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.

Spencer Rivers

Okay, so I have two that popped into my mind that I personally (looking back now) find absolutely hilarious – you know, one of those memories you look back on now and just wish you could go back in time and watch unfold like bad a reality TV show that you can’t look away from. The first one happened to me at a final walk-through with one of my most beloved buyer clients now. I was doing my thing – touching, checking, smelling everything (you never know what could have happened since you and your buyer client(s) were there last). Read more>>

Kristen Dunahoo

My craziest story is actually how I got started with photography in the first place. I think I’ve always loved photography but never thought that I could actually make a career out of it. I had a digital camera back in high school that I used to carry around everywhere, taking pictures of anything and everything. I was also the Varsity Basketball & Soccer Photographer my senior year of high school. I got to ride the bus with the players to games and cheer them on at every game. Read more>>

Kristian Ellison

One thing I hear quite often when I tell someone about being in the wedding industry and working with flowers, is that “you get to play with flowers all day?” While yes, I do enjoy the creativity and delight that comes along with designing florals, there is just so much more to the job than just flowers. Read more>>

Millie F

On this particular day I was working on a life long client (Probably the realist client, and your about to find out why). I was four years into my career. My client is a sweetheart who was attending Harvard at the time of this incident. I asked all the right questions and went through my regular client intake questions. Everything was asked properly and everything was answered with no problem in sight. Read more>>

Michael chanthanark

It was a freezing day in Houston. Bone chilling, like 60 degrees. In Texas that is basically an ice age. It was early on in my pop-up career, I was still learning how to develop my routine. Me being me, I have to show up late to the event. I promise I’m only slightly late present day. I joined in with my now business partners in their tent to sell some fried chicken sandwiches and try to grow my Oohmamipapi brand. Read more>>

Meghan Davis

After about a year of building my clientele, I reached a very exciting and nerve wracking junction where I had too many clients interested for me to take on by myself. I knew I had two options: to either start a wait list, or start looking for someone to hire. At around the same time I discovered I was pregnant (yay!) and quickly realized the best option would be to look for someone to hire, since that would enable me to have someone else to cover my clients when I went on maternity leave. Read more>>

Stephanie Houston

November of 2019 was a pivotal moment for our distillery. We had recently agreed to buy out one of our founding partners, our closest friends had agreed to invest in the distillery and we were set to start with a new distributor just after the first of the year. We started our distillery with $61K and had basically been running on fumes for almost 4 years – struggling each week to make any kind of ground. Read more>>

Caitlin Baumberger

I’m Caitlin, founder and artist behind Happy Tines, a design shop studio where my mission is to create joyful designs and products that help you love on your people. My style is defined by my whimsical hand-drawn illustrations, hand-lettering details, and use of bright and happy colors. Read more>>

Elizabeth Rosner

I helped Henry, who was in debt with $80k from his undergrad, strategize how to earn his Master’s and Ph.D. debt-free!! Read more>>

Kristian Njeri

One of the craziest but positive experiences I’ve had as a business owner is when I participated in Dessert Wars Atlanta. I saw an ad for the competition where it stated it was the largest dessert festival in America. I applied even though I was fairly new to being an entrepreneur. A few weeks later I got a call from the creator of Dessert Wars stating that out of 3,000 applications my application was accepted. I was so shocked because I am still new and not a lot of people know about my business. Read more>>

Claudia McMullin

I wish I had the celebrity photo experience! The one I got with Cesar Milan, was a self-manufactured opportunity during the Sundance Film Festival where I basically showed up to an event with a bag of Hugo Coffee and stalked Cesar until I could grab the photo. :) Same with Martha Stewart! Read more>>

Shallon Thomas

We were trying to make our first color expansion for our lunch totes. We decided to play it safe and go for a dark brown color. We were immediately disappointed when the sample finally arrived as the bag was light brown. Money was tight, so we could not immediately return to the sampling process. We sat on the bag for weeks, if not months, until we decided to share it with social media. The internet went crazy for it. Today what we thought was a big mistake is our top seller. Read more>>

Jolie Reine

On New Year’s Eve I was getting ready to celebrate with my son. I got a call from a close friend who knew someone who was requesting that I write her some wedding vows. Her friend read my book and knew I was the perfect person to put her emotions into words for her wedding day. I was apprehensive at first and then got into gear! When did she need them?!? For the next day! I got into my head and wrote some amazing vows that she read on her big day! Read more>>

Regina Robinson

Seven years ago, I discovered I had built an amazing Business; however the foundation, which was me, was crumbling. For a long period of time in my life I would wake up going from day to day with my eyes open, but the darkness of my failures, fears, doubts and lack of confidence haunted my every move. I was depressed, unhappy, and broken. However, like most women I had learned to mask my pain so well, you would have never known. Read more>>

Douglas Stanley Kuehn III

My journey for coffee industry started when I was growing up in El Salvador. My father pioneered the first certified organic coffee in the country, and it took me into the farms for many years. After graduating high school I left central America to start college and take my next step into the coffee world. I teamed up with a Turkish man named Erdal where I learned to be a barista and roast coffee. Read more>>