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.

Charisse Woods | Brand Identity Strategist and Designer

Ah, the question every entrepreneur gets asked! The truth is, there wasn’t just one “aha!” moment that sparked Creators Brand Bazaar. It was a crescendo of frustrations, aspirations, and the unwavering belief in the power of creativity. Read more>>

ROCKSTEADYY | DJ, MODEL, BUSINESS OWNER

My thought process was the fact that I did not go to college and if I wanted to be successful that means I needed a plan. I Knew that I was taking a huge risk in not furthering my education as I only have a high school diploma and did not have another degree to fall back on if this plan didn’t work. I went to college and attempted to stay focused on that goal also but found myself very distracted with the weekend gigs of modeling a djing.I also worked a part time job at a restaurant and eventually went to work at a gym. I was just doing TOO MUCH. the thought process was to have a plan and execute. Read more>>

Monica Arroyo | Clinical Director & Owner

I started Family Therapy Group of Weston out of the desire to help as many families, couples and teens as possible. I realized that there was a great need for mental health services in our community and I envisioned a place where we could serve all members of a family at once. Read more>>

Sarah MacDonald | Licensed Massage Therapist, Owner of Cape Cod Wellness Works & Old Cape Apothecary

As a Massage Therapist, I had grown tired of working for other people. From the time I had completed my Massage Therapy education, I had previously worked as an employee and as a (misclassified) Independent Contractor at Franchise locations, Spa locations and other wellness offices. I wanted the freedom of creativity, control over my schedule and the services I offer. I was well aware that it would be an immense amount of work to start a business from the ground up but I had faith in myself, the quality of the service I provide and the ideas I had about running a conscious business. It was my “Field of Dreams” moment – If I build it they will come – If I do good work, they will come back and tell their friends and family. When I told my mother in law that I was opening my own practice, she had a look of concern on her face. She asked me, “How do you know this will work out?” My reply was, “Because it has to. Because this is how I will house and feed my children.” Read more>>

Adam Lichterman | Marine Manufacturer & Entrepreneur

The thought behind starting any business is an opportunity. Big yachts, sport fishers, trawlers, really anything over 50′ all have large maintenance industries surrounding them for any and all types of service. Growing up in the marine industry, I noticed a lack of 3rd party care options for your average boat owner that has enough money to afford the luxury, but not enough time to familiarize and care for it. Salt water, being as harsh and corrosive at it is… care is everything. The knowledge and experience gathered during my time growing up made me an ideal candidate to fill this void. I saw my opportunity to fill the gap in the market and took it. Read more>>

Stephen Pickering | Creative Director, Project Supervisor

I often joke about someday writing a book titled, “Oops, I fell into business.” I’m not a business person by trade, but for some reason I still wanted my own business and I fell into my current role of “business owner” because I have a passion for filmmaking. My dad has always been self-employed and I saw firsthand the stress and hard work it takes to sustain a business. But I always liked the idea of setting my own schedule and being accountable only to my clients. Read more>>

Dimitris Harvalis | Chef / Owner of Elia cafe / the best catering company and FitbyElia meal prep.

I opened my first restaurant backin 2012 and i was a newly father of a baby girl and in a new relatioship with my now wife that was also expecting, after being in the nightlife industry for 14 years i realize i needed to change my work enviroment for many reasons, I always loved the idea of owning my own restaurant and the time just felt right, as well as my pation for cooking and sharing with everyone the knowledge and flavors that my granmother passed on to me. I am Greek born and raised in Greece and food for us is a way of life. Read more>>

Claudine Gentles | Owner of Pak N Jet Travel

I’ve always wanted freedom. Both financial and time freedom. I knew that working a 9- 5 every day, I am working and building someone else’s dreams and goal. My boss’s dreams and goals to be exact. I figured, why not put the same energy, enthusiasm and spirit that I gave to my 9-5 in my own business. Something that belonged to me, and this way I would be fulfilling my own dreams and goals. That was my thought process in starting my own business. Plus, being a W2 employee will never make you wealthy. You must invest in a second source or multiple sources of income. I decided to invest in myself. Read more>>

Deanna Marandola | Restaurant Owner / Chef

My business partner Tracy and I worked together bartending at another local business (Kleos and Rosalina) we started talking and discussing foods and drinks and our love for creating new recipes and cocktails. She had lived in LA and wanted to bring that style of eating to RI seeing there wasn’t anything like that here. We started to collaborate, made a name, an Instagram, and from there started doing pop ups in local spots for a few years and especially over the pandemic. We made a little name for ourselves before opening our brick and mortar. Read more>>

Deanna Dicesere | Personal Trainer & Owner of EMPWRD

Covid made me very frustrated and out of my routine. I saw that as an opportunity to get people together virtually and start a community called POWER30. The frustration behind gyms closing, everything shutting down, and everyone forgetting about their health for a few months INFURIATED me. I said enough is enough, I’m doing this I don’t care what it looks like but something needs to happen. I had an idea, I prayed about it and put action to the dreams/desires I had. Read more>>

Dr. Nicole King-Smith | Generational Leadership Expert

When I decided to launch NK Enterprise Consulting in 2014 it was the result of a Fortune 500 company calling me and asking me to come do a paid speaking engagement. It was in that moment I realized my passion of speaking and training professionals on building better relationships across multiple generations was now a profitable business. Prior to launching, I spent several years using my talents of speaking, teaching college, and running a career center at a university learning the major obstacles individuals and organizations were having with building opportunities. I constantly saw a need and was able to provide solutions, but now with the business I can do it on a bigger scale with a strategic plan in place to target certain organizations that could use my strategies. Now 10 yrs later I have been able to help hundreds and thousands of people connect and get results in their workplaces and overcome conflict as Generational Leadership expert. Read more>>

Mary Meisel | Creator of Meet Marie

When I started my own business I was a stay-at-home mom of 3 beautiful daughters who occasionally did consulting work and taught classes at the University. Never before had I worked in fashion but I have always loved it and learing and reading about the industry. One day I went shopping with a friend and her teenager daughter and it was an absolute disaster. They never agreed on anything and fought all the time. When I got home and looking at my girls I had an epiphany ! That was going to be me in a couple of years and multiplied by three. Read more>>

Tammy Bartels | Simplicity & Habit Coach

When I became a stay-at-home mom 7 years ago, I always felt things had to be a “certain way”, but I also didn’t know what that “certain way” was. You are not taught how to be a mom, and our world makes it seem like moms are supposed to live in chaos all the time. My anxiety and overwhelm were through the roof. I decided it wasn’t how I wanted to live my life. The only thing I knew to do was figure out routines and habits that could help me simplify everyday life. The more consistency I showed in various home tasks as well as clearing out excess clutter around the house continued to reduce the anxiety and overwhelm significantly. It required me to take baby steps because it wasn’t going to be perfect right away, but a process that allowed me to pursue the life I wanted to live. Read more>>

Edu Puertas | Stop Motion Animator and Puppetmaker

When I started making stop motion animation I found out that it was really hard to find the right tools for my job. Either they were really bad or I couldn’t afford or find the good ones. I wanted to make great animations and this was something that stopped me from achieving them, so it made me think. Read more>>

Rob Jeezz | Designer

I was around thirteen when I started to pick up hobbies other then sports like photography, sewing, digital arts, painting – drawling taking up cooking classes, architect designs, building computers really anything to keep me busy. I don’t come from stability, successful parents- money etc . So growing up I had to wear what ever my mother could afford so we got pick on here and there but my mother always did her best. As I got older anytime I could put a fit together even if it didn’t match I would, don’t matter where Aj was going . Kids use to be like “where ever JEEZZ goes he always gotta be wavy and I would just be like “pretty much” so . I would always say it’s not wavey it’s SWAVEY and you gotta think this is like back in 2003 2004 . I guess that’s where my fashion adventure started . Growing up I had a consistent melody in my head, I couldn’t leave music alone, it was all around me . I knew I wanted to be a designer but I also loved music, growing up broke didn’t help, everything I wanted was on tv screen. So to answer your question, Starting a business form zero was the hardest thing I ever had to when bot a single person in my family even graduated high school besides me, everyone I grew up with was either dead, locked up or long forgotten about. The toughest part was having zero support but just a vision . Read more>>

Ximena Salgado | Actress, singer, dancer, choreographer. Founder & Director of Rumbamena Dance Company

I had launched another business with my ex-husband. This story didn’t end well. It was my time to launch something on my own. Directing, producing, creating new shows, choreographing sustained me in all aspects. Keeping my already functioning productions and rehearsals alive kept me focused and motivated. I was inspired to design a new brand,l. I had collaborators joining the journey and we made Rumbamena happen with the purpose to celebrate with joy and free ourselves. Read more>>

Ewa Matyja | Abstract Artist

My path to starting my own business began with a deep-seated passion for art. I had spent over a decade in the fashion industry, enjoying my role in retail management. However, my heart always leaned towards art, a love that ignited in my teenage years. In my small hometown in Poland, the absence of an artistic community left me unsure about pursuing art professionally. This led me to study marketing and event management while I was in Ireland, skills that served me well in the corporate world. Read more>>

Nuno Gomes | Writter & Director

I always hated when I heard someone from the industry reply “it’s just business”. So I will give you a little bit of context before I jump directly into the answer. When I was 11 years old I knew right and then I wanted to become a Director, no questions asked. I started to do the “School Tv News”, recording the Theater plays from our Classroom and funny bits for our Art Class and I always looked up to this “Special Presentations” before the movies started, like “An UNIVERSAL PICTURES Movie” or “20TH CENTURY FOX presents” and I wanted to have something similar on my own stuff to show before my presentations right? So I read a book which was given to me by my father called “The Magician Diary” by Paulo Coelho before he became THE Paulo Coelho that we all know. Basically before becoming a renewed/awarded writer he went on a mystical journey through the Santiago de Compostela way and he wrote about it and made it into a book with all the people, adventures and crazy experiences he encountered on his trip. I found it just magical, wonderful, exhilarating and pure fun. Fell in love with it, especially all the mysticism behind the “Compostela journey” and I just couldn’t get out of my head the idea of this special place where anything can come true and just like that, It clicked! That’s it! Compostela comes from the Latin word “Field of Stars’, like this land full of dreams of so many people ready to become real and I couldn’t find a better name to call my very own dream; my “visual business’ ‘. So what started back in School, years later evolved into my company “Compostela Films & Art”; and even though its has been almost 14 years later, with many projects already done along the way, collaborated with wonderful artists, worked on different entertainment medias, platforms and clients, I never lost sight from where everything started…this idea of make peoples dream come true. I know it’s very “romantic” and probably naive from me thinking like that, but I believe everything that we do, how we think, how we behave in life, how we treat people, how me face troubles, how we overcome problems and how we succeed in life comes from who we were back when everything started, if we lose that, better starting to find another reason that makes your heart pumped if you want to be successful and happy in life. A successful business comes from a business state of mind that feeds from a purpose. A soul without a purpose, it’s an empty vasell waiting to be filled with meaning and meaning without passion, it’s just like a company without heart. Nothing good comes from anything without heart…even if “it’s just business”. Read more>>

Wendy Behar | Certified Addiction & Recovery LIfe Coach

My journey into entrepreneurship unfolded during the pandemic with the release of my bestselling book, “#YourRules.Your Life.” As an experienced therapist specializing in addiction, working for an outpatient agency, I have dedicated my 20-year career to helping individuals and families navigate the complexities of recovery. My transformational program, the Happiness Recovery System , has been a lifeline for clients and their families in recovery, offering guidance in rebuilding relationships with themselves and others. Having embarked on a personal sobriety journey spanning more than 25 years, I’ve integrated evidence-based therapies with my own recovery experience to develop this simple holistic program. It’s amazing how my book changed the trajectory of my life and has given rise to a business dedicated to supporting one-on-one clients and group programs to create a healthier, happier, more authentic life. Read more>>

Kewina Walker | MLO, Credit Advocate, Tax Preparer & Notary

My thought process behind starting my own business involved three variables: being a mom, my health and time freedom. As a single mom, I found myself always working and having to miss certain small events that I definitely wanted to be present for. If I wasn’t working, then I was always rushing and speeding through the day so much that I rarely had time to just enjoy being a mom. I knew something in my life had to change because time was running out. My son at the time was in the seventh grade and I already knew that I needed to come up with a solution prior to him entering into high school. He is a very busy athlete and I vowed to myself that I would never miss any games during his high school years. I am proud to say, I never missed a game. Read more>>