In The Business of Likeability, an Interview with New York Times Best-selling Author Dave Kerpen

Episode 26

Dr. Chloe Carmichael: [00:00:00] Hi everyone! I'm Dr. Chloe Carmichael, host of the High Functioning Hotspot. I'm a clinical psychologist based in New York City, but I'm also an author. My new book is Nervous Energy: Harness the Power of Your Anxiety.

My guest for today is Dave Kerpen and he's an author as well. He's a New York Times Bestselling Author as well as a super successful business owner. He has businesses which are up in the $10 million range, $5 million range. He just has an array of very successful businesses. So I'm really excited for the chance to talk to Dave, ask him some questions about writing, about business and about life in general. So without further ado here is Dave.

Dave, I just want to share with you that I was Googling you to just try to learn more, so I can introduce and describe more about you and your accomplishments. And I was actually a little surprised that it wasn't as easy as I thought to find online a list of your businesses and what you've done, because I’ll share the last time you and I spoke, you said like, “Oh, E-comm has never been my strong suit. I had one business that maybe did like 5 million or something in that space”. And I was just like, “Oh my gosh!” Like for me, to do 5 million in E-comm would be such a dream. So I'm just curious, do you mind sharing an overview of your businesses and the kind of revenue that they do?

Dave Kerpen: [00:01:28] Sure. Sure. So I have four businesses currently and I have some businesses that are no longer with us. Well, I guess we can focus on our current businesses. Likeable Media is a social media agency and content marketing agency. We work with big brands, Fortune 1000, Fortune 2000 brands. We do about 10 million.

And then Likeable Local is a software service that helps small businesses manage their social media. And that was the one that we maxed out at around 5 million, but we're stable and growing and profitable, but much smaller now, somewhere between a million or two.

And then I have two new businesses, Choose Apprentice, which matches CEOs and entrepreneurs with the best and brightest college students. And Remembering.Live and Celebrating.Live which are virtual memorial services and virtual event company, respectively. And we're just getting started with those. We'll be at a million this year, but we're just getting started with those.

Dr. Chloe Carmichael: [00:02:39]. That is so incredible. And I just have to say as well about the (Choose) Apprentice. Of course, a big fan of the company myself, you know, even as somebody that uses VAs I really found the Apprentice to be something that was special and different. So thank you, Dave, for putting that together.

So I'm just curious though, because I do think it's such an important thing to note that you have all of these incredible, robust, strong, multi, multimillion dollar businesses. And that's the backdrop against which you're writing these books. So I'm curious, did you decide to write books after you became a successful business person? Or did you have the writing bug before?

Dave Kerpen: [00:03:26] I think I've always had the writing bug, but like many people, I didn't have the final sort of push. You know, the world has changed a lot and now you can, anyone can truly write and publish a book through self-publishing tools. But I think for me, certainly growing up, I had the, as many people do this sort of misperception that I had to be chosen. So even though I wanted to write a book, I didn't really know where to turn.

And then fortunately the first business is a success. Likeable, we were really one of the very first companies to understand and leverage social media for big brands. And so McGraw Hill came to me and asked me to do that first book, Likeable Social Media. And I had had the writing bug for years, but it wasn't until they said, “Hey, we'd love for you to do a book”. Then I said, “Well, okay!”, and it really jumped in.

Dr. Chloe Carmichael: [00:04:28] And then is that when your speaking career started taking off, was after the book?

Dave Kerpen: [00:04:33] That was the paid speaking career, yes. So I was doing speaking, but like most marketing related speakers, I was basically being asked to speak for free with the promise of being able to generate leads for my company.

And it actually worked fairly well. But I wasn't a paid speaker until the first book came out and hit the New York Times Bestseller List. And then that helped me generate much more lucrative paid speaking.

Dr. Chloe Carmichael: [00:05:05] Yeah, I know that you had a big strategy. You did not hit the New York Times List by accident, so to speak, but I have to still ask, like on a scale of 1 to 10, when you actually hit the list, how surprised were you on a scale of 1 to 10?

Dave Kerpen: [00:05:23] I was on a scale of 1 to 10. I would say I was seven. I mean, we had worked well, no, I'll say six. I mean, we had worked very, very hard for it. But it's still, you know, it still felt really good and really, you know, I guess at least a little surprising to be able to accomplish it.

And there's so much luck involved as well. That's the reality, no matter what, you know, in terms of how, what other books come out that week? So yeah, I wasn't shocked for sure but, you know, it was a happy surprise.

Dr. Chloe Carmichael: [00:06:02] Yeah, definitely. So what you started to do there, Dave, is like almost undercut your success a little bit. You're like, oh, well there's some luck in it as well. And you know, Dave, I like this about you. I think you have a big ego. And I like that cause I have one too. So this is not any kind of a slam, I think you have a big ego and I like that. And so I'm just curious, like, Since you are an entrepreneur and you do, you've had to deal with a lot of ups and downs. Do you like, just give yourself serious pep talks or do you ever feel deflated? Like how do you get out of that if that ever happens?

Dave Kerpen: [00:06:39] First of all, this is very exciting being interviewed by a clinical psychologist. Now I feel slightly on the hot seat with respect to my own emotions, but that's okay. So yes, I definitely feel deflated.

I mean, my father has bipolar disorder and I have, I would, I mean, I sort of self-diagnosed with like a very subclinical, sort of a hypno case of it. So I definitely get deflated and you know, my hacks that I wrote about in my last book actually, The Art Of People, are gratitude and acts of kindness. I find that it's really amazing when I'm feeling down, how stepping out of my own issues and focusing on doing for others, either through gratitude or through literally random acts of kindness can improve my mood from really down to feeling okay. Or from okay to feeling really great, right.

And if I need to perform, if I need to be in front of a big audience speaking or whatnot, then I need to be feeling great. So I need to figure out an organic way, or for me, an organic way to get into the right mindset.

Dr. Chloe Carmichael: [00:07:50] Yeah, definitely. So, I'm also curious with book titles like Likeable, which by the way I love I'm just like, I do feel though, like you kind of put yourself out there to the public, right?

So with a title like Likeable, it's very, to me it's very vulnerable because you're kind of inviting the public then to talk about Dave Kerpen’s likeability and his understanding of what it means to be likeable. And wow, this guy wrote the book on likeable, right. And I know that you are using it in terms of business and corporations and how they can be likable, but you know, the books kind of took on a life of their own.

And so I'm just curious, like, do you ever read your own social media? Do you ever read the positives, the negatives? Do you read it all? None of it?

Dave Kerpen: [00:08:11] I read it all. You know, one of my core values is, and one of what I believe is part of likeability is responsiveness. And so I can't not read it all and it's not easy. But I do. And I realized to your point that when you put yourself out there, as I have with the word likeable you're sort of setting yourself up. I mean, I can't possibly be likeable to all people, right. So that's really important. I learned that way, way, way back.

Super quick story, when I was on a reality show in 2003, we had a show therapist who, you know, very unethically was not confidential. He literally took what we said and went to producers with it, but that's another story. Anyway, he was somebody that I got to know because the only way to get off set was to speak to the psychologist. So I would take advantage of that. And after the show, I would walk down the street and I would see some people like cheer for me and then some people like snicker. And I would read online and some people had nice things to say, and some people had really nasty things to say. And I remember feeling really troubled by this. I mean really deeply disturbed. And I called him up and I said, what am I supposed to do? I mean, I can't, people don't really, they don't like me, but they don't really know me. It's not fair. And he said to me, “I have two questions for you, Dave. Exactly what percentage of the world do you need to like you to feel happy?” And then he said, “And second, how would you verify that? Even if you decided it.” And it was really valuable, I'll never forget that lesson.

And it's important because no matter how, no matter what I put out there, Chloe, and I do try really hard, but no matter what I do, there will be some that don't like me or even hate me, or don't like what I have to say, or even hate what I have to say. And that's just part of life.

Dr. Chloe Carmichael: [00:10:42] I know it's so ironic. I just, I think sometimes people actually get the most agitated when you're saying what they actually need to hear the most, you know? So it can just be like, kind of ironic sometimes. But anyway I'm also curious, again, because the nature of what you write is so personal. I mean, it's business, but it's so personal. I'm curious, do you ever, if you don't want to share it's okay, but do you ever use ghostwriters or what are your thoughts about ghostwriters?

Dave Kerpen: [00:11:16] So a lot of folks use ghost writers. I prefer, I've thought about using a ghostwriter, I prefer using coauthors and I do use coauthors.

So my first book was so hard to write. I really struggled with it. I know you've been fortunate enough to be able to write yours with, I think, less pain and strife than I, but I really struggled with it. And so really all my books since then have had coauthors that I put on the front cover and, you know, give full credit to.

And I think coauthors can be very, very valuable in writing. I think ghost writers, I have no ill will towards anyone that uses ghostwriters, one of my best friends is one of the leading ghostwriters in the world. So he ghostwrites for like really big name celebrities. It's just the business. But personally, you know, again, if transparency is going to be one of my core values, then I sort of have to be transparent about such things. So I am.

Dr. Chloe Carmichael: [00:1:19] Yeah. Okay. And then I'm just also curious, do you write backwards, meaning like, do you kind of have an idea of what you want the book to be like, and then you reverse engineer it and black it out? Or do you just sometimes start by saying, you know, like, there's this little thing that I want people to know and then you build on it. Does it go top down or the other way?

Dave Kerpen: [00:12:46] I would say top down. I think I one of, now I need to decide how humble I should be Chloe, but let me say that, well, I believe that one of my strengths is thinking in titles and headlines. And so with the exception of Likeable Business, which is my best reviewed book and my poorest selling book, I think I'm good at thinking of headlines. And so I think of the headline in this case, the title of the book, that big idea. And then I build a table of contents and really the table of contents is a set of, as I see it, a set of shorter headlines, right.

So what is the big idea of each chapter or each section? And, and then I take it from there and even within most of my yeah, I mean, pretty much all of my books that the chapters have are still bulleted, right. Bulleted out and have sections within those. And I still can have subtitles within each chapter.

So I would say, I think from title of book, table of contents, title of each chapter, and then titles of each sort of subheading within the chapters and right from there.

Dr. Chloe Carmichael: [00:13:57] Right. Have you ever had a desire to write fiction or some other type of book?

Dave Kerpen: [00:14:03] Totally. So actually after my first four books, my daughters said to me, “Daddy, when are you going to write a book for us? And I said, “I guess now”, and I took the challenge. It's been very, very much a labor of love, but I have finished writing a middle grade fiction book called Normal. And after four years of hard work and I'm very. Why do you look shocked? I'm so glad that I got to teach you something. So yeah. So I'm very excited about that book now. Of course. My girls are four years older than they were when they first asked me to write the book. So I don't even know if they may find that juvenile at this point, but hopefully my son will eventually read it and enjoy it.

It's about four New Yorkers growing up and the challenges that they have coming from different families that they don't feel normal. And it sort of teaches the lesson that normal is a sort of ridiculous social construct and that we need to embrace, you know, who we are and where we come from.

Dr. Chloe Carmichael: [00:15:08] I love it. I love it. My look of shock, Dave, was in part just because I didn't know, but it was also because I was thinking what an awesome title. You're right. You really do just have this gift of thinking in titles and headlines. I love the title. Normal. It's really, it's the perfect thing, especially for that age group.

So I'm curious, Dave, for you as a man with so many ideas, so many good ideas. I imagine one of the hardest things for you is to limit yourself, right? And to not, you know, just kind of just go in all kinds of a million different directions when you're having a bunch of good ideas. And you've got a team of people that are, you know, willing to start executing on them. How do you decide which ones to pursue and which ones to stop? And then do you have like the proverbial rainy day file where you store stuff up or is it just like yes now or no never?

Dave Kerpen: [00:16:09] Yeah, so great question. You're a really good interviewer, Chloe. I'm really excited. I guess I do a lot of these and they get very stale because they're the same questions over and over again, and I love hearing new ones. So thank you.

So, first of all, I'm stealing what you just said and calling it a Rainy Dave File instead of a rainy day file, Rainy Dave File. But I think I do think of a lot of ideas for sure. Many of them are bad ideas to be clear. Many of them are bad ideas. I remember when the pandemic first hit, we had this amazing au pair who was looking after my five-year-old and I was like, “We could start a preschool right now and have like 20 kids each day in that”. And my family looked at me like, what is wrong with you? It's an ongoing pandemic. Are you out of your mind? And I was like, “okay, maybe bad idea”.

So I think what I've learned in my old age here is that I can't execute that many ideas myself. And so I really surround myself with great people. And part of what I love about (Choose) Apprentice is that I can do this with young people who are super driven and entrepreneurial. In fact, I just launched a new business on Clubhouse with my apprentice, Christina, which I'm super excited about.

So now when I have new ideas, I sort of see the extent to which they bubble up, stay with me over time. Many of the bad ones quickly fall apart, but the ones that really keep rising to the surface I bring them to others. And I say, “Do you feel as passionate as I do about this? Because if so, let's do it”.

I have learned a lot of entrepreneurs really hold onto their ideas and sort of protect them. And I have it from the way I see it, I would much rather have lots of small slices of potentially big pies than a huge slice of nothing. Right? So, this is my strategy around finding great partners and great colleagues to run with some of my ideas that maybe aren't as crazy or aren't as bad as other ones.

Dr. Chloe Carmichael: [00:18:21] Yeah. So, I mean, with choosing great teams, obviously that's a strength of yours too. So I'm curious, Dave, so just for people who may not know Dave's latest business, Choose Apprentice is really incredible.

He gets these incredibly talented college students. And I don't say that lightly, like I'm personally somebody that likes to outsource and when it comes to just, you know, people to do everyday tasks, I don't need to pay a college student a bunch of money to do that. But Dave actually has these incredible college students, like the one I'm using, she's almost like my business diary. Like I tell her all my business ideas and then she executes them and organizes my team to do it. And like, she's so amazing.

So I'm curious, Dave, how do you, I mean, it almost sounds like a riddle joke or something. How do you go and find a hundred college students and then choose which ones are more than just bright eyed and bushy tailed, but don't have any idea like how to actually organize or see anything through? And which ones are actually really going to be incredible? I mean, do you tell it by their GPA's? How do you do it?

Dave Kerpen: [00:19:33] Yeah. Happy to answer that question. First, I just want to clarify that I wasn't talking about (Choose) Apprentice when I mentioned the new business, I was talking about an actual new business that I'm starting with my apprentice, a fifth business that you haven't heard about yet.

But that said, you know, I think that finding people, people is everything in building a business even a technology business, because people need to do the work. And, you know, with (Choose) Apprentice, college students are used to this rigorous, crazy application process. So that's the good news. So we basically recreated a similar process once they're already in college and if they want to become an apprentice. So we do go by GPA initially, and what clubs they're in, their leadership activities. But the number one aspect of the round one is writing samples because I do believe that great writers are great thinkers and great communicators, which is really, really important in business. So round one, the number one thing we look at in addition to GPA and clubs is writing samples.

Then we have an interview process, a multi interview process, and then finally we have an assignment, so they have to do an assignment and show how great their thinking is in real life. They do a competitive analysis. Every single one, one of the great parts about this is we're always understanding all of our competition because we have all these kids doing competitive analysis for us all the time.

And then finally if they pass that, they're selected and we only take 5% of applicants, so we're able to truly get really, really good people. And you never get it completely right. I mean, in business I’ve, of course, made some poor choices around people hiring. But you know, the whole adage of hire slow, fire fast, I really, really believe in, and really being very, very thoughtful about our hiring processes and who we hire.

Dr. Chloe Carmichael: [00:21:37] Yeah, well, whatever you're doing, it's definitely working. So Dave, also of course, is the President of the Entrepreneurs Organization. So definitely I'm so glad that you're sharing what you know about business on a larger scale.

And I'm curious, also, Dave, as we start to come towards the end of our time, I can't believe how time flies. But with all of these activities that you're doing, businesses, I know you're a really big family guy as well, which I really respect. And of course you give back with your time. Dave actually mentors me as well. So, I mean, he does so many things. I don't know where he gets his time and his energy.

So, Dave, I'm curious, do you have, and don't feel like you have to say yes, some people don't, so I'm just genuinely curious, like what you are doing or not doing. Do you have any sort of daily practice, meditation, prayer, exercise, anything that you do every day that you feel helps Dave Kerpen to be Dave Kerpen?

Dave Kerpen: [00:22:38] Gratitude. Gratitude for sure. So I have a few gratitude practices. The only one that is super, as always daily, no matter what is we have a practice in our family every single day. We have dinner together, no phones, and we share one person that we're grateful for at the table, one person that we're grateful for who was not at the table and our favorite moment of the day. And my kids resisted at first, but it's been several years now that we've been doing it every single day without fail.

And for me, gratitude is the ultimate drug. The ultimate mood enhancer, the ultimate game changer. So I try to actually sprinkle as many gratitude practices in my day as possible, but the one that I always stick to, no matter what is that dinner gratitude practice.

Dr. Chloe Carmichael: [00:23:29] That's great, Dave! That's really such a gift and a balance because a lot of people who just want to think about gratitude, they do it at the expense of being aware of reality, right? They're like, well, my house may be burning down, but I'm going to be grateful that there's heat from the fire, you know? But it's really wonderful, Dave, that you're not a man who runs from problems. Like you love to solve problems. You're not blind to them in any respect. But then you're tempering that with this really heavy dose of gratitude, which is awesome.

And I'm very grateful that you decided to come in, open up and share today. I appreciate that, Dave.

Dave Kerpen: [00:24:08] My pleasure. Thank you for having me. And thank you for asking such smart, pointed and new questions.

Dr. Chloe Carmichael: [00:24:15] Oh, it's a pleasure. Well, thanks again and hope to see you soon on Clubhouse.

Wow! That was really fun to be able to talk to Dave. I mean his point about gratitude. Definitely, I feel grateful all the time. I mean, for me, I just, I come from a small town in Michigan and you know, for me now, the idea that I get to talk to people like Dave Kerpen about his book and talk about my book and becoming a psychologist. There's so much in my life that I definitely do feel grateful for. So I appreciate that Dave put a fine point on the importance of gratitude.

So if you want to go ahead and share what keeps you centered every day, I would love to hear from you about that. And if you have not already, please do subscribe to the show. Just hit the subscribe button and the notification bell. If you see one, depending on your platform, and I really hope to connect with you on social media, I do love to interact with people. So go ahead, and let me know what you thought of the show today. Thanks a lot!

IN THE BUSINESS OF LIKEABILITY, AN INTERVIEW WITH NEW YORK TIMES BEST-SELLING AUTHOR DAVE KERPEN

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