Daily Inspiration: Meet Jake Freedle

Today we’d like to introduce you to Jake Freedle

Jake, we appreciate you taking the time to share your story with us today. Where does your story begin?
When I was 24 years old, I found myself between roommates, living in my father’s basement. At the time, I was a massage therapist, questioning my purpose—a quest that had lasted about 24 years. My dad, a real estate agent with over 20 years of experience, kept telling me, “Jake, you should get your real estate license. You’d make a great living!”

One day, I responded, “Daaaadduhh… I don’t want to make a living; I want to make a difference.”
He shot back, “You millennials are so messed up. How are you going to make a difference from my basement?”

He had a point. Dumbfounded by the truth bomb he had just dropped, I started giving it some real thought. I decided to take the summer as a sort of final, “I’m young, free, broke, and confused” vision quest. The question at hand: Should I get my real estate license and join my father, or go back to college to figure things out there?

The three-month journey would include spending time with family, traveling the country by car, working at my favorite summer camp, and supporting kids in the greater Philadelphia area. What surprised me was how little of this journey it took to find my answer.

My first stop was Abilene, Texas. I stayed with family, and my aunt worked as a social worker. The family lived in a house owned by a charitable foundation, and her job was to live there and provide support to the neighborhood. The whole family was involved. It was one of the coolest things I’ve ever witnessed—to see the impact they were making on the community and the reciprocal impact it was having on their family.

The answer seemed obvious: Should I go back to school, take on even more debt, and spend another 4-5 years navel-gazing? Or should I get my real estate license and figure out how to make a difference in my own community?

Twelve years later, I love real estate more than ever. As a husband and father of two sweet girls, I’ve found my purpose. And as a citizen of my beautiful community, I’ve discovered my role in making a difference.

I see my job as a form of ministry. I often find myself sitting at kitchen tables with families where no social worker, priest, rabbi, counselor, or therapist will ever sit. I help clients navigate difficult transitions that often involve the largest investments of their lives.

In my spare time, I run men’s groups, supporting men to become more conscious, caring members of their families and communities. I host a podcast about my hometown, featuring community leaders, business owners, and interesting neighbors. Attached to the podcast is what we call the HRtbeat Project—an initiative to connect families in Highlands Ranch and bring more support and joy to parenting and community life. Additionally, I get to “vote with my dollar,” supporting causes nearest and dearest to my heart.

I love my job, my clients, and my community. I feel incredibly fortunate to have found my calling.

Speaking of calling… I can hear those two little girls needing me now!

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Getting started in real estate is a unique challenge. You have to find a way to be constantly available to clients—even when you’re not yet making any money in real estate.

At first, I was wrapping up my career as a massage therapist, keeping the lights on while calling everyone I knew to tell them I had started in real estate. Newsflash: when you’re 25 and broke, so are most of the people you know. For the first two years, I went months without a deal, scraping by on my massage therapist wages.

Eventually, I had to burn the bridge. I quit massage therapy and fully committed to real estate. When I had an occasional closing, I’d pay my bills, chip away at my credit card debt, and keep hunting for business. But then the credit card balances would creep back up, the pressure would build, and—just in time—I’d have another closing. It was a constant cycle of paying down debt and holding on until the next deal.

By my third year, things had changed. I was steady, stable, and comfortably closing 25+ deals a year.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
It may not sound like art in the traditional sense, but I am a gatherer and facilitator of men’s groups. Men’s work is a unique and profoundly important endeavor. In a world where writers are describing an “epidemic of loneliness” among men, bringing the guys together to share their victories, struggles, and lives has never been more crucial.

I’m part of a group called Man UNcivilized, where our mission is to end the suffering in men and the suffering caused by men. I host a monthly gathering and organize several other events throughout the year, creating spaces where men can connect, grow, and support one another.

In addition, last summer, I started a podcast called HRtbeat: The Highlands Ranch Podcast. The podcast features interviews with community leaders, business owners, and interesting neighbors, highlighting the people who make Highlands Ranch a special place. Paired with the podcast is Project HRtbeat, an initiative aimed at bringing neighbors together and fostering deeper connections within the Highlands Ranch community.

What do you like best about our city? What do you like least?
Denver has been my home for my entire life. As a little boy, I remember driving up I-25 where it crosses Broadway and seeing that breathtaking view of the city and the mountains. I would always think, “This place is amazing! Why don’t more people live here?” In hindsight, I think I jinxed it—sorry, fellow natives.

What I love about Denver is how business-friendly it is. There’s a long tradition of keeping taxes manageable and fostering entrepreneurship. Of course, people come for the mountains and the sunshine, but what makes Denver truly special is its thriving metropolis, brimming with potential. Denver is a city of opportunity for so many, and I’m proud to call it home.

That said, it’s heartbreaking to see the growing population of unhoused individuals. I’d love to see Denver take a leadership role in helping people overcome challenges like mental health struggles, addiction, and economic hardship. With so many innovators and resources in this city, I believe we can—and should—do better.

Contact Info:

• Website: https://gofreedle.com
• Instagram: https://www.instagram.com/freedlerealestate/
• Facebook: https://www.facebook.com/freedlefamilyrealestate
• Youtube: https://www.youtube.com/@HighlandsRanchRealEstate