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Chris Clews: “Leaving your job to pursue your entrepreneur journey is only the first risk you’ll take”

Know when to take a break. Without the program of a typical job and having to be somewhere at a certain time with everything scheduled out, you can quickly forget what day it is. And if you love what you do like me, it doesn’t ever feel like work. I was talking to my sister […]


Know when to take a break. Without the program of a typical job and having to be somewhere at a certain time with everything scheduled out, you can quickly forget what day it is. And if you love what you do like me, it doesn’t ever feel like work. I was talking to my sister and she asked what I was doing over the weekend and of course I said working on presentations and content. She asked when I had last gone out with my friends and I couldn’t remember. That night I put my work down and met my friends. It made all the difference.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Chris Clews. Chris is a speaker, marketing consultant and author of the book series “What 80s Pop Culture Teaches Us About Today’s Workplace”. He grew up just outside of Baltimore, MD and is the quintessential child of the 80s. Growing up in the 80s and with over 22 years in corporate marketing he knew two things very well — 80s pop culture and business. So he combined the two and created “What 80s Pop Culture Teaches Us About Today’s Workplace.”

A graduate of Elon University in North Carolina, Chris’s marketing experience included executive roles in both ad agencies and the corporate world within a variety of industries from financial services to software. He’s built brands, led brands through transition and spearheaded sports sponsorships with NCAA Basketball, PGA, MLB, International Soccer and the UFC.

He speaks at conferences and events around the country on the topic of “What 80s Pop Culture Teaches Us About Today’s Workplace” and has spoken to a variety of audiences ranging from human resources to financial services to 80s fan conventions. His latest book was recently included in an article on Entrepreneur.com titled “15 Books on Business Culture You Need to Read Today” along with books authored by global titans such as Simon Sinek and Marc Benioff and he is a frequent guest on both business and pop culture podcasts.

He’s also passionate about animal rescue and donates a portion of the proceeds from his books and speaking engagements to the SPCA International and lives by the quote from the poet laureate Ferris Bueller, “Life moves pretty fast. If you don’t stop to look around once in a while, you could miss it.”


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

I grew up just outside of Baltimore, MDduring the 70s and 80s when pretty much everything we did was outside until Atari came along. I like to think of my generation as the video game generation since we were the first to have gaming consoles in our home throughout our lives. As was pretty typical in the 80s, my parents split when I was just entering my teens, so my younger sister and I became very close and have been the best of friends ever since. Sports, creative endeavors and exploring pretty much encompassed my youth. I played soccer, football, basketball and baseball and having a game or tournament was pretty much the only way to get me up before noon on a weekend. I had a great group of friends — I think Stephen King (via the Gordie character) said it best in Stand By Me, “I never had any friends like later on like the ones I had when I was twelve. Jesus, does anyone?” From a creative perspective we made a home movie called “California Bones” which we thought was great but besides destroying my mom’s house with fake blood and an unfortunate smoke bomb incident, I’m not sure that it was festival ready. And we explored everything and everywhere. During the summer, every day felt like it lasted a year and now every year feels like it lasts a day. I think we all feel that as we age and long more for our youth. Besides multiple broken bones and stitches from sports and stupidity, a very short unfortunate stint at a private school (I was definitely a round peg in a square hole there) and my parents’ divorce, I had a pretty cool childhood and look back on it with fondness.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

I spent over 22 years in corporate marketing — a job that I loved and brought passion to every single day. My formative years were the 1980s and you could say that I am the quintessential 80s kid. I had a moment a few years ago where I wasn’t quite sure where everything was going and if I was still passionate about my career, which ultimately prompted an internal questioning about my purpose.

One day while watching The Breakfast Club I had an epiphany of sorts. There’s a moment in the movie when John Bender — the juvenile delinquent character played by Judd Nelson — says, “Screws fall out all of the time. The world’s an imperfect place”. I’d heard that line 100 times — which ironically is the amount of times I’d watched The Breakfast Club — sat straight up and thought you know I’m currently in a bit of an imperfect place and the business world is a wildly imperfect place. I decided to write an article for LinkedIn on “What The Breakfast Club Taught Us About The Workplace” and the response was amazing, so I wrote another on what Ferris Bueller taught us about the workplace.

I realized that there was this explosion of creativity and unique storytelling within 80s pop culture that provided an opportunity to re-imagine some of the content and perhaps message it in a different way that could potentially impact workplaces and our lives. At that point, I thought I might have something unique, so I put pen to paper, wrote and self-published my first book, “What 80s Pop Culture Teaches Us About Today’s Workplace” which is now a series with a 2nd book that was recently published in November of 2019. After the 1st book hit the market, I built a website and positioned myself as a speaker on the topic and began pitching for speaking engagements on the side. I was fully employed as the Head of Marketing for a global division of a large corporation, so I used my vacation time for my speaking gigs.

It was at this point that I hit a crossroads and with the help of an amazing speaker manager, Kristin Haggar of The Haggar Agency, I ultimately decided to leave the corporate world behind and pursue a passion that was really there all along — speaking and writing.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

I was ready. Sometimes our best ideas come to us when we aren’t quite ready to make the investment or maybe life isn’t cooperating at that particular moment. Once I realized that my idea of integrating lessons from 80s pop culture into the modern workplace and our lives was occupying a super large space in my head all day and all night, I decided now was the time. At that point, your passion and belief in yourself and your content/product/service pushes you to continue finding ways to make it an actual business. The coolest thing for me was the first time I was traveling for a speaking gig and someone asked me what I do for a living and I said, “I speak and write about 80s movies and music and what it teaches us about today’s workplace.” I wish I had a picture of the look on his face. It was this smile of acknowledgment and a look of you really did it, good for you. His response was one word — “awesome.”

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

There is a great quote from one of the original pop culture icons, Henry David Thoreau. He said that “The mass of men (people) lead lives of quiet desperation”. We have hobbies or pastimes for a reason — we love whatever it is, and we are passionate about it. So much so that we dedicate one of our most valuable of resources -our free time — to pursuing it, working on it, perfecting it or just enjoying it. Doing something you love for a living is the dream everyone talks about. If your passion, hobby or interest is where you feel most fulfilled, then maybe it’s time to toss your fears aside and make it your reality. I know it’s cliché but life really is short and the goal for all of us should be to minimize the “wish you would have’s” at the end of it all.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I’m not sure that the fun will ever come out of this for me. I think if you are a building a business in the traditional sense I can see where you may get to a point where you are eventually running the business from a management perspective and you don’t have your hands in the putty any more if you will.With speaking and writing you are always the driver of the content and although you may grow to a point where you have a team supporting you, you’ll still be the idea person. For creative people, that is the piece we don’t ever want to lose. Creating is my fuel. If that was ever taken away from me, then the fun would be gone. I never thought for a minute that I would make a living through the lens of 80s pop culture. It’s just awesome. I wake up happy every single day.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

Freedom. After 20 plus years in the corporate world, having the freedom to make my own decisions, work where I want and work at the times that are best for my schedule.I’m a bit of night owl so that didn’t jive well with being in the office at 7:30 a.m. or 8:00 a.m. every single day.Knowing that each day I’m building something for me and not for someone else. That I’m accountable and responsible each day to myself. In terms of downsides, there are times where the administrative piece can be daunting. Not that it’s difficult but it can be time consuming and who wants to maintain spreadsheets for accounting when you could be creating new content. And then there’s the fear. Fear of failure. Fear of going back to that “mass of men who lead lives of quiet desperation.” But the enjoyments far out way the downsides — it’s not even close. Since I’m an 80s guy and pretty nostalgic, I explain it this way to everyone. Each day on your entrepreneurial journey will be a mix of excitement and terror. For me it’s going back to when I was a 13 year old teenage boy and the excitement of putting on my football pads knowing I was going to take some punishment and dole some out, versus the terror of being at my first middle school dance and peeling myself from the wall to walk over and ask a girl to dance for the first time. Both are about overcoming fears just like making the decision to start your own business.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

How much rejection there is before a true breakthrough and of course the stability of a paycheck. Regardless of how much you believe in yourself and your product/service/content you need to be prepared for rejection. Let it fuel you. There are plenty of examples of incredibly successful people and products that heard “no” over and over again. They just kept going and didn’t let it deter them. And of course the stability of a paycheck is something that you can begin to take for granted. Once it’s gone and you are out there like a bird on a wire, it’s a “striking difference” from before. As one of my friends told me — “get ready to cave-person it!” If you are in it for the long run and you believe in yourself, then sacrificing some of the small things over the short term that you took for granted before will get easier over time.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Yes. No matter how much you believe in yourself and your product/service/content, self-doubt is a very real thing. I remember one moment where I had been grinding away for months and feeling excited about the doors that were beginning to open. I felt like a breakthrough was right within grasp. I had a call set up for big opportunity and it was pretty much locked up, so the call was just a final formality. “Pretty much locked up” is not something you want to say often when it comes to an opportunity. Ultimately the call was cancelled at the last second, never rescheduled and to this day I haven’t heard back from them. The modern day ghosting. I was devastated and really spinning in circles for the rest of the evening and into the next day. But then I did two things: (1) I shifted my mindset and focused on all of the opportunities that were still out there — some I was aware of and others that would come to me if I kept hammering; (2) I took a break. I did something I never do. I took a day off in the middle of the week and I didn’t bring my laptop or phone with me. I took the advice of Mr. Miyagi from The Karate Kid when he said, “Don’t’ forget to breathe. Very important.” Stress is like dehydration. Once you realize you have it, it’s too late. Sometimes we just need to reset but not for too long. There’s a difference between resetting and wallowing. Keep those feet moving under you.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

So. Many. Mistakes. One of my first speaking engagements, I thought we were going to have confidence monitors at the front of the stage. These are the monitors that show the speaker their presentation with notes so you can have a reminder of sorts particularly when it is a longer form presentation. Well, I practiced with the notes and felt great about my presentation the next day. At dinner that evening I found out that they did not have confidence monitors. I was on my own and I had less than 12 hours to pull it together. It sounds terrifying but laughing at the position I found myself in, made me relax and I nailed it the next day. Of course, lack of sleep from practicing caused me to put on two very different looking socks which was pointed out to me by someone in the Q&A portion of my presentation. I told them it was part of my personal brand but no one believed that of course. The lesson I learned was similar to Michael’s in the movie The Lost Boys when David the vampire leader said to him as he handed him a goblet of liquid, “Drink some of this, Michael. Be one of us.” He drank it against his better judgement and well the liquid was blood and Michael was on his way to becoming a vampire. The lesson — Always review the terms and conditions and always read the fine print. True for both the living and the undead.

Who has inspired or continues to inspire you to be a great leader? Why?

This is a really great question and a tough one for me to answer since I look to multiple people for inspiration. It’s kind of like asking me to name my top 5 favorite 80s movies which I can’t do without putting them into genres because they are so many of them.

Rather than provide names I’d like to focus on the qualities of leaders that inspire me. Things like relatable, authentic, genuine, a belief in others, encouraging, positive, driven. I relate a lot of things back to 80s pop culture and in the movie Coming to America, Prince Akeem (played by Eddie Murphy) is born into royalty but ultimately wants to earn his own way. He teaches us that unearned leadership creates pleasers while earned leadership creates believers. I gravitate towards leaders that have earned their position — they are typically the ones willing to share the stage with others when they see potential in them.

How have you used your success to make the world a better place?

Yes! I donate a portion of the royalties from my book sales and fees from my speaking gigs to the SPCA International to support their mission to advance the safety and well-being of animals. My grandmother took in every stray — dogs, cats, birds, any animal that needed a home or help — and she instilled that love for animals in all of us. I also volunteered at a local Humane Society shelter and plan to do a lot more with them when my feet are on the ground locally a bit more.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Don’t be afraid to ask for help. Good people like to see others chase their dreams and if they can help, they just might. I had a very good friend, Jim Zielinski, who is a graphic designer, help me with my first book — designing and then formatting to self-publish to Amazon which he had never done before. He learned something new to help me with my dream.
  2. Be patient. No one sees the days and nights people put into their “overnight” success. I found myself comparing my journey to others and wondering why it wasn’t happening for me as quickly. No matter what you see or hear, it is rarely quick particularly if you are creating something new. You can frustrate yourself right out of the journey if you don’t practice patience.
  3. Know when to take a break. Without the program of a typical job and having to be somewhere at a certain time with everything scheduled out, you can quickly forget what day it is. And if you love what you do like me, it doesn’t ever feel like work. I was talking to my sister and she asked what I was doing over the weekend and of course I said working on presentations and content. She asked when I had last gone out with my friends and I couldn’t remember. That night I put my work down and met my friends. It made all the difference.
  4. Leaving your job to pursue your entrepreneur journey is only the first risk you’ll take. Every day is a risk when you are on your own and trying to build something great. Each day that passes by the risk becomes greater but that’s what keeps us motivated and moving forward. I was debating whether to make yet another financial investment in my journey that I didn’t anticipate and at this time, revenues were incredibly scarce. Oddly enough I was inspired that evening by the movie GhostBusters which is an entrepreneur journey in itself. At one point Dr. Peter Venkman played by Bill Murray says, “Why worry? Each one of us is carrying an unlicensed nuclear accelerator on his back.” I realized that if I wanted to succeed, I needed to take more risks — financial and otherwise — so I did.
  5. Enjoy the ride. You are getting ready to do something that very few people do but almost everyone talks about doing. Kind of like those who talk about writing a book and those that actually do it. You’ve already succeeded by betting on yourself, starting your journey and taking your shot. As Charles De Mar said to his friend Lane Meyer in Better Off Dead as he stood on his skis at top of the highest mountain peak in their town, “Go that way really fast. If something gets in your way, turn.” I don’t have an example here because I promised myself to enjoy it from day one and I have. It was the best decision I’ve ever made.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I’m going to refer to my life lesson quote below from Johnny Cade in The Outsiders when he said, “You still have a lot of time to make yourself be what you want.” We are often programmed to believe that certain things need to be accomplished by a specific time in our life and that includes career choices and in particular major career changes or entrepreneurial journeys. Of course this is all nonsense. You can be whoever you want to be whenever you decide to be. People find their true calling at all kinds of stages in live — some in their teens, some in their 40s and some in their 80s. There’s no right time or wrong time. It’s simply when it is your time. I think we are beginning to see this now and I know that some people on social media have already begun to push this idea forward which is awesome. I’d like to see this movement take hold and grow — the idea that it is your time when it is your time. Everyone is ready at a different time and everyone’s journey is unique. Embrace it and Create You when the time is right not when you are told that you should.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

The Outsiders (a great book by S.E. Hinton and 1983 film directed by Francis Ford Coppola) has a character, Johnny Cade, who says, “You still have a lot of time to make yourself be what you want.” I was 47 years young when I truly figured out what I was most passionate about and what I wanted to spend the rest of my life doing for work and a career. More importantly, I figured out how I truly wanted to live my life. No matter your age or your station in life, you really do still have time to be who you want. Go Create You!

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Adam Sandler. No doubt about it. He has inspired me in so many different ways throughout my career and my personal life. He just seems to have the right approach to life and totally gets the proverbial “joke”.

I consume every piece of content he puts out. He perfected humor with a heart and even in his silliest of movie moments, he delivers lessons for all of us. I think most importantly, he bet on himself and he delivered. He’s one of the good guys and it is so cool to see him beginning to finally get credit for his dramatic roles as well. If you missed Reign on Me, go watch it. And as an 80s guy, The Wedding Singer is the most perfect tribute to all things 1980s. I also really dig that he seems to work with the same people — seems like a family which is very cool and difficult to pull off in any industry. He is clearly super loyal which is really great.

On a personal level, I lost a great friend at 23 years old and my very best friend at 38 years old– way too damn young — and he lost his friend Chris Farley way too soon as well. When he went on SNL and sang his tribute to Farley, I felt it at an incredibly different level. I know that pain and I’ve lived it, but I also know that we need to focus on the joy and laughter they brought to us as well and he nailed all of that in a four-and-a-half-minute song. That’s why he is so universally loved.

We also have a few random people in common within our circle, that involve, well, super random stories so it would be cool to have that conversation as well. And of course, I think he might like my books!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.


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