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.

Lawrencina Mason Oramalu | Author, Trainer, and Motivational Speaker

Before I made the decision to start a business, I had made the decision to write a book, and I later decided to use the business as a vehicle for launching my book and other programming. I have always loved writing. When I was growing up, I used to journal. I also used to submit essays for various essay contests. I wrote for my high school and college newspaper, and when I entered the work world, I had jobs where I was either writing proposals or reports. I think one of the reasons I started my business is because I wanted to have a platform to write whatever I wanted to write and speak about whatever I wanted to speak about. Although I have been able to write and speak in my traditional 9 to 5 jobs, I did not necessarily have the final say on what I could write or speak about. Sometimes there was someone who could decide whether or not my style of writing was acceptable. Now, if I want to write a blog, I can write a blog. I love acronyms, and now, as an entrepreneur, if I want to use an acronym, I can. The name of my company, Soar2BMore, is an acronym. Read more>>

James Price | Entrepreneur Transitioning into Restraunteur

My thought process was being able to determine my altitude. Legacy… I wanted to make sure my children’s education was taken care of and that they would have options later in life. Read more>>

Alison Viktorin | Beauty Blogger & Content Producer

I started my blog,, for all the Mommas out there that don’t have time to research different skincare products and procedures. I do all the work, so they don’t have to. If there is anything new and different, in the World of Beauty, I put it in my blog. As parents, we can become so busy that we don’t have time to deal with any extras…enter my blog, where I give the latest advice and do all the work, I even have links that make it easy to purchase the products I mention. I like to call myself a #truthfluencer. I like to give truly honest reviews. I want to help make feeling and looking your best, as easy as possible. Read more>>

Rosie Kaplan | Artist and Entrepranuer

I started Brushed Restorations by Rosie because I wanted to prove to myself that I had the power to make my life anything and everything I want it to be. The year leading up to starting Brushed Restorations I did a lot of soul searching and with the help of a few people, I realized how powerful self confidence is. I started to believe in myself in ways that I had not done before. I was turning 40 and felt compelled to make 2020 about pushing myself in ways I did not think possible. I am a wife and a mother of 4 kids so often I found that I always did for others and didn’t really put myself first. I wanted to show myself that I could do it and be able to share my story to hopefully inspire and give that power to someone else. Read more>>

Nan Phillips | Fused Glass and Stained Glass Instructor and Sculptor

I had been teaching fused glass, stained glass, and figurative clay sculpture classes at other art studios for 5 years. My initial thought behind starting my own business, was that, even teaching 5 classes a week, I was making too little money to survive. No matter how many students were in a class, I still made the same $50 per class. That worked to my benefit when only a few people attended class, but not so much when a class was packed with 15 students. In 2008 my children were all away in college and I had extra space in my home to create a fused glass and stained glass teaching studio, so I decided it was time to strike out on my own. In determining how I wanted to run my classes, I thought about all my previous students. One of their biggest complaints was paying the art studio up front for a specific number of classes, so if they missed class, it was lost money. Since these were all adults who had work and family obligations, they almost always missed a class or two per session. Read more>>

Woody Smith | Bicycle Sales and Repair Shop

An opportunity to serve our community and give back to God. Also to create job security for me and my family, and challenge myself. Its always been my dream since around age 12. Read more>>

Will Hooper | Recording Engineer

I started a recording studio after travelling over Texas recording friends and acquaintances for two years. Learning the craft since I was 18 years old. Finally taking it on the road to spread my wings and learn more from different people. I knew I could make it and have a successful business with the knowledge of 10 years recording and collecting musical gear. Read more>>

Kimberly Armstrong | Owner & Taste Creator

I think that one of the most important factors behind my success and the success of my brand would be my family and their unwavering support. Persistence would be a very close 2nd. Read more>>

Reese Accuardi | Aerial Instructor & Performer

I believe the most important factor behind my success is the time and dedication I put into it. Success did not happen overnight for me. It took hours upon hours in the studio, many late nights, and rejection. Success is what you make of it and is subjective – I am proud of what I’ve accomplished and the biggest indicator of my success to me is happy aerial students! Seeing my students reach goals and get stronger is super rewarding. I put into my “brand” what I want out of it, and it’s most definitely a labor of love. Read more>>

Addie Roberts | Registered Dietitian & Business Owner

The most important factor behind success of General Wellness is being authentic always and meeting people where they are. It’s not helpful at all for me to discuss macronutrients with someone who doesn’t even know how to prepare food or how to buy healthy foods. Additionally, if I’m not transparent with where my health and nutrition barriers are, then I become unapproachable. No one is perfect, and being able to tell clients we are all in this together builds trust. Read more>>

Cassie Green | Elderberry Syrup Wizard and Integrative Nutrition Health Coach

I think two big qualities that have helped me be successful (and of course we all define success differently) are my tenacity and action orientation. I’ve owned my own businesses since 2008, first an organic grocery store in Chicago and one in Dallas called Green Grocer. Then I built a robust health coaching practice which I scaled back because we started really growing our locally produced immune supportive elderberry syrup business. Over these nearly 13 entrepreneurial years, I have seen the edge of exhaustion many times, failures, disappointment, stress-you name it. But I think my (and my husband/biz partner’s) ability to just keep going has helped us to move into a business that is sustainable not only financially but also health-wise. It’s like that old Churchill quote “If you’re going through hell, keep going.” I also am a person of action. A lot of people talk about ideas of what they want to do and that’s okay but when I want to do something, I make a decision and jump in. Read more>>

Chloe Rogers-Campbell | Owner of Free Vibe Entertainment

My brand is called Free Vibe Entertainment, a company that serves as a Music Label, an Apparel Line, and produces Creative Directed Photography. Free Vibe’s name stems from the yearning for freedom from inhibitions, insecurities, and expectations. This company has become a personal journey through trying to live up to its name. My faith in God has been the most important factor behind both my personal and the brand’s success. Through this journey of growing my vision, God has taught me to not only find my own voice, but trust it. Hard work of course is important ,but at the foundation of that hard work is passion and purpose. It is a responsibility yet a privilege to be able to run your own business, and it takes confidence to trust your gut when making decisions in both business and creativity . Rather I’m writing an album , coming up with apparel designs or planning a photoshoot I often ask myself , “What are you trying to say?” It is so important to dig deep and be authentic to the vision God places on your heart. Read more>>

Davis Speight | Owner

There are 3 three things that I live my life by; Focus, Work Ethic and keeping a Positive Mental Attitude at all times. Unfortunately, I didn’t learn the importance of this until I was 34 years old but once I did, they were a game-changer for me. Keeping a positive metal attitude is critical for your success. If you have personal items in your mind that effect your mindset in a negative way, it will 100% affect your ability to stay focused on the job which leads me to Focus. I have a strange ability to check my problems at the door. It’s as if I can bottle them up and set them by the front door so that once I walk into the office, I am focused on northing but the job at hand. I realize this may be hard for most and it was for me as well, but once I harnessed this ability, it changed my day-to-day beyond belief. Work Ethic comes down to your goals. Set yearly, monthly, daily or even hourly goals if needed. Schedule your day around your goals and don’t leave until everything is done. You got this. Read more>>

Lesli Marshall | Designer – Artist

Being a creative and entrepreneur, it is so important to create a routine in your daily operation. I work from home and have the same routine every morning,..this sets the tone for my whole day. The most important factor behind the success of Articulation Art is also execution…you can have great ideas but if you don’t execute, you don’t continue to build a great reputation. Read more>>

Aaron Jackson | Founder of Aaron Jackson Designs

Originality. We use every opportunity to be innovative in our branding as well as uniquely original in our staging design concepts. Too many times I’ve seen many businesses in the Real-Estate industry who stage homes and their execution is always that same stereotypical “cookie cutter” look. Read more>>

Molly Valentine Dierks | Visual Artist + Designer

I am a visual artist and designer. I have just very recently started a nascent brand of my own design works (, from jewelry to stickers to children’s toys and vinyl wall pieces and installations for home or business. I live to create, and between exhibitions of my sculpture, I find myself making work that is visually sensual [a lot of my work features nipples, which web designer friend told me is a running joke athe best user interface design ;)] or meant for play – for example the series of wooden 3D puzzle toys with custom boxes I designed for my cousin’s children – these toys are good for children’s brains (no instructions included to encourage critical thinking). I first handdraw my designs, then use technologies like laser cutting or vinyl printing to turn the ideas into humorousgorgeous, playful products. With the onset of COVID, I realized that I wanted to start my own business, and definitely had enough ‘products’ to do so. Read more>>


Persistence,I believe in hard work and keeping at it means getting better. Everyday after work I do my practices and do more re-search on my craft. Whenever am not doing that am working on video and audio editing/production.I also teach so as to expand my team. Still under persistence, balancing between my daily job and my Dj career sometimes gets hard, I get at least 1 hour or 30 mins sometimes a day to practice and I make sure that I use that very well . I always pursue different audiences and different markets be it online or socially, I travel and do videos in Different cities to do self promotions which in the end attracts more online and physical business. Read more>>

Prudence TheAuset Sneed | Filmmaker, Writer, Poet and Mentor

My thoughts honestly reflected on when my mother had a non profit organization. It had community mentors that taught life skills as well as provided the assistance many low income parents needed from food and clothes banks to applying for jobs and trade schools. Those services made important impressions on us as youth as well as adults who were facing many challenges. We are in an era where being a bridge in the community where students and parents may need the smallest of help to make a huge impact in their lives is beyond necessary. Read more>>

Javy “JJ” Caballero | Hip Hop Artist/Producer/Brand Owner

I am an aspiring hip hop artist first. That’s what I’ve been working my towards for most of my adolescent and adult life. Not only am I an artist, I come from the DIY punk school of thought in which you learn all aspects of your craft, from inception to distribution. I just have a natural distaste for authority, so any job I’ve had growing up I always left because I was tired of being told to do that thing that I was paid to do. All of this combined naturally pushed me to starting a business. The first two I started failed, and it was a very bitter pill to swallow. I took a ton of lessons from there and got some side gigs to hold me over while I thought about the next one. On top of organizing my aspiring career in hip hop, I’ve now organized the my efforts to starting a fashion/lifestyle brand called Gang Signs. It’s progressed rather fast since the pandemic hit and forced me to run with the idea full steam. But the idea with Gang Signs is that shoes, fashion, style all have their place in hip hop culture and I’ve always placed interest and learned about this stuff growing up. Culture always has a way of molding a unifying look, and I love the aspect of unity in all of this. Read more>>

Darren Williams | Man of God, Family Man, Veteran, Entrepreneur

My initial thought process behind starting my own business was fear, anxiety, self-doubt; but at the same time excitement, adventure, and gratitude. Read more>>

Kathy Still | CPA, Partner and Firm Cheerleader

As a full-service accounting firm, we offer a “commodity”–expectation being that a good tax return or audit or bookkeeping services will be obtained from us. What makes us successful is that we believe in including everyone in our organization–from the partners to the staff to administration–in brainstorming ideas for our clients and for the firm. Lots of organizations say they are about teamwork but in my experience, few actually live up to the words with their actions. At Still Burton, we literally bring everyone to the conference table and discuss ideas. Everyone’s perspective is important, even freeing to “leadership”. Valuing our people this way naturally leads to our people treating our clients as they deserve, with respect and partnership in reaching their goals. We are not in the accounting business serving people; we are in the authentic partnering business bringing peace to people’s accounting needs and concerns. Read more>>

P | Designer , Curator, Purist

The most important factor to VSN’s success is showing people that it’s cool to support people trying to make their own way. Everybody can’t work a regular 9-5 and that’s cool. Also showing people that they can be a little creative too. It’s cool to sit down and make stuff as simple as that sounds. After I’m done I just want to leave the city inspired. Read more>>