Over the last 25 years, Jamie Mackay has worked across various sectors of the real estate market including development, investment, construction, and project management. In 2010 he launched his own real estate development company, Mackay Developments.
Early in his career, Jamie founded Teton Heritage Landscaping in Jackson Hole, Wyoming—a business specializing in the design and development of major land planning, infrastructure, and landscaping for residential & commercial projects throughout the Northern Rockies. By the time he sold THL in the early 2000’s, Jamie had grown his first business into a multi-million dollar company with over 70 employees, overseeing projects worth more than $70MM in total.
After this first success, Jamie became engaged in several different land deals around Jackson Hole that led to larger development and management projects. His primary focus now is in residential real estate developments & entitlements as well as the hospitality industry. A few of his larger projects include Benloch Ranch in Park City, UT, Vogel Hill & Fireside Resort in Jackson Hole, and Wheelhaus—a prefab construction business of modular cabins and homes—based in Salt Lake City, UT.
Throughout these experiences, Jamie has been able to nurture relationships and engage with third parties for ground-up developments from start to finish. In collaboration with countless engineering companies, land surveyors, land planners, contractors, and government officials, Jamie has continued to manage successful projects from start-up and stabilization to exit or sale.
What is your typical day, and how do you make it productive?
I wake up, put my feet on the ground, and lean straight into the day. Most of the day is spent responding quickly, solving problems, and putting out fires so projects keep moving forward.
How do you bring ideas to life?
Ideas only matter if you execute them. I start by understanding the land, the design, and the practical path to build it—then assemble the right team and move the project forward step by step.
What’s one trend that excites you?
Smarter ways of building communities through better design and more efficient construction. When architecture, land, and planning work together well, you can create places people truly value.
What is one habit that helps you be productive?
Build a strong team. I learned the hard way that even great ideas struggle without the right people around you.
What advice would you give your younger self?
Don’t hesitate once you’ve made the decision. Once you cross the Rubicon, you’ve already committed—so buckle up and make sure you have your act together.
Tell us something you believe almost nobody agrees with you on.
Most problems people think are impossible are actually solvable. Persistence and practical thinking go a long way.
What is the one thing you repeatedly do and recommend everyone else do?
Go see the work. You learn more walking a site than sitting in meetings.
When you feel overwhelmed or unfocused, what do you do?
Writing things down and putting ideas on paper helps organize the noise and clarify the path forward. Going outside and taking a walk always helps clear my mind.
What is one strategy that has helped you grow your business or advance in your career?
Start small and build from the ground up. I began with a lawn-mowing company and grew it into a landscaping business with about 80 employees, which taught me how businesses actually operate.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
One of the biggest lessons in business is that early success can be misleading. The real challenge is raising capital—working with banks and investors is often the hardest part of scaling a business.
What is one business idea you’re willing to give away to our readers?
Thoughtfully designed communities connected to nature. When architecture and land work together well, people notice.
What is one piece of software that helps you be productive? How do you use it?
My iPad and pencil. I do most of my early design work there—sketching houses, landscaping layouts, and site ideas before they ever become formal plans.
What is the best $100 you recently spent? What and why?
I bought my girlfriend flowers. I work a lot, and sometimes a simple gesture goes a long way.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
I enjoy history quite a bit. Honestly, I tend to gravitate toward good nonfiction—stories about real people, real events, and how things were actually built or discovered.
What’s a movie or series you recently enjoyed and why?
I still enjoy some of the classics—films like Gladiator and The Hunt for Red October. They’re oldies but goodies and stories about leadership, strategy, and conviction.
Key Learnings
- Execution separates entrepreneurs from idea generators; ideas only matter when someone commits to building them.
- Innovation often brings resistance; leaders should expect challenges and keep moving forward.
- Strong teams are essential to turning ideas into successful ventures.
- Raising capital and working with financial institutions is often the most difficult part of scaling a business.
- The mindset of exploration—crossing the Rubicon despite uncertainty—often defines successful builders and innovators.