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.

Ron Lee

In 2009 we received a call from an intern at a large LA/NY-based advertising and branding firm. They wanted to know if we could provide 100 skydivers for a product introduction project. We asked a lot of important questions, none of which the intern could answer. It took a while, but we finally got them to transfer us to manager of the ad account. It turned out they wanted the skydivers as a part of a t-Mobile branding and activation account where they were going to announce a new cell phone. Kicker – they wanted all 100 skydivers in freefall at the same time, over San Francisco’s Embarcadero. And, we had 26 days to make it happen. Read more>>

Kevin Sprague

I can think of two stories that come to mind. Every year since 2014 we have donated our time and product to a special event that helps people living with Multiple Sclerosis. It’s a non-profit called Meat Fight. They host an amateur bbq competition with local chefs not in the bbq community. On one particular year they had Nick Offerman (Parks + Rec, comedian) be one of the judges. He stopped by to try our coffee and actually did a little promo pitch for us. All the way to the point of “here let me turn it around so you can see the logo.” Such an unexpected thrill for us! Read more>>

Teal Cooper

has been for me. This is the lesson of detachment. Like many business owners, the pandemic totally wrecked me. Since our clients consist of corporate offices, colleges and hospitals our revenue dropped 95%. After the feeling of being in denial for the first month wore off I started to hit this rock bottom moment of just feeling so extremely low. Like many others can relate, I felt so incredibly helpless, frustrated, angry and discouraged. Read more>>

Jennifer Rohling

As a professional photographer, we hold ourselves to a higher standard of running our business. There are times we agree to takes jobs that might be better suited for someone else, but if we never jump outside our comfort zone we never know what we are capable of. Early on a Saturday morning I was waiting for my client to arrive in Golden, they called and said they were running a few minutes late. I took a little stroll along the river contemplating which yummy eatery to go to when my session was done. Read more>>

Weston Holm

One of the craziest experiences so far as a business owner was after being open for two years when a spirit brand and concept of this magnitude was starting to take notice with a local following, but then the pandemic hit. As an entrepreneur in the industry, you’re always “pivoting” to get things that work. This happens a lot in this business, then you “pivot” and “pivot” again! We rolled into producing hand sanitizer to keep income coming in and help the community. The PPP loan was only a band aid — the sanitizer helped us make it through! So, it was an unexpected amount of work that was really hard, but it was really good for our recognition after that. Then, we pivot again back to normal operations. Read more>>

Bryan Devore

This isn’t a crazy story but it’s a situation that reiterated for me why I am grateful to be able to do what I do. A business colleague was caring for an elderly woman (we will call her Jane) who was living alone in her home. Jane had hoarding disorder and her home was in severe disrepair. She could no longer cook in her kitchen or safely move in her home. My colleague wanted to move Jane to a board and care where she would be put on hospice, but Jane didn’t have the funds to pay. Because Jane owned her home, Read more>>

Monique Bright-Rodgers

Being the owner of an int’l solar company often feels like episodes of “I Love Lucy”. This story is a prime example of this. In addition to being based in South Florida, we are also in the country of Panama. This crazy story takes place there. I had a buyer from Canada, who lives in a remote set of islands in the Bocas Del Toro region. We’re talking at least an 8-hour drive outside of Panama City (on a good day), and then additional boat and ferry rides to your destination. There are no roads, very little cell signal, and no electricity. Completely off the grid! Every week they have a farmer’s market where the expats that live on the various islands get on their boats and meet for drinks and to socialize. The lack of available infrastructure means that the only way to attend this event is by boat. Read more>>

Tina Newton

Going to markets and presenting my goods is one of my favorite things to do, I love to tell people “I just made what I was craving this week” and that’s so true, I can never tell people what I’ll be making the following week because I don’t know what I’ll want but, what ever it is I know from the way I describe it, people can already taste it. I like to see myself and my family as approachable and easy to talk to when we serve at markets and events. But, one day at an outdoor market, it was truly a beautiful day and we were all enjoying our time there, something came out and of my mouth that shock the customer and me. Read more>>

Chase Davis

Our craziest time came when the world was really crazy… The 2020 Pandemic! We had to quickly figure out how we would stay in business, especially since it started at the beginning of what was supposed to be our busy season. Since most of our business comes from large festival crowds and businesses we knew we were up against a big hurdle. Our staff came together and decided families are at home and everyone still has to eat, so let’s develop a marketing plan that shows how safe food trucks are, create an online ordering service, and contact subdivision HOA’s and lets serve lunch and dinner. Read more>>

Dalton Tomlinson

I sold my first business, North Texas Painting, a partnership with my best friend in 1985 when I was 24 years old. The next day Supreme Painting was started, just 8 days before my first daughter was born. In those days we did new tract homes and our first contract was with Centennial Homes that was starting 4-5 houses a month. 5 houses a month was not going to support my growing family. After 5 weeks I got a call from a superintendent working for Gemcraft Homes they were starting 5 homes every Monday. In March of 1986 while everything was going smooth, I got a call from the Centennial Homes people to tell me that they were opening up another subdivision and they wanted Supreme Painting to paint them too. Read more>>

April Amarillas

As a Single Mom and Entrepreneur Life can be hectic and some crazy situations can arise! Over a year ago on Valentine’s Day to be exact I was a target of a Break-in and vandalism to by business. Just imagine how It could feel to get a phone call saying your business was broken into. Gosh, it was a devastating emotional experience after I had just fully recovered from the Covid pandemic closures and loss of regular business due to Covid-19. As a small business owner I unfortunately wasn’t able to get any pandemic ppp funding due to exhausted funds for small business owners thus, this situation was a setback to say the least. Read more>>

Caylon Allen

So to date, I would have to say the craziest most challenging encounter I have experienced business wise, had to be the time we cooked for high profile corporate Christmas Party were the guest list included 1,300 guest that me and my team had to fully accommodate for . The entire package included full on gourmet buffet, table set up , decor , drink service , ice buckets the whole shebang , that we were all responsible for . So preparation had to be very meticulous and timely . With that being said we executed prep very well and showed up 30 min prior to set up time , so we were ecstatic and pumped to be ahead of schedule due to the magnitude of the event ! Read more>>

Briana Campbell

One of the craziest things that has happened to me just so happens to be one of the funniest moments. The incident happened just in the very beginning phases of me starting my business back in 2010. As many people who have been following my company for some time know, I originally started creating skincare for my son. He was 4 yrs. old at the time when I first starting experimenting in our small 2-bdr apartment’s kitchen. In the beginning I did not know much about ingredients and whether they were truly natural or synthetically produced. Read more>>

Kym Feltus

I had a successful corporate career and decided to explore the arena of entrepreneurship. It was a hard transition and honestly I didn’t anticipate the amount of ground work that an entrepreneur has to endure. As I introduced myself to meeting with investors and venture capitalist, I ran across three venture capitalist who were black women. It is rare for black women to be in the space of VC’s. I was immediately drawn to these women and I was trying to figure out how to get in contact with them to help me with my series investment process. Read more>>

Shelly Lee

I have had the most challenging trouble keeping coaches. See, everyone needs help from time to time. When I started my business, I did not know about finding my audience or branding. So this year, I took the time to learn by hiring a coach. Well, my first coach quit on me. Her reason was that she was going to work with active clients. Now I have two pre-existing illnesses. I had to reschedule twice. In the other sessions, I was there and present in living color. Nor was there a contract stating that you had to attend every session. So that ended abruptly. Read more>>

Bre’Unsha Chandler

Life as a hairstylist during the pandemic. So as we know, there was plenty of free money to help many small businesses succeed. Most of the business owners were able to be successful with the help of the PPP loan, and of course I applied being a small business owner whom met all the qualifications to receive funding. I was asked to submit so many documents and I did just that, for some reason god didn’t see fit for me, and unfortunately I was denied. But that didn’t STOP ME, I tried SBA as well and unfortunately I was also denied. I couldn’t wrap my head around why I kept being denied, because I indeed met all the specific qualifications to receive funding. Now at this point I became discouraged, honestly I didn’t know which way to go or what to do to keep my business going, Read more>>