Uncommon Success Secrets from Dave Kerpen – An Entrepreneur in the Trenches

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Dave Kerpen
Dave Kerpen

Dave Kerpen

Founder & CEO, Likeable Local, NY Times Best-Selling Author & Speaker

My second “Success” interview is with Dave Kerpen. I admire Dave and all that he’s accomplished. I first became aware of Dave and his agency back during my tenure at Buddy Media. Dave and I didn’t meet in person until only a few months ago. I had been able to get to know Dave via his prolific writing. If you read any online business outlet, Dave is a regular contributor. Forbes, Inc.com, you name it – Dave has a loyal following. Silverback recently engaged Dave to keynote our Westchester Digital Summit. I knew he would be great. Our audience loved Dave. Dave also does a few things differently that intrigued me. In a world of superficial “liking” and “following” Dave engages. Upon first meeting him in the Likeable offices he drew me in. He’s whip smart, and a powerhouse sales person. His wife is his business partner, he has high profile clients, and he had three kids at home.In our “always on” world that we live in, how does Dave do it all? Excited to learn Dave’s secrets to success, I went a little overboard with my questioning. Good thing I caught him while he was flying. He was gracious enough to spend the time to answer each inquiry. So who is this guy? What makes him tick? And does he really own 31 pair of orange shoes? Let’s find out. Here we go.

Chris Dessi: Dave, currently as I write this, your most popular post on Linkedin has over 2.7million views. What is it about your writing that you feel resonates with the Linkedin community?

Dave Kerpen: I try to write simply and concisely, and I like to tell stories. If my kids can read a LinkedIn post of mine, that’s a good thing.

Chris Dessi: You recently keynoted at my event, the Westchester Digital Summit. During your keynote you discuss the importance of gratitude. What role does gratitude play in your everyday life?

Dave Kerpen
Dave speaking at the Westchester Digital Summit

Dave Kerpen: I’m a huge believer in gratitude. I hand write three thank you cards each morning, and spend each dinner with my family going around the table, all sharing someone we’re grateful for that day. Gratitude is the best drug on the planet.

Chris Dessi: You’re a true family man, and you’re business partners with your wife. What has that been like? How have you and your wife navigated the bumps in the road?

Dave Kerpen: It was very challenging at first – we brought arguments from home to work, and arguments from work to home. But with practice, we’ve become much better communicators, and leaders. Ultimately, it’s been amazing to share my businesses with my life partner.

Chris Dessi: You’re what I call “Aggressively transparent” in your writing. Did this come naturally, or was this advice that someone shared? Why should my readers become more transparent in their blogging etc?

Dave Kerpen: Transparency is actually quite freeing, and a great differentiator. Most people are afraid to be radically transparent. So if you can open up and share your heart, people will respond to that.

Chris Dessi: You’ve been a successful entrepreneur for a few years now. You were once a school teacher. What facilitated that shift for you? Was there one defining moment, or was a gradual progression? Do you think you were a born entrepreneur.

Dave & Carrie Kerpen on their wedding day.
Dave & Carrie Kerpen on their wedding day.

Dave Kerpen:  Our wedding was the biggest factor that took me from teacher to entrepreneur. I think I always had entrepreneurial tendencies, but after pulling off a sponsored wedding that raised $100,000 including $20,000 for charity, I knew we could build real businesses.

I’m still super passionate about education, and hope to one day support public schools as a public servant. Perhaps my next career.

Chris Dessi: You’re a thought leader in digital and social media. You contribute to Inc.om, and even Forbes. How important has writing been to your success?

Dave Kerpen: Writing has been critical to my success. Writing has helped me to become a better thinker, which in turn has helped me to become a better leader. Writing bestselling books and well-read articles has also helped to position me as credible.

Chris Dessi: When was the first time you felt you were a success?

Dave Kerpen: I still don’t feel like a success a lot of the time. There’s always lots of room for improvement, you know? But the first time Likeable won “Best Places to Work” in New York from Crain’s – that felt pretty awesome.

Chris Dessi: How do you define success?

Dave Kerpen: Success is being happy at the end of the day with what you’ve got!

Chris Dessi: I have two young daughters. As do you (as of this publication the Kerpen’s welcomed a bouncing baby boy to the Kerpen klan). How important do you think it is for young women to get involved as entrepreneurs? Is this something you discuss at home? Or does business never creep into your home life?

Dave's Family
Dave’s Family

Dave Kerpen: We have “entrepreneurial” in our family mission statement, and it’s one of our core values. My daughters are on their 3rd business right now. I’ve done several lessons on entrepreneurship with my 6th grader and 60 of her classmates, and my 2nd grader and 11 of her fellow girls scouts. So, I’d say it’s pretty darn important to us as a family. I think that young women (and young men!) should be strongly encouraged to pursue entrepreneurship, and that entrepreneurship, as creative problem solving, should be taught in every school in this country.

Chris Dessi: How great a role do you think luck has played in your success?

Dave Kerpen: I’ve been very lucky- most of all, to find Carrie to want to marry me and be my partner in all things. I married up at least two levels.

Chris Dessi: You’re a successful guy – and a former school teacher, so you’ve taken academics seriously. What do you say to the pundits who feel that college is a waste of money?

Dave Kerpen: I think college is a waste of money, for many! I was fortunate enough to attend BU on a full scholarship. Otherwise, I could not have afforded it. I think that for many families, college provides an opportunity for structure and socialization and learning that works. I also think that got many, it’s not necessary, or even beneficial. Personally, I would much rather spend $250,000 to fund a smart business plan that my future 18 year old daughter is passionate about than fund 4 years of school for her. But we’ll see about that!

Chris Dessi: Do you have brother and sisters? Where did you grow up? How has that shaped your successes?

Dave Kerpen & his brothers
Dave & his brothers

Dave Kerpen: I grew up in Brooklyn, New York before it was cool, in Sunset Park with 2 younger brothers. My father has struggled a lot with bipolar disorder since I was 12. So I learned at a very young age to be independent and to be a leader – I had to help take care of my younger brothers. I’m super impressed and proud of the young men they’ve become – Phil is a conservative leader in Washington and Dan is a technology marketer! 

Chris Dessi: You seem to be living American dream. What has that journey been like? Tell me about the lows – where there bumps along the way?

Dave Kerpen: There have been lots of lots of bumps along the way – and there still are bumps, every week! My wife Carrie talks about the “highlight reel” – you see people’s highlights online and even in person, but you don’t hear about the bumps as much. The first time I met Carrie, I fell madly in love with her but she was married at the time. That sucked. When I went on 31 episodes of Paradise Hotel (Fox, 2003), I was famous for a bit, but when People Magazine called me “homely”, that sucked. When I lost my first $500,000 client for going above her head, that sucked. When we nearly missed payroll, that sucked. Lots of bumps. But fortunately, lots of highs too!

Chris Dessi: Are there people in your life who inspire your success? Tell me about them.

Dave Kerpen: I’m inspired by great leaders – Mark Zuckerberg, Tony Hsieh, and Jeff Weiner, to name a few. As for people I know more intimately, my wife Carrie is my greatest inspiration. I’ve also been blessed to be surrounded by great mentors and advisors. My father in law, the late Honorable Steven Fisher, taught me to show your friendship first, and the late Senator Frank Lautenberg taught me that family is our greatest legacy.

Chris Dessi:What’s your rythme? What time do you go to bed? Do you meditate? If not – when and how do you find quiet time? When do you wake up? Do you exercise? If so – what do you do to keep fit & stay focused?

Dave Kerpen: I don’t sleep much. I typically go to sleep at 1am or so and wake up at 6. I’ve struggled to embrace meditation, and I never have quiet time. I hate to relax. That’s probably why I need to mediate. I need to exercise more! I love to play tennis, but get bored by most other forms of exercise.

Chris Dessi: You offer so much great insight to entrepreneurs via your writing. I hear from many whose businesses are failing. They’re about to give up. Can you share a moment when you were about to give up? What kept you going? What would you give to these entrepreneurs as advice to keep going?

Dave Kerpen: I have moments where I want to give up all the time. I try to embrace those moments instead of avoiding them. For example, a month ago, an investor who I was sure was going to invest $1 million in our new business Likeable Local, pulled out at the last minute. That sucked a lot, be made me want to give up. But I’m inspired by our mission to help small businesses, and by the amazing people I’m proud to call my team. So there’s just no giving up!

To entrepreneurs who feel like giving up, I say, the number one most important trait that defines whether you’re successful or not is persistence. You can do it.

Chris Dessi: You public speak often. You seem like a natural. Are you? Or have you had to work at it. If so, what advice can you offer those who want to be better public speakers?

Dave Kerpen: I love to speak – the bigger the crowd, the bigger the high I get. That said, like anything, practice has made me better. I’ve had a speaking coach who helped me to realize, that it’s never about me, and always about the audience.

Chris Dessi:You’re a prolific content creator – books, blogs, articles etc. When do you find the time? What’s your writing schedule look like? Are you an everyday no matter what type of blogger? Or are you able to put in great effort around deadlines.

Dave Kerpen: I write late at night typically (11pm-1am) or early in the morning (5am-8am), and on planes. I’m writing this long interview response on a plane.

Chris Dessi: You’re super laid back and easy to get along with. One may say that you’re “Likeble.” How important do you think it is for today’s leaders to be likeable?

Dave Kerpen: In an increasingly transparent and fast-changing world, it’s essential for leaders to be likeable. I feel so strongly about this, I wrote a book about it, Likeable Business.

Chris Dessi: Would you go back to teaching?

Dave Kerpen: Yes, I would love to teach again. Or start a school and be a principal. Or be a superintendent of schools somewhere. Or be the Secretary of Education.

Chris Dessi: Why orange?

Dave Kerpen: Orange is the most positive persuasive color. Plus, my 31 pairs of orange shoes help me stand out a bit.

Speed Round:
Yankees or Mets? METS!
What’s the best advice you’ve ever received? Show your friendship first.
Do you have a life motto? Just be likeable.
What cheers you up? My kids, and feeling grateful.
Favorite word? Likeable. (duh)
What are the names of your children, and what significance do those names have to you and your wife? Charlotte is my oldest, though technically she’s my step daughter since her birth father is my wife’s ex husband. She was named after her great aunt. Kate was named after my grandpa, and Seth Franklin, my one month old, was named after my 2 mentors above, my father in law Steven Fisher and Senator Frank Lautenberg.
What’s your worst vice? Gambling.
Good book, or Netflix? House of Cards.
Game of Thrones or Breaking Bad? Orange is the New Black.
EQ or IQ? EQ

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Chris Dessi Fox Business

Hey there thanks for reading!  My name is Chris Dessi. I’m the founder and CEO of Silverback Social.  I’m also the founder of the Westchester Digital Summit, and the author of Your World is Exploding: How Social Media is Changing Everything and How You Need to Change With It.  

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