Skip to main content

From Strikeouts to Home Runs with Jennifer Gefsky

From Strikeouts to Home Runs with Jennifer Gefsky

Episode 31: From Strikeouts to Home Runs, with Jennifer Gefsky

Jennifer Gefsky is the Co-Founder of Après and the host of the Après podcast, The Aftershow. She started of her career as a lawyer, specializing in “sports law” and moved from her law firm to MLB. When her second child was born, Jen continued to work but wasn’t happy. She decided to take a break from her very high-powered, high-stress career, and then everything changed. After having worked so long and built her career, Jen had quite a bit of an adjustment to make. In this episode, Jen talks about her career and what led her to become an entrepreneur, the importance of passion and perseverance, and being comfortable with failure.

Episode Transcript

00:13 Kristy Wallace: Hello and welcome to the Ellevate Podcast. This is Kristy Wallace, and I'm here with Maricella Herrera. Hello.

00:21 Maricella Herrera: Hi, Kristy. I'm laughing. I've listened to many people today on the phone call me Marciela, and when you did not do that, it made me happy.


00:32 KW: Well, I'm glad I can make you happy. That is what matters. No, I'm very glad I made you happy. And you know who makes me happy? Jennifer Gefsky, our guest today, will make me very happy if she introduces me to Derek Jeter. I asked her if she could, she laughed at that as well, so we'll see him. I'm taking that as a positive.

00:53 MH: I'm taking that as a no. [chuckle]

00:55 KW: Hey, glass half full. So Jennifer is the co-founder of Après, and the host of the Après podcast, the aftershow of which I actually am a guest.

01:06 MH: Yeah, we're waiting.

01:07 KW: I know, it should be fun. I go very personal in my career. So now I'm thinking back about it, and I'm like, "Hmm... " But no, so Jennifer actually worked for many years at MLB, Major League Baseball, which is the connection to Derek Jeter. She has a great story, really interesting. I will not give away any clues 'cause you're all gonna hear directly from her in a few minutes. But before we get started, I know you have some poll data for us today.

01:39 MH: Yeah. So Jennifer, as you mentioned, has quite the background and has done different things, including at some point taking a break from her career. And some of the things she talks about is how that affected her. And we do hear that from some our community who have decided to take some time off work. So we asked them, "How much of your personal identity is defined by your job?"

02:07 KW: So for me, I will tell you, in the earlier stage in my career, a large part of my personal identity was defined by my job. And I think that was a mistake. I think it's important to do a job that is in line with your values and things that you care about, but I don't think it should define you, and so I made the mistake once, and now...

02:37 MH: Do you think it's in the past that was like that because of where you were in your career, as in you were more like starting out, or because of the job you were doing?

02:47 KW: Maybe both, that's a great question, maybe both. It's just I lived, ate, breathed my job; and now I love what I do. I love Ellevate, and I love what we stand for. And so I guess it defines me in another way, but it's tied to who I am as an individual. And yeah, I think about it all the time, but I would be if I wasn't here, so I don't know.

03:12 MH: Yeah, no, I agree.

03:15 KW: So what do our members say about this?

03:17 MH: More than half of our members said that their job defines some of their personal identity, but that they balance it with other interests.

03:25 KW: That sounds good.

03:26 MH: So they're pretty balanced in that way. Almost 40% said most of it, it's their public persona or their personal brand, which for people who are experts in their fields, it is a big part of it.

03:40 KW: Sure, absolutely.

03:42 MH: I was very surprised though that only 10% said, "Not much, it's just what I do for a living" and only 1% said, "All of it, I am all about my work."

03:53 KW: Well, that's very interesting, and let's hear what Jennifer has to say on the topic.

03:57 MH: Yeah.


04:14 KW: You got a great journey, and one that I think resonates with many of our listeners. And then you're doing some pretty awesome things right now. Can you share a little bit of your career, and how you got to where you are today?

04:26 JG: Sure. I'll start at the beginning, which may be a little bit too far back to start, but I'm from Ohio and grew up really sort of very lower middle class, no wealth whatsoever. Put myself through college in law school, and was lucky enough to land a really great law job in New York City. Actually, the first time I had ever been to New York City was when I came to interview at my first law firm called Proskauer Rose right in Times Square, and I spent several years at Proskauer as a labor and employment attorney. And from there, I went in-house at Major League Baseball. And that was very exciting because shortly after I started my career at Proskauer, I was placed in their sports practice, which they have a very well-known sports practice there. Gary Bettman, commissioner of the NHL, and David Stern, former commissioner of the NBA, were both partners at Proskauer; so they had a very robust sports practice. And so shortly after I started at Proskauer, I started working in the sports world; very male-dominated, as you can imagine.

05:32 KW: I can only imagine.

05:33 JG: Yeah. And worked on some matters for Major League Baseball. And shortly after I worked on those matters, Major League Baseball brought me in-house, first as Deputy General Counsel, and then as Vice President & Deputy General Counsel. So it was a really amazing career.

05:50 KW: So tell me a little bit about that. Labor and employment with Major League Baseball, specifically what type of matters were you working on?

05:58 JG: Yeah, so that's a really good question 'cause I think a lot of people think of sports law, and what is that exactly, and there really is no such thing as sports law. There's different elements of law that relate to sports. So there's corporate, there's different finance, there's all sorts of different aspects of the sports world, but labor and employment is very important in the sports world because athletes are usually in collective bargaining units. So they're unionized employees, and as such, they have a collective bargaining agreement that basically governs their workplace policies, which is funny to think of athletes in that way, but they are employees, and so their collective bargaining agreements are negotiated between the teams that have their contracts and the union that represents the players.

06:47 JG: So labor and employment attorneys actually play a very important role in the world of sports because anything relating to players, and in baseball's case also were umpires, were unionized workforces. So any sort of arbitration relating to discipline, the drug programs, any action you wanted to take with respect to a player or umpire had to come through our group at Major League Baseball. So we served a very important role, and my boss at baseball was Rob Manfred, who's now the current commissioner of Major League Baseball. So it was great. It's an amazing, amazing, amazing experience.

07:20 KW: So can you introduce me to Derek Jeter?


07:25 JG: I wish. [chuckle] Although I did meet some really really great players, and for the most part, they're a really fun great group that loves helping the game and being with the fans, so it was really a wonderful place to work.

07:42 KW: And did you feel that, particularly your practice focus on labor and employment, made you more aware of workplace policies, particularly regarding women, but flextime and reviews or any of the benefits? Were you more aware of what was going on there?

08:02 JG: Yeah, so I think the answer to the question is yes, I was more aware. But what's really interesting, yesterday, we were working with a marketing company and we were talking about survey results that this marketing company did, and it was a survey of millennials. And millennial women almost across the board think that they're not going to get discriminated against. I thought that was really interesting because I think early on in my career, I never thought that I would get discriminated against either. It's sort of that, "Well, it won't happen to me."

08:33 KW: Of course.

08:35 JG: Not that I was discriminated against, but I think it's the mindset of someone who's young and entry level and sort of moving up the ranks. So I was certainly more aware of policies and programs in place, but to be honest, also at that time, it was a very different workplace. Things have changed dramatically. I left Major League Baseball in 2007, and even since then, things have changed dramatically. When I graduated law school, this is gonna make me sound like I'm really old and I'm really not that old, emails were kinda new. Okay, so I graduated law school in 1996, and truly, it was kind of a new thing. Emails, that sort of digital world was really just unfolding. So the world has changed dramatically in the last 20 years, it's almost shocking. And I think in my experience of what I'm doing now, I think it's gonna be completely different 20 years from now as well. So yes, I certainly did. To circle back to your original question, I was very aware of all employment discrimination laws that were out there because I did that work as well.

09:40 KW: So you mentioned you're not at Major League Baseball anymore.

09:43 JG: Right.

09:44 KW: What happened?

09:45 JG: So life happens, right? And if you would have asked me when I was 30 if I would ever stop working, I would have told you there is... Hell would have to freeze over for me to stop working.

09:56 KW: It's so funny. I said the same thing. I'm like, "If I won the lottery, I would still work 'cause I love working." Ask me that question today, I'm like, "I will be on a boat in the Mediterranean, and I will see you later."

10:05 JG: You're right. Well it's funny because not only do I love working, I feel very strongly about financial independence, and this is just because of my upbringing. Like I said, I grew up without money and I've been working since I was 11, and I had... Basically, I came from a broken home, and I learned very early on the importance of financial independence as a woman. And so for me, it was very important to have a career that allowed me financial independence. But I also really enjoyed what I did, and I really identified myself by my career. So there were all of those things wrapped into one. So if you were to ask me at age 30, "Would you ever leave the workforce?" And this was before I had kids, so that's sort of an important point. I would have absolutely said, "No way." So I had my first child at age 35. I worked the day I gave birth. I actually took 12 weeks off with my first child. I hit the ground running. I was still living in the city at that time, and back like boom! Back at it, traveling, working really hard. My daughter was born in October. In February, I had a two-week long business trip. It's almost unheard of, right? But that's the world that I worked in, and there was no...

11:19 KW: And that was pre flying the nannies with you, and drinking breast milk.

11:22 JG: Right. Right, exactly. And then I had my second child, they're 22 months apart, and that was a little bit harder because now I had a little one at home, I'm pregnant again, and it just... Everything was a little bit more difficult. Things were a little bit more difficult at home. And while I was pregnant with my second, I moved out of New York City into a suburb of New York City. And everyone had said to me, "Oh when you move to the suburbs, you'll see. You're gonna stop working in again." I was like, "Not me." My commute was, brace yourself, an hour-and-a-half each way, so it made it very difficult and I became the cliche, that I wasn't doing anything well. I felt like I was never at home, and I felt like I was never at work.

12:10 JG: When I would leave work, I would try and catch a 5:45 train, and I could see my colleagues at baseball like, "Oh, isn't it nice to be Jen. There she is, leaving at 5:45, while we're all here working." Meanwhile, it was commuting to get home, to relieve a babysitter, to be with my kids for the short period of time I could be with them, to just start all over the next day. So that cliche, where I just felt like, wow, I'm just not doing anything well. And I made the decision with my husband that I was lucky I was able financially to step away from my career. But to be honest, I wasn't thinking about the future. I wasn't thinking about what's gonna happen to my career.

12:50 JG: I was thinking I just want, I want this pressure gone. I want this stress gone, and I'm tired of feeling guilty on all fronts. And I just left and opted out. And it was, honestly, like I went to Mars. I felt like I became this entirely different person overnight and it was really, really hard. And it's interesting doing what I do now with Après, and we'll go more into that. I've learned from so many different women that they felt exactly how I felt. I didn't really talk about it back then because back then, it was like I dove right into being a mom of a baby and a toddler. I'm in play groups and I'm in this, and it was really like a very foreign land for me because I had existed in male-dominated environments. And all of a sudden, that was gone.

13:36 KW: When you and I spoke on your podcast, The After Show, I shared a similar story about my last day of work when I had my first, was I decided I can't work at this level seven days a week, 12-hour days. Work was number one priority, and have a child, and do both. And it was at that time I had taken a short break, and it was really hard. I think as a professional and particularly as a young woman, I feel like you are just working as hard as you can to prove something, to get as far as you can, to be successful however you define that. And then once that is removed, you're lost.

14:22 JG: Totally lost, yeah.

14:22 KW: Suddenly like, "Well, am I valuable?" I base my value on how I progressed in my career, how much money I made, how much clout or stature. And then there's something amazing about being with your children, but that's not always the way you think about it at first.

14:43 JG: Right, it's hard. You really face this, "Who am I?" And it doesn't happen necessarily right away, although I struggled from the beginning, and I was out of the workforce for seven years, when I did other stuff, but really out of the workforce for seven years. And you really reach this like... For me, and again I'm not talking about anybody else's journey or experience, but for me, I felt like I became uninteresting. I felt like my husband would come home from work, and we'd sit at dinner, and he would have interesting things to say, and I would have the same things to say over and over and over again. And I just felt like I lost myself, and you reached this point of "Who am I? Is this who I'm meant to be? Is this the journey that I'm meant to go on?" That was my experience, and that's me and that's my personality. And I have to tell you, I had the most fantastic friends who have the most incredible education and professional background, and they are so happy being at home. And I applaud them. I think that's amazing, but for me personally, I wanted to re-engage in the workforce. And so that's the journey that I started down.

15:53 KW: This is going off on a little bit of a tangent, but it is interesting 'cause when you talk about work and the ways you get the money you make, the deals you broker, the position, the title, whatever that is, there's many markers that you feel you can measure yourself against, and peers as well. And when you're not working, what are those markers? And I think that there's a disconnect there because there's so much value and purpose and worth in whatever you choose to do. And if it's with your family, if it's doing volunteer work, if it's working in a corporate environment, whatever that path is. And unfortunately, it feels like our society is only really focusing the value on some of those more tangible work-related.

16:42 JG: Oh there's no question, yeah.

16:43 KW: Which is what makes it so hard for any parent, or anybody who's looking for alternative paths.

16:49 JG: Yes. And this is such a broader topic, and we talk about going off on a tangent, this is such a broader topic. But for me, I'm gonna imagine a world where a woman's non-linear career path was actually celebrated. Where she could take some time out of the workforce if she wanted to, she was welcome back in the workforce, she could dial it back and work part-time in it. Imagine a world where employers didn't look negatively on that. I was just met with the editorial director of Working Mother Magazine yesterday, and she was talking about there's basically a general survey that's out that if a man in a workplace has a child, it's viewed as a positive; and if a woman has a child, it's viewed as a negative. To talk about the worst double standard you could possibly think about, and how hard it is for women in the workplace.

17:33 JG: But you're right about those monikers sort of succeeding in life, and it's hard when you're a mom 'cause you're home, and what are your... How do you measure success? That you're kid didn't have a temper tantrum that day, or... It's very complicated, and I know the feeling I had, which is people used to pay to listen to what I had to say. And now my kids aren't even listening to me, so that's always very difficult, a difficult sort of adjustment to make.

18:03 KW: Sure. So now you are the co-founder of Après.

18:06 JG: Yes.

18:07 KW: How did you get there? And tell us about it. I need to hear.

18:10 JG: Yes. It's exciting because, first, I should definitely start by saying that I do not have certainly a year ago, this entrepreneurial spirit. You hear people talk about, "I'm a serial entrepreneur." And that is not me, okay. I am corporate through and through. That's been my career. I never thought I would be an entrepreneur. But when I looked to re-enter into the workforce, I'm well-educated, I had a very good career, I honestly, naively thought that, "Oh, I'll be able to get back in the workforce when the time comes." And I remember literally sitting down at my desk in my house, and sort of getting on the computer and starting to do research. And literally, I had no idea where to begin.

18:55 JG: I couldn't find resources out there to help women like me. But yet when I was looking around, I thought, "There's a lot of women out there like me, how can there not be resources?" So I started doing research and connected with my co-founder Nikki Kroll, and we decided there's something here, so let's pursue it. And this was a little over a year ago, and we started doing research. We did some focus groups, we conducted lots of interviews, and we really decided there is a need in the marketplace, not only for women to re-enter the workforce, but also for companies who want gender diversity specifically in the mid to senior levels, which is a huge problem in this country, as we all know. And so we thought there's something here, let's start down this path and see what will happen.

19:42 JG: And so Après, and you can see our website at, is a platform that's really dedicated to helping women either re-enter the workforce or transition within the workforce. Because when I think about my career at baseball when I was sort of ready to just leap off the cliff and opt out of the workforce, I'm not sure I really wanted to exit the workforce. I would have liked to probably have transitioned within the workforce, and found something a little bit more palatable to my lifestyle then, whether that's part-time or project-based or whatever. And we're looking to help women with that too, not only dial down, but also dial back up.

20:19 JG: You talk to women who, like me, their kids are going into kindergarten or they're empty nesters, and they're like ready to go. Sally had a great... Sally Crouch had a great article I read on LinkedIn about how fabulous her career is now at this stage of her life. And it's so true because when women get to have that sort of independence, when their kids become more independent and even leave the house, it's like a new world, and many women are so re-energized about their career. So that was the foundation for us starting Après, and we've been around now for four months. We launched in May of this year and we've had an incredible launch so far, I will say, because I know a lot of people talk about wanting to be an entrepreneur and stuff.

21:03 JG: Being an entrepreneur, as you know 'cause you're an entrepreneur too, is really hard. It's not easy. I always say to people if you're starting down the entrepreneur road because you want a better lifestyle, you want to make more money, wrong. It's just not why you want to be an entrepreneur. In my view, you have to be an entrepreneur about something that you feel really passionately about because if you don't, you will not succeed because it's so hard and there's ups and downs literally on a daily basis on the same day. So yes, I think having my sort of work background and my work ethic, where I've always worked really hard, helped a lot. My co-founder and I worked really really well together. And what's great about our company is that we're mission-driven.

21:50 KW: Do you have any advice for some of our listeners that are thinking about starting their own company?

21:57 JG: Well, I would say, yes, I have lots of advice. It's so funny I laugh as I say this because I always say to people, if you wanna receive advice, start a company. You probably know this as well because people love to give advice to entrepreneurs. But I will give advice that I have found that's been helpful for me. One is one I already mentioned, which is if you are gonna start a company, don't start a company to get rich. Start a company about something you feel passionate about, and where you think that change needs to happen. That's number one. Because when things get difficult, it's gonna be that passion that keeps you going. Two, you have to have perseverance, every day. Every day there is a reason to quit. And I experience this still.

22:39 JG: Every day there's a reason to stop, and you have to persevere and keep going. And I just listened to a podcast with Sara Blakely, who is the founder of Spanx. And part of that podcast I loved, well I love the whole thing, but this one in particular, her first order for Spanx, which you hear about overnight successes in her journey, was from idea inception to actually getting into a store was two years. And then it was another year before she kind of really started becoming successful. So it was three years from idea inception until sort of like success. But her first order for Spanx, which was basically two years after she thought of the idea, was with Neiman Marcus. And the interviewer on the podcast said, "How did you get into Neiman Marcus?" And she said, "I called." And I love that because it's like, you know what, you got to pick up the phone and you got to do it.

23:34 KW: Yes.

23:34 JG: No one's gonna do it for you. No one's gonna make something happen. And what's really funny about the story is she called the Neiman Marcus in Atlanta and they're like, "Our buyers are in Dallas." She had to call the buyers in Dallas over and over and over. They didn't pick up her call over and over and over. And she was persistent. And perseverance, like I said, you just have to be a dog with a bone as an entrepreneur and you can't be... This will be my final piece of advice and something that I think all women should feel, because I didn't until recently, and for me, it's been incredibly empowering. You can't be afraid to fail. And I was raised as a person not really like my parents were around saying, "You have to be perfect" 'cause they weren't, but for some reason, I felt, whether it was society pressure or whatever kind of pressure, that I need to be perfect, and I needed to do the impressive thing, and I needed to get the job that people thought I should have, instead of sitting back and saying, "What do I wanna do?" and "I can't fail" and "I've gotta be impressive." And so when I started down this road of starting Après, I was like, "You know what, there's a good chance I might fail."

24:39 JG: You look at the stats of entrepreneurs and startups, and a good percentage fail. And it was like, "You know what, I'm okay with that. I might fail, and I'm gonna own it, and I'm gonna do my best. And if I fail, I fail. But I'd rather... " And this was an inspirational quote that I read early on that I think about all the time, and it said, "Don't be afraid to fail, be afraid to not try." And I love that quote because it's like, yeah. Maybe it's 'cause of my age, maybe it's 'cause I'm in my mid-40s and I know half of my career might be behind me, but just don't be afraid to fail. I'd much rather fail then never having tried in the first place. And maybe that's an old saying and it's like cliche or whatever, but for me, once I believed it, like, "I'm okay to fail," it honestly changed my life in some ways. So it's really empowering for me.

25:27 KW: Last question. Do you have any advice for companies that are looking to create a more inclusive culture, more diversity, maybe as you alluded to before, giving employees other paths to follow, if they're looking instead of leaving the workforce?

25:46 JG: Yeah. Well, we could have a whole podcast just on that question. And I think that companies many times have great intentions, and they really do want to make changes that have an impact. One is, they have to stop talking and they have to start doing, and a lot of companies have started that. Two is, when you implement programs and policies that sound really good, like a 20-week maternity leave or unlimited vacation or whatever it is, there has to be a game plan for actually implementing that. So a 20-week maternity leave is great, but what are you gonna do with that open slot when the woman's gone for 20 weeks? And if the concept is, oh, we're just gonna get the person to the right and to the left if they're at work to both pitch in and do her job while she's gone, that's going to fail. It's going to fail on every level because when the woman comes back from maternity leave, people are going to resent her for being out, and that they had to pick up the slack. And to know that when you implement these programs and policies, that they have to be very thoughtful in the way that they go about it, and not just to announce something to have it sound good to the public, to actually have a game plan in place so it can be successful.

27:00 JG: And I do think that companies are trying, and they truly do wanna try, and they want to make change. And I think it's hard to move. I always think of like a large boat in the ocean. You're turning this boat, and in order for these programs and policies to be successful, there has to be buy-in at every level of an organization, and that takes time. But it can happen. It just has to be really mandated from the very senior levels within companies. So I'm very optimistic, I'm very optimistic that companies are starting to lead the way to putting in really creative programs and policies. Amazon just announced their 30-hour work week, which I think is really interesting, and I'll be very interested to follow it and see how it goes. Things are starting to change. FaceTime is becoming less important, and as a result of that, it's being driven by millennials, and as a result of that, the workplace is gonna change. So I think it's really exciting, and I think that opportunities for women are only gonna continue to grow.

28:07 KW: Great. Well, thanks so much for joining us today. This was fantastic.

28:10 JG: Thank you, I'm so happy to be here, thanks for having me.

28:15 KW: Thanks so much for listening to Ellevate. If you like what you hear, help a girl out; subscribe to the Ellevate podcast on iTunes, give us five stars and share your review. Also, don't forget to follow us on Twitter at EllevateNtwk, that's Ellevate Network. And become a member. You can learn all about membership and all the great things that Ellevate Network is doing at our website That's E-L-L-E-V-A-T-E And special thanks to our producer Katharine Heller, she rocks! And to our voiceover artist Rachel Griesinger, thanks so much. And join us next week.


Continue learning with this Ellevate Playbook: