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.

Lorielle Jackson

Scaling as a small business owner is something we all dream of as we grow and develop our businesses, waiting eagerly for that first big order that will surely catapult us into great success. But then, the moment arises; you land the biggest order of your career, and before you know it, you begin drowning in your business in ways you never even saw coming. That moment for me was last year. Along came the momentous corporate order that required me to Girl Boss up in a way I didn’t know I was capable of, and in a way, that made me want to throw up my hands and walk away from the business altogether. Read more>>

Latrell Caton

My craziest story in recent times has to be the success of a photoshoot that I thought was going to be terrible. As much as I shoot, any photographer would tell you when they have a gut feeling about a shoot. I was asked to help conduct a photoshoot for a stylist named Jordyn Clark for an event entitled the Met Gala where our 46th Annual Mr.Howard, Rashan Schoffner, was celebrating his birthday. Jordyn created and designed this elegant red dress that I know had to be photographed by me. On top of this was her pairing of the dress with the Jordan 1 OG Top 3s. Read more>>

Hannah Denson

Let me first start by saying, if you expect a normal time- it won’t be with me. Wherever I go, chaotic good seems to follow and I live for a good story so I’ll always say yes to an adventure! A little background, COVID times had just begun and Nashville had also just been hit with a devastating tornado. I get a call on a random day from a client. She decided times have already been tough and you know what, she was going to get married. Even if it’s a partially zoom wedding. That same week. Read more>>

Jaelin Clay.

Wow ! Well I gotta good for you ,, being a young talented artist seeing the people I love on tv to later being stage with famousDex himself… not only did I , I also got song with his Comrades n backstage kicking with him after doing song with Warholss he like bro he call em who has videos with lyrical lemonade n songs with shoreline mafia famous Dex Diego money from Chicago Illinois….. why is this one my craziest story’s cuz my big brother twon mccoy only one who believed in me n seen my vision n my purpose n well being n helped me get there when everyone said I was lying later I do a song with rio da yung og from flint years later showed my brother n he less found dead at his job after we then made history .. Read more>>

Kayla Terrero.

I had a couple of cancellations one day, and I was packing up to leave when this client walked in to get her hair fixed after it was just messed up. I was hesitant to take her considering I was already about to leave work and she was a little stressed but something told me to do her hair anyways. As I am doing this woman’s hair, she’s giving me such a hard time just by saying things like “nobody has ever done my hair correctly”, and not being confident in what I can do, just giving me a hard time. This caused me to feel anxious and a little stressed out since I was doing a long service and was being questioned on my ability to fix her hair. Read more>>

Tom Martin

Leading up to any wedding or event, I always ask what are the priority shots for the client. What are the shot(s) that are “must-haves”. There’s always the family member that does a weird thing, or a group shot with the family members that are never in town or similar. One very small wedding I did, was hosted at the brother of the groom’s house. This brother (and host) overheard me going over the ‘must-have’ list with the couple on the day before the event, and approached me after. Read more>>

Harry Acosta

started off as a concert photographer. A fellow employee asked me to photograph her wedding. I refused, stating, I don’t want to be responsible for ruining her wedding. After some more conversations, I finally agreed. The photos turned out terrific and I realized, I should say yes to everything. Even if I’m not experienced with an event, my skills on the computer are enough to fix most anything. I agreed to every event everywhere, and quickly realized, there are some situations I cannot fix in post. Read more>>

Dr. Que Harper

Here is a story only the individual reader will have to understand, ot all started many, many moons ago, when it was all a dream and to be frank honest there were a few dreams, of myself help at risk youth also creating a platform for minority talent, business owners, products and services where they would be able to obtain there starter package such as graphics, exclusive interview, commercial and so forth so, these ideas were all in my head and i would often share these things with my mother and this and taken place over the course of several years perhaps and I believe she got tired of hearing me say what I wanted to do, Read more>>

Kellyann Alvarez.

The craziest thing that ever happened? Saying, YES! When I decided to start Kreative Kreations by KK, was supposed to be about epoxy, stickers and such; guess what? 2 years after I had done only one thing out of Epoxy and same with the stickers, funny I know. How saying yes made our business change? Well, out of nowhere, a travel agent contacted us through Facebook to request us if we can do a welcome basket for a client traveling to Disney World, without any hesitation I answered “YES! sure we can”; Read more>>

Ariene Bethea

There was this lunch spot I wanted to try with my husband for months. On the way to lunch my husband noticed a building on a street we had never been seen, he asked me “did you see that building?” and I replied “no but we can look at it on our way back.” So on the way back from lunch we stopped. It was a colorful building and it was for rent, so we wrote down the number can called the landlord. Turns out the location is an incubator for small businesses. We set up an appointment for later that evening to see the space. It was small, needed a lot of vision but it was an interesting space. Read more>>

Olyasha Novozhylova

The craziest thing that happened to me, was war in Ukraine, my family there got affected by it. At first I didn’t sleep for 6 weeks because I’ve lost communication with them, and after I’ve spent days and nights for month and half to find someone who can evacuate them, because the city I was originally from, was occupied and heavily bombed. I had to put my business behind, and couldn’t think of anything but saving them, luckily I was able to find a guy who evacuated them to the Polish border, and after I had to go out of the country, to Poland, to pick them up, and after to Germany, to get their visas, so I was out for a month again. Read more>>

Sharise Crumley.

I think you hit the nail on the head, entrepreneurship is probably the craziest ride I have ever subjected myself to, but in the best way. Rather than one culminating moment, there have been a lot of smaller great moments that collectively make me love the decision to make this investment in myself and my brand. – The support of customers who not only repeat buy, but go on to buy multiple SKUs in every color and every size, just to show support to my small, black owned business. Read more>>

Christian Schauf

There’s been a lot of crazy moments. What comes to mind is launching the company. The first product, the Seventy2 Survival System, was an idea I believed in, but very few others did. Regardless, I put my life savings into the idea and went for it. I launched in November and I promised delivery by Christmas – assuming at the best we would sell a couple hundred units. When we sold over 1,500 in a few weeks, it was a serious problem. Read more>>

Doll Thomas

I am launching an e-commerce business called CoilMeCrazie LLC. This idea came about back in early 2021 in a car ride on my way to Connecticut from Georgia. A close friend of mine was moving to Connecticut and I joined her on her trip so she did not have to take the drive by herself. While in the car, we were talking about our futures and our interests and how we can either profit from it or grow into it professionally. That is how the business NAME came about but the direction of the business came year later… Read more>>

Diahni Sample

The craziest thing that ever happened in my 5 years of entrepreneurship was my 3 month networking event being cancelled on me the day it was supposed to take place. I am originally from Roosevelt New York and I moved back home at the age of 15 and graduated from the same high school as my parents. Because of the low belief in potential or going far in life that kept my small community stagnant, I always dreamt of being able to give back once I graduated and got my businesses off the ground. Read more>>

Gabi Angelini

For 3 years we were raising money to open a coffee shop to employ people with special abilities. During the pandemic, God said to move all our coffee supplies into The Loading Dock co warehouse space. So, I said to God ” you do know there is a pandemic going on and everyone is working from home and you want me to go where?!? I have learned over the years to do what He tells me so we packed everything up and moved into Dock 1053. Read more>>

Anthony Davis

Wow! Great question, where do I start? Lol. Ok, well one aspect of our business is the car rental or carsharing space. We utilize platforms such Turo (my personal favorite) Hyrecar and Getaround. These platforms allow you to rent or share your personal vehicle for income. They’re somewhat like the Airbnb of automobiles. Operating in these spaces require you to have ZERO emotional attachment to these vehicles, because the craziest things can and will happen. In my particular case I had a vehicle listed on the Hyrecar platform that was being rented by a gig worker. Read more>>

Erica Qualy

I found this really cool looking jacket that looked like it was 90’s. I almost left it on the rack but something was telling me to just grab it while I shopped. As I did a quick search on it, I saw it was a really awesome brand from the 90’s I had never heard of- it was a bit out of my price range but if I could sell it for market value, I’d make a decent profit so I took the risk. I’M SO GLAD I DID!!! The day I listed it, I got a message request in my DMs asking to purchase the piece if it was still available- no haggling or hemming and hawing, the customer was super polite and cordial. Read more>>