Why Erin Gallagher Left a Fast Company Award-Winning Startup to Find Herself

I am disappearing. I am abandoning myself in order to serve others. And so my, what happened for me was I turned 40 and I sort of looked at the lot of my life and said, to what end am I going to continue to play a behind the scenes role? Am I gonna be the fluffer? Am I gonna keep existing only to benefit other people's ambitions.

Welcome to Big Hitters. I'm Larry Weidel, and this show is for people who are done playing small. Each week we break down what it actually takes to win at a high level— the decisions, the discipline, the adjustments that separate those who almost do it from those who do it. No theory, no fluff, just straight talk from someone who spent 50 Years Building Winners. If you're serious about momentum, you're in the right place. Let's get into it. Hello to Erin Gallagher. Hello, Erin.

Larry Weidel, we are in it.

I don't know what, you know, who knows where this is going to go today, but it's going to be fun.

That's for damn sure. That is for damn sure.

What would you think is, you know, coming up? What was the first most amazingly significant thing you did to you that you were really, you know, really aspired to do something. And then when you did it, it was just like, yes, yes, this is— good things can happen to me in my life. You know, I've kind of, kind of proving to myself I've got, I've got what it takes to do really substantial things.

My answer is going to surprise you, Larry, because It was actually the undoing of one of those, one of those big things that was the most significant and surprising to me and actually opened up my life to bigger and better things. And it was resigning from the first company that I co-founded. So, so yes, you know, maybe the answer would have been a few years ago, oh, well, Larry, founding my first company was, the most powerful thing I've ever done. We, we received funding and were the first equity investment in a majority women-owned business by global company Interpublic Group, right? A huge holding company. They never in their 93-year history had ever invested in a majority women-owned business, and they invested in us. And we grew that company over 2.5 years from nothing to being named one of Fast Company's World's Most Innovative Companies. But then I walked away. And the reason I walked away is because I started to remember who I was, and I was disappearing inside of that company. So I think a lot of times we strive for something and we have goals, and when we achieve them, we keep going to the next thing. It's inertia. It's just like if you're an ambitious, driven person, you're kind of like, cool, what's the next goalpost? I'm going to keep moving it. But if you ever give yourself the chance to sit down once you've achieved the thing you wanted years before and say, is this still it? I think a lot of us would actually make different choices. We would, right? We would say, this isn't my ambition anymore. I'm not the person I was when I set out to do this. So that was the most surprising thing to me, was that I had the courage to walk away and to go against what the naysayers absolutely came after me to say, Oh, you quit, you opted out, you couldn't hang, you couldn't handle it. Right. All of the narratives from people that didn't know anything about what was actually going on. Right. And, and so, but what did it do? It allowed me to start my own company. It's led to much bigger and better things for me.

And so as you get in, of course, everything turns, you know, the thing is everything turns into a grind eventually because, you know, you got to keep doing, keep doing and keep yourself excited because because that's how you get to bigger and bigger levels and bigger and bigger breakthroughs. But when you get into the grind and it's something unpleasant, now I need to be somewhere else. And so what were the signals that came to you?

Yeah, the grind doesn't scare me. The hard work doesn't scare me. The pouring in, those are things that have always been inside of me. So that wasn't it. It wasn't that, wow, this really is much different than working inside of a corporate company. This is entrepreneurship. This is hustle. It was, I am disappearing. I am abandoning myself in order to serve others. And so my, what happened for me, Larry, was I turned 40 and I sort of looked at the lot of my life and said, to what end am I going to continue to play a behind-the-scenes role? Am I gonna be the fluffer? Am I gonna keep, existing only to benefit other people's ambitions. At that point, I was 20 years into my career. I had 2 children. I had checked the box on so many of the things that society told me I needed to do in order to be considered a successful person. But I just kept disappearing, and I kept allowing others to tell me my value and my worth. And they weren't telling me the truth.

Yeah.

Because oftentimes when you are someone who goes after what you want and you are ambitious, that can feel very threatening to people. They don't see it as, wow, let's get together. Can you imagine what we could do collectively? There's that. That's the abundance mindset. The scarcity mindset is I am afraid of your power because I think it's going to take mine. Yeah. And so I started to look around and say, Who are the people that are looking at me as a threat versus an asset? And when I began to strip away what those people looked like, the truth began to reveal itself. So, so for me, it was, it was kind of one of a mile— it's one of those milestone ages where you just kind of have a little bit of an existential crisis, right? But it, but it was also a sort of— it was a pivotal point in, in my entrepreneurial journey where I had 2 years under my belt and we had the external recognition. We We had done huge work for McDonald's and LinkedIn and United Airlines. And so, like, we were validated, but I was disappearing. And so, like, it kind of goes back to what you said at the beginning, Larry, where there is a key differentiator between people who have ideas. When you're building something that doesn't exist, it runs the gamut of being— there being unlimited potential because you have no idea, you haven't seen how this plays out. And then you also have this other side where because there's no roadmap, there are no guidelines, there's no data to review to see how you should progress, you can feel completely stalled. And so, and so you really just have to start. I mean, that's, that's what I realized is that you can completely outsmart yourself in the wrong direction by thinking of all of the ways that things could go wrong, trying to plan and prepare. It can, it can be something that actually keeps you from even, from even going. So not being afraid to fail is, I think, the most important thing. If you want to start a business, if you want to start an endeavor, if you want to build a movement, is knowing that you are going to fuck up. It will happen. That is, that is where you learn your best lessons. It's where you then establish yourself as an expert in something because you've lived it and you've found your way out and survived. And so I think, you know, having aspirations for what you believe is the only way to enter into an endeavor where you're starting your own company and you're building something from nothing. You have to also be able to withstand all of the people who think you're nuts because so much of the time the response is, you can't do that. No one's ever done that before. That's not going to work, right? These are the messages that you will receive. And my, my, my like sort of guidance to anyone who's hearing that is good. It's working. Keep going. Right. If that's what you're hearing, you're on to something. You are on to something. If everyone feels like they know how it's going to turn out, it's probably been done before. So, you mean— that was actually— that was line for line the business plan, Larry. So if you are— if you're a dead, soulless corporate sucker and you want to work with us? Let's do this.

Yeah. So you had to be super excited about whatever this idea was.

So do you play golf, Larry?

Yes. Yes, I do.

Okay. So golf is a business ecosystem, right? It is a place to do business. And what we have seen over the past 300 years is there are the significant number of men who are out there building generational wealth, giving each other backdoor opportunities, talking about investments, they are doing this, you know, in a forum that we all have accepted and decided is a business activity. So much of this is about like, how do we actually see the world and frame it and respect it? So I saw that,. And I saw all of these messages to women coming from, coming from Harvard Business Review and Fast Company and, and neuroscientists saying, ladies, get on the golf course. You want to make money? You want to be a Fortune 500 CEO? Learn how to play golf. And I didn't agree with that because to me it was like, no, no, it's not about the golf. It's about the access. And so if we have a system golf that has absolutely supported more than not straight white cisgendered men in building their careers and their wealth, but that it doesn't always accept other people into those, into those foursomes, then the issue isn't being able to play, it's the place to do it. And so I actually created The Fairway, which is a series of— my book always falls over when I say something that's kind of intense. It's like, she's like, she's like, oh shit, it's happening. So, so I created this dinner series that was focused on creating sort of a mix of Fortune 500 C-suite, mid to senior level rising stars across every industry, and then founders and entrepreneurs. And I would bring these 20 women together into a room over 4 hours, drinks, dinner, conversation to do business. Because I had experienced as a founder and an entrepreneur coming to events where you're all founders and it's difficult to help someone else because you're building your own damn thing. You don't have more time, energy, and money to give to others because you're pouring it into your own company. And then I had been on the other side where I'm in a room of all very senior C-suite executives in corporate America, and those women had been conditioned to hold their cards close to their vest, to see other women as competition and threats, and so not to give access to their networks because they were like, if I make that introduction for you, what if I need it? Yeah. So I was watching this play out and I said, what if we just cut through all of that? And we brought these women together and we said intersectionally, we could actually do this. So there I had Asia Star Day, founder, entrepreneur, and designer sitting next to Jessica Kimbrough Munsch, who is the chief diversity and equity inclusion officer of United Airlines. And they have a conversation and they start to do business together. That was— I was breaking through that barrier of like, I don't want to talk about this. I don't want to pitch myself. Makes me uncomfortable. Money is like a sort of an inappropriate thing. I centered business in these, in these endeavors. And so, Larry, what I did over 3 years was I did these dinners, 33 of them in 10 major markets. Across the country for 1,500 women, and we increased our collective wealth by more than $33 million because, because we were doing business in a way that we had not been given the space, the encouragement, or the language to do it.

And so how— and so where— but now that's 3 years, right? You said over 3 years. And then so how from 3 to 20 years. What happened during the, during that stage?

Well, I spent 15, 16 years in corporate America. And, and so that was me inside of agencies, leading marketing communications, PR. In 2019, I left to become an entrepreneur. So my entrepreneurial endeavor has only been a 6-year stint, 2 and a half inside of the first company I co-founded, and now more than 3 inside of my own solopreneur business. So yeah, it was a, it was a full transformation of being a good girl who was following the rules and climbing the ladder at a very glacial pace and sort of doing it on the terms of, of the system I was inside of to sort of turning the whole thing on its head and creating something that I thought was new and different.

Well, and what it shows is that those are not wasted years because you, like you said, you were building, you know, you're getting your foundation in place, you're getting your family and, you know, there's there's things you have to sort out. You have to learn lessons about that. But the fact that it took you a while to get your entrepreneurial stage of your life going is, is the fact, you know, people should— what, what should the takeaway people should have from that is like, don't give up because you spend 10, 15 years inside the corporate thing and say, Well, you know, my inspiration is gone. I'm numb now. Like, no, no, no, no, no. You know, the thing is, if you're having those thoughts, you're probably right. You know, you shouldn't be an entrepreneur. But if inside of you, you're still burning and churning to, you know, you've got things bubbling up inside of you, seeing things that are wrong and you want to fix them and you want to, you know, break out. Don't worry about the time that you spend in corporate America or doing other things because you're making contacts. And you're getting skills. You're getting, you know, you're, you know, the other thing is when you're working inside a corporation, you still can have a lot of stupid ideas. But the thing is, you, you move into some kind of management or leadership inside the corporation and the corporation will wind up paying for a lot of those stupid ideas.

Right? It's like, hey, actually might, might be a better idea to try this inside of there. Figure out what works and what doesn't, and then take, take your human capital on the road. You're right. You're right. I mean, now granted, the risk you run of taking a really good idea and trying it inside of a company that is inside of corporate America is that you will lose your IP. Yeah. So, so you have to— it's a risk. You have to decide what's the risk-reward here? What do I want to sort of try so that I can see what, what this is like to to run a business this way, to take an idea like this to market, to think about this consumer, to, to launch something this way. You can build your human capital inside of a company that is footing the bill. Absolutely. And then you have to decide when is the time that you might run the risk of losing it all to them and they might reap the biggest reward from your own human capital. And do you wanna invest in it outside of this? So, I was never planning to be an entrepreneur. That was not my plan at all. And what I have said is, for the most part, entrepreneurship finds you. Like, it's something that comes and says, here's the deal. I know this isn't a convenient time. I know this is a risky idea. I know this is a financial, you know, lift that you're going to have to make, but you can't think about anything else and you don't want to try anything else. And so you have to do it. And so like, yeah, when it's something you're thinking about all the damn time, you are finding ways to work it into conversations with friends, with, with colleagues. When you are, when you are paying attention to that, to that particular market more than anything, that is a pull that you need to follow and to think about pursuing.

Follow your natural curiosity and instincts and Don't hold back. Well, one thing that I would say, you know, I didn't really think we would go in this direction, but I think you're uniquely positioned to speak to it is like when you're in those, you know, a job, you're in a corporate thing. And even if you don't have a big inspiration or an idea and you're not really sure that you want a business of your own down the road, there's a lot of incentive I think for still being proactive and looking for responsibility, looking to move up, looking to expand your skill set, you know, make contacts, things like that. Because again, that's how you learn. You know, you get out there and you try things. And the easy thing inside a corporation is to hide from responsibility or hide from that because, you know, there's a lot of blame, the blame game, you know, like, you know, you raise your head up and you get chopped off. And so there's a— you want to overcome that. I get the feeling while you were in that world, you were not someone who shirked back from challenges and responsibilities, you know?

Oh, Larry, the number of times that I was sort of pulled aside for varying reasons, like there were times I was pulled aside and it was like, run with this. Yes. What you're doing, go. We will support you. There was that. And then there was also the times where they're like, Why do you have to ask so many questions? Why are you making this so hard? Why can't you just let it go? Those were the messages I was getting all the time. So, those are very confusing, conflicting messages. Both were still me. Both were me pushing and asking questions and saying, why do we do it this way? And saying, why don't we do it this way? And I either had people who reflected back to me this is interesting. What you are looking to do is new, but we think you should go for it, right? You are going to have that, but you're also going to have the people that are afraid, that do not like change, that do not want their career disrupted or threatened. And so, you have to decide who to believe because what I found in my 15 years in corporate and then my 2.5 years with my co-founders is that You will have people that tell you lies about yourself, that say that you aren't good enough, that say that vulnerability is a liability. And if you think that they are telling the truth, you will believe it to be the truth. And on the reverse, you will have people who are seeing all of the good in you and who are telling you these beautiful truths. But if you are listening to those naysayers, you're going to think they're lying. So you have to decide, like, what is your identity? What is the truth about what you're capable of? And, and pull back from those people that are there to drain you of that life force versus to help you expand it. Well, and I think curiosity is innate. You either are a person who is curious, who wants to learn more, who wants to understand, who questions why things are a certain way, or you are a person who just takes it and does nothing with it, right? You are just sort of like an absorber. So it can be very frustrating to be working with people who are not curious, who don't want to understand more and learn more, because when you have people who are curious, you actually develop better products, solutions, offerings, because you are thinking through the 360-degree experience of the individual, the person who you've created the product for. So I want to go back for a second, Larry, to this. Toxic family member, because we all have them. We all have them. They're either— they're in our families, they're in our friend groups, they're in our social circles, they're in our whatever it is. And here is what I have— this is what I have discovered with a situation like that, with a response like that. You, you put yourself out there. You, you were vulnerable in creating a piece of content that's shared. And right, and so as soon as you Soon as you let that leave your body, you are up for critique. You're up for critique. And so that is why most people don't do it because it's scary. It's hard. It's heavy. Like, it's always great when you get positive responses, but when you get negative ones, you're like, why did I do this? So, so that family member, here is what I discovered. More often than not, under criticism, under critique, under jealousy, under envy, is desire. Right? That is so often the real feeling that's underneath those things. And so that family member, I believe, was jealous of the family that you have, that you've created, the— this idea that you put out there. And so the way for them to inappropriately engage with you on it was to be like, oh, this is so annoying. I got this again. I'm so sick of reading it. It's like, then don't fucking read it, dude. Fucking unsubscribe. Right? Like, like, and so my longtime therapist gave me this great phrase to say to people when they say something asinine to, to like something that you're doing in the world. It's like, what an odd thing to say. Right? Because it's like, it's like, I'm sorry, are you talking shit about my family newsletter? Like, like, dude, go get on some fucking antidepressants. Like, you're like, you need to figure your fucking shit out, you know? So that's my response.

Yeah. Well said and well received. Okay. I'm going to switch gears on you because you and I are now big friends. We'll probably be talking one way or the other the rest of our lives now.

Definitely. I see it for us, Larry. I see it.

I see it for us. But now tell me about the butterfly behind your and your background. What's the story of the butterfly?

Well, and here's, here's my tattoo, right? And obviously you can see on the COVID of my book, right? Hyperman butterflies. So I am obsessed. I'm obsessed with butterflies because it is, it is unimaginable to me that a crawling caterpillar can just move along at a glacial pace and then one day say, I am really sick of this slow shit. I'm sick of it. And they're like, you know what I'm going to do? I'm going to cocoon. I'm going to build this entity around me. I am going to dissolve into goo. My body is going to completely transform. And then I am going to break the fuck out and fly away. That transformation, that metamorphosis is so unbelievable to me. And I think that we go through metamorphosis over and over and over again over the course of our lives. Maybe it doesn't look the exact same as this, but truthfully, when I think about when I left my first company, I was a crawling caterpillar inside of that company. I did what I was told. I existed where I was told to exist. I was told to know my place, and I knew it, and I didn't push. And then one day, something snapped in me, and I cocooned. I pulled back in, and I said, I gotta reevaluate this. I want to look— I want to look at this. I don't— I don't like this version of myself. I am not who they are telling me I am. And then you want to scare the shit out of people that that try to keep you down, you transform into what you were always meant to be. Because when I broke out, they couldn't stop me. They couldn't tell me who I was anymore. They couldn't get me to crawl because I couldn't. I had wings. So that is my obsession with butterflies. And it is what I believe anyone who is interested in their own growth, anyone who is interested in taking a risk, anyone who wants to start a company, who who is okay to fail, this is what we go through. We go through this process of metamorphosis.

So let's talk about that process. When did that idea come into your head?

So that idea, it actually, you know, I have, I was an English major at University of Michigan.

Okay.

Go Blue. You're, you said, you said Georgia Tech? Is that your alma mater?

Yes.

Georgia Tech. Buzz, buzz, sting 'em, right? So we are very, we're paying close attention. Or paying close attention, but I was an English major, so I've always been a writer, but being an author is a different ballgame.

Tell me why. Tell me why.

I've never heard that. Yeah. So to me, I, I defined being a writer as like anyone who puts their ideas into the form of the written word and puts it out into the world, whether it's on a LinkedIn post, on a blog, you are writing for a publication, whatever it is, it's the transfer of your ideas to other people through words. And so I have been writing my whole life and being an author though was this more, it was a smaller community where you actually put this into a book, right? Like writing a LinkedIn post is a little bit different than writing a 70,000-word book. It's— it requires a different kind of stamina. And, and a— and you talk about that hot air balloon, it requires you to kind of go up and come back down over and over again, where you are saying, how is this shaping up? How do I get back in and make some adjustments? And how do I look at it again? So I actually didn't know if I was ever going to write a book. But 2 years ago, a acquisitions editor at Wiley reached out to me. Really? Yes. Victoria Savon. She reached out to me on LinkedIn and said, I'm watching you. I'm reading what you're putting out there. I think you have a book in you and I wanna talk to you about it. And Larry, I read the email and I was like, dully, she doesn't know who she's fucking talking to. Like, I was like, this was, she, she said this was a wrong email, right? We talked, we talked earlier about if, You've been told so many lies about yourself and you believe them. When you hear a beautiful truth, you think it's a lie. So a year after I didn't respond to her, she reached out again and said, still watching you, still think there's something here. So I finally met with her and that began the process of me, okay, am I really going to do this? I wrote a book proposal, I pitched it, I met with agents, I met with publishing houses, I fielded offers, and I fielded a lot of rejection. Like a lot, a lot of rejection, right? A lot of people who said, we like your idea, but we don't think you have enough followers, so we don't think you're going to be able to do this. Other people who said, we like you, but we don't think that this book is going to sell, right? I heard every— I heard every version. I heard every version. But, but she was like, we want it all, this version and you. And so then I, then I sought out to do this endeavor. And I wrote the book, I turned in the manuscript in February, and she broke out of her cocoon last Tuesday, October 14th. And this was a really, this was a totally new frontier for me of writing a book and having to think about something that was going to be this significant in terms of con— like content, 288 pages. And how is it going to stand on its own without me there sort of guiding it and having interactions with a post, right?

This is—

you put this out and it's just gone. It's out there. So, um, so it's been a really wild process and it is an act. It is an experience of self-worth where I would love to pretend that external validation doesn't matter to me, but that's just not true. It's not true. My entire career has been built on external validation determining my value, my worth, and how I was compensated and acknowledged. And so that is still in me. And so this experience now of having it out there is kind of, it's kind of exhausting.

When was it released?

Last Tuesday, October 14th.

Oh, fantastic. Okay, so let's make sure they see it again. Let's stick it up there, the COVID again. And it's behind you, right over behind.

Oh yeah, yeah. Hype Women: Breaking Free from Mean Girls, Patriarchy, and Systems Silencing You. With a foreword by Jamie Lee Curtis. Wow.

Yeah. Fantastic. And so, you know, I hope, I hope the book does well because dead gummit, we need more. We need more ladies doing well out there. We need more voices like yours out there. And I do think they are intimidated into holding back. You know, more than every, you know, men are, you know, everybody's intimidated and, you know, has to go through that. But I think more so for the women also, there's more obligations that the ladies have to do through parenting and all of that stuff. And so the other thing is, I think that's what makes you guys so good in business is because, first of all, the moms have an instinct that's frightening. And you know what I'm saying? Like, if your kid does something wrong, you know, they think they can hide it.

Oh, hell no. Women's intuition is the strongest force on the planet, which is why the patriarchy is so afraid of it. Because if we actually listened to our intuition and believed our gut instinct, extinct, like we would take over. But yeah, you're right. Women's unpaid labor is worth $10.9 trillion every single year. And so part of the, the writing of this book and the act of my life on the other side of 40 is reclaiming some of that unpaid labor that I pour into society, reclaiming it for myself. How am I going to choose myself first? How am I going to prioritize what, what I need? And do things like this that are necessary. I mean, Larry, you got to buy this book for that toxic family member.

That's fantastic. Now let's do this. Let's pull a highlight or two or three to wrap up the public part of this interview. Let's pull a couple of choice bits from the book. And, you know, just as a wrap-up, quick wrap-up here, kind of a final word for everyone. Let's, you know, and also let's mention, because I want to talk more when we get into the locker room portion that we do for our community, what, you know, what you— the podcast. I want to hear about the podcast and, you know, how that's evolved. And so let's talk about that later. But right now, what can we take away as a final word here from the book and kind of anticipation? It's available on Amazon as we speak.

It's available wherever you want to buy your books. And Amazon, Amazon is definitely one of them. I feel, I feel called to this chapter for you, Larry Weidel. Main fucking character energy. Okay, so, so I'll read you the first page of this chapter. "If you don't stand for something, you'll fall for anything." This quote was attributed to Alexander Hamilton, but let's be honest, it was probably a woman who said it without being credited. Regardless, regardless, it stands the test of time. Nike went on to use an iteration of this in a campaign in 2018 celebrating the 30th anniversary of Just Do It. The ad featured professional football player and civil rights activist Colin Kaepernick. Best known for taking a knee during an NFL game's national anthem to protest social injustice and police brutality. In white font, overlaying a black and white zoomed-in full-bleed photo of Colin's face looking directly into the camera, are the words, "Believe in something, even if it means sacrificing everything." But what if we took it one step further? What if we shifted the focus from the "something" that Hamilton and Nike reference in their messages and we turned it directly to you. Let's try it. If you try to be liked by everyone, you'll be loved by no one, least of all yourself. Right? And so this goes back to everything we've discussed here, which is if you believe in something, if you believe in an idea, if you believe in yourself and you wait for everyone to agree with you and to support you, you will go nowhere because you have got to release the control and the desire to have everyone on your side. It's not going to happen. So for the things that you believe you are here to do, you have to push through that discomfort of not having this crowd hyping you. And, and you have to, you have to just trust that your intuition and your instinct is leading you in the right direction.

It's easier to do that if you understand the process of life. And the process of life is you get a great idea, you wanna raise your head up and go do something great. Everyone tells you you're an idiot, it won't happen, especially if you have in-laws, they really tell you you're an idiot, you know? And, but then you keep your head down because you really don't have any other options. You can't escape from yourself. And then years later, you have this incredible success And then these same people come in and say, what, I knew you were gonna do it from the beginning. We used to talk about, you know, how great, you know, you had something special.

And you know, it was like, you're like, that's funny. Cause this text message says otherwise. I've got the receipts of who's invited to the party. Yeah, that's right.

That's right. Unbelievable. Thanks so much, Erin. Looking forward to checking back in with you down the road and hearing about your next book and the success of this one.

Thanks for having me, Larry.

All right. Thanks so much. That's it for this episode. If this resonated with you, do me a favor. Share it with someone who's ready to level up. Winners find winners, and the right conversation at the right time can change everything. Want to go deeper? Join us inside the Big Hitter community. Me at joinbighitters.com. That's where the real work happens. And if you haven't already, subscribe so you don't miss the next one. Remember that you're either growing or dying, and there's no standing still. Keep winning, and I'll see you next week.