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.

David Barbeschi

A lot of crazy stories come to mind. As a freelance screenwriter, I strive to be open to my clients’ suggestions. After all, most of the scripts I’m commissioned to write are personal to them. That said, sometimes you get ridiculous notes. Just last month I had a client who – with a straight face – asked that I insert a twist at the end of our “Rocky”-style story that revealed “the whole movie was just the main character’s dream”. Read more>>

Shawntay Gorman

I remember this day like it was yesterday. Me and the Stonerettes (Vanessa and Liv) we’re covering the Santa Cruz music festival. During Ghostfaces set I kept throwing up my the shirt (with the painting I painted of him on it) up, he’d acknowledge it with a head nod but never came and got it. For some reason it did cause Killah Keise to keep looking at me like I was a snack and stand right in front of me all night and look at me like he was gonna eat me but that’s neither here nor there Lmao Anyways, I painted this painting and put it on a shirt in hopes that I’d somehow get it to one of my favorite Wu Tang (P-Tone aka Tony Starks himself) members by the end of the night, but it wasn’t working. Read more>>

Lori Judd

I was hired to declutter a home in Las Vegas. The family had a home in South Hampton and NYC and was buying a home in Beverly Hills. Once I was finished decluttering and organizing the home in Las Vegas the family sent me to South Hampton (selling this home) to organize and pack the home, find a moving company and start the process. The home sold in South Hampton and they asked me to have some of the items from South Hampton shipped to NYC and back to Vegas but in the meantime they purchase their Beverly Hills home and needed the rest of the items shipped to Beverly Hills. I then proceeded to jump on a private plane back to NYC meet the movers to receive the items in their NYC apartment, unpack them and organize their home. Read more>>

Rebecca Velez

During my first few months in business, I was slowly but steadily building my clientele and was seeing around 8-10 clients every month. But then came July, my 4th full month in business, and I had 26 clients booked – a huge milestone for me at that time! But one particular appointment that month was more memorable than the rest. A husband had just booked an appointment for his wife’s first-ever birthday facial. She was so excited and even braved a summer storm to get to me! Read more>>

Sara Troy

As a Podcaster one has to deal with many things that can go wrong. A client not turning up, not ready for the interview, internet dropping happens a lot, and internet interruption that only catches every other word. But, the biggest for me was having an Ash=thma attack on the air. I was lucky enough to be interviewing a Mother of 15 children and she was calm while I gasped for breath. Once the attack was over, a laugh and now a husky voice, we resumed the conversation. I cut the attack out of the video but left an explanation for my husky voice. Stuff happens, it in how we deal with it that matters, calm light, and continue. Read more>>

Nat GJ

In the vibrant world of entrepreneurship, you never quite know what’s around the corner. From shocking moments to surprising triumphs, there’s a vast spectrum of experiences. Let me share one of my most surreal tales from my journey as an entrepreneur. Picture this: It’s 2018. Everyone is buzzing in the developer community, specifically about AI related to video sentiment tracking. I’ve always been at the frontier of technology, programming since I was 12, and had even graduated with a degree in multimedia from the Art Institute of Seattle. My previous agency, Reflection Labs, had been acquired by a Venice-based startup, Tonic, where we developed algorithms leveraging AI for video analysis. Our goal? Help publishers gauge audience reactions to their ad content. Read more>>

Tâm Nguyễn

I am grateful for the opportunity to share my crazy exhilarating back story of my journey and breaks into beauty & banking. First, mentorship matters! Minh Tâm Nguyễn, godfather of the nail industry is a legendary pioneer in the manicuring industry. He modeled social entrepreneurship and I had a front row seat as his son. As a former medical student and biology major I was headed down a career path of safety & stability. What I found out eight years into that upon completing my education was I was neither happy, fulfilled nor passionate about the future. The missing part was the social impact through entrepreneurship serving my community to make a difference. Read more>>

Elias Toufexis

When I was 21, I had graduated from theatre school in Montreal and I was working at a comic book store for about 5.50 an hour. I was doing a play I co-wrote at the Montreal Fringe Festival. I was broke, but it was a lot of fun. Someone saw the play and offered us a theatre Off Off Broadway in New York to do the play there. They wouldn’t pay us anything, but hey I’d get to do a play in Manhattan so of course I jumped at the opportunity. Read more>>