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.
Katrina Fleisher
Within the world of media/marketing, I have found a niche in the entertainment and event industry, and I work very closely with my husband’s company, Let’s Party! DJs & Events. Being around entertainers, I’ve certainly seen and heard some “crazy” things! Read more>>
Alexandra Stevenson
My first paid speaking gig, my contract involved 2 trainings approximately 6 months apart. I was so excited to have booked a gig that I didn’t pay close attention to the details like how much travel was involved (2 flights across the country and a 4 hour rental car journey across a border!) and how much that cost would eat into my profit. After my first training, I knew immediately the mistakes I had made but thought, ‘well, lesson learned, however I still have to fulfill my contract so I will make the best of it.. what’s the worst that could happen?!’. Read more>>
Suzanne Jameson
As the owner of a marketing and public relations agency, I have learned over the years that every project is unique and things, like in life, can happen. One of my most favorite projects was a wildly successful launch that almost didn’t get off the ground due to a simple online glitch. Read more>>
Charlene Fitzpatrick
Crazy or Crazy Blessing! My entry as a small business owner began with my former employer needing the services I provided them as an employee to continue as they went through a merger in 1998. As a 5th generation entrepreneur, I was a reluctant small business owner, having grown up in the small business industry. Read more>>
Lucy Schultz
One of my craziest stories has a happy ending, but seemed like a tragedy until the very last minute! I was contacted by an American couple who wanted to elope in New Zealand – a place I know well and love – and I was ecstatic to help them plan and photograph an elopement that would knock their socks off. The couple shared that this experience was one they were saving just for themselves – they mentioned that they were always giving to others; they had saved up just enough time and money to afford 1 dream vacation and wanted to elope at the same time, surrounded by mountains. Read more>>
Kedma Ough
Life is always giving you the AHA moments and you need to be paying attention. Read more>>
Isabel Madison
The craziest story I have is when one client purchased my absolute favorite lipstick, Radiate, which is the reason I started the company. She did not like it and she emailed me saying this lipstick is not Pretty, it looks like “porn star pink” and I laughed so hard I almost fell off my chair. That was the color I wore morning day and night. I was obsessed. The truth is that is our number one seller and we’ve already run out of it so many times. Read more>>
Tyler Youngs
Red Warrior Technology (RWT) was originally founded by Bill Chavis and later added myself and Mike Ferger after falling outs with other companies that we worked for at the time. Bill had spent months, developing vendor partnerships, establishing business protocols and essentially getting RWT in a functioning state. Read more>>
Nicole Sachiko
I was living in San Francisco at the start of my business. At this time I was still working full time and organizing with clients after work and on weekends. I had a consultation with a neighbor who seemed very excited to tidy. He briefly mentioned his wife having mixed feelings about the experience – a red flag that I did not see as a warning at the time. Read more>>
Andrea Leon
AS a private chef you live the lives of other. You are on borrowed time. I very funny story is that I was left behind in NYC. My client decided he had to fly to Miami on the spot. I was at Wholefoods when they decide and flew straight to the airport. I ran out of Wholefoods with my shopping bag. Checked out of hotel went to airport, Checked my bag but I was still carrying the groceries as it was too late to Shop in Miami for his late night meal. Read more>>
Loren Blazek
I recently underwent a turbulent but surprisingly successful music video production experience that taught me the absolute importance of having a strong team, but also the crucial role that self-reliance plays as a leader. To an extent, I already knew the importance of a strong team, but after this experience, my perception of teamwork and collaboration was taken to a whole new realm. Read more>>