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.

Eric Jackson

One of the best leaders I’ve ever worked with was Peter Thiel, PayPal’s co-founder and first CEO. His ability to stay calm under pressure and think strategically, even in the face of overwhelming challenges, set him apart. Startups are chaotic, and PayPal was no different. We faced fraud attacks, regulatory threats, and intense competition—all while trying to keep the business afloat. Through it all, Peter remained steady. Read more>>

Thando Skwatsha

I still remember the day I started working at the magnolia co. , I was nervous, fresh out of college, and unsure of what to expect. But from the moment I met my boss, Rachel, I knew I was in good hands. Rachel was different She was warm, approachable, and genuinely interested in getting to know me. During our initial meeting, she asked me about my goals, aspirations, and what motivated me. I was taken aback by her genuine interest in my well-being. Read more>>

Anastasia Freimarck

I started out as a bather in high school, then during college, wanted to become a groomer. When I tried to get access to go through school, my boss at the time did not think I had what it takes because they didn’t think I could do it. One reason they stated was that I was too emotional. After trying to convince them after, awhile, I grew tired and kept bouncing salons until I landed in Sterling Virginia with a great boss named Tanya! She saw what I saw in myself, and took the risk and let me go to school to become the groomer/business owner I am today! Once I came back, she allowed me to grow, and I ended up being a natural, where groomers would start asking me for advice during my first year! Read more>>

LaDeidra Stokes-Roberts

One of the best bosses that I have worked with would have to be Mrs. Cynthia W. Graham. On July 23, 2008, I started as a Family Services Advocate at Childhood Development Services. She was not only a boss to me but she was also an amazing mentor. At the time I was just graduating from South Carolina State University, therefore I was 24 years old when I pursued my very first career. Mrs.Graham has taught me so much, not only the way to become proficient in my job but also my work/life balance. Some of these ways were: making sacrifices for my family, being an advocate for myself, stepping out of my comfort zone, and working towards being a public speaker. When my mom was diagnosed with breast cancer in 2015, she was very accommodating and supportive through one of the hardest moments in my life. Read more>>

Jacob Rowell

Before starting my business, I made it a point to work various jobs and internships to gain as much experience as possible before entering the workforce full-time. Throughout those experiences, I was fortunate to work under several amazing leaders. However, the best boss I ever had was in my first job out of college. Ironically, he was the reason I took the job in the first place. We connected through a mutual friend, and he was gracious enough to meet with me. The meeting was only supposed to last 20-30 minutes, but we connected well, and it ended up lasting over two hours. None of the benefits this job offered on paper were particularly special, but I knew this would be an invaluable learning opportunity, and that was enough for me. Read more>>