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 Armstrong

The bottom line with being a business owner is that no matter what, you are responsible for everything at the end of the day. In the days leading up to the pandemic, we were in our 4th season and really hitting our stride. It was only myself and Patrick at the time, my sous chef from a previous life in South Carolina who had been with me 3 years there and had been with me for about a year and a half here in South Florida. Read more>>

Madison Blake And Ashlea O’Connor

In January of 2022, Maddie was stuck in Nashville because her flight had been cancelled to come back to Florida due to a ton of unusual snow storms. Ashlea and Maddie had always talked about how cool it would be to partner with the local NHL team, the Tampa Bay Lightning, so Maddie decided to send them an email. She figured she may as well give it a try since she was stuck in a hotel room anyway… Maddie and Ashlea expected absolutely nothing back from them and if by chance they did get a reply, it would be months before then. Read more>>

Spenser Judd

Back in 2018, I started up Clear Vision Collective with a colleague named Danny Loveless. At the time I was a college radio DJ for KCPR at Cal Poly SLO, so I’d often go out and interview bands and shoot photos/videos at events. That year I was given the opportunity to be part of the press team for the SoCal festival, Desert Daze. When we got to the fest, Friday’s headliner, Tame Impala, had their set cut short due to a huge thunderstorm. Everyone scrambled to find shelter from the storm and the rest of the night was canceled. With all of the chaos on the first day, I never received my media pass from the company. Read more>>

Amelia Ball- Moore

My very first Fashion Show was a heck of an experience!! I was approached by a guy with a model agency with the opportunity to be apart of a Fashion Show that him & his friends were putting together. At the time my boutique was located 30mins from the area that show was in & would be taking place. Read more>>

Kay Adams

Since I started my dementia coaching and training business back in 2019, I’ve found it fascinating how new referrals find their way to me. Sometimes they come from providers in various medical systems, sometimes from a friend, and other times someone discovers me while surfing the internet. Regardless of how they come about, one of the most interesting referrals I’ve received was from a lady who was in the audience during a presentation I gave at an Alzheimer’s conference in Denver. I never had the pleasure of meeting the person responsible for recommending me to her employer, but I am grateful she did. Because of it, I had one of the most memorable family meetings of my entire career. Read more>>

Marsha Stephanson

One of the beliefs I standby is that there is no timeline when it comes to postpartum. Postpartum depression generally lasts 3 to 6 months, however, this varies based on several factors. I think it’s so important that moms are supported and catered to for however long they need us. This is why I chose to create a monthly postpartum care subscription. Read more>>

Ilse Chiri

One late February evening, I found myself cozied up with my small Lenovo laptop, nervously holding my breath as I clicked “submit” on the application that—unbeknownst to me—would change my life. Yes, I boldly nominated myself and my business with this application to the First Horizon Bank Business Contest for the Tampa/Sarasota community’s business contest. Read more>>

Hansel De Haro

Ever since we launched the brand, it’s been composed of nothing but challenges of all different sorts. But, having the right mindset and attitude that nothing happens overnight, especially when you’re starting out, are key. The best approach that has helped us so far is focusing on our mission and vision, ensuring quality is where we can, and that our customers are not only happy with our product but we’re building relationships with them. Read more>>

Reggie Griffin

The Craziest thing that ever happened would be having Covid twice, which lead to a breakthrough in my Art career. In 2020, 1 week after Atlanta was shut down, I was an essential worker at a printshop still heavily in contact with people and got sick. At that time, you were seeing a lot of people going to hospitals and not making it home. Read more>>

Sharon Wong and Han Pham N/a

We’ve had some pretty crazy stories while on the job as every day is different. From seeing bugs that we didn’t know existed (potato bugs are a new discovery) to having kids and customers recognizing us outside of the job, it never gets old. Read more>>

Thomas Hayes

So about 6 years ago we had a guy come in, bright red pants on, a European tall, sort of James Bond looking. A gentleman, with a British accent and who was a legit designer, sort of worldwide. He ordered 4-5 custom pieces that we made completely custom, and then he disappeared. We were then contacted by either the Secret Service or FBI, and they told us he was sort of this international fraudster and that they wanted to get a refund for the furniture for whoever was defrauded. Read more>>

Marquita Livingston

Getting a business off the ground is hard enough! So many things you have to learn. Marketing, promoting, being consistent. None of those things scared me because I love to learn so I figured that would be easy right? Well, not as easy as I thought. And with all the work I was putting in and the learning that I was doing, I still wasn’t getting the customers that I wanted. Or at least not for my skincare line. Which left me feeling a bit discouraged, but I knew I had to think outside the box. Get out of my comfort zone and keep pushing! So I did just that! Read more>>

Christina Cowherd

We have been so fortunate to have started our business in the most supportive, encouraging neighborhood and community! Even so, of course there have been some obstacles along the way. Read more>>

Tai Edwards

At the time, it wasn’t funny, but it’s something I can laugh about now. It’s no surprise that bakeries are busiest during the holidays… Christmas was no exception. I received 30 orders… all of them were pies. I spent 3 days in the kitchen, blasting music, switching between mixing and baking, and running out of room in my apartment to store the towering boxes of pies. Read more>>

OLIVER SANCHEZ

Things will happen when your business is open to the public. The craziest thing that happened at Swampspace so far has to be the time when I ended up on the local news for saving a child from an attempted kidnapping. The kid lived nearby and would visit us after school to hang out with my daughter and learn about making art and running a neighborhood gallery. Read more>>