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.

Kay Jones Williams

Not crazy but unexpected… I was featured with other small businesses on Fox8 and Kickin’ it with Kenny November 18, 2021 as part of the East 185th Street “Pop-Up Christmas Shops’, one of my limited edition handbags-a 2022 square shiny handbag was on display during the interview and highlighted. Fast forward to the pop-up shop that was taking place the following to which I was a vendor. Read more>>

Heather McCarty

It’s no secret consumers love to shop with people they like, know and trust. I have built my business on sharing my authentic self with my followers/customers on social media. They get a first hand look in to my personal life. They see my face, they know about my family, my hobbies. That vulnerability has benefited my business in more ways than one. But it doesn’t always come without consequence. Read more>>

Ash Uss

The most interesting story about my business, From the Ground Up is its origin story. In 2020, I was working with Mike McQuaid, a local champion and expert in the areas of homelessness and housing. We planned to leverage private sector resources to build housing communities for vulnerable individuals- that is people struggling with mental illness, cognitive challenges and physical struggles. Read more>>

Elissa Onda

One of my craziest stories is a ‘fake it until you make it’ kind of story. Good Morning America called me and asked if we could do a full set design, for a segment featuring The Rock and Emily Blunt. I jumped at the opportunity, but I didn’t know if I could pull this off. Read more>>

Princess Miller

Don’t fall for deceptions…. I remember when I went full time with my business. I had a handful of clients and I was working to establish my brand as a full service creative agency. And so I started forging relationships with other agencies to partner on projects providing services they didn’t offer. Read more>>

Shaila Martin

One of the craziest stories I have to share is one that would forever impact the way I view relationships and also friendships. It was last summer, May of 2021, that I was returning from a trip celebrating my daughter’s 6th birthday. Our birthdays are are one day apart so it’s always a special moment for me and her to celebrate together, although she gets 100% of the shine. Read more>>

Rahkim Sabree

I left my full time banking career in May of 2021 to pursue entrepreneurship full time and to protect my mental health. It was during a period dubbed “The Great Resignation” where many people were leaving their jobs in search of greener pastures, whether that be a different more fulfilling job or to start their own business. I felt that I could no longer thrive in the environment I was in mentally, emotionally, or professionally and so my leaving was motivated a bit by frustration. Read more>>

Karon Wilson

I was In Atlanta and Filmed this amazing project called ” The Come Up: Atlanta” we were gearing u to wrap the project up and had a-lot of amazing footage in it an also had an Oscar winning actress do a cameo in it. The Last week of us filming the project i had been robbed of all my camera equipment and footage from out of the car we were using to film scenes with. Read more>>

Drew Henry

In many ways, I feel like I was pushed off a cliff into entrepreneurship. While other business owners take gradual steps to create their own company — working side hustles and gradually leaving their 9 to 5s — I started with some higher stakes. I quit my job in March 2020 with other offers on the table. The next day was the start of the pandemic shutdown, and all of those offers disappeared. Read more>>

Melencia Lattimore

The craziest, most unexpected thing that happened to my business was when I was contacted by an agency representing Ciroc vodka. When I was contacted, I wasn’t allowed to know who the client was, all they could tell me was that it was a liquor brand by a man with a lot of kids, lol. Read more>>

Nick Eldredge

One of my craziest stories starts back when I first got my camera! I went to a car meet with some friends of mine and I took my camera I just barely got to take some pictures of peoples cars. Then someone walked up to me and asked what camera I had and they offered to put one of their lens’ on my camera to take some better pictures. Read more>>

Trajan (Tra) Moreland

The craziest thing that has happened since I’ve started my brand is receiving love from JT from the citygirls. It was so unexpected! I was promoting my release of my Summer lot on Twitter, & before I could finish promoting I saw she tagged me in something. But knowing me & how active I am under her post I just kind of brushed it off. But something was telling me to check & see what she mentioned me in. Read more>>

Charles DeBarber

My name is Charles DeBarber and I am the Animal Husbandry Coordinator at Filbert Street Garden in Baltimore City! I am primarily a beekeeper, but care for the many animals at our garden; chickens, ducks, turkeys, goats, and a temperamental goose. Read more>>