Thinking through whether to start a business – whether to take the risk, whether to go out on your own – isn’t easy. So we asked some entrepreneurs we admire to tell us about how they thought through the process of starting a business.

Matthew Key | New American Folk Singer

When my first son was born, I wanted him to know that he could create anything he wants in this world. That’s when I decided I needed to start sharing the songs I had been creating my whole life. So I started playing anywhere that would let me and started saving up to record. From there it was just a matter of fulfilling the urge to keep going and creating. Read more>>

Derrick Wesley | CEO and Founder of Seedlyng Financial Education

The inspiration to start my own business stemmed from a desire to merge my passion for education with my financial acumen. As an educator eager to advance my career, I sought opportunities that would not only support my professional growth but also provide financial stability for my family. During this period, I applied for a particularly appealing role that promised both career advancement and a better financial future. Despite a promising interview, the agonizing wait for a response—which ultimately never came—pushed me to a pivotal moment. Frustrated by the uncertainty and lack of communication, I resolved to take control of my career. This decision led me to establish my own business, ensuring that I would never again be at the mercy of such circumstances, and securing my family’s future on my own terms. Read more>>

Summerboyz Clothing | Clothing Brand

We were all just hanging out after work one day and Posey came up with the name SummerboyZ. So ever since that day we started calling the friend group SummerboyZ. Around 2020 Reece had designed the first logo and he surprised us with some shirts for Christmas. We all are creatively talented individuals, but together were stronger and form like Voltron. So eventually we knew what we wanted to do and make something greater for the world to see. Since then we all decided it was time for us to start a business for ourselves.. Read more>>

Dr. Heidi Kay Begay | Multi-Passionate Serial Entrepreneur

Starting my own business was not what I originally envisioned when I embarked on my musical journey. From a young age, I had a clear goal: to become a university professor and help shape the next generation of flutists. But as I went through the process—earning my degrees, applying for countless academic positions, and dealing with the reality of a highly competitive job market—I found myself at a crossroads. For two years, I dedicated nearly all my time and energy to applying for academic positions, only to face rejection after rejection. It became clear that the traditional path I had set out on was not yielding the results I had hoped for. I realized that I was filling out applications more than actually teaching and playing the flute, which are my true passions. Read more>>

Deontaye Jones | Perfumer

I actually was tired of working for someone else and being told what to do and when to do it so I started my own business and became my own boss/CEO Read more>>