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.

Jessicka Anne

“One of the craziest experiences I’ve had in business was actually the moment that reminded me of a truth that changed everything.” I’d been in a functional freeze for close to 12 months — just grinding, spiralling, and trying to get myself moving again. So I decided to run what I lovingly call my “Hail Mary” one-day event. Read more>>

Kevin Wilkerson

The craziest story happened before PubClub.com was even created. In fact, it’s a big reason why it was created in the first place. I was in Amsterdam with a friend who knew the city so well I called him Mr. Amsterdam. Read more>>

Jeremy Knauff

Shortly after leaving the United States Marine Corps, I started a full service digital marketing agency that I ran successfully for over a decade until I was blindsided by a health crisis that nearly killed me and left me on my deathbed for over two years. Read more>>

Rhonda Green

My books are based on my own, sometimes crazy, life experiences. I wrote ’40 Questions Before a First Date’ from my own dating experiences and the conversations I should have had before entering relationships that ultimately wasted my time. Writing the book taught me that dating isn’t about butterflies; it’s about clarity. Initially, I promoted the book by sharing questions from the book. Read more>>