We love grabbing drinks with our entrepreneur friends because they always have the craziest stories. Sometimes it’s a big, unexpected win. Other times it’s a problem that came out of nowhere and couldn’t possibly have been foreseen. There is so much to learn from these stories and so we asked some of the brightest entrepreneurs and creatives in the community to share some of those stories below.
Shanita Williams

The craziest thing that has happened to me in regard to my business is both my parents switching from expensive $100 creams and quick fix products to using mine! When I first introduced them to my products they supported me out of love and yet were truly skeptical as to whether or not my natural skincare would match up to their bougie brands. Read more>>
Alexis Jones

The craziest story that relates to me as a small business owner also relates to finding the right mentor. This is One thing that a lot of business owners encounter is becoming educated and we usually try to find education through those that are more experienced. Read more>>
Gaurav Bali

In 2005, I was advertising my guitar lessons online and received a message from a woman named Mrs. Hill who was trying to find a guitar teacher for her daughter. I asked her some standard questions, she asked some standard questions and we set up a time for a first lesson at their house. Read more>>
Kayla Dunham-Torres

Fortunately, I have a positive and crazy story to share. It’s about the time I choked on a sandwich and how it completely transformed my life and creative career. During the height of the pandemic, while I was still attending university and working on more than one small freelance project, I was up late most evenings working and studying until my vision was too blurry to continue. Read more>>
Kata Bilanchone

Many think that opening a yoga studio was a long time plan of mine, however this all came to happen quite unexpectedly. I had no intentions of opening a studio and much less buying one. But one cannot deny their fate… I was helping manage what was Green Monkey Yoga Studio, at the time, for about 2 years before my life flipped completely. Read more>>
The Mojo Network

Wow, let me tell you about the craziest business story We’ve experienced firsthand. It’s about our creative team finally meeting in person after knowing each other for years online. We had the incredible opportunity to come together in Miami for an event we co-hosted called the Ambetter Classic. Read more>>
Ravyn Alexander

The backstory of a positive crazy story for me through my business would be one day I was on Instagram. I was scrolling through people stories and this LA known dance named “Storm Debarge” Read more>>
Jacqueline Roche

In the realms of entrepreneurism, there are no rules, no predictive abilities. Your journey is often times a captivating tale of transformation, full of the unexpected. One of the most profound character strengths of an entrepreneur is the ability to transmute unforseen change into forward movement, or in simpler terms… go with the flow. Yet nothing could have prepared me for the massive shifts in my career that catapulted me into 2023. Read more>>
Colleen Monroy

I photographed a wedding once where the entire event was drugged by a disgruntled stepdad. It made the news and everything that night. I was two years into my business and quite honestly, didn’t have the boundaries or backbone that I do now. I was willing to take any work that came to me, so long as I was paid. No amount of money is worth dealing with crazy I’ve since learned. Read more>>
Ivan Wentzel

In June of 2021, we were booked to play a gig at bike night on the square in Lynchburg, Tennessee. It ended up raining, so our outdoor gig was moved inside the winery on the square. We backed our raggedy band bus up the narrow alley beside the Lynchburg winery and proceeded to load in and set up. Read more>>