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.

Dina Lu

I started my YouTube channel in 2020 posting weekly long-form educational videos about how to start a calligraphy business (my audience at the time was calligraphers who wanted to start their first business). For a year, I made videos helping calligraphers make money, but then I had a midlife crisis in my YouTube journey. Read more>>

Sandi Ballard

Well, one of the craziest things that happened to me during a coaching session was a wife asking for a divorce from her husband in the middle of the session! And their son was in the session as well! YEP! Here’s how it all went down. Read more>>

Morgan Blackman

My craziest business story was when I made my first $10,000 in one month as a wealth coach. This was in the year 2021 when I had been running my business for about a year. Usually, in the first year of business, we’re told that it’s going to be really challenging finding clients or customers and it’s going to take years before we start to see significant revenue and success. Read more>>

Dorian Rogers

The world of real estate is a crazy place all on its on. There are a lot of ups and downs that we experience through the process but there is one file that I would never forget. This may have been the hardest loan I ever completed with one of the toughest clients that ended up being very grateful in the end. Read more>>

Alana Weintraub

What comes to mind as the craziest is the time I was setting up wedding florals at an old hotel in downtown Portland, and actually experienced paranormal activity. I was installing a large floral install on a fireplace mantle for the wedding ceremony backdrop. To save install time, I designed it in studio knowing the dimensions of the mantle and it had no issues in the studio. Upon completing the installation and standing back to photograph it, just like dominoes, each section fell of the mantle in slow motion and came crashing down. Read more>>

Gerard Jones

I have always had a passion for soccer coaching and developing people, having established a career working in grassroots and professional soccer across different age-groups around the world. I previously worked in professional soccer in England as a Head of Coaching at EFL Bristol Rovers FC, and have mentored coaches across all levels from the elite level to the grassroots for four of the six continental bodies of governance in football, including UEFA, AFC, CAF & CONCACAF. Read more>>

Rachel Hunt

There are so many stories. Some of the most heartbreaking stories are from clients who are young or otherwise dependent on family. They often feel trapped, pretending to believe things they have doubted for a long time. People are forced to fast for days on end, evangelize for beliefs they don’t subscribe to, submit to corrupt authority, even marry someone chosen by their parents or church.  Read more>>

Heather Baker

We were cleaning out the home of a hoarder after she had passed. Her daughter, who had lived with her, was convinced that her mother was the hoarder, and that she was not a hoarder. As we worked with her, it became clear that both of them had been hoarders, as it was nearly impossible to get the daughter to let go of items that were basically trash. Read more>>