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.

Isabella Johns

There is so much joy associated with wedding dance lessons – when couples accomplish a pattern that was initially difficult, when the groom earns brownie points for being a good sport about the lessons, when they flirt and laugh as they treat the lesson like the date night its meant to be, etc. One couple planned to surprise the groom’s mom with the fact they have a choreographed first dance because she would be in utter disbelief that her son could dance. I’ve had a bride be cleared from cancer between her lessons. I could tell a million stories about the small and big moments I get to share with these amazing couples during their season of celebration and love. Read more>>

Courtney Reed

I have had two really interesting situations to occur to me since the launch of Kinky Kouture. In 2020-early 2021 Rose vibrators were very popular to the point that if I announced that my inventory was restocked they were sold back out within 48 hours. One evening I had a potential customer chat to request a discount. I advised him that none were available at the time and asked if he had any specific questions about the item in question. This gentleman began to curse me out and tell me they were “cheap, POS items from China so there was no reason that I could not offer him a discount.” Read more>>

Melanie Fantus

“Crazy” is a good word to use describing my last few years. Maybe because I live with a significantly compromised immune system, on a planet overcome with an endemic that sounds like a drink my parents always have around for company (and don’t forget the lime!). Maybe because our family-owned and operated business, the one I had always dreamed of having, was up for sale. The parents wanted to retire and, despite my persistent pushback about selling, I knew it was the right thing to do. Scary pandemic and potential life-long dream crushing doesn’t sound like much fun – not until you fill in the juicy details. Read more>>

Renard Ragsdale

So the year was 2010. After starting RDG in April of 2008, I was quickly greeted with the harsh reality of a historic global economic meltdown. All my plans and projections were quickly doused with a bucket of cold water and I was forced to re-assess my next steps. Though I never doubted my decision to strike out on my own, the first couple of years were “interesting” to say the least. As we were moving forward, it became clear to me that the greener pastures lay ahead in the form of forging longer-term relationships as opposed to one-off projects. Read more>>

Katrina Karyofyllis

One of the craziest stories I have from throwing events in Miami is one from a little over a year ago. My partner and I were hired to manage and book DJ’s for a private event at an art gallery. Covid restrictions were still in place at this time as gatherings were limited in size and scope. Upon accepting the request to manage this event the owner of the art gallery informed us that it was a small private event indoor and outdoor of 20-25 people. This seemed reasonable to us and we accepted this offer. Read more>>

Rosalyn Osorto

My story happened with a popular brand name available at Target. They contacted me for a collaboration for the second time. The first time everything went well, and I enjoyed working with them! The second time, they sent to influencers the instructions to complete the collaboration. I headed to the store and bought what I needed, I got home and created the content that I needed. Few days prior to the due date I received an email saying that the collaboration was cancelled (this was during Covid time). Read more>>