How to Fast-Track Your Career, and an Exciting Opportunity with Dave Kerpen

Please share this episode with a college student in your life!!

Listen to the Zev Audio Zone podcast episode here:

They say you’ll shine brighter if you get closer to the sun. This saying is very true when it comes to advancing your career.

Spending some time working as an executive assistant to the person you admire most, or to a leader who is in a position where you aspire to be someday yourself is one way you can jump-start your professional life and gain experience, which you can ultimately leverage to become a star performer in your field, climb the corporate ladder, or start your own thing in the future.

Taking an internship or a job where you’ll be reporting directly under someone who can serve as a mentor, or a role model can be an amazing learning experience.

Today we’re going to be talking with serial entrepreneur and business influencer, Dave Kerpen, about mentorship, leadership, and how to make your business and yourself more likable.

Dave Kerpen is the founder and CEO of New York based social media marketing agency, Likeable Media. He’s a New York times bestselling author of such books as, Likeable Social Media, Likeable Business, and The Art of People, The 11 Simple People Skills That Will Get You Everything You Want. And he’s a renowned keynote speaker. He has recently launched a new venture,, a platform that connects entrepreneurs who are looking for a driven executive assistant committed to professional growth, with smart and motivated college students who are looking for real world experience and mentorship.

Read the full transcipt here:

Zev Gotkin:

Dave, thank you so much for being here with us today. I have long been a fan of your work. This is truly an honor.

Dave Kerpen:

Well thank you so much for having me. I appreciate it. And it’s too bad we can’t ride a cab together like our last interview.


Yeah, that would be great, wouldn’t it? So tell us a little more about Choose Apprentice. How did this idea come about?


Yeah, it’s really, it’s a wonderful story. As you mentioned, I’ve been a serial entrepreneur for a while, and in my last two companies, over the last 10 to 12 years, I’ve been very fortunate to hire a whole bunch of college students, while they were in school, who have worked for me as my executive assistant, and many of them have gone on to work for me full time after they’ve graduated from school.

Michelle was my first EA while she was at Syracuse, and she ended up working for me at Likeable Media for over five years, and she is now running social media for a Fortune 50 company. And then Megan worked for me while she was at St. John’s, and then she became a Product Manager, and my first employee, at Likeable Local, my second company, a software company. And Meg worked for me for over five years after she started as my EA, she was my Chief of Staff at Likeable Local. Theresa worked for me for over seven years after she was my EA. She ended up co-authoring my second book, Likeable Business. All these guys were super, super valuable. My last EA, was named Rob, and he worked for me for over two years, while he was at Hamilton. He co-authored the third edition of Likeable Social Media, he worked on $1 million project for a major brand client, for Likeable, and he ran numerous personal projects for me.

Well, Rob came to me about seven months ago, and he said, “You know, Dave, you’ve been very valuable in teaching me quite a bit while I’m in school. I’ve learned more from you than I learned in three years of college, and I think I’ve done some valuable work for you as well. I think we really should scale this and provide the same sort of relationship for others.” And I thought it was quite a brilliant idea of his, so Rob went, literally, from being my executive assistant college student to being my business partner on this latest venture, which is called Apprentice. And Rob and I launched it just a few weeks ago and we’re up and running with our first cohort right now.


Amazing. Sounds like Rob’s a real take charge go-getter. It sounds like a lot of the other students who’ve been in this program are that type as well, and that’s really amazing. You notice that there’s a trend now of a lot of young people starting businesses right out of college. There also seems to be a growing trend of kid entrepreneurs who start businesses at very young ages. Do you think that all young entrepreneurs should first spend time working for someone else before starting their own businesses? Do you think maybe, before they run and do their own thing, they should train under someone else?


Well, I think there are pros and cons to both methods. But here’s what I’ll say. I’ll say that I believe that higher education is in the process of a major, major disruption. It’s an area that has had very little disruption over the last century, and it’s really problematic because the costs of college have gotten more and more expensive, and yet, if you think about it, the value of a college education hasn’t gotten that much better. If anything, it’s gotten worse, relative to the job market. So, if you want to be a lawyer, you need to go to college. And if you want to be a doctor, you need to go to college. And if you want to be an engineer, you need to go to college. But if you want to go into business, I think more valuable, and maybe this will be controversial, but I think more valuable than a four year education is working directly in a business.

Many children, like my children, for instance, are fortunate in that their parents are entrepreneurs or small business owners, and if your parents are entrepreneurs or small business owners then you can probably get a taste of what it’s like to work in a business at a very young age. But if you aren’t as fortunate, my strong recommendation is, in lieu of, or if you want to be more comfortable, in addition to a four year education, that you strongly consider reaching out to and doing a program like Apprentice, or reaching out to an entrepreneur, a small business person, somebody you admire and saying, hey, is there an opportunity for me to come help out?


Amazing. I totally agree with that. I think definitely the value has decreased, but if they’re doing this instead, or in addition to college, I think they’ll definitely be prepared for the real business world.

What characteristics do the college kids who apply to join Choose Apprentice need in order to qualify? Do they need to be in college and what kind of traits are you looking for?


Yeah, great question. So, we have a very, very big vision for this. We want to connect at least a million entrepreneurs with college students. And the good news for us is that they’re both very, very large markets. In the future, we might be open to people that are not in school or people that have graduated, but for now we are focused on people that are enrolled in school. It doesn’t have to be a four year school. It certainly doesn’t have to be any particular kind of school. But people that are currently enrolled in school. They have to be entrepreneurial. They have to be driven. They have to be ambitious. They have to be self-starters. And we look at… we have a pretty hard application process, to be honest. But one thing that I… that’s the most important to me is writing ability.

I think that the biggest driver of success in my previous apprentices is their ability to write. I think that somebody that can write well can think well and can communicate well, and these are essential qualities in business. So, if you are not a good writer, I strongly recommend that you work on that skill. You practice until you become a better writer because writing is a skill that will absolutely benefit you and differentiate you from others. Whether you want to be an entrepreneur or not, writing is just a really valuable skill. As, obviously, you know.


Yes, and maybe I’m biased because I’m a copywriter, but our mutual friend, who’s going to be the guest on the next episode, Jeffrey Gitomer, once said, “Writing leads to wealth,” and I couldn’t agree more with that.


I had not heard that quote, but I do love it myself as well.


Yes, it’s great.

This brings me to my next question. I guess it’s a little bit similar, but, when you’re looking for an executive assistant, even outside Choose Apprentice, if you have an executive assistant or anyone who’s helping a CEO or a leader, what do you think is the most important trait? I mean, besides, I guess, good writing ability, what do you think is the most important thing they need to remember or keep in mind?


I think responsiveness is really, really important. I live a very fast paced life and I think most of the CEOs and entrepreneurs I know live similarly fast paced lives. This means that if I need something done, I need it done right away. And if it can’t be done right away, that’s okay, but then I still need to know, right away, that it can’t be done right away.

So what we do with Apprentice is we teach our kids, look, there are… apprentices rather. If you’re in class, that’s fine, but you still have to respond, right away, saying you’re in class and you’ll get to it in two hours or three hours, or whatever it is. I think responsiveness is a really, really important trait. If I want to keep going, just, like I said before, independence.

Oh, here’s another really good one! Resourcefulness. It shocks me how few people are resourceful. And the difference between somebody who’s resourceful and somebody who’s not. I’ll give you an example. Rob. Rob, I had a project, I had a client that needed a website, so I said, “Hey Rob, can you figure out… have you ever built a website before?” And so Rob said, “Well, I’ve never built a website before, but I’ll figure it out.” And he Googled it and he figured out how to build a website. It’s the kind of thing where most people probably would be like, no, I don’t know how to build a website, who can we hire? Whereas, if you are truly resourceful, you can… and smart, you can figure out how to do just about anything. That’s the beauty of the internet and Google and YouTube. You can figure it out.

So the kinds of people that I look for, not only as executive assistants, but, for that matter, any of my employees at any of my companies, I’m looking for people that are self-starters and are responsive and are quite resourceful.


Excellent. Yeah, I’ve seen in my own experience with managing people, those qualities are essential.

So, how can leaders bring out the best in their employees and teams? How can we cultivate that environment? How can we bring out the best in them?


Well, that’s a great set of questions, and I answer that a lot in my second book, Likeable Business, that unfortunately, while being my best reviewed book, is my worst performing book. Nobody buys it, which is a bummer. But, oh well.

But, for the purposes of this interview, in a nutshell, I would say that we need to be transparent and vulnerable, and we need to give a little bit of ourselves in order to… I ask lot of my people, but I give of myself and I think that helps differentiate me from some that don’t take that extra time to teach and to mentor and to give of themselves. I think that when leaders take that extra time and that extra vulnerability and authenticity, their people really respond to it.


Excellent. I will admit I’m guilty as charged. The only book of yours I haven’t read yet is Likeable Business.


(laughing) I’m telling you, nobody’s read it. It’s hysterical to me, but it’s okay. I can live with this, but it is sort of funny.


Well, I will be placing an order on Amazon right after this interview, and I encourage everyone listening here, not only to buy that book, but the other two books that I mentioned before as well. They’re all great.


Well, thank you. It’s kind of a funny situation, and I don’t want to get too into it, but bottom line is, ironically, because I’ll probably never earn out of that advance, and I’ve already earned out of the others. I actually make money on the other books, and I’ll probably never make money on Likeable Business. But it is, technically, my best reviewed book, Zev, which means, technically, it probably is my best, even though nobody’s read it. It has a very bad cover, and one thing I’ve learned through the years is that, in fact, everybody does judge a book by its cover.


That’s important to remember.

Alright, so last question, Dave.

How can businesses who value creating great cultures and wish to cultivate an enviable work environment best use that to their advantage when they’re promoting themselves on social media? How do they make it an attractive place to work? You know a thing or two about social media, how do you convey, hey, this is a great place to work, on your social platforms like Instagram and Facebook and what have you? LinkedIn.


Well, great question, but it’s really a two part-er, because the first thing and most important part of that question is to create a great place to work in the first place. You see, if you don’t take the time and energy, and frankly, money, to create a great place to work, then, when you try to promote it, it’s going to come across as inauthentic and it’s not going to resonate. So the first and most important step here is to go out of your way to create a great place to work.

So what do I mean by that? Well, the first thing is, be intentional about creating a culture, and spend money on it. A lot of folks will say, hey, we want to have a great place to work, but then they won’t actually spend money on it. What I am proudest of in all of my business accomplishments is winning Crain’s Best Places To Work in New York for five straight years. Because what that means is, we’ve been able to build companies where people are happy to go to work every day.

So this means spending money on employees, doing retreats. We just took our whole Likeable team on a two day camping retreat, which was an amazing… it was so much fun. Spend money on Christmas bonuses. Spend money on company outings. Really invest in your people.

And then, after you’ve done that, the second part of the question is, sharing it. I think Instagram is probably the best tool, but I think you can really use any of the social platforms and take video and pictures that help to demonstrate the kind of culture that you’ve built, and share that out with the world.


Absolutely. It’s interesting you say Instagram. I would think LinkedIn also, because a lot of people put their resumes there. Do you think that’s also a good platform, or would you do it differently on LinkedIn versus Instagram?

I’m hugely bullish on LinkedIn, and I think I would point specifically to LinkedIn Live as a tool that is going to see increased use, and folks will be able to use LinkedIn Live to showcase their company culture. I think that today, in September of 2019, it’s probably still Instagram over LinkedIn, just because that’s where people expect to see slices of life, even in workplaces. But I do think that’s changing pretty quickly and I am very, very bullish on LinkedIn continuing to be, and even evolving to be, an even better place to showcase your company culture.


Excellent. Well, thank you so much Dave. I really appreciate you taking the time to do this interview, and it was really valuable insights that you shared with us today, and thank you so much.


It’s my great pleasure. And you know, I talked about responsiveness earlier in my EAs and in my employees and I like to practice what I preach, so one of my personal core values is responsiveness. So if anyone’s listening to this interview and has a question or a comment, you can hit me up on any social network and I promise to respond to you. No matter how many inquiries I get every week I do work hard to respond to everybody.


I can vouch for this. He really is very responsive! You often respond to my tweets and emails, and it’s pretty impressive because I know you’re a busy guy.


It’s my pleasure and thank you for the shout-out.


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I'm a writer and digital marketer. Communicating your brand's message and helping you to connect with the right audience is my specialty. If you are interested in: branding, marketing, copywriting, social media, search engine marketing, inspiration, success, and enjoying life, then my blog is the right place for you.

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