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.

Soverign Anthony

The craziest business story that I ever had to go threw was when I was getting ready to drop a music video and I had to look for a promoter/ marketing and so I had found someone great like everything about him was great like his business did my research so I said ima take a chance so I was asking for donations and man a took a chance on me to give me money to invest and when I did the dude that was great business man took all the money that was donated to me and my video didn’t do the views it was post to and like everything about that’s business went down Read more>>

Kyleigh Rumpca

It may not be the craziest story but it was definitely one I’ve learned from and look back on and just laugh. It was when I was just beginning my business endeavors. I hadn’t even officially launched my business, wasn’t really on social media yet and just doing craft sales. It was when I experienced a total flop at a market event. Read more>>

Meghan Bowen

Exhausted and overworked sums up 2022 for me. Being a small business owner is hard. That’s putting it lightly. I suffer from anxiety and panic attacks. I have been on medication now to manage my anxiety for almost 10 years now. These medical issues are stemmed from PTSD but are also hereditary. I’ve spent most of my life learning about mental illnesses as my father was a Vietnam Veteran and suffered an immense amount from mental illness. Read more>>

Davon & Tavon Woods

We are working around the country for kids in the foster care system. Read more>>

David Neely

So many people ask me how I got into this business. I simply say “I didn’t get into it, I was born into it….Nashville Tennessee, St Thomas Hospital, 1950. Read more>>

Brian Hofer

Aloha and thank you for taking the time to read my crazy story about how I doubled my revenue month after month. I’m a young entrepreneur on the beautiful island of Oahu and I have thriving laundry service startup named Tama Laundry. We offer a wash and fold services with pick up and delivery where you can choose your own detergents, softeners, etc all within a few taps on your smart phone or laptop. Read more>>

Degaryia Witten

One of the most extraordinary experiences that unfolded for me was receiving an unexpected spotlight for my business in the Facebook group of one of my favorite authors, Ashley Antoinette. It was a day that will forever be etched in my memory. As I followed my usual morning routine, my Shopify app suddenly started chiming with notifications, causing me to wonder what was happening. It was around 8 or 9 am, and little did I know, something incredible was about to unfold. Read more>>

Latarsha Giles-Ansah

The craziest thing that’s happened to me/my business has been receiving shoutouts on the radio from a local reggae dj. It all began during the 2020 pandemic quarantine when there was nothing to do and no place to go. My family and I love to listen to DJ Rickey Lee play reggae music on 99.7 FM every Sunday from 6-8 p.m. Instead of sitting at home listening, we began to drive around town listening to the reggae. Read more>>

Stoney Monroe

It has always been my dream to be in the beauty world to have some type of beauty business. I started my online beauty supply in 2019 and I knew that’s what I wanted to do for the rest of my life. I still do but during that transition i grew a love for modeling. I’ve always been told I should be a model but I never took it serious until I got my first paid opportunity in 2020. Read more>>

 Suzanne Lucey

So we have a large sign saying Page 158 Books above our store. You would think people know that we deal in books. However, we have had people drop off coffee machines for us to fix. ( I did find the warranty for her) I had a woman come in during the pandemic and cut her hair. Someone wanted us to place a bid on his old porn magazines. Read more>>

Lee Johnson

When I was dropping my Fall/ Winter 22 collection. A guy I follow led because I like his brand and he was influential in the Streetwear community, so he posted on his story he was trying to collaborate with upcoming designers. So I messaged him and said let’s work. He responding and we started sending each other mock ups and ideas. But the only thing was it was 1000 dollars. Read more>>

Matias Whittingslow

This story definitely has a few chapters. One thing for sure, is that through all of our ups and downs, we have always committed to being the authors of our own story knowing that once we started something that was OURS we were going to do what is best for us, and write our lives the way we see it. Read more>>

Timothy Cameron

As the Founder of a non profit public charity designed to provide underserved youth with an opportunity for a brighter future, it is often a challenge to break through cultural and social barriers to effectively inspire change. At Stella’s Child, we strive to help youth overcome the stereotypes they grow up with merely because they come from poor families. These talented and creative youth simply lack access to opportunity by mere circumstance of birth Read more>>