/ / / Michael Bosstick Interview: Serial Entrepreneur, CEO of Dear Media + Husband to Lauryn Evarts

Michael Bosstick Interview: Serial Entrepreneur, CEO of Dear Media + Husband to Lauryn Evarts

Sharing is caring!

michael bosstick interview

Michael Bosstick Interview || Serial Entrepreneur, CEO of Dear Media, co-host of The Skinny Confidential Him & Her Show and so much more. Michael shares his insight on what it takes to build a successful business from the ground up, advice for entrepreneurs both new and old + how to execute efficiently.

If you don’t already know who Michael Bosstick is then get ready to thank me in about ten minutes. But really. Michael is husband to the ever so popular Lauryn Evarts of The Skinny Confidential, and If you follow me on Instagram you’ve probably noticed I tag them in my stories EVERY Tuesday when their podcast episodes come out.

I’ve been following this duo from the beginning and when Lauryn started putting Michael in the spotlight due to her jaw surgery, it added a whole new layer to her business. Michael Bosstick is the CEO of Dear Media, founder of Bosstick Media, co-founder of Jetbed, Inc., co-host of the TSC podcast + much more. Michael’s business advice is consistently on point (as well as his reading list), and I always look forward to his tip of the week since it’s normally geared towards business owners and entrepreneurs like myself. He is truly a wealth of knowledge with incredible insight on how to build a successful brand and business.

Not only is Michael an incredible mentor when it comes to business, but he’s also extremely down to earth. How do I know this? I e-mailed Michael asking if he would be interviewed on Hello Spoonful and he responded with a yes less than 24 hours later. This spoke volumes to me about his character and humility. I cannot wait for y’all to meet him.


If you were getting introduced on Good Morning America, how would they introduce you?

Ugh! I hope at this point it wouldn’t be too confusing. I have trouble introducing myself at this point and it’s something I need to refine and work on. I think they would probably say… “Our following guest is a serial entrepreneur and the CEO of Dear Media, a podcast network specializing in female content and hosts. He is also the founder of Bosstick Media a digital agency that has helped clients sell and build brand in the direct to consumer e-comm space. He is also the co-founder of JetBed, Inc. a company that creates beds for corporate and private aircraft for some of the World’s leading companies as well as the co-host of the popular podcast; The Skinny Confidential Him & Her Show which he hosts with his mega star wife Lauryn Evarts Bosstick of the popular online brand, The Skinny Confidential.” See what I mean? Needs refinement.

michael bosstick interview

What three pieces of advice would you give to college students ( or anyone since I know you’re not always pro-college 😉 ) who want to become entrepreneurs?

  1. I would say, do you need a degree for the field or career you want to go into?, if Yes, stay the course. If no, why are you there? If your parents are paying, by all means stay and have fun. If you are accumulating personal debt… ask yourself – “Is this debt worth the degree I am pursuing for the career I hope to go into?” As an entrepreneur I have not seen my degree since I walked across the graduation stage. No idea where it is. Have never used it. Certain career paths require it but the entrepreneurial path does not.
  2. Use the first 10 years, 20-30, 25-35 to take chances and make mistakes. You have no idea how valuable this will be later. I am 31 right now and feel like i’m 20 years old. You have so much time to correct course later.
  3. You don’t have to have it all figured out. Just start. The path will present itself once your walking down the entrepreneurial road. Too many young entrepreneurs hold themselves back by waiting for all the answers. Here’s the secret, you can’t find the answers without starting, so get started!

What do you look for in an employee?

A self starter. Someone who takes personal accountability. An individual who wants to grow past the initial job offering and bring elements to the brand or business that don’t already exist within the organization. Someone who doesn’t complain and blame others. The last one is a deal killer.

How long do you stick with an idea before giving up?

This is tricky. Most of the ideas and businesses I have started have changed and evolved over time. I think it’s more important to be willing to pivot if something isn’t working. I also think it’s really important to move on from bad ideas that don’t work. Use your audience or customer base for honest feedback and really listen to what they are saying and requesting. Don’t be stubborn or hurt at the idea of changing your path. Remember, as a business owner, content creator, or brand; your job is to provide value to the customer or audience member. If you aren’t doing that in a meaningful way. Move on. Take your self serving and ego out of it.

michael bosstick interview

What is your greatest fear, and how do you manage fear?

I don’t have a lot of fear in business. Probably why I take so many chances and make so many mistakes (which I later have to correct). I have a much greater fear of loss (death) of family. This is completely impractical because death comes to all of us. It’s so unproductive to think about the loss of a parent or sibling or spouse. I would throw away everything I have to make sure the people closest to me could live forever and stay safe. I manage fear by reading history and stoicism.

Understanding that the only thing, and I mean the only thing, that we truly have control over in this life is our minds.

Take care of your mind and use logic and reason to manage your greatest fears. Check out: “How To Stop Worrying and Start Living” by Dale Carnegie

You read A LOT — what are your top 5 books for entrepreneurs?

Ugh, again really tough. I don’t think these would be my top 5 but they are good places to start. I don’t have a top 5 because I think there are so many books that speak to you at an individual level. Let’s say these are all great and well rounded places to start.

  1. The One Thing by Gary Keller
  2. Managing Oneself by Peter Drucker
  3. Total Recall by Arnold Schwarzenegger (seriously, the guy has lived an amazing life)
  4. Poor Charlie’s Almanack by Charlie Munger (anything by Charlie Munger)
  5. Think and Grow Rich by Napoleon Hill

I have an email list that I will launch soon that will provide monthly book recs.

What sacrifices have you had to make to be a successful entrepreneur?

Personal time with friends and family. Personal time with myself, there is always a fire to put out or something that requires attention. In another interview, I also said it can be lonely and isolating. As a self starter and the last line of defense in the organization it can be hard to relate to everyone. There is never a clock out period. My businesses have become the majority of my life (I wouldn’t change this). It’s not for everyone and I think it’s important to let people know that’s ok. For me it’s what makes me happy and keeps me driven.

How did you feel when Lauryn started putting you in the spotlight? Did this spark new business ideas for you?

I have always been a behind the scenes guy. Probably still am. That’s probably hard to believe at this point, now that I have taken on some more public roles. We had a conversation and realized it was impossible for her to continue telling her story without bringing me into the mix. It sparked the idea for the podcast for sure because we both started receiving a lot of questions to our social channels on a wide range of subjects. The show started as a Q&A from people following our content.

What are some mistakes you see entrepreneurs, bloggers & influencers making?

They lack patience, they want it all now, and that’s not how this works. At least anything lasting and truly valuable. It takes a lot of time. They try and use someone else’s formula (which only works in the short term) and they look at where audience or customer is instead of where they are going. Read the book “Mastery” by Robert Greene.

michael bosstick interview

Were there any key moments or things you did that were pivotal to your success?

Deciding to go full force and unapologetically pursue my now wife Lauryn. From that marriage and partnership their have been many successful ventures created and that partnership has given me the confidence to keep pushing the boundaries.

Tell us about your newest venture, Dear Media!

Very excited about this. Lauryn and I started our podcast out of our living room with nothing but some sub par equipment and an idea to provide entertainment or value to an interested audience. The show has since done over 15 million downloads and reaches a couple hundred thousand people per week. From that growth an idea sparked in my head to help other podcasters (specifically female) find the same success in the space. I have an amazing partner in the business called Digital Brand Architects that bring an expertise in digital talent management while I bring the distribution and marketing to the shows.  We currently have 6 shows on the network and are in contract phase with 8 more. We are going to help bring the podcast space into the digital age.

What wakes you up in the morning and what keeps you up at night?

If i’m being honest, its my two chihuahuas, Pixy and T. Boone Pickens (yes we named him after the billionaire) They are up at the crack of dawn begging for food. My wife’s fingers clicking on the keys of her laptop keep me up at night. I know you were looking for a more exciting answer 😉

What can we expect from you in the next few years? Ultimate goal?

You can expect me to keep pushing and testing my limits. I am very much someone who gets off on the chase more than the destination. I think this is very important in staying happy along the rocky road that is entrepreneurism.

michael bosstick interview

Talk to us about mindset, creating your own future + what are some tips?

The first tip and the hardest tip is to start asking yourself what makes you happy and start disregarding the noise from others for what doesn’t. This can be hard because we hear things from our parents, and friends, and spouses and want to make them happy. In order to make others around you happy, you yourself have to be happy first. Then I would take a play out of Warren Buffet’s play book and start looking at your future in terms of 7 years and 2 months. First, what do you want to accomplish in 7 years (long term vision). Second, what can you do within the next two months to move towards that accomplishment (short term action). Then I would really work on staying in the present moment. Again easier said than done. There is a quote I keep on my computer backgrounds. It goes like this:

“Two elements must therefore be rooted out once and for all, the fear of future suffering and the recollection of past suffering; since the latter no longer concerns me, and the former concerns me not yet” -Seneca

If you were conducting this interview, what question would you ask?

After interviewing high performers and being on the other side of those interviews for the last 3 years, I think the most important questions are always the questions that get those performers away from their talking points. When you do a lot of interviews and answer a lot of questions you can get stuck in a rhythm of saying the same thing. Think about questions that get people in touch with their emotions and feelings so that they can open up from the heart instead the head. I myself am working on what these questions look like to better my own interviews. I understand this was not an answer with specific questions but I think it’s more valuable for anyone interested in the interviewing process.


+ Instagram + Dear Media + The Skinny Confidential Him and Her Show


MORE INTERVIEWS + BUSINESS POSTS ON HS: Krista Williams, Emilie Hebert, Samantha Bowers, How to Grow Blog Traffic in 2018.

x, elizabeth.

Similar Posts

Leave a Reply

Your email address will not be published.