We’re excited to introduce you to the always interesting and insightful Kim Bosley. We hope you’ll enjoy our conversation with Kim below.

Kim, thanks for joining us, excited to have you contributing your stories and insights. What was the most important lesson/experience you had in a job that has helped you as a business owner?

I worked for almost 30 years as in Orthopaedics & Sports Medicine as a Certified Athletic Trainer. Now at 52 years young, growing up in and navigating that space was always challenging. It’s a world dominated with big male ego.

I worked very hard as a young professional to take any and every opportunity to network and be exposed to a variety of sports, people, and experiences. I took a chance and found my niche in cheerleading and performing arts, which landed my a gig with the NFL Baltimore Ravens Cheer & Dance team. A position I held for over 26 seasons.

I was also very committed to advocating for the profession by educating hospital systems and school systems on the advantages of hiring ATCs to care for patients and athletes.

I ran my department like it was a small business, taking pride in every aspect. Also, taking responsibility for the good and bad. I was always very passionate about growing a team and empowering a safe work space.

As I continued to develop as an Athletic Trainer and grow as a leader I always carried my core values as a healthcare provider first.

I topped out my career in a Regional Director role with a staff of over 50 people.

There are so many lessons that I have learned through my years-

I think that all that i have done running a department taught me everything I needed to know to effectively run a small business.

I have also learned many many painful lessons about people. Countless lessons- when people show you who they are, believe them.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I spent 30 years in healthcare. I had a big job. Balancing a staff of over 50 people, taking care of more than 50 NFL cheerleaders, while navigating all of the politics of a large hospital system really started to effect my mental health.

I had a supervisor who grew to be wildly disrespectful and dismissive, a HR department that was inept and turned a blind eye. Every day felt like a fight for what was right.

I turned to a work coach and the EAP but was eventually ‘restructured out’.

I have lived in my home for 22+ years and Chesapeake Wine Company has been a staple in my neighborhood for 28+ years. The Gals that owned the shoppe had become very very good friends. I have made so many memories and created so many relationships visiting there during their 10 year span of ownership. They had been trying to sell for over 2 years, so they could enjoy a retirement and their grand kids. They were prepared to lock the doors and walk away at the end of their 10-year lease.

I couldn’t stand the thought of the neighborhood losing such an amazing space- so I risked everything and bought it!

Let’s talk about resilience next – do you have a story you can share with us?

My entire journey is one of resilience. Trusting my healthcare system, putting so much of myself into my position that I was Very Very good at, that also really became my identity- to then so easily be pushed aside so quickly and easily for no really good reason was devastating.

The entire process of dealing with banks, the SBA, real estate companies, management companies and then Baltimore city with those politics…… Everyday was a lesson in getting knocked down. Everyday was a reminder of how isolating it can be owning and building a business as a single gal. Everyday it was difficult to rely on others to have to do their job so thay you can make your vision a reality.

Can you tell us about a time you’ve had to pivot?

Getting restructured out of healthcare after 30 years.

Having my Cheer team taken from me after 26+ seasons.

I always had a side hustle in the bar/restaurant industry.

I tool those skills, my love of wine & spirits and bought a business in my neighborhood.

Contact Info:

• Website: https://chesapeakewineco.com/
• Instagram: @chesapeakewineco
• Facebook: https://www.facebook.com/share/19coQFf3o7/
• Linkedin: https://www.linkedin.com/in/kimberly-bosley-13691214?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=android_app
• Yelp: Check out Chesapeake Wine Company! https://yelp.to/rsjqlbbxtN

Image Credits

All my photos