Many business owners we’ve spoken with didn’t start with a huge team on day one. They had to learn how to be a good boss, but the problem is the books on leadership are often highly theoretical and so we wanted to hear practical examples of what it means to be a good boss. So, we asked some brilliant, insightful folks to share stories about the best bosses they’ve had.

Jamie Poole

When I moved here to the Houston area 15 years ago, I started a job as a medical assistant in a Dermatology practice. The Dermatologist that owned the practice was a fierce female doctor who really held education to a high priority. She knew that when I started, that I wanted to become a Registered Nurse, and supported me in my journey. After I finished nursing school, I decided that I wanted to possibly get into Plastic Surgery Nursing. After a few months, I missed the Dermatology world, I missed Aesthetics, and her guidance and wisdom. I had watched her for about 4 years doing Aesthetic procedures, lasers, filler, neurotoxin, peels, and many other things. Read more>>

Sherard Sharpe

Had a great boss whom when everyone gave up on me a wrote me off, he believed in me and set a team around me that helped me to become #1 as a banker in loans and investments. Read more>>

Robbie Kaye

Many years ago I gave up my job at a university in California and moved to NY to be with my then, fiancee. I kept in touch with my boss, who after years of working together, became a good friend. The relationship in NY became abusive and I had to leave. I gave up my car and apartment and didn’t have any money. I didn’t know where to go. I had been attending school when I left and was lucky enough to have attended NYU for one class in NY, so I kept up my studies. He suggested that I go back to CA and continue school. Read more>>

Brandye Kemp

Lauren Quinn is our Founder and Creative Director at Bromelia Swimwear. She first employed me as a sales associate in early 2022. I remember being so awed by the advancements Lauren had made in such a condensed and precarious time (the pandemic). She had not only relocated her life and family from Brazil to Los Angeles; she had reimagined her strategy, uprooting and replanting her business in its the earliest stages: when foundation is crucial, constant pivoting is inevitable, and anything can change everything. Read more>>

Robyn Carter

The most amazing boss I’ve had is CK Chin, a restauranteur based in Austin, TX. I had the pleasure of meeting CK when I worked for him in Austin, TX at one of his restaurants, WU Chow. CK is amazing because he is a real person. Very authentic and genuine. The same person every time you meet him. He wasn’t afraid to say things that needed to be said and he knew how to say them in a diplomatic way. He made split second decisions all the time and stuck to them. All the while, still knowing how to pivot. He is the same age as me and was actually born in the town where I grew up. Small world! Read more>>

Larry Dean Harris

Fresh out of college, I landed a job at a creative company in Toledo, Ohio, that did 3-D design (events, displays, art exhibits, a little marketing). My boss, a man named Ron McKinney, took a big chance on me. I stayed with him a year, and he taught me everything I know about business (and kindness). Ron came to visit a few years later when I was living in New York. We went to a Broadway show and afterward over desserts at Cafe La Fortuna (John + Yoko’s favorite place, gone sadly) I pitched a silly little idea I had for a show. A year later, I was back in Toledo at my desk. The phone rang. It was Ron. “You know that show you pitched me? Read more>>

Kate Gaffney

Emily Rex is a Creative Director from San Diego who changed the trajectory of my life and showed me what actual leadership should look like/be. She is a wonderful boss and was the first (and only) female boss I have had that empowered me, gave me autonomy, and REALLY let me be creative. I was working in advertising in San Diego (too scared to move to Los Angeles for acting at that stage) and Emily had an enormously important client pitch for one of the largest businesses in San Diego. I was fresh out of college and she knew my ambition was to go to LA and make a career out of acting, not be an advertising professional. Read more>>

Alexandra Benaim

My dad. He inspired me to really get involved in the fashion world. I loved what he was designing so thats why I jumped onboard. It was a chance to show him and the culture we come from a lot of respect and adoration. He has an eye for things and the more time spent, the more I got to realize this. That is in all honesty why I do what I do. For him, for my family, for the artisans of Morocco. I love my culture so much. Read more>>

Matthieu Piriou

There’s a lot of items on that list I could have chosen. Being happy doing what I do, talking about meaningful projects or about how you sometimes have to take risks to take your whole career to another level, but I have a tricky answer for a story about that one : “the best boss I ever had”. Growing up and craving for independence, I did a lot of odd jobs, and had a lot of different people I called boss among these years. Read more>>

Anthony L. Robinson

The best boss I had was my family. While in high school my grandfather started a local janitorial service, and he allowed me to work within the business throughout high school. This job was an opportunity for me to develop work ethnics and understand responsible.. My grandfather My grandfather held my accountable while working and I continue to practice those ethnics today. Be kind and polite to everyone. Read more>>

Jana Stern

I am lucky enough to have had a number of really wonderful mentors and leaders who have helped me along my journey. The most impactful would be the woman who interviewed me for the first high-end retail job I ever held, Debra. As soon as I started my role, she made ever effort to help me to understand every facet of the business – from the clients to the merchandise to the importance of understanding relationships, she truly made it her job to show me as many parts of the business (as a part time employee) as she possibly could. Read more>>