It’s wild out there and the struggle is real. Entrepreneurship is no joke, everyday is a new challenge, a new up, a new down, it never stops. The action, the drama, the energy is addictive and it’s why so many never want to retire from entrepreneurship. We’ve asked some very talented entrepreneurs to share some of those crazy stories with us.

Alex Ioannou

Craziest story, and this is both positive and negative with a huge aha at the end… Read more>>

Dawn Dagger

The craziest thing that has happened to me when it comes to my business is the founding of it! I have dreamed of owning my own publishing company since I was a little girl. I toyed with the idea again as I started the Adult Writing Group at the Massillon Public Library. Read more>>

Lisa Rodriguez

I often get the question, What made you start the ” Cookie Business” ? I always start off by offering a slight chuckle and then lead in to the story behind Lisa’s All Occasion Cookies. So, the story is really this simple, I was at a child’s birthday party and at the end of the party when everyone was saying their goodbye’s I was the one packing up my leftovers and ensuring I grabbed a goodie bag on the table when I noticed the cutest Minnie Mouse cookies in cellophane bags spread all over the table, so, I took the initiative of grabbing a few and putting them in my purse. Read more>>

KAITLYN STONE

One of my wildest business stories is where my husband took me out to celebrate a win in our lives at a popular chain steakhouse restaurant the night before scheduled mini sessions. About 5 hours or so after I had eaten the food, I woke up in a panic because I felt very sick, and I knew I had minis in a few hours. I started downing bottles of Pepto and doing everything I could to try to feel better. But unfortunately, I had food poisoning. Read more>>

TJAY Jones

I relocated to South Carolina primarily due to a promising job opportunity within the retail sector. It felt like my broadcasting days were behind me. However, a serendipitous moment occurred when a coworker and I were assembling a Bluetooth speaker capable of tuning into local radio stations. Read more>>

Nicole Spencer

On a Purse and a Prayer Read more>>

Judy Ryan

One time I was starting a culture change process with a client of 550 people. The CEO contracted me to take their 20 top executives through our “deep-dive”, yearlong, guided culture transformation process. Our immersive implementation process required them to do individual work (online training and filling out a workbook and post-training reflective survey), then lead small groups on a rotational basis to review, discuss, and practice what they learned, then mentoring each other (in peer and reverse mentoring) on what they learned, their barriers, fears, and how and when to apply it if they determined they would. Read more>>

Mary Wiegand

A hallmark of Boon is that whatever inventory needs that a small business has, we have the team to help you tackle it. And sometimes, that is because we have a team member (Mary) who happens to live in Columbus, OH with a garage. Thanks to that garage, Boon facilitated a big win for an intimate apparel client, who was embarking on a partnership with a major specialty retailer. Read more>>

Sierra & Angel

During a recent job, we were prepping and realized a tool we’ve used on every job was suddenly missing essential parts. This realization occurred one day before the event with just enough time to meet the overnight shipping deadline. The arch arrived on time and the client never knew how panicked we briefly were. Read more>>

Devin Perreault

Becoming a co-owner of Uplift Boulder was not something I had set out to do. Through a combination of good timing and good preparation, my business partner Jena Franz and I were presented with the opportunity to purchase a gym. In July 2020, interest rates had plummeted and I refinanced my condo with the expectation that I would use some of the equity to purchase a second home. Read more>>

David Je’

Crazy things indeed happen all the time when running a business, and in the music industry. The craziest story for me would have to be the recording session that ended up being the reason I am Grammy Nominated today. At the time my former business partner and I had a recording studio in Glendale, California. Read more>>

Shadia Derbyshire

Let me tell you about the craziest way I ever landed a contract… Read more>>