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.

Jessica Ringer

The (Literally) Wild Story Behind One of My Most Memorable Wine Launches In the fall of 2023, I had the privilege of helping design a new wine brand and label for Archway Wine, a California Pinot Noir created exclusively for The Keg Steakhouse in Canada. Read More>>

Peter Young

Two stories to highlight that the biggest entrepreneurial successes come from taking the biggest risks… Before launching my software business, I was selling used books on Amazon. I was 35 with no resume, no skills, no degree, no family money, and no backup plan. Read More>>

Olga Gabris

“Can You Cheat?” We were in the middle of yet another pre-production meeting. Six crew members at a dining table, coffee in hand, sleep nowhere in sight, we got up for a quick break. In the hallway, the director KD Karnati looked at me and casually dropped this bomb: Read More>>

Jamie Parker

One of the craziest stories happened during the crash around 2010. I was mowing the yard at one of my short sales and I saw a car drive by the house. I told myself when they come back to the stop sign I was going to stop them and speak with them to see if they’re looking to buy a house. Read More>>