We had the good fortune of connecting with Jessica Charlesworth and we’ve shared our conversation below.

Hi Jessica, can you walk us through the thought-process of starting your business?
It started as a dream during Covid. I imagined a shared piece of land with my closest friends, each of us in our own tiny home, with a pocket park, a lazy river, and space to connect without giving up privacy. After so much disconnection, I wanted to feel rooted again, in community, in nature, and in a life we define for ourselves.

That vision lingered. But it wasn’t just nostalgia…it was a blueprint.

At the same time, I noticed the conversations I was having with my friends (especially women) kept circling the same themes: Where will our parents live as they age? How do we help our adult kids afford housing in this insane market? I started paying attention.

Then the laws in Colorado began to shift. Cities were becoming more ADU-friendly. The regulatory environment was opening up. And suddenly, the dream wasn’t just personal, it was practical. There was a real opportunity to help people solve very real problems with creative, legal, and scalable solutions.

That’s when Rocky Mountain Tiny Homes was born. I used my background in corporate sales to build a company that guides people through the complexity of zoning, permitting, and construction, but with heart. We’re not just building structures; we’re offering freedom and flexibility. For families navigating elder care. For young adults priced out of the market. For property owners looking to add value.

People need alternatives. We’re one of them – and we’re proud to be part of the solution.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I never really felt like I fit the corporate mold, though I spent years trying. I worked hard, showed up early, stayed late, hit the numbers, played the game. I wanted to feel like I was adding value, like I was part of something meaningful. But when you get laid off after doing what you truly believe is your best work, it cuts deep. It shakes your sense of worth and forces you to ask some hard questions.

The hardest part isn’t the layoff. It’s the slow erosion that happens before it. The micro-lies you tell yourself to stay compliant. The quiet compromises. The feeling that who you are isn’t quite right, but if you could just tweak this one thing about your personality, you might be “a better fit.” That kind of culture chips away at your soul.

That’s why Rocky Mountain Tiny Homes means so much to me. It’s not just a business. It’s a place where I can finally do things on my own terms, where I get to lead with authenticity, build something real, and give back to my employees, family, friends, and community in a way that actually matters.

The road here wasn’t easy. I’ve overcome most challenges the only way I know how: with wildly inappropriate humor, and the support of the people who know me best. I’ve learned that the parts of you that don’t “fit” in traditional environments aren’t flaws. They’re clues. They’re signals. They’re your superpowers. And when you finally stop trying to contort yourself to fit in, you start building something worth belonging to.

What I want people to know about me and this company is simple: We’re not here to follow the rules. We’re here to rewrite them, to offer alternatives, to serve with heart, and to make space for the kind of freedom and connection most people are quietly craving. That’s the work. And I wouldn’t trade it for anything.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
Favorite Spots in the City (and Beyond)

If my best friend were visiting, we wouldn’t just stay in the city, we’d take the ultimate Colorado road trip. It’s all about mixing nature, music, food, and connection. Here’s how the week would go:

Denver
We’d kick things off in Denver with a night at Red Rocks- because there’s no better way to set the tone than live music under the stars. Post-show, we’d head to a laid-back patio like Lowry Beer Garden or grab a bite at Illegal Pete’s for that perfect combo of music, margaritas, and conversation.

Fort Collins
Next up: Fort Collins for a casual beer tour. The downtown area is walkable, fun, and packed with great breweries: Odell, New Belgium, and more. It’s got that college-town energy but with grown-up vibes.

Glenwood Springs + Palisade
We’d head west and stop in Glenwood Springs for some downtown shopping and people-watching, then continue on to Palisade for a vineyard bike tour. Nothing beats sipping local wine in the middle of peach country. We’d hit Clark & Co Distillery, Peach Street Distillers, and grab a peach ice cream at McLean Farms.

Grand Junction
In Grand Junction, we’d stroll down Main Street, explore local shops, and treat ourselves to dinner at The Winery or The Ale House (but let’s be honest- it’ll always be Gladstone’s in my heart). We’d cap it off with a scenic drive or hike through the Colorado National Monument or up on the Grand Mesa – nature’s version of therapy.

Telluride
Finally, we’d head to Telluride for those jaw-dropping views that make you question why you live anywhere else. Whether it’s a hike, gondola ride, or just relaxing with coffee in town, Telluride is the exhale at the end of the trip.

The whole week would be about reconnecting with nature, with each other, and with the good stuff: family, friends, great music, and a chill vibe that reminds you what really matters.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
This journey has been shaped by an incredible community.

To my friends who inspired the original vision of shared living spaces, your love of connection helped plant the seed. To my family, thank you for standing by me as I left corporate life to build something meaningful from the ground up. And to my kids, thank you for supporting me while I make bold, brave choices. Everything I’m building is part of the legacy I want to leave for you. You’re the reason I push forward, even on the hard days.

To the mentors and professionals who helped me translate a dream into a business, your guidance made the impossible feel manageable.

A special shoutout to Crossroads Montbello, and its fearless leader Monique Penner, for being a force of good in our community. The work Monique does alongside the incredible volunteers who show up every day to support the kids in our neighboring community is nothing short of transformational. Their dedication to lifting up others inspires me constantly and challenges me to lead with the same heart and purpose.

And finally, to the women I serve – those navigating the complexity of caring for aging parents, supporting adult children, or simply trying to find a sustainable housing solution in a tough market, you are my why. Rocky Mountain Tiny Homes exists because I see you. I’ve been you. And I want to build for you.

Website: https://www.rockymtntinyhomes.com

Instagram: https://www.instagram.com/rockymountaintinyhomes/

Linkedin: https://www.linkedin.com/company/105047366/admin/dashboard/

Facebook: https://www.facebook.com/rockymountaintinyhomes/

Nominate Someone: ShoutoutColorado is built on recommendations and shoutouts from the community; it’s how we uncover hidden gems, so if you or someone you know deserves recognition please let us know here.