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.

Elizabeth Herrmann

For starters, I am a graphic designer and letterpress printer and manage the bespoke letterpress studio, Humanity Letterpress in Tampa, FL. Read more>>

Jessi Pagel

The craziest story I have as a makeup artist/hair stylist is about an 80s band. In 2008 I was booked on this job on Sunset Boulevard. Read more>>

Jerome Serra

I had a client who I already fired, But for about two years he was one of my most profitable clients, but it would come at a cost. Read more>>

Justin Gardner

We sell a natural skin and wound care product online. Not exactly the sexiest product but we had found some traction with mom and natural product influencers and decided to put more money into influencer marketing. Read more>>

Jheneal McDuffie

A customer was referred to my business for resume writing services. When he finished the services, he called his credit card company to request a refund, claiming he’d never received them. Read more>>

Andrea De la Torre

The story I’m about to tell is a bit of a bitter-sweet one. What I now remember as a funny anecdote, back then, was a moment I had to face all my fears. This is the story where we first realised the impact we had with our business. Read more>>

Laurel Mintz

At my first company Elevate My Brand, our team is and has been 100% diverse since day 1. Because that’s always been part of our core value set, I am extremely clear that in order to shape the culture of any company, inclusivity, communication and diversity have to be core tenants of the leadership of the team before it can trickle down. Read more>>

Sonya Grenell

Do you have any advice for creating a more inclusive workplace? Are there any moments from your journey that shape your view? Perhaps moments where the workplace wasn’t inclusive or where it was and why you think it was impactful/ important/etc… Read more>>

Olmos & Flores

As a part of the LGBT+ community we have always tried our best for people who work or have worked with us to feel free to be who they are, to express creatively and to explode their talents. Read more>>