The Learning Leader Show With Ryan Hawk - 586: Erika Ayers Badan (Former Barstool Sports CEO) - Deserving Great Mentors, Learning From Failure, Building Your Career, Earning Your Dream Job, & Other Hard Truths About Life As A CEO

Episode Date: June 9, 2024

Read our book, The Score That Matters https://amzn.to/3VrogOC Full show notes at www.LearningLeader.com This episode is supported by Insight Global. Insight Global is a staffing company dedicated to empowering people. Please CLICK HERE for premier staffing and talent. Notes: What Erika learned from her dad: "He loved his work and was so full from it. Three weeks before he died he was doing Zoom calls with students from the ER even though it was beyond unnecessary and impractical to do so. If you love what you do it can add so much dimension to your life and the lives of others. He liked people and to learn from them. There's something to learn from everybody. And the best control was no control - let things happen and learn from them & adapt. Career advice: Know what your company is paying you to do. And the better you make your boss look, the better it will be for you. Find problems and clear the path for your boss. Make their life easier. Make them look good. That's the role when you have a boss. Must-Haves When she's making a hiring decision: Be able to share stories of how you've gone for something that failed, and learned Be curious, ask thoughtful questions Do research on the company. CARE.  Test the product. Be able to demonstrate that you know what it does. Bring a point of view. Articulate what you could bring to the role and how you could make the company better. Joanne— I wanted to be you until I realized I couldn't, so I decided to be me. I studied you for twelve years. You are the architect of all my work dreams, and you are the scaffolding I built myself on. You put force into my nature, and for that I am so grateful. Getting the Barstool CEO role: She earned the job over 74 male candidates. "I wanted this job because they were considered too rogue, too untouchable, too badly behaved, too unproven. Dave Portnoy (the founder) was powerful, seemingly unmanageable, and volatile." In 2012, when Chernin bought a majority stake in Barstool, the company was worth $12 million. You sold it to Penn Entertainment seven years later for $550 million. Make Your Own Luck – When Erika was nearly graduating college, she applied for an internship at Converse no less than 45 times. She never got an interview. Why? "I didn't do anything unique enough, passionate enough, or memorable enough to deserve a chance at the job." "It was a heart attack every day for nine years," Erika said of being Barstool's CEO. As the first-ever CEO of media magnate Barstool Sports, Ayers Badan led the company through explosive growth (+5000% in revenue and significantly more in audience), expanding the company from a regional blog to a national powerhouse brand and media company. During her 9 years steering the company, Barstool became a top ten podcasting publisher in the US, with the world's #1 sports, hockey, golf, and music podcasts, and a top 6 brand globally on TikTok.

I really believe in failure. People who do not fail a lot are either without a pulse or they are refusing to leave a very safe comfort zone. Multi-time CEO, senior leader at multiple companies, earning the CEO job at Barstool. I knew just by taking the job that it would be polarizing. I'm a against the world type of person. So I'm very motivated by being slighted or being disliked. or being dismissed. What were some of those early ideas

that you brought to the table that helped the company grow from 12 million bucks to 550 million? It was following the talent who were following audience. What would you say was the best and worst parts about working with Dave? Dave knows what he doesn't know

and is not afraid to say, I don't know, you don't find a lot of work ethic like Dave Gordaigne. One of the things that I think is very underrated in work is caring, but actually caring goes so far. We're living in an era of information overload. We have more knowledge than ever before, but what do we do with it all? If you're in Notion, you put that knowledge to work.

Notion is a place where any team can write, plan, organize, and rediscover the joy of play. It's a workspace designed not just for making progress. but getting inspired. Try Notion for free when you go to Notion.com slash learning leader. That's all lowercase letters, notion.com slash learning leader. And start turning ideas into action. And when you use our link, you're supporting our show. Notion.com slash learning leader.

Welcome to the Learning Leader show, presented by Insight Global. am your host, Ryan Hawk. Thank you so much for being here. Text Hawk to 666866 to become part of Mindful Monday. You, along with tens of thousands of other learning leaders for all over the world, will receive a carefully curated email for me each Monday morning to help you start your week off. Right. You'll also receive details about how our new book, The Score That Matters,

will help you become a more effective leader. Text Hawk to 66866. Now on to tonight's featured leader. She's a great one. Erica Ayers-Badon is the CEO of Food 52. Prior to that, she was a CEO of Barstool Sports, one of the most influential sports, lifestyle, and entertainment media brands on the internet. From 2016 to 2024, Erica led the company from a regional blog with 12 employees

to a national powerhouse with over 300 employees. She has been named one of Forbes' most powerful women in sports. She's also held leading roles at Microsoft, AOL, and Yahoo. She's the author of a great book called Nobody Cares About Your Career, Why Failure Is Good, The Great Ones Play Hurt and Other Hard Truths. During our conversation we discuss how she beat out 74 male candidates to earn the CEO role at Barstool. That's an amazing story. Then Erica shares what she learned from her late dad about showing up

people. Then she talked about the best and worst parts about working with barstool founder Dave Portnoy. She shares how to build the career you want and how to earn your dream job. And so much more. Ladies and gentlemen, please enjoy my conversation with Erica Ayers-Baddon. Erica, it is so cool to have you here on the Learning Leaders Show. Welcome. Thank you. All right. I was reading your acknowledgement section of your latest book. Nobody cares about your career. And you wrote about a woman named Joanne. You said, I wanted to be you until I realized I couldn't. So I decided to be me. I studied you for 12 years. You are the architect of all my work dreams and you are the scaffolding I built myself upon. Can you tell me more about

Joanne and the impact she had on you? Yeah. Joanne Bradford is a beast. She's the best. I was working at an ad agency in Boston and kind of fluke. I got the opportunity to go to this MSN. Joanne ran MSN at the time. She ran sales for MSN. And this was probably in 2000, the year 2000. And I got an opportunity to go to this women's retreat. And I think, quite frankly, I was a last minute invite and probably because somebody

else bailed and I was probably the youngest person there and the least qualified. And I got seated with Joanne at a dinner and she was very provocative and she asked a lot of questions and she was very bold. And I knew in that moment that I wanted to work for Joanne. And I took a job at Microsoft probably six months later and then followed Joanne across four different companies over 12 years. And what I really loved about Joanne was she was a very powerful woman, a very powerful person in a time that there were not many powerful women. She was very strong. She was very blunt. She was very matter of fact. It was interesting at Microsoft, there was a lot of brains and there was a lot of brainiacs and there were a lot of MBAs and there were a lot of pedigreed people. and Joanne was always very proud. I think she went to San Diego State and she was a C student.

And she had a very, you know, hit the road, matter of fact, way of doing things. And she was very generous with feedback, which a lot of people didn't like and felt was destructive. But I really felt like, gosh, what a gift that this person is telling me that I stink. And the more she tells me that, the less I'm going to stink. So Joanne is a lifelong friend and a lifelong friend. and a lifelong mentor, and I was very, very fortunate to work for a lot of really interesting, capable people, but in particular that she let me essentially tag along and study her for over a decade. What do you think she saw in you that made her want to invest so much time in you?

I think she saw that I was up for it, that I could take it, that I had the stamina to run at her pace. Joanne is a person who it didn't matter if you were traveling around the world for a month or a day, you never checked your bag. And if you checked a bag and you were traveling with Joanne, she would not wait for you. So, you know, I think there were a lot of people who wanted to be around Joanne, but I don't know that she found someone that was so interested in picking up what she was putting down and so eager to move at her pace. I love those stories. It's amazing the impact that those type of people can have on our lives and they can change the trajectory of our lives. And now us as the leaders are trying to do that for others. Another person who I loved reading about, and especially because of the name of this podcast, it was just focused on learning and education and bettering yourself. And that's your dad. You wrote this beautiful letter to him or about him after he died, a few months after he died, which I know was still fresh. So I realized. that there's probably some sensitivity here. But I love this part.

You said he loved his work and was so full from it. Three weeks before he died, he was doing Zoom calls with students from the ER, even though it was beyond unnecessary and impractical to do so. If you love what you do, it can add so much dimension to your life and the lives of others. He liked people and to learn from them. Can you tell me what you learned from your dad? Oh, so much. My dad was great.

He, um, you know, my dad, was very driven in a, in a, I learned a lot from watching my dad. I think my, a lot of who I am and how I do things is really just because I always watched everybody else and I always watched my dad. My dad was getting his PhD when we were kids, when my brother and I were kids. And in the downstairs of our house where most people had a TV room, we didn't have a TV. There were just papers and books. and he was writing his dissertation, and he would work on it at night, and he would work on it over the weekends. And he always showed up for everybody else. So I would, you know, on a weekend, we would be going to the volleyball game, and we'd go to the softball tournament, and we'd go to

the math league. And I learned a lot just from how my dad showed up for other people and also how he kept challenging himself. And I learned he always would, tell me that the best control is no control. And I also, that was a lesson I needed to learn. And I felt that he was very gracious in giving it to me, which was he would kind of let things play and then subtly influence the outcome versus being more directive or dictating about how things went. And later in life, especially when I got to barstool sports, that lesson really, really came out for me. So, you know, I learned so much, so much from my dad. I think about my dad all the time and mostly just how he was so curious and kind about other people, but also how

committed he was to lifelong learning and to surrounding himself with other people who wanted to learn. I wrote that, actually, that quote down, the best control is no control. And I was like, I need to ask Erica about this. Because, to me as a self-described control freak, I want to make all the decisions. I want to be in complete control, even though that's not how life works. I still want it. So I think it would probably be more healthy to learn from your dad here. And I'm curious, like, especially you're a CEO, right?

You're multi-time CEO, senior leader at multiple companies. So like, you're in control a lot. You get to make the call a lot. But this seems like useful advice maybe for people like you and I. So I'm curious, how did you implement that? advice. Yeah, it's hard because your instinct here is like, I want this done my way. I want this done now. I want this done the way I want it done. And I had to learn over, I found early in my career that I was exhausting myself because I wanted it done a certain way and I wanted it done on my timeline.

And I found that I was exhausting myself and frustrating myself. I was finding. quite honestly that I would get very depleted in a job within a year. And I think partly it was that desire for control. And so over time, I really worked on it myself, to be honest, which is like, okay, like let people do their thing. Let people do it their own way and still hold people accountable to, hey, on this date, I want to see the thing. But don't be so maniacal. Don't be so micromanaging about how people get there and to change and channel your energy into briefing people on a vision like here's what you want to achieve or here's what we want to achieve. Here's what I'm looking for.

Here's a couple ideas of how you might tackle it. And then to say, come back to me in a week, come back to me in a month, come back to me in a day with what you think that looks like. And I found that more rewarding, to be honest with you. And I think this is in part where my dad got it, which my dad was a teacher. So he was very used to imparting knowledge or giving a direction. But then you got to let people toil through it. You got to let them arrive at it at their own time and in their own way.

And I was a very non-traditional learner. And he did that with me. And what I realized is the more that I could apply that to work, the better off I would be, but also the better off the people around me would be. Eric, I love that. And I love learning about how people earn big roles. And I remember reading about this when it happened, but you earned the role. You build up an amazing career prior to earning the CEO job at Barstool.

Now you're going for this job to be the CEO. And I loved reading about how badly you wanted it. And that's why Mr. Churnin, it sounds like, ultimately picked you. but there were 74 male candidates that were also going for this role that, I guess, were in some way, shape, or form a part of the process. And the Churning Group and Dave Portnoy, they and others, they said it was you. Could you take me inside the interview process to become the CEO of Barstool, the highs and lows,

some of the funny things about it? But I'm just fascinated by the process of people earning big jobs. I love that you ask about it. You know, pivoting your question a little bit, when I was right after college, I wanted to work for Converse in Boston. And I applied to Converse, I think 45 times. But I mailed in the resume. I filled out the form. I like did the requisite stuff.

But I never did anything special. I never, I never showed up at Converse. I never built a sneaker. I never made a port. I didn't do anything special to get the job. I didn't network. I didn't call people. I didn't do anything creative. And if you had asked me at the time, why did I want the job at Converse? I would have said because working at Converse is cool. I didn't really even have a good reason for the job. And when I, I've really had two jobs in my life that I desperately wanted. One was I wanted to be a digital

marketing coordinator for a third of the pay I was making when I was at Fidelity. And the second one was Barstool Sports. And I remember when I heard about Barstool Sports from the Charnan Group, I was so jealous. I had anxiety. I got sweaty. I was jealous. I was like, they're going to find someone else a white guy with a vest and a button down who has an MBA and works for Activision. You know, like, I knew, I knew exactly who they were looking for. And I knew because I followed Barstool and I read Barstool, I was like, that guy's not going to, that's not going to work. And I really worked hard to get the meeting with Dave. I stalked a friend of mine to introduce me to Dave, introduce me to Dave, introduce me to Dave, please introduce me to Dave. And finally,

she made it happen. And I felt like it was an eternity. I'm sorry to swear, but I bug the the shit out of this lady to get me the interview. And I met Dave in a coffee shop with this person, and we hit it off. And we had a huge conversation about the vision and the history of barstool and what it could be. I was already hooked, but I was really hooked in that moment. And, you know, the interview process was a little bit awkward, quite honestly, because they had been through so many candidates. And I came out of nowhere. I didn't come through the recruiter. I didn't come recommended. And I came ultimately through Dave. Dave went back to the recruiter and went back to the Charnan Group and said, hey, what about this person? And if you've ever searched for a job with a

recruiter, recruiters don't love when the recruiter doesn't find you. And so it was kind of a little bit of an awkward process, but I studied hard for it. I showed up with ideas. I showed up with perspective. and questions. And mostly I listened. And I wrote big emails after every interview I had about what I had learned from the people I had met and what I thought about it and where I thought we could take it. And I really feel like since that first interview I had with Dave, I was working for barstool. So in that case, there's a little luck involved too.

The follow up is big, though, showing that you're a good listener, showing that you're a learner, showing that you had ideas and you were willing to state them. You said I wrote big emails. What were in some of those emails? Who did you send them to? Because I think this could be helpful for a lot of people when they're going for a job they really want. Yeah, I think, you know, for me, I wrote a very heartfelt note to Dave.

I wrote a very heartfelt note to Big Cat and KFC and KMarco. Like the people hit Dave's original crew who I met with, I treated them with, respect. I thanked them for giving me the benefit of their time. I shared why I loved what they created, why they made me laugh. Like I didn't talk like a business person or, you know, I'm going to increase the EBITDA, blah, blah, blah. I talked about what they loved, which was really entertaining people. And I talked about how that affected me. I talked about the T-shirts I bought. I talked about, you know, how I felt about deflate gate. So I think one, I'm a little bit of a stickler for thank you notes. Like if if I interview someone, I always check my inbox like two days

later and search for the person's name and did they send a thank you note or not. If someone doesn't send a thank you note, I won't even consider them for the job, which is harsh, but it's if they care, you can fire off a four line email saying thank you. I think if you really are moved by something, one of the things that I think is very underrated in work is caring. And I know it sounds stupid, but actually caring goes so far. And if you care enough to get a job, then show you care. Don't be a psycho about it. You don't want to drool all over yourself and trip all over yourself,

but do be convincing and convicted about why you love what this company does and how you could play some small and be humble, some small part in taking it to a new place. What was it like right after you got hired people? Was it Deadspin or others calling you the token CEO? Things like that. What was that like? Yeah.

I mean, I think when I took the job at Barstow, people really didn't think I should take it. It was a very good lesson. It was a good lesson in resilience because I knew just by taking the job that it would be polarizing. And I really, I didn't think it should be polarized. you know, I didn't really agree with it, but it really didn't matter what I thought. That's how people felt about it. I got removed from two boards. It was, it was very alienating. I was alone. But it actually was quite beneficial for me because what I realized was that nobody's coming to help me and we need to do this ourselves. And it made me very focused inward inside of barstool sports

versus outward. And that was a very important lesson. And I, you know, my second lesson was I realized I could spend all my time apologizing to people who had an unfavorable perception of Barstool or didn't like Barstool or was offended by Barstool. And what I realized was that was a fool's errand because every breath and minute that I was spending on capitulating to someone else was a minute that I was spending not building this company. And I think that's a good lesson for people. That's a good lesson for me personally in my life. And then three is, you know, people called me every name in the book. You know, the token CEO was very widely said, which was that the only reason I was at Barstool Sports was because I wore a skirt and I was supposed to wash them and make them look good.

And the reality is, you know, that pissed me off. But then when we grew the company, thousands and thousands and thousands of percentages over eight years, I was like, you can call me whatever you want, you know, the success is what it is. That brings up motivation. There's like different forms of motivation, things that inspire us as well. How much are you driven by doubters and people who don't think you can do it versus how much are you driven by the people who love you, the people who support you? And I'm curious about that mix in your life. Oh, I'm a, you know, Barstow made a great t-shirt that's essentially New England against the world.

And then, you know, it was Philadelphia against the world. I'm a against the world type of person. So I'm very motivated by being slighted or being dismissed or being underrated. I love working with people. And I love seeing the change that you can create in an organization and the impact you can have on people on a personal level and on a professional level. But I'm really in the, they hate us because they ain't us depart. which is a good Barstall slogan. And I think it's important where, you know, I think you can't be to, you can't drive all over

the road and it's probably best to stay somewhere in the middle, which is if you're so wedded on the attaboys and the accolades, it motivates some bad behavior. I think it creates a desire for superficial recognition versus substance. if you're so motivated to, you know, turn down the haters and to defeat your naysayers, you can become spiteful and vindictive and then you look just like the people who are spewing negativity at you. So I try to be a little bit healthy in the middle or as much as I can, but, you know, I really believe that it is, it's up to you. And this is why the book is called Nobody Cares About Your Career, which is you should do what makes you happy. You should push your

career and your jobs and your limits as far as you humanly can. And you should stop being so dependent on other people to validate your success or to, you know, put the nail in your failure. You're going to succeed. You're going to fail. At Barstall, we succeeded and failed. I succeeded and failed at every job before that. I continue to succeed and fail. And that's just part of living. And that's part of that's part of work. One of the sections in the book you write about is, Basically, you are going to succeed when your boss does. And so your job for all of us building careers is to do whatever we can to help your boss do well, to help them succeed, to make their life better and easier, solve their problems. What advice do you give the people who have a boss and they don't fully yet real?

This is definitely me for chunks of my career. I didn't realize, like, how a big part of my job was to make their life better, was to, was to, was to, serve them in a way. What advice you give to people and maybe draw from the book of how they need to understand their role is to help their boss? Yeah, I think, you know, I write about this in the book, which is the dumbest person at your company is the company that is the person who doesn't know what your company is paying you to do. And one thing that happens a lot at work is you get distracted by the mundane and the minutia of the Mondays and the Wednesdays and the Wednesdays. the conference calls and the deliverables and the Excel spreadsheets and blah, blah, blah, blah,

that you forget what you are there to do. And I also think there is, there's a little bit of resentment having a boss sucks, right? Who wants a boss? Like, I don't want a boss. Like, I get not wanting a boss, but I think people also forget the better you make your boss look, even if you think your boss is an all-time idiot, the better you're going to do. And that the work you do and the time you spend doing things that ultimately serve your boss, it's really a Trojan horse because doing those things serve you. And what I write about a lot in the book is, look, there's all different types of bosses. There's the absent boss. There's a micromanaging boss. There's the friend boss. There's a toxic boss. You know, there's all different types of bosses. And what I write a lot about is how do you navigate

each type of boss? What is the benefit of each and the pitfall of each? And I think a lot of times people become victim to the persona or the archetype of their boss. My boss is absent. I can't be successful because my boss doesn't care about what I do and who I am and what I achieve every day. in my opinion, and the book is really my opinion about work, is what a great luxury to have an absent boss. It gives you more latitude. You can do more things. You can take more ownership. You can learn faster. You don't have anyone like nipping at your heels or biting at your neck. What an opportunity to take this time to self-educate and to self-propelled. Same with a micromanaging boss. I hate a micromanaging boss personally.

micromanagers make me absolutely crazy, but a micromanaging boss can teach you precision. And while you don't want to work for a micromanager forever, early in your career, being micromanaged and learning how to do things a certain way and with excellence is a pretty good skill. So it's all to me how you look at it. I really like the fact that you write a lot about taking ownership of your career, take ownership of your development, take ownership over the decisions you make. And I think one of the issues at times is somebody complaining like, well, my company doesn't invest in my development or there aren't any upward trajectory. That's a big thing on employee opinion surveys that

people complain about. As opposed to saying, no, this is my career. I am in charge of my development. I'm in charge of interviewing for my next job every day, which was advice given me by my mentor Rex Caswell, hey, you're interviewing for your next job every single day. Act like it. And don't wait to the interview process. It's too late. The job's already been decided at that point. You're interviewing for it right now. And I think it taught me early on take ownership of your career as opposed to saying, well, my company doesn't do it for me. No, you need to do it for yourself. And I feel like that is your like the entire synopsis of you and what you've done and certainly what you've written about as well.

Yeah, I'm with you a thousand percent. I think a lot of times people expect that their career, you like get on the work conveyor belt and somebody is going to water you and feed you. And, you know, it's kind of like the old time. It's like babies on the conveyor belt. Someone's going to burp you and change your diaper. And work isn't like that. You know, work is what you make of it. And a lot of times, I, I think people get very lost. One of the things I write about in the book is that your environment is relentless. And you need to put yourself, or not you need, you don't need to do anything.

But the environment you put yourself in is very important. And if you are in an environment of people who are negative and naysaying and there's a huge malaise and they don't care, then you know what? even if you are the strongest human being alive, that's going to infiltrate into you. If you surround yourself with people who are motivated and curious and ambitious and embrace failure and are learning, that too is going to infuse you. And I think there is a challenge right now in the workforce where people are coming into the workforce less resilient. Parents are more involved ever before in how their kids are raised, how their kids are schooled, how their kids play sports. You read the

headlines at any given point and people are interviewing for jobs and they're asking their parents to make a choice for them or someone's interviewing for a job and they want their mom to talk to the potential boss. No way. Oh, yeah. Like this is happening. Like this has happened to me. Really? Yes. I mean, is it just, you just cross them off the list or like, come on. I was like, that's not going to work here. Okay. That's not going to work here. So I think the notion that you are going to be, that people owe it to you to grow you is a

misnomer. And the faster you get out of that and the faster you start trying things and failing, the better off you're going to be. I really believe in failure. A lot of the book is about failure. The reason I like failure is failure is just a code word for trying and experimenting and pushing yourself. And I think people who do not fail a lot are either without a pulse or they are refusing to leave a very safe comfort zone. And when you stay stagnant,

you kind of calcify. It's like your body. If you don't exercise, you don't move your body. Your body just becomes kind of flabby and soft. And I think the same is true in work. If you're not failing, that means you're not pushing. You're not pushing. You're not fine. I think like Navy SEALs fail all the time because they're constantly pushing, constantly pushing and going for it. And that's a signal. I'm curious, Erica, I know you write a lot about this, but I'm curious.

What is maybe one of your favorite failures, the biggest learnings you took from a failure at some point in your career? Oh, I mean, I fail every day, literally every day. I've made a lot of really bad decisions. I've made a lot of mistakes. I've gone along with the plan when I knew I shouldn't have. I've made mistakes in hiring. I've made mistakes in firing. I've made mistakes in strategy.

And, you know, I've made mistakes in execution. I fail all the time. And I like it actually because I think what it says to me is like, it gives me something to chew on on the train home. You know, when I look back at a course of a day and I say, I really miffed on that. I got this wrong. And then it gives me a conversation to have with myself of like, how would you have done that differently?

And what would you have done? And do you owe an apology? And how would you make this right? And who's someone you can learn from that does this better than you? And I like having that conversation with myself all this. time. One of the things I talk about in the book is the game where I really try to make games myself in my head all the time. I get bored very, very easily. And having a game in my head helps me stay focused. And the game could be like, how am I going to make this situation right?

Or how am I going to get everything done on my to do list? Or how am I going to get this job? or how am I going to leave this job? And always talking to yourself, it sounds crazy, but I think having a very rich dialogue with yourself is really, really important. I think a lot of times you have these two sides. You have this ego and then you have this insecurity. And a lot of times it's either your ego doing all the talking and you become arrogant and then you're very likely to mess up or it's your insecurity.

talking and you find yourself anxious and being held back. And I think always talking to all these sides of yourself is really important because then it kind of gets you to the end right place. You mentioned earlier about the fact that it's important to surround yourself with people who are ambitious, who are growth oriented, who are moving forward, right? Because if not, if you're around others who are just kind of slow, you could become part of that environment. And we talked about one of your mentors, Joanne, to start this conversation, I'm curious to learn more about this idea of mentorship and how you've intentionally went out and found them, how you attracted them to you, because it takes two to be in a relationship. And I think this is a question I get

asked a lot. Like, I want and need more mentorship. How do I go about doing it? It's just like that Charlie Munger advice of how to get a great wife. Someone asked them, how do you get a great wife? He's like, deserve one, right? So be the person, be the type of person that someone wants to mentor, but I'm curious, what have you done to be so good at both being mentored by others and you now as the mentor for others? Yeah, I really believe you can learn from everybody. And I think you can learn from the lowest person on the totem pole and the highest person. I am allergic to people who only manage up. I find it very, very unbecoming. And in a lot of ways I think sometimes when people want mentors, they're just trying to suck up or look up. And I think you can be

mentored by all different types of people. My first job, my first internship slash job was as a receptionist at Fidelity Investments. And I was very bored. I stared at the door and I let people in the door. And the only people who would talk to me were the secretaries. So I was like, all right, to your Charlie Munger analogy, I'm going to do whatever the secretaries need. I'll get the coffee. I'll file the cabinets. I will clean the desks. I'll organize the bathroom. Whatever. There was no job that I would not do. And finally, I ingratiated myself to the secretaries, which then enabled me to ingratiate myself to the next group of people and the next group of people. So to me is you have to create value for other people to get benefit and knowledge in return.

And the second piece is mentorship is kind of like a job where you may want this lofty, perfect dream job, but you have this like, okay job. And it's all the little jobs, it's all the little learnings, it's all the mentors along the way that gets you to a new, bigger, better place. And I think a lot of times people look for mentors who are very lauded or very removed. and there are mentors all around everybody. There's something to learn from everyone. I really believe that you should watch and listen to people.

I watch everyone. I learn from people who work for me. I learn from people who work for people who work for people who work for me. I learn from, speaking of Charlie Munger, like I watch the Berkshire, every year I watch the Berkshire Hathaway Conference. One, because I just, I thought Charlie and, you know, Buffett were just so funny and charming together. But the questions, you can learn from the questions.

You learn from how they answer the questions. You learn from how to people at the top of their field perform and more importantly how they think and how they work with the people around them. Now, Warren Buffett wouldn't know me from a hole in the wall, wouldn't care. I don't even know if he would like me. I wouldn't say, but I can learn from him from watching a YouTube video.

And I think that's the other piece, which is people want mentorship in a very specific way, shape, and form. And you're really, I think your aperture is too low. You should have a very wide view of you can learn truly from anyone. And what a time to be alive where you can access anything on the internet. I also enjoy learning about partnerships. We're talking about Charlie Munger and Warren Buffett and one of the most epic partners. partnerships of all time. I think yours and Dave Portnoy's is another one that I'm curious to learn more about. What would you say was the best and worst parts about working with Dave?

I loved working with Dave. I don't actually think I'll ever like working with anyone the way I liked working with Dave. Dave was a once in a lifetime partner, truly once in a lifetime. I've frankly kind of resolve myself that I will never have that again because if I think I look for it, I will be disappointed. I think that was a magic partnership. I think I appreciated him for who he was and what he was. I think he appreciated me for who I was and what I was. I think if you were to ask him, he would say, oh, Erica's in charge. She'll make the decision. If you were to ask me, I would say, oh, Dave's in charge. He'll make the decision. And we always kind of came to a right great place together. And we were, most of the time, we were right. And when we weren't right,

we were honest with one another and we corrected it. I don't think there was a worst part of working with Dave. The other, you know, I really like Dave. Dave, Dave's very confident. And Dave knows what he doesn't know and is not afraid to say, I don't know. I don't know. And a lot of times in business, I think the more senior you get and the more expertise you're supposed to have or the most more experience you have, you're supposed to know more answers. And I write a lot about this, which is sometimes being like, I don't know, I don't understand what you're saying or I don't know what the right thing to do here is, is the most powerful thing of all that you can say. And I think Dave and I had a really, really great partnership because we were both entirely committed to

something. We both knew what we didn't know and weren't afraid to ask for help from the other. and from others. And we both shared a work ethic, which was, you don't find a lot of work ethic like Dave Portnoy. I also enjoyed reading the actual emails that you sent to your team at Barstool, both like when you got the job, when you left, and then certainly ones in between, some funny ones.

I feel like I can hear your voice in your writing. So it doesn't feel like it ever went through legal or a comms team. It was just Erica sitting down writing a note to a company that was growing rapidly. I think communication as a leader is so, so important and not necessarily talked about enough. What was your overall philosophy on communicating

with your team when you're the CEO of Barstool? I've always been a rabid over-communicator. I learned it really, I had a job at Microsoft in the early 2000s, and I was in Boston, and my team was in London and Tokyo and Seattle, in New York. And it was a scary moment and kind of an alienating moment. It was my first job in publishing. And I was in Boston. I had never been to Japan, let alone run a business operation in Japan. Same for London. Same for Seattle. And I learned that I had to over communicate. Communication was the

only way that I was going to give something so that people would give something back to me. It was the only way I was going to create a feeling of cohesion and team. It was the only way that I was going to create relationships being, you know, thousands and thousands of miles away. And it was the only way that I was going to be able to motivate a disparate group of people in disparate countries with disparate agendas to marshal together to do something. So I really at Microsoft learned how to communicate, I would say. That was a huge, painful journey for me, but it was a very valuable one. At Barstool, by the time I got to Barstool, it was funny, Barstall communicates on Twitter. So Barstall is also always communicating and was very unique

about Barstall is what happened inside of Barstall very often ended up outside of Barstool. I think I'm with you. I think communication is so, critical. I think people underestimate the power of, hey, here's what we're doing or here's what we're struggling with or here's where we failed. It's funny, I took a new job about a month ago and we were debating. I want to have a Friday email from me to the company. And actually, I would prefer a Friday email from the entire management team. And one of the things I wanted in the email was what we fell down on this week. You know, where? did we fall short? Where did we fail? And I got a lot of pushback from the management team of like,

why would we tell people where we failed? And I was like, because they already know, like, they're seeing it as much as we're seeing it. We should acknowledge it and talk about it. And I think real honest communication is really important. I think that is one thing. You know, I love that you love the emails. Like, I loved writing the emails. I love email. I work now at a company that communicates in Google Docs, not email, and I'm finding myself like a little bit like, I don't know how to exist in that. But I think email can, when used the right way, can be a very powerful way to communicate. I think picking up the phone is not something people do anymore and they should do way more of. I think in a world where most of work is remote and over Zoom,

how you create connection and trust with people is entirely vested on how you communicate. And you've got to be an expert. If your company is communicating in Google Docs, you got to learn the Google Docs. If it's an email, you've got to learn the email. If it's in Slack or text or Discord, whatever it is, you have to learn how to do that. And then you can't be afraid to pick up the phone. Speaking of having a senior leadership role, you have a new job now. So you've been in these senior leadership roles for a while.

I'm curious, Erica, when you're making a hiring decision, let's say for a leader who's going to work for you? What are some of the must-haves in that person? I know they have to be specifically good at whatever the task is. Those are table stakes. Obviously, they got to be good at whatever that thing is. But beyond that, what are some of the must-haves for a leader to work with you? You have to have failed and you have to be able to talk about how you failed. And not in the stupid, like, tell me one time about how you made a mistake at work. Like, you have to have shown a journey to me where you have tried things and you've learned from the trial and error. Curiosity, trial and error, those things are very important. Two, you have to have done enough research so that you can at least

bullshit caring about the company. I don't like, you know, I would see this a lot at Barstall Sports where people would be like, oh, I'm a huge fan of Barstall sports. And I would say, well, what's your favorite podcast and they'd be like, uh, and, you know, or they'd say, I love part of my take. What, what do you love about part of my take? And so you can't bullshit a bullshitter. You need to have done your homework. I write about this actually in the book, which is if you're going to work at a consumer facing company, you have to test the product. If you can afford it, buy something. At the very least, sign up for somebody's emails, have an opinion on their emails. So you have to show enough initiative and curiosity to learn about the company.

And then I think it's, I think you have to be able to articulate what you could bring. It's a little risky, but I sometimes feel that you having a point of view in the interview process, I don't actually sometimes all the time I feel that having a point of view in the interview process and you can couch your point of view, which is, hey, I don't know nearly as much as you. I don't work at the company, blah, blah, blah. But having a point of view on how something should be done is also something that I feel strongly about. I like that last one a lot because it also shows some guts. You have a perspective. You've probably thought about it. And maybe you've even identified a potential problem and you've thought of a way to solve a problem or you thought of a

an idea that could expand or grow the business. And that feels like what you did with Barstool thinking about, I believe there were like $12 million company when you get there and at the end sold the Penn Entertainment for $550 million. So $12 to $550. I'm curious going back to the beginning and you've said publicly that those were some of the most fun days, like the earlier days when you were scrappy and gritty prior to the sale for $550 million. What were some of those early ideas that you brought to the table that helps the company grow from $12 million to $550 million? There were a lot. You know, one, we hired really smart people.

Exactly. You know, we hired a lot of people. We grew from maybe 15 people to at the peak for over 400 people. So we hired a lot of talent. We went through a lot of talent. Two is I, in the early days, I needed to keep them busy. The busier the barstool talent was the less they got in trouble on the internet. So for me, it was very self-serving that, you know, the more time they were on camera, the more time they were on a stream, the more time they were writing, the more time eventually we were podcasting, the better off we were, because then I had more assets to work with and I had more ability to monetize. And I had more proof points of where and how we could grow. For me, it was really, it was following the talent who were following audience. And in the media business, that to me is the media business. You are, it is a business of audience. It is the business of harnessing talent and IP to grow audiences and to serve the audiences you have and to find and nurture and engage those audiences in all the places they may live. And I think that's, that's really what set barstool sports apart because when you look at most media companies,

they say, I have a distribution format. You know, I make this, I put it here, and I think people buy it. And I'm like, that's not how it works. Start from the other side. Who's reading this or watching this or talking about it or socializing it or chatting about it? And then how do you reverse engineer back into the quote-unquote media company. And so we had the benefit of a bunch of things. The summer I got to Barstool Sports, Twitter bought Periscope, and Facebook launch Facebook Live. That was a lucky break for us because it was cheap. It was easy to produce. And people talking was not that different than people writing on a blog. So I was able to make a transferable skill between blogging and then podcasting and then live streaming on social. And that was a game

changer for Barstool because one, it was the same cost basis. It was the same talent. We created a production format that was also low cost. When you look at most media companies, they start with someone in an office says, here's the show and here's the producer and here's the director and here's the associate producer, and here's the PA, and here's the lighting guys, and here's the camera guys, and did it all the way down and finally you cast the talent. And at Barstool, and this is really because Dave was so brilliant at this, we always started with the talent. And that's what, that's a Dave thing. And when you start with the talent and you build a little bit of pieces around them, you get a lot more value because you're following the talent who is closest

to the audience. And that's really doing those things and then building a very diverse monetization strategy underneath it. And the reason we needed diverse monetization is some days they pissed off the advertisers. And other days, the commerce business was slow. And I needed to cover payroll. So I was like, I got to have some options here. How do you judge and make the call on talent? Is this just a gut feel?

Or how do you know if someone's going to be good on a podcast or good on video, prior to them actually doing it? You don't really. And, you know, I give a lot of credit. There's a gentleman at Barstool named Paul Gulsinski. He was Dave's first hire. He's incredible at finding talent. Dave is incredible at finding talent.

We interviewed a lot of talent who you knew pretty immediately wasn't going to be great. And those were mostly people who were trained by traditional media. And one of the things about Barstool is it's all about the reaction, right? So we're in an era of opinion and opinions happen after incidences. And I remember interviewing a talent with Dave and he was a basketball person, I think. And Dave asked a question of like, all right, so the game ends at 11.30. Are you jumping on Twitter? Are you going live on Facebook?

What are you doing? The guy was like, oh, well, you know, my producer will tell me what to do. And we always knew immediately that those people wouldn't work. It was the person who had to say something about the Red Sox or had to say something about the Eagles that was going to be the most successful. I think that actually plays beyond the media world. Again, I personally like people who have a point of view and they're willing to say it. And I think Adam Grant may call them disagreeable givers within corporate America, maybe, where you have a point of view, hopefully backed. There's some emotion there, but there's also some factual backing.

And you're willing to say it immediately. You're willing to say it in the meeting, in the actual room it's happening. Or in your case, like with media, you say it, you broadcast it on a social media website or whatever. The people who are making a difference, the people who are making a dent, they have a point of view and they're willing to say it. And they're wrong, a good amount of the time. They're wrong. Or people disagree with them. They're polarizing.

Those are the ones who make a dent versus the ones who just play it safe and don't speak up. If you want an audience, you have to say something that gets people attention. Whether that's right or that's wrong and you can argue the social consequences of that and the echo chambers we all live in. But that's the name of the game. Yeah. Yeah. One more, Erica, you left Barstool. and you talked about the fact that it was a heart attack every day for nine years.

And so maybe it was time to not have a heart attack every day. So that's probably one reason why you left. But I'm curious, what are some of the other reasons why you decided to leave? Yeah. I mean, it was the best heart attack ever. I say that a little bit in jest, which was you just never knew what was going to happen. And that made it exhilarating. It was, you know, the most exhilarating run of my career.

And I'm so infinitely grateful. For me, the acquisition from Penn was difficult. And in 2023, we sold the company twice. We sold it to Penn for $550 million. And then we sold it to Dave for a dollar. And I really came to Barstle in 2016 to grow it and to see what it could become and to legitimize it. And it exceeded on every dimension beyond my wildest, wildest, wildest, wildest, dreams. It was nothing I could have ever anticipated. And August 2023, as I'm looking back on the year, and I'm like, geez, I've sold this company twice in a year, 2024 was never going to beat 2023. I was like, I'll never, I'm never going to have this ending again. And I felt really good that Barstool was back with Dave. I felt like for me personally, I had come full circle. I had joined just as Dave had sold a majority stake. And I felt like, gosh, it's kind of the perfect circle of I'm going to leave as Dave gets it back.

And it's in its rightful home. And I was here for a time and I helped take it to a new place with a lot of really talented people. And it also got me thinking about, you know, what next? What's the next mountain to climb? I think a lot of times in a career, people can choose to be. complacent and choose to be happy with the status quo. And for me, a lot of people were like, geez, this has been a crazy eight years. Why would you not just enjoy it now? Like, you made it. And I'm just not like that. I'm like, I don't want to stay too long. I want to be in a place where I'm

still scaring myself. I want to do something that I haven't done before. I still have a lot of energy and feel young and want to do things. And I honestly felt like it would have been disrespectful to barstool for me to stay when I wasn't needed. And what I felt really good about was, gosh, I was going to leave the company in a great place, was with the right owner. It had the benefit of the eight years before. And I also felt like I still would like to learn from other people. I'd like to learn a new business. I'd like to have a different type of customer. I'd like to go really deep on retail and commerce. And that for me, you know, plus, you know, I was writing a book at the time about the chapter I was writing in August was stay or leave. And I was like, oh, I should actually

listen to my own advice. And so that's really what made me decide to go. Always pushing, always pushing. Getting too comfortable is uncomfortable. We got to push. I love that. The book, which I highly recommend because it's very entertaining and there's just so much to learn. It's called Nobody cares about your career. Why failure is good, the great ones play hurt and other hard truths. Erica, this is so good. I appreciate you investing your time with me and I would love to continue our dialogue as we both progress. Absolutely.

Thank you so much for having me. I'm so grateful. Awesome. Thank you so much. It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learningleader.com. Let me know what you learned from this great conversation with Erica Ayers-Baddon.

A few takeaways from my notes, what she learned from her dad. Quote, he loved his work and was so full from the work. Three weeks before he died, he was doing Zoom calls with students from the ER, even though that was beyond unnecessary and practical to do so. And she writes that if you love what you do, it can add so much dimension to your life and the lives of others. She said he liked people and to learn from them. There's something to learn from everybody and the best control was no control. That was interesting to me.

Let things happen and learn from them and adapt. I really enjoyed the smile it brought to Erica's face when I saw her talking about her dad and there's so many life lessons from him. And then how about some career advice from her? know what your company is paying you to do. Understand that. And also know that the better you make your boss look, the better it will be for you. Find problems and clear the path for your boss. Make their life easier.

Make them look good. That's the role for all of us when we have a boss. Then the must haves when she's making a hiring decision. A few things. Be able to share stories of how you want for something big and fail. as well as what you've learned from that failure, then be curious, ask thoughtful questions, do research on the company, show, prove that you care, test the product, be able to demonstrate that you know what it does, and then I think most importantly, bring a point of view, articulate

what you could bring to the role and how you can make the company better. It's about them, not about you. Once again, I would say thank you so much for continuing to spread the message and telling your friend or two, hey, you should listen to this episode of the Learning leader show with Erica Ayers-Badon. I think she could help you become a more effective leader because you continue to do that. And you also go to Spotify and Apple Podcasts and you rate the show, hopefully five stars and you subscribe to it and you write a thoughtful review.

And by doing all of that, you are continually giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so, so much. Talk to soon. Can't wait.