What It Really Takes To Build a Successful Brand & Business - From Scratch To Scale With Michael Bosstick
The Skinny Confidential Him & Her Podcast
Dear Media
4.5 • 14.5K Ratings
🗓️ 18 August 2025
⏱️ 56 minutes
🧾️ Download transcript
Summary
#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.
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Produced by Dear Media
Transcript
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| 0:00.0 | The following podcast is a Dear Media production. |
| 0:04.4 | She's a lifestyle blogger extraordinaire. |
| 0:07.5 | Fantastic. |
| 0:08.5 | And he's a serial entrepreneur. |
| 0:10.8 | A very smart cookie. |
| 0:12.2 | And now Lauren Everts and Michael Bostic are bringing you along for the ride. |
| 0:16.3 | Get ready for some major realness. |
| 0:17.9 | Welcome to the skinny confidential, him and her. |
| 0:21.8 | Uh-huh. |
| 0:24.8 | Hello everybody. |
| 0:25.6 | Welcome back to another episode of the skinny confidential, him and her show. |
| 0:29.4 | Today you have me, Michael Bostic, once again, solo while my wife, Lauren, is still |
| 0:33.8 | on maternity leave. |
| 0:34.7 | She will be back soon. |
| 0:36.4 | But today, I'm very excited to do a business focused podcast show because I haven't done |
| 0:42.8 | one in a while. |
| 0:43.5 | And obviously for the entrepreneurs or the career focused people out there or people that |
| 0:47.5 | are thinking about starting a business, many of you come to this show for some of the business |
| 0:51.9 | content. |
| 0:52.3 | And we have amazing entrepreneurs that come on here regularly. But I also have a thing or two to offer in the realm of entrepreneurship. For a little bit of background, for those of you that maybe don't know me, I'm sure many of you do. But for those that are wondering, you know, why is this guy credentialed to give us any advice? I've been an entrepreneur, basically, my whole professional career. The last actual |
| 1:11.5 | job I had where I worked for somebody other than myself was when I was 15 years old, working at |
| 1:15.9 | McDonald's. It was great experience. But ever since then, I've always kind of done my own thing. |
... |
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