183 Carrie Kerpen: Work It To Crush It

Entrepreneur and CEO of Likeable Media Carrie Kerpen shares her badass secrets for women who want to crush it in business. Carrie has built a successful business around HER life, rather than building her life around her business. Author of Work It: Secrets For Success From the Boldest Women in Business, Carrie shares her go-to advice ond ‘work-life integration’, alignment, and how women can be their boldest, badass selves.

Melinda Wittstock:         Carrie, welcome to Wings.

Carrie Kerpen:                  Thank you so much Melinda. I’m excited to be here.

Melinda Wittstock:         It is great to have you on and I’m so intrigued always with what was the a-ha moment that made you think, yeah I’m an entrepreneur? I’m going to go, you know, start a company, build a business?

Carrie Kerpen:                  Gosh, Melinda, it’s an interesting question because ultimately I think I’m always envious of these entrepreneurs who are like, “This was in my bones since I was three and I knew I wanted to be an entrepreneur and I’ve got the spirit.” And for me it was a little bit different. You know, my husband and I decided to get married in a sort of a … I mean it was a fabulous wedding but it was also a bit of a publicity stunt. We were married on a baseball field in front of 8000 people in a sponsored wedding that raised money for charity and got international and national press. So this was like an idea we had to help get our wedding paid for… that turned into this big marketing thing and our sponsors were very pleased with the press and they came to us and said, “You know, this was so great. Would you do it again?” We were like, “Uh, can’t get married again. Not going to have a sponsored baby. No sponsored divorce. Okay I guess we’ll think about starting a company.”

And we kind of thought about it for awhile and I was afraid to take the risk. My husband had a good job with good benefits. Wasn’t prepared to leave at that time. And so I had a great job too but it was ultimately the thing that pulled the trigger for me was that my commute was really long. My daughter was really not getting a lot of time with her mom. I was driving very far to work, coming home very late and I realized that ultimately if I only had a little bit of confidence in myself, I could start a business tomorrow and get the time and flexibility I desired.

Carrie Kerpen:                  So a lot of entrepreneurs go for the brass ring. They’re looking to build unicorn companies, they raise funds, they want to make lots and lots of money and I think ultimately, for me, it was much less about making a lot of money or building a huge company and much more about freedom of time and ultimately when I was able to build a company and the company took off and did start to grow, I ended up working harder than I’d ever worked before. But I felt like my time was my own. So I guess the way I learned I was an entrepreneur was understanding that I valued my freedom of time above everything else.

Melinda Wittstock:         That’s really beautiful because so many of us have a tendency to go create businesses that enslave us rather than businesses that support us. Right? What is the business that’s going to allow me to live the life I want rather than what’s the business that I’m just going to end up being an employee like of my own business? And it’s an interesting distinction because you can start to become a slave to your business rather than the other way around.

Carrie Kerpen:                  I think there’s a whole stigma around that you have to hustle non-stop. You’ve got to hustle, hustle, hustle. If you look all around the Internet, all you’ll see is people saying, “Hustling 24/7 to make my business grow.” But I think ultimately if you come at it with, what is the life I want? Who am I authentically as a human? What do I have to offer to the world and how can I build a business on my own terms? I think you’re going to find much more success that way and abandoning the perception that you need to be like everybody else in doing this.

Melinda Wittstock:         Well all too often, I think we all can fall into this trap of living a life of should’s. It’s all the things that we’ve been brought up with … some of it’s conscious; some of it’s unconscious. We’re social media 24/7. We hear all those stories about the hustle and the way it’s done. And we end up turning ourselves into pretzels trying to be like other people rather than just being like ourselves. And I think it’s so true that when you do step into your authenticity as a person and you’re doing something that’s aligned with your purpose or your talents, whatever, it’s easier. It’s so much easier.

Carrie Kerpen:                  Yeah it doesn’t feel like work right?

Melinda Wittstock:         It doesn’t feel like work. It feels like flow. It’s kind of like this podcast. It’s just, it’s easy. It’s flow, it’s fun. I mean it doesn’t feel like work. Not at all. Totally natural. And then there have been other businesses I’ve done certainly that have felt like this Sisyphean thing, like literally pushing the boulder up a mountain. And I’ve caught myself in the should’s by literally listening to myself. Listening to how I talked to other people. A couple of businesses ago, I was like, “Yeah I should do this.” I should, should, I should. And someone said to me, “Why should you? You’re an entrepreneur. You can do what you want.”

Carrie Kerpen:                  Yep, yep I agree. I think should is a very damaging word in our vocabulary especially for women who are so much more open to feedback. Men don’t care what other people think they should be doing, they just do it. And for us, we’re always worried about what others think and I think that that’s very powerful once you can abandon the concern about what others think.

Melinda Wittstock:         Well this is true. So on one hand it’s really great for an entrepreneur to be coachable but on another hand, they can be easily over coached to point where they lose themselves. I’ve seen that happen to a lot of female technology entrepreneurs like myself who depending on which investor you last spoke to, your business model should be completely different. And never mind that this person doesn’t know you, doesn’t know your market. Even isn’t necessarily as smart as you are. But we’re more likely to take all that to heart.

Carrie Kerpen:                  Yeah I think ultimately especially. Yeah if you’re raising funds… Forget about it. You want to talk about learning how to deal with rejection? Go try and raise funds. Because what you’ll have is every different person has a different opinion of what you should be doing with your business. You end up feeling totally confused and stressed unless you have complete and total confidence and real passion and commitment to your own vision. And I would write your vision down everywhere you can just to remind yourself, as a reminder. It’s a key important piece of the puzzle. And don’t let them break your stride.

Melinda Wittstock:         And so, it’s so important obviously to know yourself and also know where you’re going, know what you want. Do you, like a lot of entrepreneurs I know, do visualizations or vision boards or meditation or sort of like imagine yourself where you’re going to be as if you have that thing right now?

Carrie Kerpen:                  Well I’ve never very good at things like meditation. So, for me, the quiet time that I take to get in touch with my gut is done when walking, is done just sitting. I don’t do anything formal with meditation but I do believe that meditation is important to the future of our collective wellness. So I would like to be better at it. And certainly focus on getting quiet time with myself. That being said, in terms of visualizing, I’m really big on setting goals and writing them down and being accountable to them, even when I miss. Just being able to look at the goal, whether or not I hit it or miss it, having it there in front of me, having something that inspires me is key.

For instance, an area … and I think it’s different for different things. An area where I struggle all the time is maintaining healthy eating and fitness … all the time. I mean it’s a big struggle for me. So, in the gym where I work in my house, I have a home gym … I have all of these not only motivational quotes but actual pictures of myself over time. And being able to have that accountability is what keeps me in check. So I think there’s … I use that stuff for accountability versus future visioning and I use quiet time with myself to really channel my gut to get in touch with what I want in the right now.

I don’t believe really that the five-year plan or the ten year plan and all of that stuff. These are not things that I focus on because I think things change so quickly that we can’t always project that far out.

Melinda Wittstock:         That’s really true because so much of the entrepreneurial journey is just dealing with the unexpected and what you’re going to do in the moment that you have something unexpected happen. How do you react? And I suppose if you really do … you mentioned your gut feeling … if you really do know yourself and you know where you’re going, you have a much better chance of reacting to that in alignment or in authenticity with who you are. So your reactions are going to be better. In a way, I think that’s where true confidence comes from. Is just knowing that whatever happens, you know you’re not getting blown around in the wind … like you know who you are, you know where you’re going so you can trust your reaction even if you’re missing payroll that week or something like that.

Carrie Kerpen:                  It all ties back to the understanding of self.

Melinda Wittstock:         Yeah, it’s really true. A couple of times now, on this podcast, I found myself saying that entrepreneurship is therapy. It’s like the shortest, fastest way to personal growth in a way.

Carrie Kerpen:                  Entrepreneurship is therapy. I think, yes, one might say all entrepreneurs need therapy. For sure.

Melinda Wittstock:         They’re related.

Carrie Kerpen:                  We definitely need a little therapy. Right.

Melinda Wittstock:         Well they’re related … I think I come to this conclusion because I just in my own journey with … I’ve just always been entrepreneurial but with every step of the process you come up against a new challenge and how you react to it often, there’s so much learning all the time. I guess. And there is some introspection. There’s certainly, a lot of it’s humbling. But I found that it’s really kick started a process for me, anyway, around personal growth and interest in things like meditation, which in turn helped me as an entrepreneur. So when I started out … you mentioned meditation and that it wasn’t your gig … I was terrible at it all my life.

Carrie Kerpen:                  Oh good. Maybe you’ll help me be better at it.

Melinda Wittstock:         I don’t know. I really sucked at it. Really, I could not just quiet my mind to save my life and … but I started in a gentle way … first by doing yoga, walking the dog, having silent time and then I just got more practice … it’s just like anything, you know, just more practiced at it. And trying to get myself out of judgment with it whenever my mind like would override …

Carrie Kerpen:                  And go somewhere.

Melinda Wittstock:         Yeah because I’d start thinking about the product or I’d start thinking about my kids or anything but quieting mind. And learning how not to judge myself was the important thing there.

Carrie Kerpen:                  Wonderful, wonderful. Yes I think for me I did use Headspace a little bit but you’re definitely inspiring me to get back into my attempts at meditation practice for sure.

Melinda Wittstock:         Well you know …

Carrie Kerpen:                  I do. I think meditation is like therapy actually. You could do a whole s     how on why we all need to meditate. Because that’s pretty good.

Melinda Wittstock:         But, does this happen to you in your business as well? I find with mine that all my best ideas happen when I’m not working.

Carrie Kerpen:                  Oh my God, the shower. I talk about this all the time. My best ideas only come to me in the shower. I’m basically useless unless I’m in the shower. I like to say, although far more controversial, I often like to say my best ideas come to me when naked. Because it’s really true. It’s when I’m actually naked meaning stripped down from not in the day-to-day of the business. Not doing anything else. Because it’s quiet time! It’s away from your phone. It’s away from electronics. You’re able to really just think. I think that so much of what hinders us is about a lack of time to actually think.

Melinda Wittstock:         Yeah I’ve gotten so radical about this now that I’ve actually put quiet time in my schedule. I don’t always stick to it.

Carrie Kerpen:                  Good.

Melinda Wittstock:         Sometimes I like over-ride it.

Carrie Kerpen:                  See I’m more flowy. I’m more flowy. I need like a little. If I schedule quiet time then I feel forced. But if I just allow the quiet time to happen, like the shower or I’m taking a walk, then it has to be organic for me. But I think it’s very interesting. Maybe I will try that and learn to schedule it in.

Melinda Wittstock:         Well the only reason I try and do it is because I am such [crosstalk 00:24:30]

Carrie Kerpen:                  Otherwise you won’t get it right?

Melinda Wittstock:         Yeah, well I’m such a people pleaser. I want to make sure that … literally it’s like the hostess with the drinks tray. Like everybody else … make sure everybody else has a drink and then sometimes you can be left with nothing left for yourself. Or no way to replenish or your creativity is gone because we’ve been so busy making sure that everybody else is okay. So, as a metaphor, if I apply that to myself with the quiet time, if I don’t block out my schedule so nobody can book me at that time or nobody can bother me, I just know myself. I know that I’m more likely to just keep giving to the point where there’s nothing left for me. And that’s one of those kind of personal growth realizations that has come along with my entrepreneurial journey.

And just knowing to do that… Like Sara Blakely, she talks about all her … from Spanx … she talks about all her ideas when she’s driving.

Carrie Kerpen:                  Yeah I think driving is another great team because hopefully you’re not using technologies. Anytime we are not distracted, it helps you just think freely. It’s key.

Melinda Wittstock:         So I want to ask you a bit about your business? Because I know you got an award recently. I mean you’re Crains’ number sixth best place to work in New York City. So that’s saying something because it’s hard to create an awesome culture where all the team members kind of really love it. So what was the secret because companies that do that really do much, much better. Like when people are happy, they do better work. So congratulations first of all on building that. How did you build it? What are some guidelines for building a great workplace culture?

Carrie Kerpen:                  Well we’ve won Best Places to Work in some capacity or another … one award or another … for over six years now. And, for me, I think it’s ultimately about identifying your core values and staying true to them. If you hire people who are true to the culture of the organization, then they’re ultimately going to be happy there. If you hire people who are wonderful and talented and brilliant but don’t really subscribe to the core values of an organization, then you’re going to have people who are going to have a bit of a culture clash.

So I think ultimately it’s hiring for culture versus hiring just for pure talent or experience. It’s … you have to make and take culture into account when hiring people.

Melinda Wittstock:         This is so true. So again it comes back to know yourself. Cause your culture’s going to emanate from you.

Carrie Kerpen:                  Exactly.

Melinda Wittstock:         As the leader. And so how do you do it? We also have a lot of advice as entrepreneurs to make sure that we’re hiring our weaknesses? I mean there’s no point in cloning ourselves. Better to double down on your strength. Do the thing that you’re really great at doing that brings you joy because you’ll do it great. But then figure out how to fill in the blanks and hire the people who are different from you. So how do you reconcile that? You need people who are different from you. Different skills but at the same time you need alignment on values. Are there any practical tips for how you do that?

Carrie Kerpen:                  I think having very clear descriptions of core competencies versus core values are really what’s key. So your core values need to all be the same however the core competencies of different roles are entirely different. For instance, I could need someone in strategy who is a great thinker and can independently evaluate data. I need someone in accounts who has a core competency of being a killer relationship person. I need somebody in design who is creative and free spirited and has a lot of great thinking and thinks creatively. However, when I’m looking at all of them I need to make sure that all of them are inspired and passionate. I need to make sure that all of them are driven towards a common goal together and really understand the collaborative power of collective drive.

I need to make sure that they’re accountable. That they’re people who don’t pass the buck… Because if you’re at a company where it’s okay to pass the buck, that may work for some people but here it does not. And ultimately, the core value that’s the most important to me, honestly, that’s very challenging especially in today’s day and age and with women and after the election but a core value that I hire for is likeability. I think likeability is key. And it’s an important component.

Melinda Wittstock:         I think you’d have to be. Yeah you’d have to be

Carrie Kerpen:                  Well the company’s name is Likeable Media, right?

Melinda Wittstock:         Right so if you’re not likable, there’s no way you can fit … so yes. That would make perfect sense. I mean it would be really awkward, I think, for a customer if they called up Likeable Media and somebody yelled at them or something, right?

Carrie Kerpen:                  Exactly, exactly. I mean we have a saying here that we offer likeability guaranteed. If you don’t like us, we will let you out of your contract. It’s an important piece of the puzzle.

Melinda Wittstock:         That’s interesting. Well so culture ties really to all aspects of a business and so I love that you’ve tied that to your contracts as well as just the day-to-day culture.

Carrie Kerpen:                  Oh yeah. It has to be. You have to be able to put your money where your mouth is. When you have a promise like that, you have to be able to feel pain when you don’t meet the promise. So I think that’s part of our commitment to culture, is if you … what happens when you’re not living up to your culture, you’re not living up to your core values. There has to be some kind of pain that the company feels.

Melinda Wittstock:         Right. Absolutely. And so, you’ve written a book.

Carrie Kerpen:                  Yes.

Melinda Wittstock:         Work It: Secrets for Success from the Boldest Women in Business. What is the secret to working it as a woman in business?

Carrie Kerpen:                  The secret to working it in business is really understanding your strengths, your weaknesses, and your own personal self, in order to figure out what you need to do to grow and get to the next level. It’s really about abandoning the should’s, abandoning the directives of other people and really thinking about … instead of looking for other people to give you direction, look for other people to inspire you to be able to make your own choices and build your own best life.

Melinda Wittstock:         I love it. So in your book, you talk about the concept of “non-trepeneurship “… non-trepeneurship. I’m trying to say that. I actually managed to say that. I was looking at that word thinking I’m going to trip over that. What does non-trepeneurship mean?

Carrie Kerpen:                  Well it kind of comes back to what I was talking about earlier where what we think of as an entrepreneur is a risk taking badass who puts themselves out there and they go for it and they know exactly what to do all the time and I really suffered from a crisis of confidence. My husband and I founded the business together in 2007. There were no social media agencies at that time. We started it and we took off because we were in the right place at the right time. And then, my husband wanted to launch a tech company and raise funds and so he left in 2012 and I took over as CEO of the agency in a time where it was much, much, more crowded and it was a crowded marketplace. Different time … starting to flat line and I really did not feel like, at any point, in my career that I was this badass killer entrepreneur.

But what I did realize was that in my own journey to entrepreneurship, of course I was an entrepreneur. Of course, I was taking risks. Of course, I was doing all this. It’s just the whole time I was questioning myself. And so the concept of being a non-trepreneur is understanding that all entrepreneurs, especially female entrepreneurs, feel like non-trepeneurs sometimes. We feel like, “Oh shit, these guys are really doing this well and we … I stink.” Or I’m not really like, oh look at this successful entrepreneur; I’m nothing like her. I’m only … I’m questioning myself every moment.

Melinda Wittstock:         Oh we all do that.

Carrie Kerpen:                  You see what I’m saying?

Melinda Wittstock:         Yes we do.

Carrie Kerpen:                  We do.

Melinda Wittstock:         And it’s so interesting. So, I, on this podcast, Kara Goldin who is the founder and CEO of Hint.

Carrie Kerpen:                  Love her.

Melinda Wittstock:         Yeah she’s awesome and she’s on her path to building a billion dollar unicorn. She’s going to get there. But she said, “My goodness, look around at any room with entrepreneurs. No matter how successful they are, is going to think that everyone else has it figured out. And you are the only person that does not.” And what she said, which I just think is really bears repeating is that everybody else is thinking that same thing.

Carrie Kerpen:                  Exactly, exactly. I always like to give this quote, which was actually originally shared by a pastor, which is, “The reason we struggle with insecurity is because we’re comparing everyone else’s highlight reel with our behind-the-scenes.” So we’re living our whole life, right? We see all the crap. We see all the good, all the bad, all of it. We know everything about ourselves right? But when we’re looking at somebody like Kara we’re seeing only their success because that’s what she puts out to the world. However, Kara has her own behind-the-scenes. She has her own life, her own challenges.

We’re looking at all these highlight reels and we’re like, “Oh boy, we’re the only one that’s stuck on this island alone.” We don’t know exactly what we need to do next but the reality is, we are all living a full “highs and lows” of life and we all are in the same boat.

Melinda Wittstock:         Well as a social media expert, I mean this is really interesting to get your take on this as well because we have so many highlight reels to look at right now. And it’s really hard not to get into that comparison. But for a woman in business, whose personal brand is so vital, social media is really, really critical. How do you think women CEOs and founders are doing on social media with the personal brand? Are they stepping up as much? Are we stepping up as much as we could on personal branding? Cause one of my guests said personal branding gets confused for women with personal bragging and that we don’t like to brag.

But how can we all [inaudible 00:35:35] with social media better for ourselves?

Carrie Kerpen:                  Yeah I think we’re uncomfortable talking about ourselves. Look the whole way I built my company was all of these men had social media presences … they’re running social media agencies. All the founders were loud, they were extroverted and they were male. I didn’t’ feel loud. I didn’t’ feel extroverted and I certainly knew I wasn’t male. So when I was doing this, my entire strategy was, “I’m going to start a podcast to highlight other women’s stories and then they don’t have to.” And then I really don’t have to talk about myself. That was a great strategy but it was a limited strategy.

Ultimately, we all have to get comfortable talking about ourselves. That was a strategy that definitely benefited our business. It doubled the company. It did all this great stuff. It built my network but it ultimately allowed me to continue on a path of fear, which is that I’m going to talk about other women, I’m not going to talk about myself and I’m not going to promote myself. And we do have an intense fear of bragging. And what I would tell you now, looking back with this experience is that it is key to be able to talk about yourself … to be able to highlight your successes and not see it as bragging.

Of course, there are certain ways to do it, right? If you’re good at social media, then it looks like you’re never really bragging. It looks like you’re simply highlighting your accomplishments. However, we all need to be highlighting our accomplishments because honestly it’s just practical. Before any meeting, what do you do? Before you meet with them, you Google them. Right? You look up people; you’re doing research on people. You want to be able to see who they are, what they do and how they do it. And ultimately more and more, as this more social economy begins to happen, that message has an ability to not only be controlled but really highlighted, highlighted by you. What a great thing that it used to be that you’d Google people and it was like well whatever someone else says about you comes up. Now you have the ability to really craft that message and I think that’s what’s key. I think it’s essential for women.

So the answer to your original question is, no I don’t think we’re killing it as much as we could but I think we’re getting a little better every day.

Melinda Wittstock:         Yes that’s right. And so you mentioned the word fear and I think fear is at the root of so much that goes wrong with ourselves, with society, where we hold back and it manifests in a whole bunch of different ways. It could be like perfectionism, procrastination. How do we and how do you overcome fear? I mean you gave some practical tips on the social media side and what you did there but just on the day-to-day basis, how do we get past our fear?

Carrie Kerpen:                  Okay so I just got this advice … there’s a book out now. I just got this advice from my trainer, okay, I love this. To get past fear, whenever I’m trying to rationalize, I don’t want to work out, I don’t want to la, la, la … it really comes from fear. I don’t like it. It’s annoying. It’s like I’m afraid to do it because it hurts or it’s frustrating.

So, okay, I want you to think about the five second rule, which is every time you’re feeling fear allow yourself to feel the fear for a second then you’re going to count down from five and you’re just going to do it. A different five second rule than the one I give my kids, which is when you drop the popcorn on the floor, you can eat it as long as it’s not more than five seconds. But just count to five and go. Feel the fear and do it anyway. So it’s just go and just do. The act of doing … I talk a lot about having the time to think … you know thinking to yourself, we don’t have enough time to think however, sometimes when we’re paralyzed by thinking or we’re paralyzed by fear, the thing we need to do is just do.

So in those situations where you’re feeling fear, you have to just push forward and just do it anyway. So count to five and go. Do something that faces that fear in some experience in whatever way. Let’s say you’re afraid of skydiving, then pick up the phone and call a skydiving place and find out where it is. If you’re afraid of raising money, email ten VCs in that moment. Just really, after the five seconds, do an action that helps you to face the fear.

Melinda Wittstock:         Carrie that’s wonderful advice about kind of feeling that fear, acknowledging it, not judging yourself, but then just doing it. Because the more you do that, the more confidence you have. The more confidence you have, the more good stuff is going to happen for you.

Carrie Kerpen:                  Exactly.

Melinda Wittstock:         So as we wrap up the podcast for today, are there any last bits of advice that you would like to share? And, of course, want to tell listeners how to find you on social media and obviously get your book as well.

Carrie Kerpen:                  Sure. In terms of last pieces of advice, I would say stop worrying about working it the way that everyone else and start thinking about working it your own way. Really ask yourself how well you know yourself and look at some of the exercises. I have a bunch of exercises in the book that will help you get there. In terms of how to get in touch with me, pretty easy on social media I am Carrie Kerpen everywhere, C-A-R-R-I-E K-E-R-P-E-N. You can find me all over the place or on carriekerpen.com. And you certainly can buy Work It: Secrets for Success from the Boldest Women in Business, either through carriekerpen.com or on Amazon.

Melinda Wittstock:         I can hardly wait to read it. It’s going to be great. So carriekerpen.com for that and we’ll put all the details in the show notes as well so people can find you easily and work with you and we’ll share everything. If you need social media work, likeablemedia.com, we’ll put that all in there. Carrie, thank you so very, very much for being my guest today on Wings of Inspired Business.

Carrie Kerpen:                  Thank you so much Melinda. It’s a pleasure to be here.

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Listen to learn the secrets, strategies, practical tips and epiphanies of women entrepreneurs who’ve “been there, built that” so you too can manifest the confidence, capital and connections to soar to success!
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Review on iTunes and win the chance for a VIP Day with Melinda