Readers often email us asking us for advice about new businesses they are thinking about starting and we often find that many of them don’t have a framework for thinking about a more fundamental question: why should or shouldn’t you start a business?

Below, you’ll find how successful entrepreneurs from across the city thought about this very question when they were considering whether to start their businesses.

Devin Masone | Professional Videographer

I started editing video footage in early 2009 as a hobby. I later found out it would jump start my own recruiting process. I spent hours editing my own school footage to help with my basketball recruitment process. As I published my work, my peers asked if I could do the same for them. In 2010 I started my first production company business that was known as M- Squared Productions (Masone Multimedia) at the time. I ended up receiving multiple offers from the Division One level to JUCO levels. My career ended early due to injuries and that is where I really found my passion. Since 2009, with some stops along the way, I have created a platform that allows me to help student athletes achieve their dreams of playing collegially through my video services. I have been fortunate enough to have had my work on some of the biggest sports platforms (ESPN, USAToday, Ballislife & SportsCenter) and worked for some of North Carolina’s premier sports teams. As we step into 2024, my goal is to showcase our talents outside of the sports world including videos for corporate company’s & weddings. Read more>>

Ilona Kossoff | Founder of 18Chestnuts, Soup connoisseur, Yoga and pilates practicioner, Mom

18 Chestnuts is a passion and purpose driven company. I could not diget food and after yet another unsuccessful doctor consult and medical tests, I decided that I had to find natural solution to my problems. Soups are my favorite food group! I completed Cornel Universtiy Healthy Living Program and learned about plant based diet. I became a yoga instructor, start to meditate and journal. Slowly I was able to reclaim my health with my soups as powerful healing companions, my “secret” weapons. I wanted to share my journey, experience and results with people. I realized quickly, my digestive troubles did not leave me in the minority. In fact, over 70 Million Americans struggle to digest food and women are 3x more likely to experience the symptoms. I wanted to share the gift of my vegan, gluten-free, low sodium and no sugar added unique soups with people to improve thier journey to health as well. I wanted to educate people, to help them, to provide an alternative that was convenient, delicious and environmentally friendly to people and our planet. Read more>>

Hannah Dilday | Owner, Traditions Silhouette Co.

I have always had a love and appreciation for silhouettes but it wasn’t until shortly after college that my first silhouette was born. I needed artwork to furnish the walls of my new home and a silhouette painting of my dog was the perfect fit. The piece quickly became my favorite in the house. It was timeless and classic yet personal and meaningful. Friends would always ask about it when they came over so I started making them for gifts here and there. Read more>>

Nicolette Jacobsen | Wedding & Event Planner for Christian Couples

I come from a family of entrepreneurs so the idea of starting a business wasn’t super foreign to me. I also began to notice my traditional 9-5 work schedule did not allow me the time freedom to steward my relationships, household responsibilities, and other passions well. That said, I started to explore the logistics of starting my own business, and through research, prayer, and seeking wise counsel I decided to go for it! Read more>>

Karla Holley | Licensed Massage and Bodywork Therapist

My thought process behind starting my own business was deeply rooted in my desire for autonomy and fulfillment. I’ve always harbored a longing to be in business for myself, and my journey into massage therapy felt like a natural extension of this aspiration. It stemmed from my genuine passion for aiding others and my fascination with the intricacies of the human body, particularly muscles. Thus, venturing into massage therapy felt like the perfect avenue to combine my entrepreneurial ambitions with my innate desire to make a positive impact on people’s lives. It was a seamless convergence of passion and purpose, making it clear that this was the right path for me to embark on as my first venture into entrepreneurship. Read more>>

Tequila Michelle | Prophet, Entrepreneur, Author, & Mentor

Embarking on my journey before college, career uncertainty was my trusty companion. I wandered until a light bulb moment hit me in my sophomore year – I had an undeniable affection for numbers. Naturally, I fancied myself as the future number cruncher extraordinaire. However, a stint in a cubicle revealed that my personality craved a grander stage than a sea of spreadsheets. Read more>>