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.

Mitzi Starkweather

In June of 2022 I went to Italy for a photography workshop. This was my first time traveling since the pandemic, and I was over the moon to meet some of the top photographers in the world at an Italian castle and create and learn together. Read more>>

Scott Boateng

The quicker you learn the lesson the faster you can grow your business. As the first entrepreneur in my family, I didn’t have a role model to call on or to help me avoid costly mistakes. I had to take the long route. Which meant there were a lot of trial and errors, but honestly, I think that was driving force to my success. “Bought sense is better than taught sense” as mother would tell me quite often. Luckily, I was a quick learner and there were so many tools online to help you figure out. Before I knew it, I had learned so much about running a business. Of course, I didn’t know it all, but I was pretty proud of myself. Read more>>

Makayla Miller

Off the top of my head, the craziest thing that has happened to me in my business was just last year. I was booked for my first bridal shower and I got there early like so do with all my bookings. As I’m getting setup, I realize I don’t have a single SD Card on me. And I usually do pretty well with having multiple on me. So I had to leave and speed to the closest CVS and get whatever SD Cards they had. And I bought two just to be safe and sped back to the function. I felt so much embarrassment within myself even though no one knew what was going on. Thankfully I was early so everything ran smoothly after that. But it was definitely a big moment of panic. Read more>>

Heather Ekola

My business was an accident. Not as big and accidental as Play-Doh, but it happened purely without a lot of planning, and grew as organically as a pumpkin does from last year’s jack-o-lanterns. I started out as a piano teacher. For twenty years I taught beginner level piano, and during that time would have a piano recital twice a year. I would make caramel apples for my students as a parting gift. That went on for a number of years. Read more>>

Nida Jalal

what a roller coaster it was, being successful or being into a world full of amazing creators is never easy. It always comes with love and hate, for me it was a crazy journey, I had to face criticism on every step of my success but I am blessed with great support system from my family and friends. There were times when I decided to quit as I was not getting enough responses but then I would go back look at my work and realize the amount of time and work I spent on all my content. Read more>>

Jazmine Scott

I believ craziest thing that happened to me was being selected to be the lead stylist for a film sponsored by Queen Latifah for her Queen Collective series. I was only 2 weeks into stepping out on a leap of faith for my braiding business. I signed and created my website via Styleseat. From there, the director, B. Monèt contacted me and it was honestly a no brainer! She later invited me to the screening of the film in New York and I got to stand two feet from Queen Latifah herself! Read more>>

Delilah Porche

Man, where do I even begin? Throughout the years, I can say I’ve seen, been through and heard it all, if not almost everything. I’ve had some crazy things happen to me before, but I’m going to talk about one particular situation that happened to me about a year ago, ha! As a freelance hairstylist, I would always be open to help others any time I was available on occasions where they may have needed an extra hairstylist. Read more>>

Michele and Danelle Pino

Danelle and I grew up dreaming about having our own art gallery. Our parents loved traveling and especially visiting galleries and museums. This was a huge influence for us. In 2013, we opened Wyn 317, a small gallery in the heart of Wynwood. It was exciting but scary at first because we didn’t have any experience in running a business. We were lucky to find a space that gave us a 4 month lease to see if we could make our dream a reality. Read more>>

LaTesha Conyers

As a rule in pop up: I never break down or leave early. I also never count my money before its over. One Saturday I was at one of my regular markets in Gibsonville, NC. The hours of the market are 8am-12pm. I usually do well and customers flow from beginning to end. But this one particular Saturday I was not doing well and it was obvious that my sales were 0. it was already a quarter to 11 and I had not sold one bar of soap! I was surprised and I was getting discouraged. I gave myself some positive self talk and kept my head up. Read more>>

Manu Goffer

The craziest story and journey of our business is the popularity vr campus tours with athletics over admissions. The idea behind CampusVR was brought to light when co-founder Zvi Goffer was trying to get his children 15,13 interested in college. Bringing them to the website of his Alma Mater, Binghamton University, he was quickly met with resistance. Images of buildings, & a birds eye view of the campus did not hold their attention. So Zvi asked, Why wouldn’t every school in America have a virtual reality tour? Read more>>

Va’nese & Keisha

As we all know, owning a business is not for the weak. Keisha and I found out the hard way. We leased out salon suites to 10 stylists and one small boutique owner. We were understanding to everyone’s needs because we know that everyone has to start somewhere. We allowed the boutique owner to have their packages with inventory delivered to our the building. The owner of the boutique seemed to be doing very well. They had a lot of clientele, and new inventory arrived weekly. Read more>>