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.

Natasha Teocel

When I started my entrepreneurial journey, I did so with a Venezuelan arepas business. It all began at my university, where my classmates were my first customers, and then word of mouth spread, leading me to start selling online. It was a successful venture that I launched in 2014, which confirmed my passion for working in the digital world. Read more>>

Danalyn Savage

No one in my family was an attorney. I didn’t know any attorneys. But I went to law school anyway, graduating in 2005. From Virginia where my law school was located, I moved to Phoenix, Arizona to study for the bar exam. I have family in Phoenix, but was on my own with studying for the bar exam. I did not know any attorneys in the city and had no prospects for work. Read more>>

Sophie Taylor

To this day, one of the coolest experiences I’ve ever had was seeing my lettering on network television. I’d signed up for a listing with a popular vendor site and was “discovered” by a wonderful man over at NCIS. The episode he was working on centered around a series of hand written letters and he needed someone to write those letters. Read more>>

Mallorie Babcock

In May 2023 I decided to use the last of my savings to open my business full time! It was exhilarating, exhausting and so fulling to see my dreams start to unfold. It was also terrifying, banking on yourself to provide a living, knowing that failure is not an option. I found a quaint room to rent out of another business, in a trendy and up and coming neighborhood. Business was steady, until it wasn’t, and I was booked and busy quicker than I anticipated! Read more>>

Paris Scobie

The craziest thing that happened to my business was the origin story of it’s creation. Before I could launch Live Well Bipolar, I had to first overcome my own internalized fear and self-stigma. I spent over a decade telling myself two things – I don’t know anyone else living with bipolar and I can never publicly share this. I thought I experienced my “full circle moment” when I went back to work at the same hospital I received my diagnosis at. Read more>>

Parker McMullen Bushman

Creating a more inclusive workplace is not just a goal but a necessity, especially in industries like the outdoors and environmental sectors where diverse voices have historically been underrepresented. My advice for organizations aiming to foster inclusivity is to start by acknowledging that this work is ongoing and requires a deep commitment to learning, unlearning, and action. Read more>>