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.

Tim Schmidt

Back in 2012 I was in the early stages of growing an e-commerce business in the anti aging sector. We were doing a steady 30+ orders per day with an average ticket of $96. On a Friday afternoon, Dr. Oz had an episode on anti aging creams, and he praised an ingredient that we used in many of our best selling products. Read more>>

Jane Wagman

We launched in June 2020 during the height of Covid. We had about 800 bottles of dog shampoo and conditioner in our basements and we were sending it out to friends and family to try. (Backstory: I met one of my partners, Regina, a very long time ago when we were both working at Vogue Magazine). Regina woke up one day a few weeks later and said “I kind of know Adam Glassman (Oprah Winfrey’s right hand man) and I’m going to DM him on Instagram. He wrote back immediately, “You are not going to believe this but Oprah HATES the shampoo she uses to wash her dog and she especially hates the smell. If you can get product out to Monetcito in two days she will be washing her dogs and will try it”. Read more>>

Khyler Vick

I flatlined once… One day I had this brilliant idea to strap light tubes to my back and ride a bicycle neck first into a rope. The plan was to get clotheslined and fall flat on my back, breaking the fluorescent glass tubes into little pieces, only giving me small, minor cuts. I was gathering a bunch of different footage to put together a Christmas special full of different Xmas related stunts like dressing up as Santa clause and jumping off the roof, kissing a tazer with a mistletoe above your head, chugging eggnog, etc. So when it came time to film the clothesline stunt, we decided to paint the light tubes with red stripes to make them resemble candy canes and tape them to my back in the shape of a cross… Read more>>

Dominique Bradley

The craziest incident that has happened to me thus far is having celebrities and/or their publicists, staff, or other members of their “entourage” follow me on Instagram and solicit me for travel services. I never in a million years thought that my reach could be that broad, and I’ve enjoyed the partnerships and relationships that have manifested as a result of me simply taking a risk and betting on myself. The unique logistics of planning travel for this caliber of people has given me a crash-course in advanced travel that I would not have otherwise gained in my 3 months of travel planning experience. I still have to pinch myself as reminder to be gentle on my progress, as I have only been doing this for 3 months. Read more>>

Fredrick Lawanson

I never really liked writing. For me, writing was a chore even in school I relied mostly on textbooks instead of taking down notes. I ventured into the entertainment business starting with music after school, but I failed. I decided to try my hands on movies next but it was worse. It was so bad that I almost committed suicide. In retrospect, try to identify where I went wrong and looking for answers, I ended up with the bible. I was able to draw a lot of insights and strength through this dark period. I learnt so much to the extent that I told myself, I can’t keep all these insights to myself, I must share it. Then the idea to write my first book came. I titled it “Real hustle” which is an exposé on how to find and fulfill purpose especially in making a career choice backed by biblical insights. From there, I started enjoying writing and have written and published a couple of books on Amazon kdp which has helped me expand my network paving the way for me to delve into other business areas of interest such as tech and the circular economy. Read more>>