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. 

Kayla Brown

I can’t believe I’m going to share this, but this genuinely is the craziest thing that’s happened to me in my career, and I truly consider it the start of a butterfly effect that shaped the entire trajectory of where I am today. In May of last year, I had a huge opportunity to photograph a show at First Avenue. Read More>>

Tamara Whitted

One of the craziest parts of entrepreneurship for me has honestly been realizing how emotionally attached people become to your brand, especially when your business is rooted in intimacy, confidence, wellness, and a ton of vulnerability. People don’t just buy products from me. They project onto me, confide in me, judge me, celebrate me, and sometimes completely misunderstand me all at once. Read More>>

katrina kelley

One of the craziest and most unforgettable moments in my business happened while running **Cigar Bella**, my live cigar rolling entertainment company. We provide **luxury cigar rollers for weddings, corporate events, private parties, golf tournaments, brand activations, and high-end celebrations** across the country, so every event is different — but one event truly reminded me how unpredictable entrepreneurship can be. Read More>>

Alexi Dinerstein

I guess this is the craziest and funniest story with a good ending. I had completed a job in June of 2024 and the homeowner posted a review on Facebook. A woman contacted me a couple weeks later via the review to install some belgian block pavers that had been removed elsewhere from the property and were to line a newly poured concrete path. Read More>>

Nick Mechak

At the first commercial kitchen I operated at the owner was a nice guy but a bit… sketchy at times. I’m not great at time management and when I left late at night he’d sometimes be sleeping on a couch in the cafe, usually alone, sometimes not. He rented a pallet in the basement to a student at one point. Read More>>

Danielle McGill

Once during a client’s appointment, she accidentally passed gas after dozing off. It startled her so much that she jumped awake and asked, “I think I farted—can you confirm?” Without missing a beat, I kept working on her lashes and replied, “Fart confirmed.” We both burst into laughter and carried on with the appointment. Moments like these remind me why I love what I do. Read More>>