Jessica Berman: A New Playbook for Women in Sports | E99

business person I could be. And I wanted to learn areas that I would not have the opportunity to learn if I had stayed at the NHL. And I had to understand that that came with some sacrifices, and I was okay with that.

today is Jessica Berman. Jessica is one of the most influential executives and professional sports. She's the commissioner of the National Women's Soccer League, where she completely reformed the leadership of women's soccer, and has presided over its explosive growth in the last 18 months. Prior to this role, she served as the Deputy Commissioner, Executive Vice President of Business Affairs for the National Lacrosse

League. When she took that job, she was the highest ranking woman in a man's professional sports league. And prior to that she spent 13 years with the NHL, ultimately serving as its vice president and Deputy General Counsel. Jessica, it's a true pleasure to have you on my show. Welcome to In Search of Excellence.

on you, and your future? And what it was like coming from a Jewish background where you were the minority?

looking to make money. Like, you know, my children want to get a job because they want to have financial independence, he was really forced to work because their family was very poor. And they needed money to actually buy food. And that really is what stuck with him his whole life. And he constantly reminded that of was a reminder of that to our family always, which is that your hard work is ultimately the thing that you

have control over. And that it is the thing that people remember most about you and really leaves people with the impression that you deserve to have what you have. And so that's really what what stuck with me and my my dad ran a very sophisticated business, but in a not very sophisticated way. He really always kept it to the basics with a Mead composition notebook and a pencil and a

ruler. And he did all of his inventory phone calls to his gas station to determine how much gas they had and really put all of his feelers out into his network. And it was a very sort of like, grassroots operation. And I always appreciated that about him. Even though we all tried to introduce technology to help make his business more effective and efficient. He genuinely believed that he didn't need that in order to run his business in a sophisticated

way. And he actually was able to prove that he was able to do it, at least for his lifetime. I don't think it would have passed the test of intergenerational support and being able to have his children or my children be able to work in the business and the way that he ran it, but it kept him very fulfilled throughout his life and And he ultimately became a provider for our entire both immediate and extended family. And my mom, you know, she, she actually was a

teacher before I was born. And that really drives her actually even still. But she decided when she got married to my dad, which was later in life, it was the second marriage that she wanted to become a psychologist. And she approached my dad and said, I could either become a psychologist and get my PhD, or we could have a child and my dad said, I don't want you to have to choose, you can do both. And she was 30 years old at the time, restarting her career in

1977. At a time when certainly the gender equity movement was was far from cool or accepted. And my dad who was very old school and traditional, didn't think twice about saying, well, I'll just lean in at home so that you can live your dreams. And they really embodied a wonderful relationship where they shared responsibilities in our home, and allowed my mom to go back to school and ultimately have the career that she wanted to have becoming a psychologist. Because

the path I took. And it allowed me to be around sports because of cheerleading, and allowed me to feel the energy around team sports in particular, which I loved. And I also through that got to know a lot of the coaches and the administrators around athletics. And once I started to sort of unlock my interest in

working in sports. In the management or administrative side, I volunteered my time to work as a manager as a student manager for the teams, which of course now is like a path that exists as a formal internship. But when I propose that to the various coaches, and in particular, the high school baseball team, he was like, Sure, you can sit on the bench and keep stats instead of my

assistant coach, why not. And so I just tried to find odds and ends jobs to make the coaches lives easier so that they would invite me to hang around and learn more about the business of what it meant to play sports in high school. And it gave me a great learning experience. So I just I just found ways to make make myself useful and offer a value proposition when I knew time was limited for these coaches, and they were all teachers and needed an extra set of hands.

in Brooklyn. And so I created an opportunity for myself to go to public school, which my parents were confused about why I would want to leave private school, I my stated goal was really to understand the community where I came from. And I just wanted to be around what I described as like different people, real people, people who came from different backgrounds. I didn't want to just drive past them in my car as we went to. And from school, I wanted to actually meet people who, who had

different life experiences. And so I went to James Madison High School, in 1991, as a freshman, and it was my junior year. So this was after really two years of me, having had the history before high school of wanting to learn being very interested in people who are different from me, but not feeling like they were accessible. And then being in a school where I was very much the minority, it was the opposite of being in private

school. And I was always interested in understanding ways to combat social challenges and racism in particular. I was always very interested in trying to understand the experience of the black community. My neighborhood was very much that embedded within the black community. And a lot of my friends in high school were part

of the black community. And I spent a lot of time in their homes and trying to understand what their life experience was like, and really trying to understand, although I don't know that anybody called it then privilege but really trying to understand what privilege meant. And as a result when I was at this Islander game when I was 16, and I was just happened to be sitting next to these two people, and was just engrossed with this vision of the way that sport had the power to unite

everybody in this arena. 20,000 people were cheering and screaming for the same thing, everyone wearing their blue and orange jerseys, but also coming from very different backgrounds. But in that moment, when the islanders scored and I saw these two people embrace I had an epiphany moment that really changed the course of my life and decided that I wanted to work in this industry that I felt really truly had the power

to change the world. And my my accuracy check my fact check is that yeah, I did have a have a boyfriend in high school and he has since validated that my memory serves me right that I told him when I was in high school that I wanted to one day have I had the aspiration of being a commissioner professional sports league, which of course seems like a crazy goal and fortunate that made a lot of the right choices but also got very lucky along the way to end up in, in the situation that actually

manifested my my life dream

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notes. I think it's amazing that you were born it sounds like with the desire to participate in a diverse community and you were interested in social change in high school, I don't know many people who are I went to private school, and it was very racially and religiously diverse. My younger kids go to public school, my kids in college went to private school, I can tell you the demographic makeup is completely different. And I love the fact they go to public school. But what's your

advice to people? Who are parents listening? Because there are a lot of 16 year olds listening my podcast to get their kids more aware and more involved with this social change? Because I think right now we're seeing an all time divergence or a hardening of social views and canceling culture. And I don't think it's good for anybody.

a private school. But in my, in my Jewish Day School, we were taught that every human has basic human rights and deserves an opportunity to be successful in life should be treated with respect and dignity, that no matter the person's background, no matter the color of their skin, no matter their socioeconomic status, no matter their religion, no matter their sexual orientation, no matter their gender, that it's our

responsibility. And this was actually this was taught to me as, as someone who as part of our Jewish identity, that it was my responsibility to look out for other marginalized communities. This is part of what is embedded within our traditions and culture. And as a result, yeah, I've been I've just been on this life pursuit. And it was reinforced in my home with with my parents, where we, it's part of our culture to retell stories of the past and understand historical

oppression. And recognize that history repeats itself, and that it's our responsibility to change the future if we don't like the result, and to make sure people understand what has happened in the past and why so that we don't make the same mistakes again, one of

there? I know so many people want to be a head coach of a professional football team, soccer team hockey team. They're dying to get a job and internship at these professional teams. What's your advice to all the people out there who say, gosh, am I ever going to be able to get one of 10 jobs or even 100 jobs or a job at Goldman Sachs or Citadel, for example, where they had the you can get this 29,000 applications for summer internships?

achieved this goal. But I think I could also say with certainty that If I would have been happy in my life and felt fulfilled, with the variety of other things that I've accomplished and experienced, and would have experienced to have this opportunity not happened. So I think both can be true. You can relentlessly pursue the thing that you think you want to do.

And continuously ask yourself what that opportunity is offering to you and be open to the things that you get to learn along the way and the people you meet, because something may take you on a different path. And maybe that's the right path. Also,

So go blue. Yeah. So you transfer to Michigan, majored in sports management? I believe most of the reason was because your cousin Eve Roski was there and shout out to Eve for introducing us and making this happen. So I appreciate you so much. You tell us what you do with our hockey, football and baseball teams? And what's your advice to us where there isn't a clear path to get the kind of experiences we want, and need to pursue that we're passionate about in our future?

business. And they actually didn't have formal internships, there was no stated path to go and be the manager of the Michigan hockey team or the manager of the baseball team or the football team. And I found jobs to do that would help the coach and the administrative staff. So I wrote press releases, and I prepared

athletes for interviews. And I kept stats during the game and prepared the media notes that would be distributed after the game so that the press would write articles about the players I worked in. It was a form of PR for the for the teams and used it as a way to really learn more about the business and to get work experience in the industry. So

door? And then how do you add value once you do that right out of the gate to get that opportunity when there's 500 or 10,000 people who want that job?

initial screening. I did well enough in school, but I certainly wasn't a plus student and the person who would stand out on paper necessarily, I was the person who was always willing to outwork everyone. And I was super diligent and left my colleagues knowing that they could count on me to get the job done, which is hard to

communicate on paper. So I I've actually said to, for example, my former law firm when I've screened candidates who are all from Harvard Law School, or Yale Law School, or Penn, which are great schools, and I'm sure very deserving, but like I've actually said to them, like where is the me this is the person who went To like a really good school, but not the best best school, and did well enough in school, but maybe wasn't a straight A plus student because I don't know that whether those

people are able to break through today, it's so much more competitive, and everything is so much more formalized. I think it's really hard to be a teenager or in your 20s These days, I'm I am lucky that I grew up in a time where the things that I'm good at allowed me to stand out. And I often wonder if life would be different if I

were growing up today. But that's, that's sort of a side note more of a just referendum on the state of the world being so, so difficult and so challenging for kids, the pressure is just so high.

Are they just going to show up in your lobby, and I hate to use that word, because it's stalking, but I've had people just show up at my door, we get a lot of emails, I probably get 50 on LinkedIn every week, which is, Hey, Randy, I'd love to meet with you, I'd love to have a cup

of coffee with you. I do give meetings to people who are in the meetings, that would be a single space letter, talks about my background and career, the details show me they've done a ton of work, to want to get 50 minutes of my time, and that 15 minutes usually turns into one hour. And in some cases, it turns into a job with me or one of our portfolio companies. But what what's your advice? What would work with you? And what's your advice to those who need to break through today?

Probably more often than, then I should, because it's, it tends to be on weekends, or late at night or early in the morning. And I do it mostly on my personal time, because I want to, I want to give back, I want to give young people an opportunity to learn and grow. And I'm always amazed at how few of them actually follow up and stay connected. I'm so amazed. I tell my kids this all the time.

What was the point of them taking that 1530 4560 minutes with me did it maybe it made them feel good and gave them confidence to do whatever it is they're doing next. But I find it so strange that if you spend that amount of time with someone who's in a position of authority in an industry that you're interested in, that you wouldn't then take the next step to at

least stay in touch. And I would say if I had to like, do the ballpark, less than 10% of the people that I do informational interviews or conversations with actually turn it into something that is not transactional, less than 10%. And to me, that's a travesty. So I I actually don't think it's that hard to stand

out. Because if you do, the sort of basic things that we were taught when we were growing up, which is to make a lasting impression, to be authentic and genuine, to stay connected to reach out when you don't have something to ask for, to build trust in your relationship. It could go a long way. And the people who actually do that and it pays back in spades for them in terms of the value for their career, I would think certainly has for me,

home and abroad. And to make sure you're never disappointed by a beach visit again. Plan the perfect beach trips. today by visiting sandy.com That's www.sand.com. The link is in our show notes. Stay Sandy my friends. We have a summer internship program here, it's a 12 week program eight to six. Do not show up one minute later, we're going to have a gnarly meeting don't pack up at 559. We got 17 150 job applications this summer. And we hire 36 every

summer. And it's amazing. Some of the kids at the lesser rank schools, run laps around the kids from Harvard. And I hate to even say Michigan because I do favor Michigan students. So if you're going to Michigan send us, you know, contact us. But this year, we hired a guy named Matt Hickerson and went to Biola. And I'm gonna guess you've never heard of bio I have not either. It's a small religious school about 90

minutes from Los Angeles. And he shows up to tie in a suit and tie his first day, we sent a very detailed memo about what to do when you show up your first day we give them reading. And by the way, I call on people, I tell them 10 hours of work before they show up. And there's a demo I'm going to call on you. And first impression you better know the answer to some of these simple questions. 90% don't, they're embarrassed? And I say why not? And the room goes silent, like, where am I? What

did I do this summer. But NAT continued to distinguish themselves showed up at 630 in the morning and left at nine o'clock. And he was gunning, I think, as most people were for my mentorship for life. And we

have so many interns. It's sort of like a bell curve, Jessica, we've got a third who are there who just go through the motion, we've got another third and they want to put my firm on the resume, we got another third, who you know, they do okay, and then we got a top third, who just kill it and of a top third. This is where the margin gets so thin, right? And this is what you're saying it's the it's the 2% or 1% that just go off on a

different path. In the end, they set them self up for tremendous success in their future. I'm writing a book on this right now. Extreme preparation, it's called and we'll talk about this a little later in the show. But people say it's, it's hard to do that. No, it's simple to do that. It takes a few hours. And it just it like you it just boggles my mind. Why people don't follow up. Don't do things differently. Listen to people

say nobody does that. I mean, I get that all the time from my own kids, you know, follow up? How about FedExing a thank you note to someone after a zoom call, you'll be the only one who's ever done that your entire career, that person will remember you forever. And if there's 1000 people applying for that job, you're now top five if not number one, because nobody does it. But this stuff is so easy to do.

represent the players. And I realized early in my college days, that understanding that foundational relationship and respecting and recognizing that being able to impact the stability of that relationship could unlock the growth of our industry of professional sports. And that was the real reason that I wanted to go to law school and become a labor

lawyer. I knew I knew I wanted to work in collective bargaining, and wanting to really understand that relationship and be able to negotiate the terms and conditions that really drive the players experience and the There's a piece about labor relations that I was very interested in, is really this idea that it's a relationship, that you have to learn how to work together, you have to learn how to compromise, you have to learn how to listen, you have to learn how to communicate, you

have to learn how to prioritize. And that is the reference that that you're making, which I've said, some times when I've talked about labor relations, where it's a marriage where you can't get a divorce, because you have to learn how to be together. And you can take different positions, you can fight for the things that you care about. But you do it in a way that allows the other to know that they you respect them, and that you need to work

together. And it is different in that way, then doing mergers, acquisitions, transactions are other sorts of deals, more business deals like venture capital deals where you might initiate or engage in a transaction, and then you may or may not have to actually work together on in the future. The way that collective bargaining works is that you negotiate agreement, and the real work actually begins when you're administering that agreement. And there's numerous opportunities to have to solve

problems together. And that's really what I enjoyed most about my time at Proskauer and my ears to the NHL, and even still today, working with our with our union, it continues to be the underpinning of the professional sports industry.

my legal background. But there are plenty of people who are leaders who do an incredible job, who are not lawyers, and not all of the commissioners are lawyers, and they, most of them are but not all of them. And so I'm sure there's lots of different paths that could make someone successful, I think you just have to lean into the things that make you uniquely you make you uniquely successful, that gives you confidence that you can perform the tasks asked of you in a

particular role. And for me having a legal background really built my experience, my skills, my confidence. I went

was rich. And when I graduated I bounced around i three jobs the first eight months of school, it's kind of a long story, but I was fired from my job five and a half weeks after moving to Los Angeles there were layoffs as $3,000 in the bank. I thought this isn't going well. But ultimately I ended up working for a firm McDermott, which you probably know, a large Chicago firm. Then I went to work at Sun America, I got an amazing job.

Eli Broad was my boss. He was a one of only three people at the time to start to Fortune 500 companies. And I would have never gotten that job without a graduate degree. And in my situation. Even though I learned really almost nothing practicing law. I felt like I'm still feel like today. The intellectual training and the way I look at things has been immensely helpful to me. So when people say to me, Oh, should I go to law school? I say Well, number one, do you like it? You want to

be a lawyer? And even if you don't, you should really map out pen and paper if it really makes sense. I know so many people who don't go to good law schools. They spend 150 to $200,000 to graduate, and they don't get a big firm job, which today pays $250,000. To start, which is just asinine to me. That word the starting salaries to 15 and get this they bill out at 495 an hour, some 595 per hour, these

New York firms. And this the only profession by the way, where the clients pay for the professionals to learn on their dime. I've never I've never heard of another profession like that. But for me, I think it has been very valuable. But for most people who go to law school, they're not working across power or Scadden or white in case you're making 40 or 50,000 a year to start. And I don't know whether the benefit really pays for itself in the long run. What do you think about that? Yeah,

normally do. And I had to really focus on studying and getting good grades, knowing that my one L year in law school was going to dictate where I was able to ultimately work after law school. And I really wanted to work at Proskauer, so I had to get good grades. And so it was very humbling for me, it forced me to focus and become a good reader, which I really wasn't a particularly good reader before law school, which I think has has helped me a lot in my career.

of all acknowledge that. And I think that's a very important thing to acknowledge when you work for a high profile company, a high profile brand, it's okay to say that you enjoy that there it has an outsized influence on society, separate and apart from the substance of what you're doing, or the size of the business. It's, it matters to people and matters in people's lives. And I had to really ask myself, Is that enough for me? Like, is that going to be the

driving force? Will I do, will I be satisfied with my career, staying at the place that opens doors and provides fodder and a cocktail conversation, if I if the if the sacrifices that I don't actually get to achieve the ambitions that I have in my, in my future in my career, and I made the choice, understanding the risk, that I may be going to a place that no one will ever care what I do, or where I am, that it was more important for me to learn and develop as a

leader. And even if it meant I made a right turn and that I was going to be hard for me to come back into the sort of sexy pyramid of professional sports, that that was okay. And and, you know, it's it sort of goes back to what I said earlier about being relentless in your pursuit of what matters most to you, and sometimes what matters most changes, right? Like I, what mattered most to me, when I made that choice is becoming the best

business person I could be. And I wanted to learn areas that I would not have the opportunity to learn if I had stayed at the NHL. And I had to understand that that came with some sacrifices. And I was okay with

that. I also think I had to sort of dispel this notion that because I left the NHL, it meant that I no longer had it As part of who I was, I really embraced this idea that no one can take away from me what I learned and experience during my 13 years there, and if that's something that feels like it has value to me, it's still part of who I am even today. And that leaving doesn't mean you've left it behind. You can take it with

you. And you can take the things with you that continue to provide value and maintain those relationships, which I've which I've done, and realize that that will keep opening doors for you throughout your career in ways that you can't even imagine.