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.

Dennis Armstrong | Second hand reseller

I worked in restaurants since I was 12 years old and it was my “career” that I saw no future in. I didn’t realize how unhappy I was because it was all I knew. I didn’t go to college so it was the easiest way to make quick money, but I always had side hustles that supplemented my income. I made many attempts at being self employed but was overwhelmed with fear, stressed out and broke and always ended up back at a restaurant job. Looking back, I wasn’t passionate about any of the side hustles I tried to make a living off. Reselling was something I found joy in, and it came with financial freedom and I loved doing it. I could make money to pay my bills and not have to clock in to a job Read more>>

Niamh Bergeron | Wedding Planner

I have loved weddings for as long as I can remember. I made the first steps towards starting a wedding planning business about ten years ago, when I completed a certification program and had the opportunity to coordinate weddings for several friends. I loved both the organizational as well as the creative side of planning, and the opportunity to help facilitate a truly memorable day for a couple. But, I did not feel ready to leave the security my long-term job, which I also loved. I returned to the world of weddings four years ago with a part-time stylist position at Encore Bridal. I just love interacting with the brides! Recently, one of my past brides reached out to me, and connected me with a friend of hers seeking a wedding planner. Read more>>

Stephanie Engels | Board Certified Behavior Analyst & Executive Director

I have worked with people with autism of all ages for nearly 20 years in various settings and states. During this time, I became more interested in supporting teens and adults navigate adulthood. My mentor and co-founder started another nonprofit organization many years ago with several families who had young children. Those children had now become adults and reached the age where they would graduate from high school and no longer receive services through educational settings. They weren’t sure where their young adult children would go. This is a concern for many families as services drastically decrease as individuals reach 21 years of age. We wanted to help and that is how REVEL was created. Read more>>

Alex Cummings | Macrame & Candle Artist

I started working with Macrame after graduating college. I’m a busy bee and after finishing school I felt like I had so much time on my hands, I knew I needed a hobby. I’ve always been drawn to crafting and art, inspired by my Grandmother who was always crafting something magical when I was younger. Once I started, I fell in love with the process of creating things. I was making things for my friends and family, and at the end of the day I still had too many things in my house. I come from a family of entrepreneurs and small business owners, so I felt like this was a good opportunity to sell the things I was making and to own a business of my own. Read more>>

Melinda Frandsen | CEO of Tobiq Family Bags

I honestly saw a gap in the market. I’m the mother of four young kids and I never have enough hands to carry all our people and their things. When we would travel, packing a bag for each kid just wasn’t working for me. We carried more than we needed and could rarely find what we wanted. I went looking for a bag to help me simplify and organize our travel experience. When I discovered a surprising lack of options for family travel bags, I went to work making one. Read more>>

Isaac Olson | Co-Owner: MECO Coffee Collective

My partner, Shane Stinn, and I have worked in the corporate and independently owned Food and Beverage industry for our entire working careers. We worked the day to day, helped open other peoples businesses and also ran some of those said business. While working as a Food and Beverage Director for a locally owned business, it became clear that our 60 hour work weeks dedicated to someone else’s business could be and should be executed for ourselves. The amount of time and dedication towards making another small business owners establishment thrive had always been a passion of ours and some day you just wake up and say, “why not do this for us”? We had always had a spark inside ourselves to own our own business and at some point, you need to just ignite that spark and take that risk. We weighed out the pros and cons of starting our own company and knew that the passion, ambition and hours that had been put forth for others would set us on the right path to be successful on our own. Read more>>

Teresa Shishim | Graphic Designer/Illustrator

I worked for non-profits for years, wearing multiple hats and honing a diverse array of skills. One of those that I enjoyed the most was graphic design. About one year after I became a parent, I realized I wanted a more flexible schedule for our kiddo. I told my husband I was going to quit my job and go freelance–which totally freaked him out! I did it and have been at it for over nine years now. Read more>>

Shima Tern’a | Black ButterFly Records CEO.

My thought on starting my own business was to take advantage of the music industry from the top down,then with the information and knowledge obtained on the highest levels implement it in a fair and evenly spread manner threw out my label.While minimizing the possibility for my artist and creators to be taking advantage of. Read more>>

Ri Ganey | Visual Storyteller & Mountain Bike Coach

I was struggling to find peace and mental stability in other jobs. I’d tried my hand at desk jobs, labor work, and multiple service industry gigs ranging from food and retail to outdoor recreation. Jobs with more flexible schedules that facilitated experiences for others were by far more fulfilling but still felt like they were lacking, and I felt like I was struggling to fit in. I figured the worst case that would come of me trying to start my own business were some dead end roads and valuable life lessons, and the best case would be figuring out a career and lifestyle that filled my soul. So far I’m thinking the latter is the more probable outcome. Read more>>

Alana Kaufman | Food Blogger

I have always been a foodie, long before social media began claiming #phoneeatsfirst. From a young age, I always had a sweet tooth and my first love was definitely ice cream. As a fourth-generation Colorado native, I always enjoyed scoping out new restaurants and really saw the city change as the restaurant scene has grown. In 2019, when I returned to Denver from college, I decided I wanted to turn my passion for food into something a bit more tangible. I wanted to share with everyone that was interested my favorite places in town, new places I tried and all the amazing things popping up within the Colorado food scene. This is how 5280foodiez (the name deriving from Denver’s elevation of 5,280 feet) came to be. Read more>>

Cody Bennett | Owner and Operator of Friendly Mechanic

My brother and I happened to both be in between jobs. He had the idea to make some cash on the side while we hunted for new work. This eventually grew when we realized that this could turn into something big if we really wanted it and really put our hearts into it. He eventually grew tired of it, but I’ve always been entrepreneurial at heart. Always thinking of different ideas and plans. It really was just a matter of finding something worth the effort. I’m highly critical of my ideas and myself, so most of my ideas don’t make it past “dreamer” stage. Friendly Mechanic just happened to withstand the scrutiny and has encouraged me to think on other ideas that may come to fruition in the future. In the meantime I fully intend to put my all into Friendly Mechanic. Read more>>

Shelby Lewis | Private Chef

I started my own business at the age of 23 after grinding in fine dining restaurant kitchens for the prior 5 years. I had completed a Chef’s Apprenticeship under a Chef who had 5 James Beard Awards who taught me that the only way to be a real Chef was to never stop learning. Once I was in a position where I stopped learning, it was time to move onto the next challenge. I wanted to be the creative driving force behind my food, rather than being told what to cook. I wanted to be a strong Female Chef without answering to the male-dominated industry I felt hindered by. At the time I started Eat Dank Food, I was working (and still am) in Vail, Colorado and had met some other Private Chefs. The idea of more intimate, creative dining experiences appealed to me and I thought, “let’s give it a go.” Read more>>

John Epp | Realtor/musician

I was in a transitional period of my life 28 years ago at age 32 in Salida, Colorado. I was housesitting at my parents and was planning to move back to Denver or even out to L A to continue pursuing my music ambitions. I met my wife and step kids and decided to settle here. I had limited job skills having been a professional musician most of my life. I was waiting tables, DJing, playing in bands, anything I could do to make a buck. I had to find a real “career”. A friend suggested I consider the Real Estate industry as I had good people and negotiation skills from leading my bands for so many years. I had no previous experience or knowledge of the business but decided to go for it. Read more>>

Karl Sona Minority Business Development Consultant | I help minority business owners scale revenue to 8+ figures

Ownership. In march of 2021, the start-up medical device company where I worked at for 7 years was acquired for 9 figures. As an early employee and top performing contributor, I realized that my talents and efforts had been making the C-level executives and board of directors, none of whom looked like me, more wealthy than what they were before. So when several opportunities came my way to do the start up game again, I figured it was time to pass on the instant cash, and take my talents to the open market as an independent. It’s important that as a person or color, we normalize building and owning wealth so the next generation can believe that it’s possible for them as well! Read more>>

Bri Poehler | Wedding Videographer

I have dabbled in film and photography my whole life. From making home videos, to being on the yearbook staff in high school, to making promotional films for organiztions in college, the art of filming and photography has alwyas been in my wheelhouse. It wasn’t until I married my 8th grade sweetheart in 2017 that I learned that the wedding sphere was super fun and intriguing to me. My sister in law got married the following summer in 2018 and I asked her if I could carry my camera around and try to make her a film and she was kind enough to let me! Little did I know, this was the start of my new passion. Filming weddings quickly became something I did not want to live without. I was a special education teacher at the time, so I began filming weddings with “name your price” mindset to get more experience and build my brand. I had so much fun figuring out how to film the way I had envisioned. Read more>>

Gabe Ramsey | Creator of Petrichor Candle Studio

Starting my own business was never in the plans, it just kind of happened. When covid hit I missed traveling and the comfort it brought me. I knew I was not the only one feeling this way, so I looked for something I could use for comfort on a day to day basis. That is where my love for candles began. By starting my own candle company, I have been able to give others comfort through fragrance while giving back proceeds to the national parks I love traveling to. Read more>>

Sydney Guan | Digital Media Marketing Manager & Strategist

I started Blissful Media Marketing with cannabis and smaller businesses in mind. There are a ton of ways to get your brand out there, unfortunately, most business owners don’t have the time it really takes to invest in these key aspects of marketing. My goal is to give small business owners the chance to be visible on all platforms while still being able to give 100% into their business! Read more>>

Kasey Harvey | Owner

For the last six years I’ve worked in the magazine publishing industry. I am the digital editor for two home and lifestyle publications, and the content I work with inspires my creative side—a favorite part of my “day job.” When the COVID-19 pandemic hit in March of 2020, my priorities began to shift. The media/publishing industry was hit hard by the effects of the pandemic (as were so many other industries), and after my hours and salary were cut in half for more than a year, stress and fear consumed much of my daily life. I had time to reflect and explore opportunities that would take my mind off the state of the world while helping me reach some creative fulfillment. Flowers were my saving grace. Inspired to share the joy of flowers with my fellow Denverites, I started Queen City Floral. Read more>>