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August 18, 2025 55 mins

#877: #871: In this raw and unfiltered solo episode, Michael Bosstick breaks down what it actually takes to build, scale, and sustain a business in today’s world. Drawing from 20+ years of firsthand experience as the Founder & CEO of Dear Media, an investor in high-growth startups, and a serial entrepreneur, Michael shares hard-earned lessons from both wins and failures. He dives deep into the biggest mistakes new founders make, how to choose the right business partners, the importance of financial discipline, and how to protect your energy while building something that lasts. Whether you're launching your first company or growing your tenth, this episode delivers tactical insight, mindset shifts, and a no-BS playbook for long-term success.

 

To Watch the Show click HERE

 

For Detailed Show Notes visit TSCPODCAST.COM

 

To connect with Dear Media click HERE

 

To connect with Michael Bosstick click HERE

 

Read More on The Skinny Confidential HERE

 

Head to our ShopMy page HERE and LTK page HERE to find all of the products mentioned in each episode.

 

Get your burning questions featured on the show! Leave the Him & Her Show a voicemail at +1 (512) 537-7194.

 

To learn more about DM IRL Dallas and purchase tickets visit https://dearmedia.com/events

This episode is sponsored by Cotton

Cotton is The Fabric of Our Lives. Learn more at http://TheFabricOfOurLives.com.  

 

This episode is sponsored by Fatty15

Fatty15 is on a mission to replenish your C15 levels and restore your long-term health. You can get an additional 15% off their 90-day subscription Starter Kit by going to http://fatty15.com/SKINNY and using code SKINNY at checkout.

 

This episode is sponsored by Astral Tequila

House Marg Summer is here!!! Time to stock up! Go to .css-j9qmi7{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-flex-direction:row;-ms-flex-direction:row;flex-direction:row;font-weight:700;margin-bottom:1rem;margin-top:2.8rem;width:100%;-webkit-box-pack:start;-ms-flex-pack:start;-webkit-justify-content:start;justify-content:start;padding-left:5rem;}@media only screen and (max-width: 599px){.css-j9qmi7{padding-left:0;-webkit-box-pack:center;-ms-flex-pack:center;-webkit-justify-content:center;justify-content:center;}}.css-j9qmi7 svg{fill:#27292D;}.css-j9qmi7 .eagfbvw0{-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;color:#27292D;}


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