Are you thinking about starting a business? If so, we think you’ll enjoy reading about how these seasoned entrepreneurs thought about the question when they were in your shoes.

Curt Howell | Professional Outdoor Educator and Guide

Owning my own business wasn’t really an intentional goal for me. Most of my career has centered on training and mentoring college students in outdoor pursuits programs. Helping students develop as people and learners through various outdoor adventure activities has been my focus for nearly two decades. I’ve enjoy teaching and being part of the university scene on both the campus recreation and the academic side. I started my own guiding company initially as a casual side gig for me to provide a new service in the San Luis Valley (SLV) and keep my own guiding skills up. Plus, selfishly, I thought that I’d better do it before someone else does. I’d been in the SLV for about 8 years at that point and heavily involved in the outdoor recreation scene. The SLV was gaining attention as a tourist destination and has significant potential for guided trips to become more and more of a demand. I thought I’d just do a little rock guiding during the summer and ice in the winter while still on the faculty for Adams State. However, maybe a year after, I was approached with an opportunity to purchase a Mountain Man Rafting. It had been around since 1985 up in Creede and the current owner was ready to let it go. As a climber and paddler, I was intrigued by the chance to expand into the river scene and to build up my own crew of guides. I recognized the benefit of taking over an established river operation and how some of the rafting clientele would likely also want to try out other guided activities. Plus, running a larger guide service would be a way for me to still teach and develop young (and not so young) outdoor professionals. My wife, kids, and I tossed this idea around as we knew that it would likely mean a shift out of higher education. But, it would give me the chance to explore and diversify my skill sets in a way that I couldn’t in my current position. We’re a family that likes a bit of risk and so we decided to go for it. Read more>>

Alec Mastovich | Owner

The idea for The Downhill Dog came during frequent walks in Downtown Breckenridge with our dog, Penny. For years, we were frustrated because there wasn’t a dedicated shop in the heart of town and became motivated to solve this issue. We began looking into the possibility of opening a store and learned that Summit County is a haven for canines with an average of 2 dogs per household locally. We began looking for a storefront convenient to both locals and tourists alike. It was important to launch our concept in a hot spot, yet we knew that finding a place to park is a problem anywhere in town. With our location in Main Street Station, customers have 2 hours of free garage parking! You’ll find us open 6 days a week in-between Teton Gravity Research and LoLo Juice, while only a few steps away from Lululemon. Read more>>

Heidi Nisbett | Artist, Hiker, and Outdoor Enthusiast

After college, I worked a few desk jobs where I had little passion for what I was doing. While I am used to being an overachiever, I found myself mentally checked out and struggling to maintain a strong work ethic. I realized quickly that in order for me to mentally show up for work, it needed to be something I was passionate about. I started making art in my free time, as a side hustle. For a few years, I built up momentum as an artist while working another job full time. Slowly, more opportunities came my way until it seemed like making a living as an artist seemed possible. It was at this point that I took a leap of faith and decided to start my own business as an artist, in the hopes that I could wake up excited about “work” each day. Read more>>

Katie Moore | Founder Of Filosophy

When I first embarked on my sabbatical from the hustle and bustle, stepping away from my career as a family therapist to immerse myself in the vibrant culture of Thailand, I didn’t yet know I was going to start my business. It was the mesmerizing artisan markets in Chiang Mai, a charming city nestled in Northern Thailand, that first got my entrepreneurial curiosity going. But my initial vision was selfishly simple: create a business that would offer me a perpetual passport back to this enchanting city. As I plunged into the unknown, parting with $10,000 to invest in the intriguing handicrafts that caught my eye, I was, admittedly, paddling in the deep end without much business acumen. Questions like who my customer would be, where I would sell the products, or even how to market them, were all a mystery to me. My plan was modest – bring these treasures back home and host a cozy, informal home party for my friends. The overwhelming response was a pleasant surprise and my first hint that I might be onto something special. This led me to set up shop at a local farmers market, a real-time laboratory where I quickly learned the dynamics of demand and supply. My strategy was simple – buy more of what sold, and drop what didn’t. This is how I began, step by step, market by market figuring it all out as I went along. Read more>> 

Mary Quinn | Lower Left Improv co-owner

The thought process behind starting our own business was all about building community around improv. Cindy and I met a few years ago. We both have extensive backgrounds in improv and some how magically ended up in a tiny mountain town together. I was in another improv group holding auditions when Cindy stepped on stage. The moment I saw her play, I knew we would be improv soulmates. Read more>>

Nhi Dang | Nails artist

I’ve worked for multiple traditional salons before, but I always dreamt of building a unique salon studio where talented nail technicians with a passion for nails don’t treat each other as owners or employees, but rather as independent artists building their careers together. Read more>>

Shianne Wright | Life Coach & Mindfulness Guide

I have known ever since I was a teenager that I wanted to work for myself. Having my own coaching business seemed to tick all the boxes; I have always loved supporting people by holding space, asking questions, and encouraging them to keep going. And although I believe that you can make a difference no matter where you are and what you’re doing, my heart was set on creating an impact in a way that allowed me to be free, too– in time, money, and energy. I am one of those people that loves to share what has helped me in my own healing, whether it is through fitness, health, or spirituality. I wanted a way to integrate all of my education and personal experience into something helps others transform their lives, too, from the inside out. Nothing gets me more excited than witnessing someone take their personal power back and begin to feel themselves again. Starting my own business was my way of contributing to the healing of humanity and our planet. Read more>>

Lucía Alonso Garrido | Photographer & Cinematographer

Of course, the road to becoming an independent freelancer is neither linear nor constant, there are many moments of instability particularly at the beginning, when jobs appear in isolation and you don’t always get as much work every month as you need. I think it takes a mix of hard work, consistency and faith, sometimes you need to trust that things will work out as we don’t work with the stability or the guarantees that regular jobs offer. In my opinion, it is important not to doubt yourself in those moments and to keep the focus on the long term to keep going in the most difficult moments. Read more>>

Hannah Norris | Social Entrepreneur & Humanitarian Advocate

The journey to founding Arboretum Coffee is deeply interwoven with my personal and professional experiences, which have shaped my understanding of the complexities surrounding community development and refugee and asylum-seeker resettlement and integration. As a caseworker with The Matthews House, I was at the forefront of addressing the multifaceted needs of individuals striving to navigate their new lives amidst numerous challenges and systems. This role, coupled with my volunteer work at Genesis Coffee in 2021/22, provided a unique perspective on the power of community spaces in fostering connections and supporting personal growth. My academic journey, culminating in a M.A. in Humanitarian and Disaster Leadership from Wheaton College in 2023, equipped me with a deeper insight into the structural challenges faced by refugees and the potential for innovative approaches to promote dignity, equity, and flourishing. This educational background laid the groundwork for envisioning a social enterprise that could transcend traditional aid models. Read more>>

Josué Oquendo Natal | Graphic Designer, Art Director, Creative Director and Illustrator

Originally it started as a means to create income and pay through college, since I started my design practice / business at the same time I was studying in art school, my family was having a though time and it was important for me to be able to sustain economic needs on my own, but also be able to provide support to my family as well. Read more>>

Heath & Alyssa Padgett | Entrepreneurs

We both got office jobs right out of college and were immediately under impressed with the standard adult life of commuting in traffic, sitting in a cubicle, and working all day. I remember sending Heath a pizza to his office and he called me so happy and it was the highlight of his week. That’s kind of when we knew that we wanted to break out and start something of our own that would propel us forward. Read more>>

Danette Munoz Shaifer | Founder & Chief Empowerment Officer

My best friend and husband launched his business in 2016. Observing his transition from a corporate employee to a successful consultant and solopreneur inspired me. However, I didn’t contemplate starting my own venture until pursuing my graduate degree in 2021. During one of my classes, we were tasked with deeply exploring our ideal “That Day” scenario, as if we had a magic wand. This exercise led me to realize that my path involved branching out on my own, leveraging my skills, and pursuing my passions Read more>>

Paul Hields | Entrepreneur, business founder/owner, passionate skier and biker.

The answer to this question is really two fold for me. Long before it became the well known buzz phrase, ‘Work Life Balance’ i was looking for the freedom to be able to work in an industry I was passionate about and to be able manage my own life, my daily, weekly and monthly schedule. To be be responsible for my own actions that really only affected me and my customers and of course with the ultimate objective of becoming financially stable from a business perspective. Needless to say as a business owner, ones responsibilities grew and demands on my time took over and that work life balance got tipped dramatically one way and it became all work and not much life. That said I wouldn’t trade it for anything. Read more>>

Erin Carpenter | Psychedelic Therapist

After working in various mental health settings, I felt ready to move into private practice. This gives me the flexibility I need to meet my client’s needs as well as my own. After encountering therapeutic psychedelic work in my own life, I knew I wanted to add these powerful tools to my toolbox as a therapist. I enjoy building systems, leading teams, and improving my business. As a small business, I can implement changes quickly to improve services. In larger settings like hospitals and mental health centers, there are layers of red tape that get in the way. Read more>>

Claudia Schauffler | Registered Respiratory Therapist and Small Business Owner

I have worked my entire life in non profit health care and when I was reflecting on retirement, I came across and opportunity to purchase a small used clothing store. I have always loved fashion. As an activist for women’s issues the history of fashion is of particular interest to me because it reflects what is/was happening in society at any given time. Read more>>

Teddi Domann | Co-Founder and Chairperson

The Pro Football Camp was started in 2006 by Craig & Teddi Domann, former TE Rich Griffith and Darlene Warmouth, who wanted to give back to the Colorado Springs community. Inspired by business entrepreneur, Steve Bigari ,and his encouragement to “just bring what you got,” they felt like there was a need in the community and they had the skill sets and contacts to run a successful youth football camp. After 213 kids, ages 7 – 14 years old, showed up at camp, they knew they had created something that the Colorado Springs community wanted and needed. Read more>>

Emily Boksenbaum | Leather worker and artist

I have always wanted to make things by hand. Being fully in control of a creative process like that just brings me so much joy. After college I worked for a leather worker who created tooled leather creations for interior design applications. Watching her run her own business as an artist that sold decorative work inspired me to find my own product that I could eventually make into a business for myself. Footwear was a natural fit for me and though I didn’t see many people doing it for a living, I started making shoes by hand. Read more>>

Lisa Avery | Cowgirl & Jewelry Designer

I have been self-employed for many years, as my first venture was breeding American Quarter Horses. My husband and I have bred, raised and trained American Quarter Horses since 1992. I honestly never thought I would be a jewelry designer. One day we were having lunch with friends in Gunnison, Co., and when we came out of the restaurant, I spotted a sign advertising, “Turquoise beads 30% OFF.” I went in and bought a few strands of turquoise, and the materials and tools to string the beads with and came home and made necklaces for all of my friends. I started selling jewelry in a local restaurant, and then I made jewelry as a creative outlet while caring for my father-in-law. It started out small, and I kept buying more beads and sterling with my earnings, and before I knew it, my creative outlet had grown into a business. I started setting up a tent with my jewelry at craft shows, and farmer’s markets, and a few private parties. Then my goal became offering quality gems and sterling at affordable prices. Read more>>

Allison Hayek | Co-Founder of Earthside Birth & Wellness Center

When we started our venture, Cheyenne, WY lacked a quality midwifery care option. My business partner, Sarah, and I each had our own positive out of hospital birth experiences with a home birth midwife – sometimes traveling 1.5 hours each way for prenatal visits! We wanted to bring midwifery care for prenatal, birth, postpartum, and well-woman care to the families of Southeastern Wyoming. We desire to be a hub for maternity, birth, parenting, and wellness in our area. Read more>>

Natalya Khorover | Artist, Educator, Artivist (art+activist)

It was all very gradual. I was a freelancer in my earlier career and always loved having my own schedule, so when I started creating art, selling it and teaching it while being an at-home-mom, I didn’t even realize that I had started my own business initially. But the more work and teaching requests I received, the more I started thinking that there was a business here that I loved. Then I started educating myself about running a small business and fine tuning my offerings and the reasons behind them. Read more>>

Tim Jewell | Tattooer/ Co-owner Heart Tattoo

When we opened Heart Tattoo, the thought process was pretty straight forward. We wanted to open a shop in Sioux Falls, that had all the parts about shops we’ve been to or worked at here in our city. We wanted to create a space that felt like a tattoo shop. I think there is certainly a place in the world for private studios, with white walls, and fine art on the walls, but that isn’t what we wanted to create. We wanted a space where you felt like you were in an old school tattoo shop. Designs all over the walls, music playing, tattooers and clients talking with each other. As one of the owners I wanted to create a space where we can all grow and learn from each other, bounce ideas, and push each other to be better tattooers. Read more>>

Aboud Hemed | Founder of Late Bloomer Brand

Starting my own business was always something I wanted to pursue growing up. My troubles early on we’re figuring what type of business I wanted to start and how I could connect it with something I was genuinely passionate about. Read more>>

Jonathan Betz | Portrait Artist

The start of my professional photography career was with a multi-location portrait studio in St. Louis. I gained valuable insights from this job, not only in my craft and expertise behind the camera, but importantly, watching all the aspects of the client experience in motion. That being said, I have always had an entrepreneurial spirit and knew that I wanted the ability to choose every aspect of my own portrait studio. Shortly after my wife and I married in 2004, we set a timeline to move out West within two years. While I know she already knew that move would launch a portrait business, she wasn’t expecting an invitation to do that together. I’m thankful she accepted that invitation as our unique strengths fill all the essential roles and responsibilities for our studio We wanted our own business for a variety of reasons…we have full control over every aspect of our business; we give our personal touch to everything; we are able to choose our schedule; and we serve our clients from our hearts. We work incredibly hard yet love all the rewards of owning our own business. Read more>>

Sonjay Shrinivas | Physician & Co-Founder of Jettison, MD

I have been a practicing physician for 18 years now. I started my career as a hospitalist. As a hospitalist, I was responsible for taking care of patients at their sickest. I would treat patients who were hospitalized and coordinate their care with other specialists. As they improved and were ready to be discharged, I would also coordinate their care with primary care physicians. I did that for nearly 7 years, and immensely enjoyed helping people get better. It was rewarding to see patients come to the hospital in a very sick condition only to improve enough to get back home to their loved ones in a timely manner. However, as time went by, I started to see the gaps and flaws in our healthcare delivery system. Patients would bounce back to the hospital because they couldn’t get to a pharmacy to pick up the medications that were prescribed to them when they left the hospital. Primary care physicians had a full schedule and couldn’t quickly see a discharged patient for needed follow up. Self-employed patients struggled to make it to appointments during standard business hours, unless they were willing to take time off work. Read more>>

Paula Lowrey | Founder and Owner of Padoca Brazilian Bakery and Market

We both left our corporate Jobs and Paula always wanted to work in the culinary industry. So Paula had the idea to start selling pastries to the Brazilians in Denver. In the beginning she would cook in our house kitchen, fry the pastries in the garage and deliver them herself. Once we got on our feet we decided to get a loan and open in the lovely neighborhood of Mayfair. We live what we do because we are able to bring some Brazil to the Brazilians in Denver who miss their country and we can also show Americans and “gringos” what Brazilian food and culture is like. It’s a win win for everyone. Read more>>

Lucy Yun | Founder of Lucky Lucy Creative Inc.

Starting my own business was a natural progression in my creative journey. It stemmed from a deep-rooted desire to channel my artistic vision and marketing expertise into a platform where I could offer a diverse range of creative services tailored to meet the needs of my clients. The freedom to shape my own creative direction and foster collaborative partnerships was a pivotal motivator in founding Lucky Lucy Creative Inc. Read more>>