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.

Darian Jarrett

For years, my wife and I lived a steady life in Little Rock, Arkansas. We’d built up our cleaning business to a point where it was manageable. I was still doing most of the cleaning myself, but it worked. It was comfortable. Then came our fifth wedding anniversary. We decided to celebrate with dinner in Northwest Arkansas, thinking it would be an exciting night. Instead, it was the opposite. The food was great, but the whole experience just felt off. My wife, who usually keeps things together no matter what, had what I can only describe as a meltdown right there at the table. She looked at me, frustrated but hopeful, and asked, “What do you think about moving to a different state? Maybe we could have a different kind of experience.” Read more>>

Brooke Greer

The most unforgettable and emotionally challenging moment of Decorum Elite’s first season came during a time when we were already navigating what felt like an impossible journey. As a first-year youth football program, we knew we’d face growing pains—figuring out our identity as a team, earning respect in our league, and dealing with injuries here and there. But nothing prepared us for what unfolded mid-season, when one of our players lost his mother to breast cancer. This wasn’t just any player—he was the heart of our team, a kid who carried himself with humility, grit, and an unshakable positivity. His mom had been an ever-present figure at our practices and games, cheering with pride and supporting her son in every way. For many of us, she was a reminder of why we do this: not just for the wins, but to help raise kids who know they’re loved, on and off the field. Read more>>

Tracey Boateng

Daringly Posh has had some incredible milestones this year, and two of the most memorable moments were being invited to host our very first pop-up event at Creative Artists Agency (CAA) during their Mental Health and Self-Care Retreat and being featured on KTLA5 News. As a new business, being recognized by such a prestigious platform like CAA was an incredible opportunity to showcase our mission of empowering individuals through luxury and self-care. CAA, home to global icons like Zendaya, Ariana Grande, and Doja Cat, invited us to create an immersive self-care experience for their team—a significant recognition of our brand. On the day of the event, we transformed a conference room into a chic self-care space that truly reflected the essence of Daringly Posh. Watching CAA’s team engage with our products and hearing their positive reactions was a proud moment that validated our vision. It was an inspiring reminder that something as simple as beautifully designed, high-quality press-on nails can elevate confidence and joy. Read more>>

Gili Mor

We had a high-end client inquiring about the most expensive ring on our website, he wanted to come and take a look at it in person since it was exactly what he was looking for and within his budget. We set up a time for him to come in and showed him the diamond ring which was in the 70k range. He was impressed but wanted to see another option, knowing that I have a really good diamond and that I priced it very competitively I would probably bring another one in and eventually sell mine. Read more>>