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.

Heather and Steven Cole Hughes | Co-founders & Co-Producers, Gunnison Valley Theatre Festival

We’ve both always dreamed of having our own theatre company, deciding to actually try and make that dream a reality on the heels of a pandemic felt like both the best and worst timing ever, but we decided to lean into the reasons why it felt like a good idea. Stories and storytelling are life lines for people in the best of times, so when things are hard they become that much more crucial. The evidence of that was clear when the pandemic took hold and all anyone was talking about was being nervous and what they were watching on Netflix. Theatre-making was paralyzed for all of the obvious reasons, but the second we thought of a way to do it safely, we ran with it. Read more>>

Alexandra Franzen | Co-founder of Get It Done, a company that offers writing, editing, publishing, and marketing services

When I became self-employed, 11 years ago, I didn’t have a specific business plan. I just knew, “I don’t want to work in a cubicle anymore. I need to get out of this stuffy beige box! I’ve got to figure out another way to earn a living.” I wanted more freedom, more control over my time, more income potential, and a workspace with less fluorescent lighting. Those were the motivating factors, back then. I asked myself, “What’s something I could do that would generate money? What’s a skill I’ve got that somebody would be willing to pay for?” The first thing that came to mind was: “writing skills.” Read more>>

Alyssa Karrasch | Mom/Owner/CEO of Linden Lane Boutique

The idea behind Linden Lane Boutique was to bring the fun back to shopping during the pandemic. One of the things I missed most last year was going out shopping, browsing and discovering beautiful things. Ordering online is convenient but its just not as much fun as browsing in a store and having someone help you pick out super special things. What I set out to do was to create a space that is just as much fun as going out to your favorite boutique; we bring the fun [online] to our customers with detailed product reviews, social channels and curated assortments. I want people to smile when you shop Linden Lane Boutique and maybe even giggle at a few items in the shop – that’s ok! It’s how we connect and make shopping fun again. Read more>>

Amanda Doherty | SEO & Marketing Strategist

As an experienced copywriter, I learned early on that brands who appear first in the Google search results are not necessarily the best in the business — they’re the most effective marketers. And this is by no means a criticism of these brands. They’re playing the game and they’re playing it well. Unfortunately, the effectiveness of a marketing strategy is often directly correlated to the size of the marketing budget which means thousands of hidden gems remain unseen. Read more>>

Dan Grim | Cannabis Beverage Maker

As I’ve grown older, I’ve become more acutely aware of what role my work plays in the greater environment. After years of offering products or services through my sales career that directly benefited large corporations, I really wanted to offer something that helped everyday people. That in combination with a sense of adventure lead me to cannabis. I went to a convention for cannabis professionals in 2015 with no experience in the industry looking for a new opportunity. I spent three days walking the expo floor, learning the business models, and talking to anyone that would engage me. When I was done I had three clear takeaways. Read more>>

Joel Tyson | Commercial Real Estate Photographer

I have a bit of a two-fold answer to this question. The first and most basic was to do it all and see what sticks! When I first started doing photography as a side hustle, my thought was, “I’ll photograph anything!” It’s hard enough to start and build a successful business, why limit myself to a certain niche? So I took every opportunity, studied and practiced hard and built things up. This helped me learn new and different techniques as well as learn what I enjoyed and more importantly, what I did not. Special shout out to all those photogs that work with children and family photos…. they have a grace and patience that I do not. Read more>>

Jessica Patterson | Inventor + Entrepreneur

When I created Jeanie Clip, I didn’t set out to create a business, but I wanted to solve a problem for people. I kept finding these tiny little holes in my shirts which meant throwing them away because shirts with holes in them don’t get donated, they end up in landfills. The “holey shirt” problem was so frustrating for me and when I found out so many others had the same problem, I wanted to find a solution! Jeanie Clip is the only patented solution to preventing holes in shirts. The demand for a product to solve this problem is the reason I created a business out of it. Read more>>

THC Samuel | Professional Photographer and Entrepreneur

I have always wanted to work for myself. When I started MHPC Media back in 2016 I had just finished with a company that treated it’s employees terribly and I decided that it was a great time in my life to give it a go at my first business. If it didn’t end up working out, there would always be another “job” out there but the chance to start something for myself and work in an industry that I love doing work that I love is something I could not let slip, so I started MHPC Media and it was the best choice of my life. Read more>>

Grace G. | Fashion Blogger & Student

I started my fashion blog in 2016 between my sophomore and junior years of high school. I used to get home from class every day and excitedly sit down at the kitchen table so I could catch up on my favorite fashion bloggers’ posts. I loved seeing their style and reading about their glamorous lives, but I quickly realized the clothing items they shared weren’t always affordable or practical for a high schooler like me. Sure, I loved their tulle skirts and neon heels, but I would never wear something like that to a regular day of classes. I finally thought to myself, “Heck, I should start a blog, too!”, so I purchased a domain name and set out to provide the everyday outfit inspiration I was missing from my favorite fashion bloggers. Read more>>

Wendy Beltran | Cake Stylist

I remember that when I started to cook, I only had one mold for pound cakes, I had no idea where to start on what was needed to start baking cakes or how to get organized, I just knew I wanted to do it. My apartment was very tiny and I didn’t have much space to work, I used to mix everything by hand and the buttercream I had to puff with a manual mixer, it was very challenging, exhausting and took way too long, but I was determined to make it work, so I started to save money to buy the tools I thought were needed. Read more>>

Abbie Blossom and Afton Neal N/A | Wedding Industry Professionals & Gift Makers

Abbie and I are both in the wedding industry in our own businesses and decided to do something that combines something we both enjoy doing, giving gifts! Abbie is a wedding planner and I (Afton) own a bridal shop in Western Colorado. As we started working with each other more, we realized that we both enjoyed the relationships you make in this industry and also in life. We value that connection and are always wanting to show people that we care or are thinking of them. The more we learned that not everyone knows how to put gifts together, has the time to put gifts together or maybe has a short deadline, we thought there would be a need for it in our community. While we both thought it may be used in the wedding industry we really felt the every day “thinking of you” or “congratulations” gifts would be the focus. Read more>>

Mike Gentile | Overland Gear & Supply Shop Owner

The overland and vehicle accessory market has experienced massive growth, A majority of the products are expensive and the only p[ace to see them other than online is at a semi annual overland expo on thee East & West coast. Meaning, unless you live in one of the two show regions, seeing these products are nearly impossible. With the price tags high and interest levels growing, we wanted to create a place for consumers to shop these items in person and allow for an experience that encouraged folks to climb inside, compare and contrast. With so many manufacturers and multiple styles to choose from, our goal was to minimize decision fatigue. Read more>>

Lisa Cosme | Hair Stylist and owner of Studio 5280

When I was 17 in high school I had created a vision board of where I would be in 10 years. Here is where I made the goal of opening my own salon within that timeframe. I’ve always had a passion for hair and the beauty industry. When I first started I gave out free hair cuts as I was learning the trade. Now I am so thankful to all my clients that I book out 6 months in advance. Read more>>

Dave Spates | Hiking Photographer and Videographer

I’ve always loved the outdoors. Hiking in nature, mountains, the middle of nowhere is so rewarding in itself. Recording this via photos and video is something I’ve always liked to do. Now it’s something I can do and get paid for it. Although it’s not enough to make a full time living off of yet, it’s nice to know I get a little bit of extra income from it. Getting paid to do what you love is life. Read more>>

Heather Jackson | Wedding, Elopement & Couples Photographer

Really I just wanted a career that didn’t make me miserable. I had a slew of corporate and service jobs from 15-24, alongside a seasonal outdoor sports photography gig starting at 19, and none of them quite seemed to fit the bill. I was either bored, stressed out, or just totally uninterested in the job I was doing. Then around 24 some of my friends started getting engaged, and asked me to shoot for them. One thing kept leading to another and I realized I was happy doing this couples and wedding photography thing. Like really content and grateful. So I kept chasing it, harder very year. Now I make my own schedule, shoot 50+ weddings and elopements a year, and the momentum seems to keep coming. Read more>>

Rex Buchanan | DJ / Producer / Teacher / Entrepreneur

I started Discosapien to bring the joy of music, dancing, singing and entertainment to my life and to the events of my clients. There is no better feeling than working for yourself, so when my pops offered to help me out with my first set of speakers to get my DJ business going I gratefully accepted and the rest is history! Today our team performs at multiple events every weekend throughout the year at weddings, corporate events, photo booth events, nightclubs, festivals and beyond. Couldn’t ask for a more fun profession and it was well worth the effort of getting it going over a decade ago. Read more>>

Leanne Alaman | International Thought Leader, Inclusive Leadership Coach, Certified Reiki Master

My business grew out of a commitment I made to myself at age 8. I promised myself I would take responsibility for healing racism. I was not sure how to do that. But I wanted to live in that world, so I kept adding what was missing to bring it forth. In my 20s, I noticed that education and awareness were missing. So, I got trained to facilitate workshops on antiracism and anti-oppression and guide people to impactful insights. Read more>>

Carrie Wingfield | Branding Strategist & Entrepreneur

Having THE WORST boss in my entire adult career transformed me into the female empowered entrepreneur I am today. Never in a million years would I have thought anyone, let alone my boss, would tell me that I was a dime a dozen, that as a creative I could be replaced in a heartbeat, that I would never amount to anything without his approval, and that he would “forgive me” for taking leadership action in the company without his permission first. This man, whom mind you had zero experience in marketing got the VP of Marketing role because he knew the CEO, would sit me in his office for hours trying to convince me to quit and that I was worthless without him. But I was no quitter and I wanted to prove to everyone I was worthy of being on the team. Read more>>

Amber Ryan | Movement Facilitator + DJ

Freedom is very important to me; creative freedom, the freedom to make decisions that feel in full alignment with who I am. My business is first and foremost a community, so alignment is foundational. Kate Shela, my partner in The 360 Emergence, and I are very much aligned. Our alignment, our similar ways and our unique ways in the creative process is in part how The 360 emerged. Read more>>