One of the most under-the-radar benefits of entrepreneurship is its ability to build fortitude and make the entrepreneur a more formidable person. Challenges – particularly the crazy, unexpected ones that take on a life of their own – build character and confidence. And the unexpected surprises to the upside, the crazy good moments offer a high that’s hard to reproduce elsewhere. The charm and the challenge of entrepreneurship is dealing with the crazy things that happen and so we’ve asked some fantastic business owners and leaders to share some of their stories with us below.

Kevin Moody Jr.

This year, our organization was blessed with the opportunity to create what has become our flagship program, “Handshakes Over Handcuffs.” This program was pitched to key decision-makers in the Baltimore City Public School System, and we were able to conduct a total of four programs within three schools this past year. Read more>>

Kenya Wright

The craziest story was an elaborate funding scheme that involved winning $27,000 worth of the exact prizes I wanted on the Price Is Right! Read more>>

Nicole Uphoff

One of the craziest projects I worked on was a Photo Shoot in the mountains surrounding Payson, Arizona for a print publication! Read more>>

Akua Robinson

The craziest thing (in a good way) that has happened to me so far in business is receiving the phone call sharing that I was being awarded as the recipient of the Black Beauty Roster 2023 AJ Crimson Trailblazer Award. Read more>>

Manny De Los Santos

One thing about my profession is I come across lots of unexpected and crazy situations that make my career never boring in the slightest. One particular story was when I was hired to shoot a beach wedding out in Destin, Florida. Read more>>

Carrielynn Fournier

I recently encountered the most unprofessional “professional” while on a job site. My small business, Busy Bee Cleans, works with local construction firms and contractors, many of whom are well known in the area for their professionalism and excellent craftsmanship. Read more>>

Ebony Everette

Being in this business we all know that you can not please everyone as hard as we may try and want to it’s sometimes impossible. Read more>>

Laurie Guest

My most memorable negative, unexpected moment in my speaking career happened when I got fired by a client in the middle of my speech! Read more>>

Kara Zone

When I started working as a ghostwriter, I did it for me. I wanted to become the best writer I could be, with the eventual idea that I’d write and work on personal novels while helping others turn their ideas about books into reality. Read more>>

Jamie Taylor

They say entrepreneurship is like being on a rollercoaster but I’ve always loved them so I was game. But I was not mentally prepared for this type of rollercoaster ride. Read more>>