Having to overcome unexpected problems is a hallmark of entrepreneurship. Almost every business owner, artist, maker, and creative we know has had to deal with countless unexpected problems that arise in the journey and so we asked some brilliant folks from the community to share their stories of the unexpected problems they’ve faced along the way.

Lea Tran

Turning Hardship into Legacy: Why True Financial Freedom Starts with Protection Throughout my life, the greatest lessons have never arrived gently. They came disguised as interruptions, detours, or storms that shook the ground beneath me. Yet these moments, unexpected and often unwelcome, have shaped my path more than any title or achievement ever could. Read More>>

Michelle Arnau

Our business is built on a truly breakthrough innovation: an EPA-registered insect repellent featuring the first new active ingredient approved in this category in more than 25 years. After five years of rigorous testing, we secured full federal registration in the summer of 2023. From there, we entered the state-by-state approval process—expecting it to take 12 months—and raised capital to support a mid-2024 launch. Read More>>

Zach Mathews

One of the biggest challenges in my career has been learning how to handle public scrutiny. The more visible your work becomes, the more likely it is that someone will have a negative opinion. With tattooing now being widely shared online, more people than ever are viewing and commenting on our work and not all of that feedback is constructive. Read More>>

Christina Jovanna Olivarez

I hit 10 years in business in 2025, and it was also one of the hardest years I’ve experienced in business. One of the most unexpected challenges I faced in my business was recognizing that I was no longer aligned with what I had been building. Especially when I think about my next decade in business and next chapter. Read More>>