To Top

Meet Michael Bosstick of Dear Media, Bosstick Media, JetBed, Inc.

Today we’d like to introduce you to Michael Bosstick.

Thanks for sharing your story with us Michael. So, let’s start at the beginning and we can move on from there.
I am an entrepreneur and business operator. I try to be as concise as possible when doing these things. I am a graduate of The University of Arizona (some call this the Harvard of the desert) and in 2008, got my start in the residential and commercial real estate space. As many of us know now, that was not the ideal time to enter that industry and necessity caused me to pivot and switch gears. With my father Gary Bosstick, we started a company called JetBed, Inc. which is now the World’s leading provider of beds for corporate and private aircraft. We service some of the World’s largest companies and high net worth individuals. Operating that business as the CEO I needed to learn how to market in the digital space. I started Bosstick Media as a marketing machine that has since marketed in the online space for multiple brands as well as my own. Most recently with my partner Digital Brand Architects, an LA-based influencer management company; we have launched Dear Media which is a podcast network focused on female voices and audiences. I have taken on the role of CEO for this business and currently represent about 10 shows in the space while constantly looking for more great talent to sign.

Has it been a smooth road?
I don’t think any entrepreneur or businessman/woman will ever say there weren’t and aren’t struggles. If they do, they are probably lying. It’s a constant struggle. Managing people, working with brands, coordinating teams, representing talent. People have their own issues and when you add a work dynamically to those issues challenges arise. I think an entrepreneur is someone who can take those challenges and turn them into opportunities. There is an author named Robert Greene who I love, he said, “Even the worst shit that happens to you can be converted into gold if you are clever enough” I think this is true.

So, as you know, we’re impressed with Dear Media, Bosstick Media, JetBed, Inc. – tell our readers more, for example, what you’re most proud of as a company and what sets you apart from others.
Let’s talk about Dear Media because it’s the most recent. We specialize in producing high-quality female-focused podcasts in multiple categories. My wife, Lauryn runs a successful blog called The Skinny Confidential. A couple years ago we had the idea to start a podcast. We started it out of our living room, self-producing the show, having no knowledge of the space. We grew it week over week with many hurdles along the way. Eventually, we joined a network, had a rough experience and went back to self-producing. During this time, I learned the ins and outs of Podcasting. I learned how to produce, market, and brand the shows. We learned how to work with brands and advertisers. The show currently reaches about 150,000 listeners per week.

In my opinion, the current podcast space needs an update. Most of the talent we represent are also heavily immersed in the digital space. We are hyper-focused on helping them add relevant podcasting channels into their brand and storyline. Most podcast networks are not set up to create a full digital experience. They are stuck in the radio age selling radio spots.

Podcasting is one of the only current digital mediums that you can be fully immersed in while also doing something else. You can listen while you commute, while you work, while you train, etc. In my opinion, audio is the future because it’s a time saver. The same way Uber and Postmates is. As a company, I am most proud that we are a place women can come and feel completely confident and comfortable getting their message across. No edits, no limits, pure creative control. I am proud to help amplify their messages.

Let’s touch on your thoughts about our city – what do you like the most and least?
My favorite thing about San Diego is the pace. It’s a laid-back city. Still a major city but very laid back. In San Diego, I get a reset. I split my time now between LA and SD now. LA can be very chaotic, constant stimulation. When I get down to San Diego I can slow down and reset.

My least favorite thing about the city is also my favorite part of the city. I live a fast-paced life and like a lot of stimulation a lot of the time. San Diego can get a little slow for someone who likes to constantly move. It’s a big city but not quite LA or NYC. It can feel sleepy at times.

My wife’s a Gemini… is this how it feels?

Contact Info:

Image Credit:
Lauryn Evarts of The Skinny Confidential, Kristen Cavallari, Gary Vaynerchuck, JetBed, Dear Media

Getting in touch: SDVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

Leave a Reply

Your email address will not be published. Required fields are marked *

More in

  • San Diego’s Most Inspiring Stories

    The heart of our mission is to find the amazing souls that breathe life into our communities. In the recent weeks,...

    Local StoriesSeptember 25, 2023
  • Hidden Gems: Local Businesses & Creatives You Should Know

    Every day we have a choice. We can support an up and coming podcaster, try a new family-run restaurant, join a...

    Local StoriesSeptember 18, 2023
  • Portraits of San Diego

    It’s more important to understand someone than to judge them. We think the first step to understanding someone is asking them...

    Local StoriesAugust 31, 2023
  • Community Member Spotlights

    It’s more important to understand someone than to judge them. We think the first step to understanding someone is asking them...

    Partners SeriesMarch 16, 2023
  • Fashion, Selling Online, Charity & Nonprofits

    SDVoyager Podcast Episode 5 We’ve got some incredible guests on on the podcast today.  Lindsey Radoff, Sybil Golin and Madison Pollard...

    Partners SeriesFebruary 15, 2023
  • SDVoyager Holiday Guide

    Discover truly unique gift ideas that will leave your friends and family smiling all season through our Holiday Gift Guide below....

    Local StoriesDecember 8, 2022
  • San Diego’s Most Inspiring Stories

    Every neighborhood in San Diego has its own vibe, style, culture and history, but what consistently amazes us is not what...

    Local StoriesNovember 8, 2021
  • The Folks Solving The Problems You Need Solved

    One of the most important benefits of a thriving small business ecosystem is the myriad of problems and niche issues that...

    Local StoriesOctober 31, 2021
  • Community Member Spotlights

    It’s more important to understand someone than to judge them. We think the first step to understanding someone is asking them...

    Local StoriesOctober 11, 2021