on.” And I looked at him and I go, “You are disgusting. No. Don’t say that to me again.” And he was my boss.
But I don’t know what percentage of the world would go, “Oh, shit. It’s my boss. I guess I better do that.” And I just posted him up and threw the ball at him. I was like, “Dude, no. What?” And I’m grateful for that.
There was another circumstance where I had to go bring a baseball player balls to sign. I needed to go… He was in town. I’d done a deal with him and I needed… He played for the… I can’t remember what team but they were in town playing the Atlanta Braves. And so I went down, he was at the hotel, and I brought him up a dozen baseballs to sign.
And I called his room. This is pre-cell phones. So I called his room. There was even that world, right, Tori? But I called his room from the front desk and he goes, “Hey, just come on up.” And I remember going, “Ooh, this is weird.”
And I go up and I sit and I’d had all the baseballs opened and I got to where I would turn the baseball perfectly. So all they had to do was just sign. They didn’t even have to pick the ball up. So I line them all up and I walk in and I was like, “Hey, man, what’s up?” And I’m sitting on the bed next to him and he’s signing these baseballs and I’m like, “Oh, this could go wrong.”
But I did a couple things. Number one, the way that I walked in, the confidence that I tried to demonstrate the distance that I sat away from him. I handed him the balls and then there was a chair in the corner and I went and I hooked the door how they have those hooks on the door. I put that in there. So the door was propped. Little things like that.
But I remember when I got up and he was a really nice guy and it was no big deal. He did nothing inappropriate at all. But it was a moment where I thought that could have gone weird.
And it’s hard to even have that placed upon anybody. The thing I think about all the time is it’s like we live in a society that doesn’t teach men not to harass. We live in a society that teaches women to do everything they can to prevent it. Of course, the first question, if there’s some sort of assault, it’s not like, “What is this guy doing? What happened?” It’s, “What skirt were you wearing? How drunk were you?” That’s the response.
So it’s even interesting of you and you’re like, “Okay, I took all of these precautions.” And it’s like you shouldn’t have to. You shouldn’t have to be thinking, “Oh, okay, I’ll put a chair between him and I and I’ll make sure that I walk in with confidence and professionalism,” because at the end of the day, it doesn’t matter. We live in a society that conditions us to think that. And at the end of the day, it doesn’t matter. I’m just so glad that you’re okay.
Well, and part of it is the… Yeah. Well, no. And part of it is, he’s physically stronger than me too, right?
And you’re in a position of he’s in power. He’s the one with… He’s the famous, probably has money, the one… And he’s physically larger. Yeah, yeah.
But the truth is I will say I had absolutely no reason to be skeptical. But what I knew is as that happened, and maybe I should have done a better job preparing that. I don’t know but-
No. That’s not you. That’s not you. Don’t… Yeah.
Yeah. When he… It makes sense, right? He’s incredibly famous. So the last thing he wants to do is go sit in a lobby where people can see him and get hammered by things.
But I hear come up to my hotel room after me too and I’m like…
Yeah, yeah. Oh, yeah. Yeah, for sure.
But no… The good thing is after games, I remember once, so as the baseball division grew, for example, I hired agents that had played, met a couple guys that had played at a really high level and didn’t make it to the big leagues and they wanted to work in the business. And one of them was a client of mine. Great guy. And after a game against the Rockies, we go to the game and then we go across the street to this bar and the players would just come over there after the game and drink beer. And these guys can drink so much beer so fast, it will blow your mind.
And I’m sitting there with my former client who now works for me and had come with me to go see a couple of the players. And I remember… And I was still fairly young, I was definitely under 30, no kids, not married yet. And they were buying me beer so fast and I don’t really like beer. I don’t drink beer much at all. And I couldn’t keep up.
But then as the night progressed, I looked at my agent that worked for me and was a good guy and I said, “Dude, we need to go. I need to get out of this… I want to leave.” And I would always do that, Tori.
These guys live in a different world. And I grew up in a pretty naïve, candidly environment. And as a Midwest girl, like you said, white girl in Michigan… And I didn’t really have a clue maybe that they were buying me beers as fast as possible for other reasons than they wanted to just be really nice and buy me a beer. And as I got more mature and more exposed, I began to see that.
But my agent had my back too. He looked at me and I go, “I don’t want to be here. I don’t want to see these guys like this. I don’t want to know this side of them.” But I’m really grateful. I feel like…
I had two older brothers, Tori, who treated me a lot more like a little brother than a little sister. And they were also two older brothers who were wild. They had a lot of fun.
And I remember as a young girl watching them run around a little bit with some girls. And I remember thinking, “I’m never going to be that girl. I’m never going to be that girl. I’m not going to be that girl. Nobody’s going to have any piece of me that I don’t want to give away.” And that was a big deal.
And I think that always helped me just make strong decisions all the time and keep my core values, my faith at the center of everything all the time.
Yeah. And it’s just difficult because… Yeah, I don’t want to harp on it too much, but we can have all of the intention of us setting our boundaries and doing that and then there’s people that will violate them. There’s people that will cross that regardless of how we carry ourselves. So I appreciate you sharing and being vulnerable.
It’s going to be a weird pivot, but I want to make the pivot.
You’ve landed more than $500 million worth of deals throughout your career. No small chunk of change. That’s crazy. Can you break down your process of negotiating and making sure you’re getting paid what you’re worth even if you’re not a sports agent, just the average person listening? And can we talk about your five pillars of negotiating?
Yeah, yeah, for sure.
Now, 500 million bucks, half a billion dollars isn’t even really a lot. That’s maybe a half of a big time which is insane. But then it was. I had several guys that were the highest paid baseball player, coach, whatever.
For me, relationships are the foundation. And when we can build great relationships with the people that we negotiate. And this is again why I think women have an opportunity to have an unbelievable advantage in negotiating if we can just start practicing more and building our confidence.
Because one of the main reasons people don’t negotiate is because of a lack of confidence. And the more that you practice, the more reps you get, the more confident you get. And I didn’t have a ton of confidence when I started, but I started doing small things and then you get more comfortable.
And what I found is foundationally relationships are key. You’ve got to build great relationships and connect with the people that you want to negotiate with.
And I think one of the biggest mistakes people make is they spend way too much time, Tori, thinking about what they want in a negotiation and not nearly enough time thinking about what the other party needs, wants, the problem you’re solving for them, what are they navigating on their side financially, strategically, what are some logistical things, every
And so I would almost go so far as to say that we have to spend more time in the head and the heart and in the world of the person we’re negotiating with than in our own world.
And curiosity is a linchpin for this. Asking great questions, doing our research, getting in the world. Anytime I was negotiating a baseball player’s contract, I knew exactly what their payroll traditionally was. I knew exactly what the market bared for a middle infield or a pitcher or whoever it was. I knew exactly what was on the free agent market in the minor leagues, arbitration eligible guys. You had to know all of that so that you knew where they were coming from and what mattered to them.
And then I think it’s counterintuitive but I think the other thing next up at some level is adding value to the people that you want to negotiate with. And this is so counterintuitive and people go, “Wait. As an agent, dude, you took your gloves off. You went at people. You got on the other side of the table. That’s what that is.” And I’m like, “Actually, I had way more success when my relationships were super strong with the people that I was negotiating with.”
Molly, I always joke when I negotiate and I do coaching with people, people think it’s like unsheathing your sword, pulling out your boxing gloves, and I’m like, “No, this is a collaboration, not a conflict.”
You are not on the opposite team with the person you’re negotiating with whether that’s a client or your boss or your potential boss. You’re on the same team. And you have to figure out, “How can I add value or how can I prove that I’ve added value in order to confirm that, ‘Oh, I should be getting this raise because look at all of the things that we’ve been able to do together?”
And I joke with people that you are great problem solvers, it’s what makes you good at your job, right? That’s probably a huge trait for you. You’re simply solving a problem of you not being compensated fairly.
There’s not these massive stakes where you feel like you have to fight to the death to get to what you want. So it’s really funny you say that because I take the exact same perspective.
That’s cool. And you take it from the lens of somebody going in and asking for a raise.
Yeah. That’s really what I’m thinking of when we’re negotiating. If I am… The average person listening to the show right now is, “Oh, I’m trying to prep for my raise,” or “I am a freelancer and I have to ask this client to pay me more money. I’m raising my rates. How do I go about doing that?”
Well, and I think when you can… And here’s the other thing, Tori, to your point, and I can speak to this a little bit through that lens given that’s the lens that your listeners are, but people have amnesia. Your boss has amnesia. They have amnesia. They don’t remember all the stuff that you’ve done for them. They don’t remember it.
So you have to keep track of the extra and the more and the oh, yeah because they won’t remember and they don’t even really want to because all it does is build your case. So you got to keep track of it.
I did that with my clients because when my guys would call me up and go, “I’ve only got half a million dollars off the field and deals.” It’s like, “Right. Because you turned 400 down. Remember this, this, this, this, this.” So people have amnesia.
But I think to your point, you’ve got to remember the way you’ve added value and continue to add value so that at some level, Tori, I talk about the favor column is so high that no becomes almost impossible. You’ve leveraged yourself to a point where without you and not creating an environment that you are excited about becomes a significant detriment to the person that you’re having that conversation with. Right?
And to me, negotiation’s just a conversation. That’s all it is. It’s funky, it zigs and zags, but that’s what it is.
And so to me, if you’ve build that great relationship, if you add value, if you do those things over time a little bit, then you ask for what you want and you shut up.
One of the biggest mistakes I think people make is they go… Because just when you think about… You’ve already done all that. You’ve built the relationship, you’ve reminded them of some of the things that you’ve done. Now, when you walk in and ask for what you want…
Can you imagine when I got that free apartment deal if I would’ve said, “So here’s the thing. I just moved down to Atlanta. You know what I mean? I’ve got 1600 bucks. I taught tennis for a couple months. Help me out. I need a little bit of help. I don’t have a job.” No. Tone matters. Timing matters. And when I said, “Let’s just waive it,” I didn’t go, “Let’s just waive it.”
Because remember, I’m going to stuff the coupons in the newsletter and remember, I could get more stuff from Wilson and remember, I didn’t do any of that. I just said, “Because I’d already done all that.” So now you can ask. And I think that’s a big mistake.
So often, we ask for what we want and we just keep… Shut up. Pause. So we got to pause.
I think inside of these conversations there’s going to be moments where you feel defensive. Get curious. There’s going to be moments where you maybe need to pause and sometimes, that pause is right after you’ve made the ask. Sometimes, the pause is, “Hey, I need a minute. I’m pretty frustrated right now. I need to take a minute. Can I come back to you tomorrow? Can I come back…” Whatever.
But we got to ask with confidence and then pause. And then I think the biggest thing is practice, practice, practice. Practice.
Tori, I took our girls when they had… Now we live in a world where you don’t have the opportunity to just get one set of braces as a kid, you get to get them twice. It’s just fantastic. These orthodontists are killing it, right? Did you know that?
No. I was told as a kid that I didn’t need them and then my teeth got really crooked. So I was lucky enough to do Invisalign a couple years ago. But literally, I was the kid who I was like, “Oh my God, I get to get scot-free, I get to get out without braces.” And then as I grew older, especially my bottom teeth were all crooked. And so-
Do you make your parents pay for that Invisalign since they neglected you so fiercely?
No. Stop. No. Literally-
No, no, no. Not at all. No. It was one of those things where… Yeah, this is a story for another time. But we had a company who was like, “Actually, we’ll pay for it.” And I was like, “Great, I’ll talk about you.” Yeah.
One of those fun things. Or I wouldn’t have done it because for me, it was not a priority. I was like, “I don’t care about my crooked teeth, that’s fine.” But I didn’t know it was two rounds of braces.
So I go in… And so this is an example of practicing in low stakes and also helping people recognize that there’s so many opportunities to negotiate and to ask for what we want that we miss, that we over… That we don’t even pay attention to.
So I walk in and negotiate to get the girls braces. And of course, the doc comes in and says, “Yeah, they all three need it.” And they really did. All three of their mouth looks like a landmine.
And so we walk into the office and the office manager walks me through and she’s like, “So this is how we do it.” And she walks me through and it’s nine grand, three grand a kid. And the whole time I’m looking at this entire practice. It’s busy, it’s in a great location. They’ve got two docs, a pretty big staff.
And I said, “Wow.” And so she said, “What you’ll do is you just pay monthly.” And I was like, “Okay.” And I go, “God, so all these people…” Every chair was full. There was five or six chairs. I’m like, “You bill all these people monthly? That’s got to be a nightmare.” And she goes, “Oh, yeah. It is, man. It’s unbelievable. You wouldn’t believe it.” She said, “Sometimes, they don’t pay. I got to chase them down.” And I was like, “That sucks.” She goes, “Yeah, it’s a nightmare.” And I was like, “Wow.”
And I just looked right at her and I go, “What if we do buy two, get one free, and I’ll write you a check for six?” And she goes, “What?” I said, “Yeah. Like a buy two, get one free.” And she goes, “Well, I got to go… Let me ask the doc.” She came back and she did it. And I was fortunately in a position financially where I could do that, but I saved three grand, saved them the hassle of having to bill.
So I share those because that’s a weird person to negotiate with. An orthodontist. Most people don’t think about that. But if we can be curious and look at the world that someone’s living in and get inside their head and heart and try to ask great questions so we can understand maybe what their pain points are, then we can begin to solve for that.
And I think that applies if you’re stepping into a conversation with your boss. What matters most to them? How can you solve for that? Serve that at some level, add value in that way. That positions your case.
One of the mistakes I made, Tori, was when I started in that job, I think I started at $24,000 a year and a mentor of mine gave me some advice. And he said, “Do this, Molly.” He said, “Agree to the…” And this was, by the way, a great job for me at the time because I’d gone down, I was in an agency, really good man that I was going to be working for. It was a good situation. I was excited about it.
And he said, “Do me a favor. After three months when you take the job, just have him or the COO at the time have them agree to just do a sit down with you and review your compensation package instead of waiting maybe for an entire year.”
Well, I hadn’t done a lot in three months. And so when I went into that conversation and reminded them of it several times, they looked at me like, “What do you want? You want a raise? You haven’t done anything.” So that was a bit of a lesson for me.
When we can add value and when we can make an environment a lot better in a significant way, then we can start to position ourselves more effectively to get those pops, to get those raises.
And I just want to call out with the orthodontist what you did as it wasn’t… You were thinking, of course, how can I get this for cheaper. But the question wasn’t, how can I pay less or how can I get this for cheaper. It was asking questions and realizing, “Oh, their pain point is they’re having to bill people all of the time,” and they probably, as a business, would just a lump sum of money once because what if this person defaults on their payment at one point. So I would rather, as a business owner, get that money all in one. So what if I pitched that to them and so that… I just want to call out.
That was the subtle change that I saw. It’s not like, “Hi, I would like to pay less. How can I do that?” It was like, “Wow. It seems…” And again, asking questions. “It seems like there’s a lot of people here, you’re billing them monthly? Oh, that’s crazy.” And you’re empathetic towards that person. And that’s not fake empathy. You’re like, “Yeah, that’s really hard. What if I made your life easier? Right?”
Yeah. It’s very smart.
And Tori, and that was a win-win. That was a win-win, everybody won. And I really think there is a lot of scenarios like that where… And we had a great relationship with them. It didn’t impact the service in any way. All those things.
So I think curiosity is a real secret weapon inside of negotiation, inside of critical conversations. And practice is huge.
I want to wrap up today by asking you a fun question. When you were scouting athletes or coaches or broadcasters, what personality traits stuck out to you? What are you looking for and how does this translate to industries that aren’t sports as well?
Boy, that’s awesome.
Yeah. So when I was recruiting clients, what did I look for? I would say reputation was the biggest thing for me because when I would go see a baseball player, sometimes, I would go try to see them when two teams were playing each other and I could take both guys out to dinner. Or when I would go see my golfers, I would want to go see guys and then be able to walk a practice round with a couple players at the same time. So I n
eeded them to like each other. I needed them to know each other, respect each other.
And so their reputation was everything to me because I was certainly an extension of them representing them, negotiating for them. But they were an extension of me. If they’re in a locker room or a clubhouse talking about their agent and they’re now an extension of me and I wanted somebody that was going to represent me the right way in the clubhouse to other players that I wanted to sign. I wanted…
And you know what? Tori, it’s a business where you work 24 hours a day. My phone was on all the time. It was on all the time. Literally, I bought pajamas with pockets in them. I would nurse on the phone with clients. I’d be pushing my kids on the swing with my phone.
So the other component of it was I wanted to like them.
I just wanted to like them. I want to go look down and see their name and not go, “You got to be joking me.” And trust me, I had a couple of those that slid through and then I either had a tough conversation and realigned expectations or let it go. But reputation, I would say was the biggest thing.
And I can speak as someone who now hires people… It would be crazy to people. I would say probably competency in your job is of course a good chunk of it. But the majority of what I’m looking for is can I trust you, not just trust you to do your job, but do I trust you as a person and do I feel like you’re always going to assume positive intent and not only… I don’t need to always like you, but I need to have a mutual respect with you. And that is something… I always say, “Skills are teachable, character isn’t.” That is huge.
And so I love that you said that because I-
Yeah. Integrity and character… Yeah. And to the second part of your question, through the lens of our world as business people maybe, it’s absolutely, certainly reputation, but it’s character integrity. All those things, to me, those are just non-negotiables. They’re just not negotiables.
Molly, thank you for being here. You were kind enough to have me on your show as well and that’s how we connected. And you’re just incredible. And I have so many questions for you too. We need to… I want to trade numbers with you. It’s so cool.
Where can people find out more about you?
mollyfletcher.com. M-O-L-L-Y fletcher.com. And that’s just a great place to start.
And then my podcast I would say is really a great one. And Tori, you were on, as you said, which was awesome. And like you, I’ve been fortunate to have some… Everybody from Matthew McConaughey to [inaudible 00:55:27]-
Priyanka Chopra Jonas I think was on, right? Yeah. Which is amazing.
She was. And so cool. So cool.
Yeah. I, like you, have been super fortunate to have some awesome people. So my podcast is Game Changers with Molly Fletcher. And you can go there and hear Tori and I on that side of the coin which is fun.
Amazing. Thank you, Molly. Appreciate it.
A huge thanks to Molly again for joining us for this episode. As always, we’ve linked her socials, website, and books in our show notes that you can find below on whatever podcast platform you’re listening to. And you can also check out her podcast, Game Changers with Molly Fletcher, including my episode on that podcast wherever you get your podcast, wherever you’re listening right now.
We are fast approaching 100 episodes. I have to lean back [inaudible 00:56:11] I’m blowing your ears out. We are so grateful truly for this community that we’ve built here at Financial Feminist. We want to thank you for listening every week. We have a special little surprise at 100 episodes. So stay tuned for that.
Crazy to think about how this show’s only been alive for two years and I think for a year of that we weren’t releasing episodes. So the fact that we’re at a hundred, we’re still here, we’re still kicking, just it’s so kind. And thanks to all of you.
We appreciate you listening every week. We appreciate you leaving reviews, sharing the show with your friends and family, and it means so much to us and allows us to continue doing the work that we’re doing. We can’t wait to see you next week. We hope you have a good one. And we’ll talk to you soon.
Thank you for listening to Financial Feminist, Her First $100K podcast. Financial Feminist is hosted by me, Tori Dunlap, produced by Kristen Fields, marketing and administration by Karina Patel, Cherise Wade, Alena Helzer, Paulina Isaac, Sophia Cohen, Kahlil Dumas, Elizabeth McCumber, Beth Bowen, and Amanda Leffew.
Researched by Ariel Johnson. Audio engineering by Austin Fields. 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 team and community for supporting the show.
For more information about Financial Feminist, Her First $100K, our guests, and episode show notes, visit financialfeministpodcast.com or follow us on Instagram at Financial Feminist podcast.