
Today Ted speaks with Kenny Anderson of Highland Custom Homes.
With over 20 years of experience in the real estate space, Kenny made the foray into home building just after the 2008 Recession when he met a custom builder known for their quality craftsmanship but had lacked in the marketing department. That company was Highland Custom Homes.
Kenny, along with his business partner Matt Yates, offered to collaborate with Highland and offer their expertise. In 2016, the two bought out their original partner, giving Kenny and Matt 50/50 ownership of the firm.

Listen in as Kenny does a deep dive into what drives him as a business owner in the real estate world. He speaks on his core values, decision-making framework, and how he balances an incredibly busy schedule and time with the family.
He then gives his thoughts on the future of home building and how company owners and those in the trades can adapt to changes in technology and consumer trends.
Topics Discussed
- [02:33] Kenny’s background and how he got involved with Highland Custom Homes
- [05:53] Overcoming rejection
- [06:57] Highland Custom Homes’s core values
- [08:00] Kenny’s ventures outside of Highland Custom Homes
- [09:27] Why Kenny loves real estate
- [10:37] What Kenny is most excited about right now
- [12:05] How Kenny makes big decisions
- [13:15] Achieving work-life integration
- [14:55] Kenny’s advice to young entrepreneurs
- [15:12] Why Kenny loves travel
- [17:24] The most special thing about being in Park City
- [19:21] Building in the valley versus building in Park City
- [20:32] Changes in technology for home builders
- [22:03] Architects that inspire Kenny
- [23:23] Kenny’s predictions about the market and supply chain for the next three years
- [26:24] Qualities that Kenny looks for in trade partners
- [27:19] The next stage for Kenny
- [27:50] Kenny on how anyone can live the American Dream
- [31:20] What Kenny learned about success from interviewing countless leaders
Connect with Highland Custom Homes
Key Quotes from Episode
- It doesn’t matter the industry—excellence is excellence.
- Something that looks great today has got to be timeless. It’s got to work 10, 15, ideally 20 years from now if possible.
- As interior designers, we are very focused on the nuance of the human appeal of all the textures and tactile layers that go into the interiors that we work on. Architects are more interested in the form and the shape of the house.
- Being an intern is probably one of the best things a young person can do to really understand if they want to be in the industry.
Connect with the industry’s best tradespeople in your area.