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.

Katie Fanizza

In 2017 I joined the world of real estate for the first time as a Marketing Assistant at the corporate headquarters for a Long Island based company. Being completely green to the industry, there was a lot for me to learn to say the least. During this job, I wore several hats, but my favorite one was working on marketing for New Development properties across Long Island. Although she was not my boss at the time, this is where I first met my now team lead – Gail Holman. Read more>>

Vincent Howard

I have had a number of highly influential bosses – Staff Sergeant Theresa Washington took a brand new 18 year old, saw potential, then laid the ground work for someone who would lead thousands. Major Matt Lewin was one who demonstrated every day that he was unconcerned with his own advancement but totally committed to the men & women in his command. But the leader I want to spotlight is then-Colonel John Cherrey. Read more>>

Jake Mackey

The best boss I ever had was early on in my career, which I think is a pretty common thing. His name is Nick McGahan, and he was my boss when I was an undergraduate production assistant for the athletics department at UMass. It started out as just a part-time gig that I took because I liked sports, and someone else had hired me before Nick started. When he took over at the start of my junior year, he quickly realized that I was into the job more than others, taking on every role of the production every game. At the end of my junior year and into my senior year, he made me one of the full-time interns. Read more>>