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.

Michael B. Chadwick

In the 15 years that I’ve been a real estate agent in NYC I’ve had my share of crazy experiences. In 2018 I was a contestant on a dating reality show on ABC called “The Proposal”. All expenses paid, the network flew me from NYC to LA , put me up in a hotel, I was treated like a rock star. After being booted off the show in the 1st of 4 rounds, I eventually became friends with the particular Bachelorette of our show Celine Thum and was asked to represent her on the purchase of her first apartment in NYC! I got a buyer from being on a reality show !:) Read more>>

Kenzie Mayberry

In December 2023, I moved from apprenticing in a large shop of 17 artists to a single booth studio to continue tattooing as an artist. The space needed a lot of renovating before I could get it inspected. My dad and I took a month to transform the place into a clean, safe, and functional tattoo studio. In early march, I was finally able to get licensed and start taking clients. I decided to keep the location pretty discreet; by appointment only. I didn’t put any signs outside that said “tattoo,” and the blinds on all of the windows stayed closed so no one could peek in. I kept the address out of all of my social media and off of my website. I planned to only send the location to my clients after setting an appointment and getting a deposit, and that’s exactly how I operated for nearly three months. Read more>>

Christina Beaulieu

I was honored with running a tarot booth at a pet adoption event this year. It was really cute and fun. There were booths with puppies, kittens, a crepe station and yummy Mexican food. My sister tagged along to promote her nail business as well. While it was a great event, there wasn’t tons of foot traffic and I grew a little concerned I wouldn’t receive many clients. Determined to make it work though, I walked around to other booths offering a reading. One young woman asked me if I could read for her rat. At first I was taken aback. Some small part of me felt like I was being mocked, but the young woman insisted this rat meant the world to her and she wanted to know what spirit had to say. I agreed laughing. To be honest it really made my day. I decided to take it very seriously and opened my heart to the opportunity. I held the little guy in my palm as I spoke to him about his long legacy and beautiful life. Read more>>

Ambrie Schumacher

I was contacted by a local musician to essentially come up with an idea for a short promotional video to promote her upcoming single. I was given complete creative control and tasked with building the set. I excel in these situations as complete creative control is any artist’s dream job, right? I built an entire 70’s style living room in the back of a U-Haul… a MOVING U-Haul. The hardest part of this job was securing the furniture to the truck so that the musician wouldn’t get hurt while in motion. I have never used so many zip-ties in my life. After adding the finishing touches and securing all of the props, I was informed I would also be driving said U-Haul. I have never had so much fun on a set; this was the craziest and most creative set I have been a part of. My favorite to date. Read more>>

Shiloh Wilde

Becoming a shop owner, I hardly expected to get any orders outside of the country due to the shipping cost. At the start of my business, I got an order from the UK for a custom rosary. When I saw the amount they paid for shipping, my jaw dropped. It was well for $70, for a rosary that costed $20. That made my whole month, I never thought people would care that much for my work that they would be willing to pay an arm and a leg for something. Read more>>

Brandon Yousko

Firstly let me say that my business should be a show cause we have a lot of crazy stories but mainly gunna focus on the one that got me pegged as the manic mechanic and made my business take off. So I’ve been doing crazy things for years but this one was a bunch of emotions built up I was freshly rehabilitated off of drugs and alcohol and just served my divorce papers I could not sleep at all I was about to start my manic episode which usually ends bad for me. I a week earlier order a brand new Mopar 6.2 hellcrate supercharged engine for a replacement in a hellcat red eye the customer ended up not having the funds to do the build and I had a 1991 Chevrolet s-10 sitting in the shop well one night I got a idea which was not a good idea. Read more>>

Jackie Errico

I had been in the fitness industry for over 15 years and I had worked from the private sector, to the corporate sector, to the Division 1 Athletics level, and I finally decided to start my own business and take everything I loved abut the health and fitness space and everything I wanted to see done better with the space, and make it my own. When I opened my training facility on February 20, 2020, it felt like the culmination of a dream—a space I had carefully crafted to serve my clients and community. But just one month later, on March 20, the world shut down due to the COVID-19 pandemic, and that dream faced an unimaginable challenge. Read more>>