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.

David Jaffe

When I was a teacher, I had a group of students who struggled with the subject matter. I wished to create a student movie and requested funds from my boss to pay for the video camera. Read more>>

John Conde

Being in the military exposed me to various leadership styles, but most of my commanders were respected because of their position, rank, or the fear of consequences. The boss who truly inspired me was a social worker. Read more>>

Valeria Mason

After finishing college, I started working as a Violin teacher and the Administrator of Arts at Colegio Monteverde, a private school in Mexico City. I was contacted by Gabriel Pliego, the director of a partnered school, who asked if I might be able to create a similar program in this new institution. Read more>>

Alexander Coulter

The best boss I’ve ever had would be myself. Whats interesting about being your own boss is that you have to answer yourself honestly about how much work you’re putting in. I’ve learned the most through trial by fire. Read more>>

Danielle Mendez

One of the best bosses I ever had led me to become a supervisor at a non-profit organization. I think one of the most difficult things about being a supervisor is helping an employee realize their full potential. Read more>>

Morgan O’Brien

To tell you about the most influential creative leader I ever worked under, I first need to take a few steps back, and share the story of how I got that specific job… as it was nearly a disaster. Read more>>

Matthew Perdoni

The best boss I ever had was my father. As a sewer contractor back in Boston we spent summers in trenches laying pipe and during winters, we’d brave the snow plowing parking lots. Read more>>