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.

Akeeme “DJ BlacqueStarr” Martin | DJ, Host, & Curator

After doing radio for 10 years, I had built up this network, or better yet an institution that consisted of creatives and people who were fans of what I did as well as a number of solo and collab projects that didn’t get a chance to see the light of day by the end of 2014. I didn’t want to let any of that go to waste, but since I no longer had that platform (the radio station), I had to look into what it would take to start up my own business, but more importantly, create that platform for the independent arts without the nonsense that industry tends to bring on. But I wanted to be sure I did it the right way. By Winter 2015, I attended a music business and law panel discussion where a friend of mine was a featured panelist. Our ties dated back to our time at the radio station and she eventually became the music editor of Flagpole that was an underwriter for many of the station’s shows including mine. She was in her third year of law school at the time of the conference, and I expressed my interest in starting up my own business. Read more>>

Dylan Marie | Autistic Artist

There were several thoughts and reasons for starting our art business. However, the main reason was to establish a foundation for Dylan to be able to support herself in the future without relaying on the government. We have always wanted her to have all of the normal teen years experiences like receiving a drivers license and her 1st job. Dylan is not a typical 16yr old girl and a typical 1st job setting just wouldn’t do! Dylan is autistic and being over stimulated sometimes intensifies her anxiety. She loves to draw and write stories to express herself, why not do it to support herself? Dylan Marie’s Paintings & Illustrations was born just a week after her 16th birthday. Read more>>

KaShanna Hale | Master Cosmetologist, Certified Hair Loss Specialist, Certified Wellness Life Coach

I just felt it was time! I really got tired of people telling me their standards/ rules and they were not upholds their own standards and rules. Everyone can’t be a boss. Read more>>

Kathryn Farrell | Anesthetist and Inventor-Entrepreneur

I have actually wanted to start my own business for a long time, but previously hadn’t found an idea that seemed worth pursuing. My day job as an anesthetist is very fulfilling in some ways, but has left me wanting more for a few years now. While I enjoy taking care of patients and I love the science behind anesthesia, I have felt stagnant for a significant part of my 10 year career in the field. This feeling had been nagging at me for a while, and then the pandemic happened. My job suddenly went from routine to terrifying, and I was now putting myself and my family at risk every day for a job that was no longer my passion. On top of the exhaustion from my professional life, I had two young children at home. My son was 2 at the time, and my daughter was not quite 1 and she was (and still is!) quite a handful. She wanted to be held during all waking hours, and only by me. Read more>>

Brandon McCrae | Preacher, Professor, Producer

The crazy thing is… I never set out to start a business! I saw. need and simply supplied a service. That service happened to be something that I love and am personally passionate about. Everything literally evolved from there. I made a great number of mistakes in the beginning. Time is the ultimate learning curve. The longer you give yourself to any process, with perseverance, you gain knowledge. It was literally the press for me. The more I did, the more I learned, the more I grew. As you can likely tell, I am a spontaneous kind of guy. Read more>>

Emerald Arguelles | Photographer & Editor-In-Chief of Aint-Bad Magazine

My thought process behind starting my business was, “how do I control my future?” I wanted to control my vision, goals, and creative processes without conforming. There is a sense of independence that I always strive for, and starting my own business was something that I saw as a necessity. Read more>>

Max Hall | Filmmaker, Actor, and Musician

My business began slowly, over a period of time, as an extension of the lifestyle I’d already established. In other words, if I didn’t have my business, I’d still be spending just as much time creating videos, films, and music – I just wouldn’t be making any money. I can’t recall a decision or a thought process or a pivotal moment – only a slow transition from making videos all the time for no money to making videos all the time for the occasional paycheck. In fact, I’m still in the middle of that transition! In a few years from now, I hope to look back at today with thankfulness for how far I’ve come. Read more>>

Jasmine Shaw-Lunsford | Wig maker

My thought process was simple I wanted to make women feel good and look good with my wigs that I provide. Especially because I was getting so many compliments. Read more>>

Nicole Tyler | Professional Photographer

Starting my business back in 2010 was more of a “snowball effect” than a “thought process”. At that time, I was a massage therapist and I knew that because of how much of a toll that work took on my body, I was not going to be able to do that for very much longer. I asked my husband for a camera for Christmas and he bought it. I was determined to teach myself how to use the camera in Manual mode using the owner’s manual and Youtube University but there were still some dots that didn’t connect for me. Eventually, I decided to go to photography school and, long story made very short, 2 years later, I was awarded “Best Portfolio” of my graduating class. I hit-the-ground-running post-graduation. I took my camera EVERYWHERE and people seemed to be drawn to me asking me if I could take their photos. So, I built a quick website to display my work, bought a box of business cards and said “Yes! I can do that.” to every opportunity that came my way. Read more>>

Jade Williams | Money Mindset & Financial Coach

I was actually employed, at the time, with a CPA firm, literally doing ALL the work. One day I just got tired. I was tired of working 9 am – 9 or 10 pm. I was tired of being the one that had all the answers, especially because it wasn’t my company. I was tired of being asked to train unqualified individuals to do my job. I was just over it and I started to think, “If I can do all this work for someone else and only make $15/hour, I can do this for myself and get the full check.” Aside from the money though, I felt like I wasn’t operating in my purpose. So it wasn’t just my own thoughts, I also had to get clear on what it was that God had called me to do. I knew that everything I’d done up to October 2018, didn’t get me far, so I asked myself, “Why not try God?” Read more>>

Clare Henderson | Artist and Computer Science Student

Selling my art was a bit unexpected. I minored in Studio Art at UVa, but before quarantine began, it was more a hobby than anything else. After being sent home from college for quarantine, I began using my mother’s art studio to complete my projects for painting class. When a friend of mine asked if she could buy one of my projects, it gave me the confidence to start posting my pieces on Instagram. I quickly sold most of the paintings I had already done, and people began asking to commission paintings. I soon created a website with listings of my pieces, and my sales picked up more and more. It all happened so fast that I can’t say there was much of a thought process at all, and I am still learning every day. Read more>>

Antwan Aiken | Entrepreneur, Philanthropist & Psychotherapist

I wanted to be in control of my own financial freedom and impact communities that look and feel like me. Read more>>

Stacey Lynn Emerson | Fashion Designer & Wardrobe Curator

I originally started my business because I had a deep love for fashion! It was tradition to go window shopping/shopping every week when I was younger and I wanted to bring my view on style to one store! The thoughts that went through my head was how I want people to feel when shopping because it always bought me so much joy! I wanted people to experience a shopping experience online that felt like they were shopping with family or girlfriends. Read more>>

Jaelaun Moses M.S. | Master of Science & Entrepreneur

When it came to Jae Taj boutique, I had to first ask myself, “Is this your passion? What do you want others to take from this? How can you be more than just a boutique? What makes you stand out from everyone else? How can you relate?” I ask myself these things to make sure I outline my purpose; my mission. It’s never been a get money quick thing for me. I always consider my personal relation to the matter and make it work for me and not against me. Growing up, I always had a fuller figure and expressing myself through fashion was the best way for me to identify myself without any restrictions or limitations. Problem with that was, finding cute AND affordable clothing in plus size growing up was extremely slim. Everything seemed so basic, and frumpy. When I did find nice pieces, they were so much more expensive. I felt like I had no one speaking to me and my body frame/type. I knew at some point I had to step in and make something happen. Everyday, I still ask myself these questions. Read more>>

Ginger Windham | Jewelry Designer

I started Gemini Flyii because Of my love for jewelry. I’ve always loved wearing jewelry since childhood. Handmade jewelry has always had my heart because of the personal touch and love that goes into creating it. I wanted to have that same connection when it came to making jewelry and someone knowing that I made it especially for them. Read more>>

Michele Bell | Accounting and Finance Navigator | ClearPath Associates

I have a love of numbers and a passion for connecting with small-business owners and helping them grow financially into their vision. I grew up through the ranks of corporate finance and accounting at several Fortune 500 and 100 companies and with a stint as a CFO at a start-up. All of those experiences have given me a well-rounded insight into large scale financial controls and analysis and how to cater those to fit a small-business without over burdening it. At a pivotal point in my career, I realized that if I am going to work this hard then I would rather work for myself. I wanted to build a business that afforded me flexibility and control over my financial future. So, I took the plunge and created ClearPath Associates, LLC. I am motivated by all the entrepreneurs out there that have a passion for their own business and I love being able to help push them forward by providing my expertise in finance and accounting. I am always excited to hear about new business ideas and ventures. It is so inspiring. Read more>>

Denise Lawson | Boutique Owner & Hospitality Specialist

My thought process behind starting my business was how, when and why. We all have been affected by COVID-19, being in Hospitality industry was hit extremely hard. I had to think about adding income due to the possibility of becoming temporarily unemployed. It was the uncertainty of how I was going to move forward. With moving forward I had to really put thought into my “why”. It has always had a dream of owning my own Boutique. As a woman that has always stayed in tune with the trends, styles and seasonal colors, it was really a no brainer. Having the love for fashion has always been my niche. My “why” became a little more clearer, because I love to see a well dressed woman. Whether it’s simply casual or elegantly beautiful but yet stylish. Read more>>

Stefa’nie Ross | Business Manager and Founder of EBW VA

There were multiple things that aligned during a time in my life when I needed additional support. As a wife, mother and black professional, I was constantly in search a group of women, outside of my close friends, who I could professionally bound with. I was also transitioning between jobs and found my past career did not value me as an employee as much I valued them. I gave myself three months to figure out exactly what I wanted to do in my professional life. I wrote down the top three things I had a passion for- supporting black women, networking and events. After much planning and pivoting because of the pandemic, EBW VA was created. Read more>>

Thamicha Isaac | Life Purpose Coach/ HIV Counselor

The thought process behind starting my business was I needed someone that looked like me, there were no one that could relate or modeled what I was looking for. In 2017 when I was homeless, jobless and living in a hotel with my kids. Being HIV positive not receiving the medical care I needed in a state that receive funding for HIV adherence and continuum of care I found it very difficult to continue to stay in that state and remain stable mentally, emotionally and physically. I made the hard choice to return back to a state and city I know would take my care seriously and I would continue on my adherence journey. In returning back to NY I knew I had to create a program where others could relate and benefit from the services I would be offering to people who are newly diagnosed with HIV, living with HIV and don’t know where or how to start navigating their new way of life. I started Openly Positives because for far to long people living with HIV have been stigmatized, isolated and believed to be less than. Read more>>

Sara Pelaez | Leadership Coach, Psychotherapist, & Counselor

I came from a family of entrepreneurs. My father was self-employed, and he created much of his financial reality. There is great joy in designing your own path. There are a lot of sacrifices tied to this, but you can go as far as you want to go without false ceilings. In my late twenties when I started a family it felt like a natural progression. I liked the flexibility it afforded me and opening opportunities for myself became necessary as a minority woman in the early 1990s. I am measured in my risk-taking now that I am older. I do more research before jumping into a new opportunity and there are a lot more paths for growth in my field right now. It is not only about growing the business but having a balanced lifestyle and living within my values and sense of integrity. Risk-taking is necessary and I start with the “why”. By being conscious of the values that I am satisfying and starting with the goal in mind, I follow it up with research and what others may have done. Small sustainable steps build into bigger accomplishments. Read more>>