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.

Cait Cassagne

One of the craziest stories would be when Spoiled Bitch Dog Boutique’s Reactive Dog Private Shopping Sessions went viral worldwide, several times! Read more>>

Meghan Pelley

Several years ago I was hired to assist a woman in her late 80’s with the sale of her home. This particular home owner had a 3rd grade education and was a widow with two adult children. Read more>>

Remi Swen

One thing I love about runway shows is the energy and anticipation. Witnessing the culmination of months of creative work as the final looks come to life on the runway is incredibly rewarding. Read more>>

Christopher Scott-Dixon

I’m an early riser, as was my client. He needed a conference call. I said, “Okay great, does 6AM work?” He told me it didn’t. And I falsely assumed that he wasn’t the early riser that he declared himself to be. Read more>>

David Berman

One afternoon I was doing my normal Facebook scrolling and saw a post from my good buddy Lorenzo Beronilla. I was a little excited because he hadn’t been posting for a little while and whatever big secret he was about to unveil. Read more>>

Dana Collins

As an independent contractor, there was a point where I didn’t think I could make the business work. I had built two teams that quit; they believed the business was just too hard. I called my mentor and told her I was quitting. Read more>>

Manesha Dowdell

In 2017 I had my first on location Bridal party that I had ever done as an entrepreneur. I was so excited. It was that feeling you have as a small child on Christmas Eve or the day before your birthday. Read more>>