Trust your gut - literally. Take a risk. Two philosophies that define Carrie Kerpen's career, family, and life. Listen in to hear how.

Learn more about Carrie at carriekerpen.com.

Podcast Transcript:

Julie: 00:01 Hello. I am here today with the fabulous Carrie Kerpen. Carrie is the co-founder and CEO of Likeable Media, a digital agency that was named Crain's sixth best place to work in New York City. A serious accomplishment in this city. In recognition of her work championing change in the advertising industry, Carrie was honored by the inaugural campaign US Female Frontier awards. She is also the author of Work It: Secrets for Success From the Boldest Women in Business. And a little side note there, I'm happy to say that over again because I was one of the people interviewed in it. So I will say it again. Work It: Secrets for Success From the Boldest Women in Business. She's also a columnist for Inc and Forbes. And she's been featured all over the place in New York, to the New York times, ABC world news tonight, Fox news, and CNBC, and she's keynoted conferences literally all over the world, in all the major markets. And she is, in and of herself, a powerhouse, and just a huge agent, not only for women in business, but I think, small businesses in general.

She and her husband Dave, have done a ton of work together. And I promise this is going to be a fascinating podcast because she has lived an extraordinary life. So thank you for being here, Carrie.

Carrie Kerpen: 01:22 Thank you so much, Julie. And as you know, I'm a huge fan of yours and thrilled to be on the podcast today.

Julie: 01:28 Thank you. Well this is fun. So, as you know, this is a passion project. And my goal is to try to get people's backstories because all that I just read is typically what people see. But there's so much that goes on behind the scenes and I think your history, your how you grew up, and those things that happen to you, are fascinating. So tell me a little bit about your childhood. Where are you from? What's your family like?

Carrie Kerpen: 01:54 So I grew up in Queens, New York, and it was an incredible experience. Queens is the most diverse County in the world. And so I grew up in a thriving, diverse urban atmosphere and loved it. I had two parents who were government employees. My dad was a judge, and my mom worked for the Board of Ed and for special education. So I'm not exactly sure where I got my entrepreneurial bug because they were not risk takers. But grew up in an awesome in Queens working class. Great.

Julie: 02:33 Interesting. So you had these like, to your point, but very conservative, but I have to believe that, we're similar age, but growing up in New York,-

Carrie Kerpen: 02:43 Yes.

Julie: 02:45 Even though your parents might've been more conservative, you can't help-

Carrie Kerpen: 02:48 They were risk averse. My parents were risk averse. But they always encouraged me and believed in me. And so when I was in New York and watching all of this incredible, I remember when I was a kid I used to watch like Secrets of My Success or Working Girl or any of those things. And that's totally what I identified with. The kid who wasn't expected to necessarily thrive in business, who really wanted to.

Julie: 03:13 Right. And so being, I was, look, I was a Midwest kid so I lived in the, not necessarily idyllic, but what you kind of envisioned, the neighborhoods. Your neighborhood far different than what I grew up in, and I have to imagine that being a city kid you learned to be independent. So to your point,-

Carrie Kerpen: 03:34 Yes, yes.

Julie: 03:35 You know,-

Carrie Kerpen: 03:36 Took the subway at 11 years old to school. The streets were the playground and it was a very New York City experience. But a borough experience. It wasn't a fancy New York City. There was no private school or any of the things you see in Manhattan. It's like a different world in the boroughs. The boroughs is a real gritty New York experience, which I loved.

Julie: 04:02 Yeah. Is it like Welcome Back, Kotter? That's what I think-

Carrie Kerpen: 04:06 It's totally like Welcome Back, Kotter. Welcome back, Kotter is actually based on Hunter High School, which is where my husband went to school.

Julie: 04:13 Oh, your kidding.

Carrie Kerpen: 04:14 No. Yeah, it was exactly, actually, it's exactly like Welcome Back, Kotter.

Julie: 04:16 So as a kid from the Midwest,-

Carrie Kerpen: 04:17 Yes. Mr. Kotter.

Julie: 04:17 ... it was that,-

Carrie Kerpen: 04:17 Yes. Totally.

Julie: 04:17 ... Laverne & Shirley.

Carrie Kerpen: 04:17 Yes. Yes.

Julie: 04:17 These were the-

Carrie Kerpen: 04:24 Yes, that was my experience. Welcome Back, Kotter.

Julie: 04:24 That's hysterical. So, I've talked about the fact that I always think that there's these holy shit moments that happened, or [hoshimos 00:04:33]-

Carrie Kerpen: 04:33 Yes.

Julie: 04:34 ... trying to shorten it, that happen to people that basically form either who they are or informed their careers, their life, et cetera. You had a very interesting one at a very young age, sort of linking into that independence thing. Will you share a little bit about what happened to you when you were 14?

Carrie Kerpen: 04:53 I will. I was 14 years old and I woke up in the morning with horrible, horrible stomach pains, like awful, awful. And my mom took me to the equivalent of an urgent care or one of these places. And they were like, "Oh, it's gastritis. She basically just has a bad stomachache."

 And I came back home and I was like, "Mm, I don't think I have a bad stomachache. I think something's really wrong." And it kept going. My parents sort of were like, "Really? Are you sure you need to go to the hospital?" And I was like, "No, I need to go to the hospital." And so they took me in the hospital. They were concerned but not really. But I was, at 14. And I went and they did a variety of exams. And then they said, "We really can't find what's wrong but you seem to be in a lot of pain. We're going to give you two options. You can wait. We don't have an available CAT scan. It will be about four hours. Or we can do exploratory surgery. It doesn't appear to be your appendix. We're not sure, but we can just kind of open you up and see what happens."

Julie: 05:57 That seems crazy to me.

Carrie Kerpen: 05:58 Crazy,

Julie: 05:58 Exploratory.

Carrie Kerpen: 05:59 Crazy.

Julie: 06:00 We don't know but let's just cut you open.

Carrie Kerpen: 06:02 It could be a cyst, it could be this, but we want, you're in a lot of pain, we want to get you in. And I remember at 14, sitting there and saying, "Okay, let's go." Now this is the kid who never had a blood test in my life. I mean there were no needles, no nothing. I mean I was a kid.

Julie: 06:18 Were your parents there?

Carrie Kerpen: 06:18 They were there. They were there. They were trusting me at that point. I mean it was, it was intense, intense pain. So I ended up going into surgery. My parents thought it was going to be a couple of hours. Because they thought it was either a cyst or something related to that. They couldn't fully tell. And it ended up that I had a tear in my intestine. And they had to remove, I think it was about eight to 10 feet of small and long intestine that they had to remove. And it was major, major surgery. I remember my mom always tells the story like she was there two hours. All of a sudden it was six hours. All of a sudden, just waiting, waiting, waiting.

Julie: 06:53 She must have been-

Carrie Kerpen: 06:53 Yeah.

Julie: 06:54 ... as a mother, right?

Carrie Kerpen: 06:55 I cannot. When I think of the story now, as a mom, I just really shudder. But so it ended up being that if I had waited, I actually would have died.

Julie: 07:06 For that CT, that four hours.

Carrie Kerpen: 07:08 Yes. If I had waited four more hours. It was an emergency, emergency surgery. And so what that hoshimo would be was, when it matters, the person that you have to trust is yourself, and you have the answers within you. For me, especially with parents who are not risk takers, I was, I had never had any kind of surgery or anything like it. Never a medical complication in my life. Never an allergy. Never a bee sting. To make that choice was kind of crazy, but my body knew. And so I always like to say that was the first experience of trust your gut because it was trust my literal gut.

Julie: 07:46 Literally.

Carrie Kerpen: 07:46 My literal gut. I had to trust. And so yeah, that was the first, my first encounter with understanding that you have to be able to depend on yourself.

Julie: 07:54 Oh, well, okay. So I want to skip forward because I want to get as much as I can because you've got such, your track has been so unusual, and as a self-starting co-founding of a big company-

Carrie Kerpen: 08:10 Yep.

Julie: 08:10 Fast forward now. So through school I'm going to move you to you were already working, in the working world. So how did you, now you've got this bug and how did marketing become a bug for you? Where did that-

Carrie Kerpen: 08:25 So I knew in school I want it to be a marketer, and I started on a pretty traditional marketing track. Until somebody, who I had had an internship with at Disney, came back to me and said, "You know, you'd be really great in sales." And I was terrified to try sales. Especially because with sales you really control your own income, for better or worse. If you don't, you can't hide in sales. You either make the numbers or you don't. And if you make them, you can be compensated really well. And if you don't, you don't have a job.

Julie: 08:51 Right.

Carrie Kerpen: 08:52 So I tried. I took the risk to do that because I thought might be okay at it. And I ended up being really good at it. And that started a career in media sales. And then I didn't leave that until I launched my company with Dave.

Julie: 09:05 So how long was that, that you were doing that?

Carrie Kerpen: 09:09 How long was I in sales?

Julie: 09:10 Yeah.

Carrie Kerpen: 09:10 I was in sales for about five years.

Julie: 09:10 Oh my god.

Carrie Kerpen: 09:13 And I got to sales manager. Yeah, it was great. It was great.

Julie: 09:15 But five years and then you were like, "I got this, I'm moving on." What was the impetus to then leave and do your own thing?

Carrie Kerpen: 09:22 Well, my husband and I had been dating. We had worked together. We were in sales and we competed against each other actually.

Julie: 09:28 Fun.

Carrie Kerpen: 09:28 He was, yeah, he was the number one salesperson in the country at Radio Disney. And then I dropped into number two.

Julie: 09:33 Until you got there. That's right. You go, girl.

Carrie Kerpen: 09:35 So that was it. That was always a fun part of our story. But when we wanted to get married, he wanted a large wedding. Really, really larger than life.

 And I had already been married and divorced. I had a starter marriage, failed miserably in two years. Big wedding, short lived marriage. So I knew there was no way, I wasn't going to ask my parents to pay for a second wedding. And I wasn't going to be able to afford the type of wedding my husband wanted.

 So we had to get really smart. And so we came up with an idea to get married on a baseball field. And we went to a minor league park. We pitched them. We said, "We're going to call the night Our Field of Dreams. We're going to sell in sponsors to your game. Instead of Pepsi tossing t-shirts in the audience, 1-800-FLOWERS will toss bridal bouquets. It'll be amazing. We'll get married on the field afterwards. We'll raise money for charity."

 And this was another real hoshimo where we were like, "Oh my gosh, we could really do this." We did. This was while I was now leading a media sales team. And we got the sponsors all of this press. So it was a huge success. Both because we were able to raise $100,000 for the wedding of our dreams, raise $25,000 for charity, and got all of this press.

Julie: 10:41 Oh my gosh.

Carrie Kerpen: 10:42 And so all of the clients, all the sponsors came to us and were like "We would bet on you guys. This is a cost effective, amazing promotion." So we came up with the idea to start a word of mouth agency, but I still wasn't ready to leave. Because it's a big risk to start, when you start your own company. It was only, when I really took the chance to leave was when I was commuting out to that media sales management job. And I had my daughter at the time, and I was dropping her at daycare and she looked at me and she was like, "Don't go." And I just felt like, "Okay, I won't." Something came over me that gave me the confidence. It wasn't even this huge event that I had that was so successful. It was the discovery that I really just wanted my own freedom to choose my time, how I spent my time.

Julie: 11:28 So when you, this three year old and I-

Carrie Kerpen: 11:31 Yes.

Julie: 11:31 Look, I know you have children.

Carrie Kerpen: 11:31 Yes. Yes.

Julie: 11:32 I have two boys and I was a working mom, like you. And I definitely had those moments where the kids were crying and you'd drop them at daycare. And luckily then my husband decided to stay home, which was great. But I remember those tugging moments. But, and I have to imagine that this wasn't the first time she was like, "Mommy don't."

 What was it about? And I know it wasn't anything grand, there wasn't lightning and stars. But what was it about that, there must've been something else going on with you as a combi, is my thinking,-

Carrie Kerpen: 12:05 Yes.

Julie: 12:06 ... that made this like,-

Carrie Kerpen: 12:07 Yes.

Julie: 12:07 ... this is what I have to do.

Carrie Kerpen: 12:09 It wasn't such a mom guilt moment. When I tell the story, people always say like, "Oh, you wanted to be a stay at home mom. That's amazing. Look at this fairy tale story." It wasn't that. It was that what I realized was that when I worked for somebody else, my time was controlled by somebody else. And I wanted to own my time. And that was the thing, as an entrepreneur, that has stuck with me for the rest of my life, was that I wanted to own how I spent my time. And it wasn't that I didn't want to work. It was that I wanted to work on my own terms. And I wanted to be able to take her somewhere when I wanted to. I didn't want to have to drop her off for early am, I wanted to drop her off at this time. Or I wanted to be able to do something, go to her recital or whatever it was. And I wanted the freedom of time. And that was a big hoshimo for me.

Julie: 13:02 So you made this decision, sort of on the spot,-

Carrie Kerpen: 13:04 On the fly, like a nut.

Julie: 13:05 Okay.

Carrie Kerpen: 13:06 Yup.

Julie: 13:06 Like I'm-

Carrie Kerpen: 13:07 Walked in and gave notice. In a minute.

Julie: 13:10 Really?

Carrie Kerpen: 13:11 Gave notice. You know why though? Because the thing with the wedding was, I knew people were willing to take a chance on us. I wasn't willing to take a chance on myself, until I had that light bulb moment.

Julie: 13:20 So you were holding yourself back?

Carrie Kerpen: 13:22 I was holding myself back and then once I removed that layer, once I had that realization, that it was actually me that was holding myself back. And once I nailed the desire, which was, the desire was I want to control my career and my time. Once I had that, it was limitless.

Julie: 13:40 So did you do this with Dave, or did you call David, and are like, "Hey, guess what I just did."

Carrie Kerpen: 13:45 I called Dave. So here's the thing. At the time, Dave had become a teacher. He had gone back, he had an education degree and he's had many different careers. And he wanted to, at the time, he wanted a job that felt really stable, and secure, and something that was a passion for him. So he went back to teach. And so I called him. So I made a lot more money than he did at that time. As a middle school teacher, he wasn't making a ton.

 And I called him and I was like, "Do you think that we're crazy if I do this?" And he, who is the biggest risk taker of all time, was like, "No, of course not. This is what we want. This is great." And so I started, and I just started consulting. And then summer hit and he was like, "I think we could scale this." Started getting really like, "We can make this huge." And I was like, "Okay, go get us three more clients and then you can leave too because we'll be able to afford health insurance." Because basically the teaching was for the benefits.

Julie: 14:35 Sure.

Carrie Kerpen: 14:36 And so he did. And then there we go. And then that was it.

Julie: 14:39 And Likeable Media was born.

Carrie Kerpen: 14:42 That's how Likable Media was born.

Julie: 14:44 Okay. And so I have to ask this question because I know all about Likeable Media. I know what you do. I know the guts of that.

Carrie Kerpen: 14:44 Yes.

Julie: 14:50 But now hearing your story, have you set up the working environment at Likeable to be that which you were seeking when you made this choice?

Carrie Kerpen: 15:02 Yes, because it was my exact motivation for starting a company was to be able to-

Julie: 15:05 I kind of was setting you up to because I didn't know the answer. So this is-

Carrie Kerpen: 15:07 Yeah. I think that's why we win Best Places to work in these things. Because I'm so focused on giving people control over their time. So it's very interesting. We do things like, we have unlimited PTO, but we also have minimum PTO. Because unlimited PTO can really be a farce because what it does is discourage people. If you don't have parameters, you feel guilty taking it. So we have a minimum, you have to take at least this much time off, and then you have unlimited. We have a variety of different benefits and things that we do to make sure that people have their time. Great work from home policies and all of that. And that was something that was very, very important to me.

 Early in my tenure, actually when I took over from Dave, so Dave was a CEO for several years. Then we launched another company and I took over. And I was struggling to find a vision for the company because I was so focused on creating a work environment that was incredible. Where the company would go, felt secondary to me, to how the employees would feel. And that was something I had to learn to balance over time. I had to, because I was more of an operator and more focused on the people.

Julie: 16:15 Obviously you've got a quite a few of these hoshimos in your life. But this one is obviously driven decisions for your career, and your family, because your career was informed because of your family. And then this career that you've chosen, you've embedded that family consciousness.

Carrie Kerpen: 16:32 Yes. It's all linked.

Julie: 16:33 And so I have to imagine that, now I'm going to move over to your book and some of your, I would love for you to talk about what you're doing. Really tell people what you're doing, but what the why is. I'm very curious as to where the bug then came on, like women in business and the book.

Carrie Kerpen: 16:50 For the book.

Julie: 16:51 Yeah. The whole, obviously you're inspired because it's not just the one book. And this isn't just a plug for your book. Because you do, I follow your videos. You're interviewing the most amazing women.

Carrie Kerpen: 16:51 Yes.

Julie: 17:02 And you're doing it to give them a platform.

Carrie Kerpen: 17:04 Yes.

Julie: 17:04 You're not selling your agency capabilities in those.

Carrie Kerpen: 17:09 Not at all.

Julie: 17:09 It's literally just spotlighting these amazing women.

Carrie Kerpen: 17:12 Yes. It definitely benefits me as much as, or more than in some cases, than it benefits them. What happened was we started an agency in 2007 around social media. At the time, nobody was doing that.

Julie: 17:12 Right.

Carrie Kerpen: 17:30 So we grew and that, at that time, we grew,-

Julie: 17:33 When was Facebook? When did Facebook start?

Carrie Kerpen: 17:34 Facebook opened beyond the college market in 2007. So we were right there. We were with them. So we started growing and growing and growing, and it was fast. And then we started to flat line. You'd grow just a little bit, a little bit, little bit.

 And then Dave launched a second company. We've decided we wanted to launch a software startup. And so we launched that and I became CEO. Now in 2013, when I took over, it was a very different world and a much more crowded landscape. Most of the leaders were male thought leaders who were on social media all the time. And this is not how I felt about myself. And so, at that time, what I decided to do was start an interview series and talk to other women in my industry. And I thought that would help me build my network. It would help me add value for them by telling their stories. And it would really, ultimately, I felt lead to business without selling. I know you, you know so-and-so, let me introduce you.

Julie: 18:32 Right.

Carrie Kerpen: 18:32 Just creating a large network and being able to tell the stories of women. And what happened was, it did work. I doubled the size of the business, but I also just fell in love with the stories of women. And I fell in love with the fact that two women could end up in the same place, with totally different philosophies of how to get there. So there's no one right answer. And so I wanted to highlight as many different stories as possible.

 And that became a passion project. And then what I did was take that passion project, and produce it using the agency. So if I say like, "Oh, I produced this show." So I wrote the book and then I produced a show that airs on Facebook Watch. Well, we produce shows that are on Facebook Watch all of the time for the agency. So it's a good case study and example of what we do, and also taps into a passion project, and builds the network.

Julie: 19:22 So another, I'm springing questions on you out of nowhere. So as you've done this now, I have two questions. So first when you got started, how did you decide on your subjects? How did you say I'm going to reach out and try to get this person?

Carrie Kerpen: 19:39 So first I went really niche. So I said, "Okay, the podcast is called All the Social Ladies. And I'm going to interview social media managers and directors." So because I knew, at that time, I didn't yet have a credibility to interview a C level executive, or anything like that. I wasn't yet there. Although I will say, that in this world, everyone is accessible. And once you get over that fear, you really can reach out to anyone. But I started by interviewing social media managers and directors, which was very targeted for the podcast that I did.

Julie: 20:08 Yeah.

Carrie Kerpen: 20:09 Which was great because we did social media at Likeable, so it all worked. Then I started writing for Forbes, and I asked them if I could do an interview series with video, because I liked video and thought I was good at it. They agreed. I started doing that. That's where we met.

Julie: 20:21 Yeah.

Carrie Kerpen: 20:22 I started broadening my base of who I interviewed. And then I was approached to write the book. And at first I was like this is not really on focus for me because it doesn't directly link to the agency. But then I realized that sometimes things don't have to directly link. As long as you're passionate about them and you feel that it's time well spent.

Julie: 20:42 Right.

Carrie Kerpen: 20:43 And so from that I was able, when I wrote the book, I just started, by that point I had credibility, I reached out to everyone and-

Julie: 20:48 Yeah.

Carrie Kerpen: 20:49 So I had people, [Sheryl Sandberg 00:00:20:50] and [Barbara Corgrin 00:20:50] and a lot of these incredible ones.

Julie: 20:52 Oh, no and this was, so this is,-

Carrie Kerpen: 20:54 And you, of course.

Julie: 20:55 Oh right. I'm was certainly the highlight of your,-

Carrie Kerpen: 20:57 Yes. Your story's amazing though. So it is a very good story.

Julie: 21:01 Well thank you. But you're, so that aside, what is the most, what story, I don't want to say what's the most interesting one? Which story has had the greatest personal impact on you?

Carrie Kerpen: 21:16 It's a simple story, actually. It's from somebody who used to work for me, who was then heading up marketing at ClassPass, which is the startup for boutique workouts.

Julie: 21:16 Okay.

Carrie Kerpen: 21:26 Okay. So you subscribe to ClassPass, you can go workout in any of the the boutique shops. Okay. So she talked about when she was negotiating, and when she was first learning how to command a higher dollar, a higher position, about using the mental mute button. Which means that you, if you are on the phone with somebody and you say, "Well this is the salary I require." or "This is what I'm looking for." You could actually put them on mute. But when you're looking across from somebody, don't underestimate the power of silence. And actually feel yourself putting yourself on mute.

Julie: 21:59 Oh my god.

Carrie Kerpen: 22:00 And it's such a small tip. It's my favorite story in the whole book. It's just, and she talks about how she did it to negotiate for her job, but I use it all the time. I use it in supervisions with people who work for me, and I say, "And what do you think we should do in that situation?" And I'm like, "Mental mute." Or I do, I use it with clients. I use it all over. The power of silence, and just by calling it a mental mute button, it allowed me to visualize turning a switch.

Julie: 23:52 Because I think it's just human nature to want to comfort, create a comfort, and try by just rambling.

Carrie Kerpen: 23:59 Also what has damaged that and the reason that has to be taught so much with kids today, is because of texting and messaging. You just can't stop.

Julie: 24:07 Yeah.

Carrie Kerpen: 24:08 It's like diarrhea of the mouth via text. They just, it's like everything they feel they text. And then it's like, "No, actually don't say that." And then there's a written record of it. So you don't want that. Yes, I have a junior, so I'm right there with you.

Julie: 24:22 Don't post anything that [crosstalk 00:24:23].

Carrie Kerpen: 24:23 Yeah. Stop it. Oh, stop talking, stop talking.

Julie: 24:25 Which is the height of irony for a woman who runs a social media agency.

Carrie Kerpen: 24:31 Don't even get me started. I work with the Family Online Safety Institute for parenting in a digital age and I do all of that stuff. That's basically to relieve my guilt of all of the social media, of the children in the world. And I mean it's different, but we working on brand stuff is a little different, but it is, it's challenging. It's definitely challenging when you see the impact. I don't think anyone could have imagined the impact that social media has had today. If we looked back in 2007, when we were starting. It's wild.

Julie: 25:02 It's crazy.

Carrie Kerpen: 25:03 Wild.

Julie: 25:04 It's amazing. Well, you have been fabulous. I knew this was going to be super fun. And your story is so inspiring, so thank you.

Carrie Kerpen: 25:13 Well, thank you Julie for having me. It was a pleasure.

Julie: 25:16 My pleasure.

Carrie Kerpen: 25:16 It was a pleasure. I love hoshimo. I'm going to use it all the time.

Julie: 25:16 You like it.

Carrie Kerpen: 25:19 I'm going to tell my staff.

Julie: 25:20 Hash tag hoshimo.

Carrie Kerpen: 25:21 I'm going to hoshimo it. Yup.

Julie: 25:23 I think we're going to have to make tee shirts.

Carrie Kerpen: 25:24 We do. We do. You need hoshimo tee shirts.

Julie: 25:27 Well, you're the expert.

Carrie Kerpen: 25:28 Yes.

Julie: 25:28 So you need to help me.

Carrie Kerpen: 25:29 Oh please. We need to, yes, we have to write about hoshimo.

Julie: 25:29 Okay.

Carrie Kerpen: 25:34 For sure. For sure.

Julie: 25:34 Thanks so much.

Carrie Kerpen: 25:35 Of course.