Dave Kerpen is a serial entrepreneur, New York Times best selling author, and global keynote speaker. Dave is the co-founder and co-CEO of Apprentice, a platform that connects entrepreneurs with the brightest college students as well as the co-founder and CEO of Remembering Live, virtual memorial service company. Dave is also the founder and Chairman of Likeable Local, a social media software company serving thousands of small businesses, and the co-founder and Chairman of Likeable Media, an award-winning social media and content marketing agency for big brands.  Dave’s newest book is The Art of People: 11 Simple People Skills That Will Get You Everything You Want.


  1. Go all in. It takes a little courage to just go for it when there’s the possibility you are going to be laughed at, ignored, or misunderstood, but you never know where it can take you.
  2. A so-called “traditional path” into entrepreneurship doesn’t exist. Part of the beauty of being an entrepreneur is the creative and unconventional ideas and choices you make to stand out. There is no “right” way.
  3. Find contentment both personally and professionally. Building strong, healthy personal relationships is the key to finding happiness in work, too.


BRYAN WISH: What is your One Away moment that you want to share with us today?

DAVE KERPEN: In 2002, I fell madly in love with a woman in Boston when we were working together at Radio Disney. I was the number one salesperson in the country until she started working at the office and dropped me to number two. We became very close friends. I fell madly in love with her but there was one problem: she was married already.

She ended up leaving the company, moving to New York with her husband to focus on her marriage. I did what anyone with unrequited love would do. I went on a reality TV show to find true love. Paradise Hotel. Sexy singles at a luxury resort and me. After the show, I was living in L.A., a celebrity, and I had to let her go, of course, and try to move on but I had a weak moment. It had been about a year since we had last talked and I was on the red carpet at the American Music Awards and I missed her still so much.

My One Away moment was calling her from the red carpet and trying to brag. I said, “Hey, I’m hanging out with the people from American Idol. What are you doing?” She said, “I’m going through a divorce.” I said, “I’m so sorry to hear that.” Did a little fist pump secretly. Told her a little white lie. I said, “I had to be in New York the following week to meet with my agent,” which of course, didn’t exist. I flew to New York. We started dating and the rest is history. 15 years later, we have three wonderful kids and have built 3 or 4 wonderful businesses and written a bunch of books. I couldn’t be happier. Thank goodness for that One Away moment.

BRYAN WISH: What about her made you connect?

DAVE KERPEN: I love that question because people don’t ask me that a lot, especially on business podcasts. It was definitely love at first sight. She was so radiant. People have described that I could sort of own a room and take over a room. I’m a very high energy, very positive, but it was like she walked into the room and it was like, “Oh my God. There’s a female me and she’s better than me. She’s the better female me. Much, much more attractive to me.”

She was and continues to be, this many years later, completely radiant and completely able to own a room but also when she’s having a one-on-one conversation with me or with anyone, she’s so focused on that person that that person feels like they’re the only one in that room as well. That has made me a very lucky guy and I am very fortunate to have a terrific wife. She’s also an incredible business person, leader, and salesperson because she’s able to do that.

BRYAN WISH: Where do you think she compliments you and where do you compliment her?

DAVE KERPEN: I was just doing some coaching and talking to an entrepreneur about how it’s really hard, if not impossible, to focus on growth and profit-building at the same time. You need somebody that’s the growth guru and somebody else that’s making sure that you actually make money at the end of the day. I’d say with Carrie and me, we have a really nice mix where I’m the growth, top-line sales, and marketing guy. She sort of was that person but she’s just so darn skilled and able to focus and refocus that in many ways, she’s become a really strong executor, profitability person, a leader with respect to the bottom line.

It’s a really good combination. In terms of personal, I think we have worked really hard to both become really good listeners and turn into each other. For those of you listeners that are Gottman fans – John Gottman, a brilliant psychologist. He and his wife, Julie, have done a ton of work on maintaining healthy relationships in couples. We’ve followed them, love their work, and work on turning towards each other and complementing each other each and every day in ways that we can.

BRYAN WISH: The entrepreneurs that are happy both personally and professionally are the ones I look up to the most. As this story continues, you called her up. She’s getting divorced. You guys started dating. The next thing you know, you’re getting married. Tell us about that experience. You did it differently than most.

DAVE KERPEN: It was such an amazing experience. Boy, am I blessed to have been through it. We had been dating a little over a year. We weren’t quite engaged yet. Carrie sat me down. We were at a diner in New York City. She said, “I have this really idea but I don’t want it to influence your decision about where we go.” I was like, “All right. Tell me.” It was a brilliant idea.

The truth is, of course I was ready to propose soon anyway. I certainly couldn’t resist once we agreed to this idea which was we would take our sales and marketing background and put together a unique, sponsored wedding promotion. We both had some really great contacts because we’d both been doing sales and marketing and advertising for several years. I really wanted a big wedding. I’m kind of a larger than life guy. We had a reality show. We had a social media thing. I wanted to be able to invite everyone I’d ever met at this wedding.

Meanwhile, she’d been married before and had a traditional, New York, expensive wedding that led to a divorce 2 ½ years later. The idea was could we pull off a wedding for essentially free by partnering with a minor league baseball team. We pitched the Brooklyn Cyclones and affiliated with the Mets. The general manager said to us, “This is the craziest idea I’ve ever heard but there’s something about you two. I think you can pull this thing off.” We said, “Yeah, absolutely, we can.” He gave us the promotional inventory for the whole game in exchange for letting us get married afterward. In other words, all of the in-between innings promotions that you typically see were ours.

Instead of throwing out t-shirts in between the third inning, we threw out 1-800 Flowers’ bouquets of flowers and 1800flowers.com was our floral sponsor. We had an official drink of the night from our alcohol sponsor, Smirnoff. David’s Bridal did our wedding dress and bridal gowns and did a promotion in between innings. We ended up raising $100,000 in-kind for an amazing wedding. $20,000 for charity for the MS Society which is an important cause for us. For me, being a big baseball fan and being able to invite 500 friends and family and being married in front of 5,000 strangers, it was an amazing dream come true as a wedding.

It turned out to be a super successful marketing event. We generated about $20 million worth of earned media for our wedding vendors. Pretty much every network was there, ABC, CBS, CNBC, The New York Times, thousands of blogs. Our vendors had such a great experience. They got so much ROI in terms of their investment versus the buzz that was created online and offline from the wedding. They literally said to us after the wedding, “This was amazing. What can you guys do next for us?” We couldn’t get married again. So, we started our first company, a marketing agency.

BRYAN WISH: This is priceless. When you met with the Brooklyn team, did you go to them with the vision that you were going to run the in-game promotion or they came to you and set the inventory?

DAVE KERPEN: I’ve gotten 3 or 4 dozen requests from brides and grooms over the years that have read about our story and they were like, “We want to do a sponsored wedding.” What I told all of them is, like anything, you need to create value. It had to be a value exchange where we were offering our sponsor something real. Why else would they give away all that valuable product and service? The pitch to the Cyclones was we’re going to sell out your stadium.

We’re going to generate national press for you. What we need is the sponsorship inventory which we can resell to our wedding vendors who we can also promise, at a minimum, exposure to 7,000 people in the stadium and hopefully some great PR beyond that. Everyone got what they wanted. It was truly a dream come true. Carrie’s parents were nervous about negative publicity like people thinking it was tacky. There were a couple of pieces. The New York Times was a little bit challenging in their review of our wedding and About.com wrote a piece. It’s funny. The About.com couple’s expert wrote a piece saying our marriage would never last. We sent them a bouquet of flowers every year on our anniversary for the first 9-10 years and then About.com went under. Our marriage lasted but About.com didn’t.

BRYAN WISH: You had a lot of great marketing experience growing up in the relationship that we built and what you’ve shared. What were you doing as a kid where you maybe learned some of these initial branding and marketing skills that maybe were rolled into this event experience for you and your wife?

DAVE KERPEN: I don’t know that anyone has a so-called traditional path into entrepreneurship but mine was particularly non-traditional. I was studying elementary education and psychology. I wanted to be an elementary school teacher for most of my childhood. I was in a school in Boston and I had no money. To put myself through school, I got a job working at Fenway Park where the Red Sox play in the Boston Garden where the Celtics and Bruins play. I was a ballpark vendor and what many people don’t know about the ballpark vending business is you’re really an entrepreneur within the business because you only get paid based on what you sell. It’s a commission only. It’s a seniority-based system.

When you start, you have the worst selling products. If you work there for years and years, like the lifers, as they call them, you get the beer or the peanuts where you’re really making a lot of money. My first day on the job, I had the worst-selling product in the building; a product called Crunch ‘N Munch, buttery toffee popcorn with peanuts. I sold six boxes on my first day. I got paid a grand total of $10 which was the legal minimum they could pay me. I came back the second day determined to make more money.

It was fun being at the ballpark but I wasn’t there to watch the game. I was there to make money. I started shtick singing and dancing, juggling boxes, anything I could do to get people’s attention. I had no talent at all. The only thing I had was a little courage to look foolish and potentially be laughed at but not really worry about that and it worked. People started buying boxes by the dozens. I was selling a lot more boxes. I attracted the attention of the Boston Herald that wrote an article about me.

The one night, my One Away moment early on as the Crunch ‘N Munch guy was the night that that first article came out from the Boston Herald, somebody asked me to sign a box of Crunch ‘N Munch. I guess they sort of brought a sharpie in hoping the Celtics would give them an autograph and they hadn’t gotten an autograph from one of the players and they figured “Try this kid.” I signed a box but the smart thing I did that night was I asked if I could borrow the sharpie for the rest of the night.

I proceeded to sign every box I sold that night unsolicited. I made the assumption they all wanted an autograph. Lo and behold, by the end of the night, I sold 150 boxes or so and I somehow created the perception in the building that you had to buy a box and get it autographed by the Crunch ‘N Munch guy. That moment, my sales shot up. At its peak, I was on ESPN Sports Center. The Crunch ‘N Munch company flew me down. I did a Monday night football game as the Crunch ‘N Munch guy. I was making about $1,000/night selling boxes of Crunch ‘N Munch. Not bad for a kid in college. Most importantly, it really helped me fall in love with sales, marketing, promotions, PR, and business, and building brands and businesses. I really haven’t looked back since.

BRYAN WISH: What would you say the fundamental building blocks are from what you learned as a kid to how you actually create a perception that you’re going for?

DAVE KERPEN: It goes all-in. As a poker player, I’m all about going all in. The same can be said for the way I look at life and the way I look at brands and businesses. I wear orange shoes every single day. I go all in. I’m committed to orange. It takes probably a little hutzpah, to use a Yiddish word, or balls, to use a more dangerous word to sign a box of Crunch ‘N Munch at a ballpark assuming you should. It was that going all in. It probably takes a little courage to just go for it even if I’m going to be laughed at, even if some people aren’t going to like it, even if some people are going to think it’s silly. That’s a lesson that I’ve continued to use and pursue.

When I start a new business idea or have a new business idea, every single time, some people are like, “You’re an idiot. That’s horrible.” I could let that stop me but I don’t. I just go for it. Sometimes I am an idiot. I had a business idea the other day during the quarantine. I was like, “We should start school. We could have like 20 kids in here.” My daughter was like, “That’s the worst idea I ever heard.” It was a bad idea but the more bad ideas we get through, sometimes a good idea will strike and then I think it’s about going all-in with the things that we do and end up going for.

BRYAN WISH: Because of the wedding and what you put together, you were able to create something off of it which was your first company. Maybe tell us about the formation, the company, and how you thought about orchestrating it and putting it together.

DAVE KERPEN: We got married. Some of our wedding vendors like our DJ and invite people, cake vendors, probably not applicable to hiring us. A couple of the big sponsors, 1800flowers.com that had sponsored our flowers, and Entenmann’s who had sponsored our desserts. The terrific baked goods company out of Long Island. They both said to us, “This was great. What can you do for us again?” We sort of racked our brains and came up with a couple of ideas. We ended up doing this really crazy, random promotion.

Our first paid promotion after the wedding was 1800flowers.com wanted us to work on their non-Christmas December holiday business. What does that mean? Basically, they wanted to improve their Hanukkah business and their Kwanza business which let’s just say, there was a lot of room for improvement. We put together a promotion where we went into a bunch of senior centers in predominantly black areas and Jewish areas and actually worked with the seniors on teaching them how to use the internet. It was all sponsored by 1800flowers.com. There were redemption codes. It was a pretty good success. We generated some more earned media and we generated a lot of buzz in the centers that we visited.

We ended up doing a bunch of grand openings, various offline promotions, guerilla marketing. We actually did a couple of other baseball stadium events for a client. About a year later, this was 2007, about 10 months in, Facebook opened up beyond college students to the general public. I actually had an intern that said to me, “Dave, you should join this Facebook thing. I think it’s going to be a big deal. It’s a pretty big deal for us, college students, now.” I said to her, “Just set up my profile. I’ll figure it out.” She set up my profile and then I eventually jumped in and like learned it and was like, “Wow, this is a really cool tool.” It’s probably a better tool for marketing and creating buzz than baseball stadiums and visiting senior centers and the stuff that we had been doing.

The moment I really knew – and this could have been a One Away moment too – I was doing recruitment for a promotion for Verizon. We were doing house parties for Verizon. It was still offline but we were looking to find people that had Verizon Fios and we were going to reach out to them and set up these house parties. They could invite their friends and tell them all about Fios. I said, “What if we tried to recruit people on Facebook?” We did and within an hour, we had thousands of applications to have a free house party with Verizon. I was like we will do the house parties but this is a much bigger deal.

We pivoted pretty early on in our business from offline word of mouth to what we call online word of mouth which has quickly become social media marketing, content marketing, online digital marketing, online marketing. We were very fortunate to be very early and timing in business is really important. We were a really early agency in the space and we were able to build up a very strong roster of clients that we helped with social media back in 2007, 2008, 2009 which has helped us to become the sort of leading agency that we are today.

BRYAN WISH: It must have been fascinating to see it first hand and so quickly. Any comment on that?

DAVE KERPEN: It was totally incredible. I was very fortunate because I have these young people that worked for me and it helped me get a lot faster. I got to this a lot faster than my peers, people my own age which was cool. It was a real blessing. Young people, like you, and I’m sure lots of the listeners take this for granted because you grew up with it, but for me, when I went to college, there was no email and certainly no social media. It’s really revolutionized and of course, I ended up writing books about this and becoming an early thought leader on this but it’s such a massive shift in the way humans interact and at this point, 2020, pretty much everyone takes it for granted because it’s been around for so long. 10-11 years ago, it was really a massive shift in thinking.

BRYAN WISH: For the listener who cares, it’s a 17-year difference here. For the shift in marketing, I can’t even imagine. For those who don’t know, Dave has written three books, Likeable Social Media, Likeable Business, and The Art of People. To speak to Dave and his brain consistency, another story here, I met Dave at an entrepreneurs organization (EO) event and I knew I was going to have to go up to the front and talk and I was kind of looking at the nametags and Dave just popped out because of his big orange shoes. I looked him up on LinkedIn and he was like my anchor, my presentation to call out. That’s how we formed an initial connection because he did stand out. He did draw attention. Back to your business, how did everything grow from there?

DAVE KERPEN: We said to Verizon, “We’re going to do your house parties but we have a better idea. We’re going to set up your Facebook page.” They literally had no idea. Corporations didn’t know what the heck we were even talking about at first. We were very fortunate. We set up Verizon’s first Facebook page and 1800flowers.com Facebook. We just worked with big brand after big brand and helped them establish their social media presence, helping them create content. We got great referrals because we were doing good work. We won a bunch of awards. We took it from there.

After I wrote the book, I think that was a very big – the first book Likeable Social Media – was a very big driver of credibility and leads, reputation. I got increasingly dissatisfied with just helping big companies out. We had established a reputation as a thought leader in this space. We got so many inbound leads but the law of numbers, in terms of the number of businesses, suggests that most inbound leads aren’t going to be Verizon and Johnson & Johnson.

Most inbound leads were all small businesses that we really couldn’t service based on the model that we’d established. They just couldn’t afford the retainer rates that were charging. I had this vision to build software that small businesses could use to manage social media.

My wife, God bless her, she said, “Go for it.” I was the CEO at Likeable Media at the time and she was the COO. She took over as the CEO of Likeable Media. I launched Likeable Local which is our second company which is a software as a service that small businesses and agencies that work for small businesses use to help manage their social media and content. I continued to launch companies from there.

BRYAN WISH: It’s an inspiring story and similarity and thread line throughout you as an early childhood to college to your marriage story and just going for it and really making it happen. Where can people find you?

DAVE KERPEN: I host open office hours every Thursday afternoon. If anyone wants to chat with me for free on Thursday afternoon, you’re going to have to wait a bit but you can go to scheduledave.com and set up a time to meet with me. I’ll talk with anyone about anything that you want to talk about. Of course, I’m on every social network imaginable. Yes, even TikTok. You can follow me on all those social networks. If you Google Likeable, you can learn more about those companies and books and Apprentice, you can learn more about what I’m up to there.

Happy to chat with anyone that’s listening. A lot of people have said I’m fearless. I want to say with great certainty that I am the opposite of fearless. I am filled with tons of fear. I think we’re all filled with tons of fear and I think the challenge isn’t to try to be fearless. It’s to recognize our fear, to work through our fear, and to be courageous, i.e. go for it. It’s okay to be afraid. Life is freaking scary. It’s terrifying. To me, it’s not okay to let that hold us back. The challenge is how can we be afraid and still go for it?