We love grabbing drinks with our entrepreneur friends because they always have the craziest stories. Sometimes it’s a big, unexpected win. Other times it’s a problem that came out of nowhere and couldn’t possibly have been foreseen. There is so much to learn from these stories and so we asked some of the brightest entrepreneurs and creatives in the community to share some of those stories below.

Olufunke Tonye-Preghafi

One morning while, we had just arrived work, my team and I are prepping for the day.A lady came to the door requesting to be let in. We opened the door and. the first words out of her mouth was ‘I left him’. I saw she had been crying. Read more>>

Danielle Spires

When I first started my pet portrait business, it was because I was trying to pay off almost $30k in vet debt from my senior cats getting diagnosed with cancer. My cat Noguchi passed away suddenly from lymphoma, and a few months later my cat Panton was diagnosed with thyroid cancer. I rushed him into surgery and he survived this incredibly rare cancer. This was all so sudden, but with senior pets these sort of things happen (I just wasn’t totally aware of it!). Read more>>

Tanya Ball

Recently a major Instagram (IG) influencer featured one of our pieces on her page. Prior to posting, we talked about availability of the dress and the best time to post. After working out the details, I ordered the dresses and was ready to go! The feature brought an influx of sales and new followers. Oh how exciting it was to hear the cha-Ching from each sale and all the new follower notifications from IG. I was elated. I thought, let me check the order to make sure everything is good. Read more>>

Meg Royston

From surprise flash mobs & fireworks for the Bride and Groom, to a Groom skydiving into his wedding for a grand entrance, to an unruly passerby getting arrested before the Bride walked down the aisle, to a wedding vendor not showing up to fulfill their duties on Wedding day, as owners of a Wedding Planning Business, we have seen and heard it all! Below we will tell you about one of our craziest experiences as business owners, how we felt at the time, how we dealt with the unexpected, and what we learned from it. Read more>>

Jessica Pinto

Hello, my name is Jessica.. I was born and raised in Brooklyn Ny . I have 3 wonderful children, jalyssa , jelicity and Xavier . I started my business when my son was 2 years old . I was a employee at Home Depot . I started to do empanadas and sell them to my colleagues. I noticed everyone was loving it so I started to go up a notch and I did plates . Read more>>

Sara Benzie

I’ve had SO many more wild experiences as a business owner than I could have ever imagined when I first started on this journey. I think even starting this business may have been one of the craziest. In the fall of 2019 I’d been working for years in bars, as a nanny, and all sorts of other random jobs that weren’t leading me down a path I felt like I could build something on. After months of thinking about it, I *FINALLY* decided to invest in some online courses in graphic design hoping it could help me find a career for myself. It turns out I am NOT a designer buuuuut…. taking those courses did start me down the path to finding my first opportunity to work with a client as their VA. Read more>>

Erin Alexander

I think the craziest story, although I have many, happened when I launched my business. In March 2020, I decided I was tired of working in the mental health field and I was ready to launch my business. I spent every waking moment, including when I was at work unattended on the weekends, researching how to become a successful virtual assistant. You see when you find something you’re passionate about you want to research every fiber of that industry. You spend your nights dreaming about what it would feel like to have that lifestyle and you spend your days building towards that goal. Read more>>

Lauren V. Davis

When I was 19 my boyfriend then, (who later became my husband, and now my ex-husband) and I dove headfirst into owning and building a legendary midwest record store and gift boutique called Culture Shock. Read more>>