This is the Leadership Journey series on the Choosing Leadership Podcast.

I believe we all have a lot to learn from each other’s stories – of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name.

Meet Kurt, a seasoned entrepreneur who embarked on his business journey at the tender age of 13. With a knack for operations and systems thinking, Kurt has been a part of over 60 acquisitions, wearing different hats as an investor, buyer, and seller in the technology space. 

Recently, he wrapped up a three-year stint with the largest real estate company globally, a company that didn’t even exist 15 years ago. In a candid interview, Kurt shares the story of his early LLC ventures prompted by his dad’s wisdom about taxes, leadership lessons learned from letting people fail, and his unconventional approach to sales – emphasizing cold calling and genuine conversations.

Reflecting on his evolution, Kurt delves into his experience scaling a company from $85 million to $1.44 billion, highlighting the common pitfalls in assumptions about hiring key positions. 

He emphasizes the importance of hiring individuals with a bias towards action, strong opinions held loosely, and a belief in healthy conflict. Kurt’s leadership philosophy centers on transparency, acknowledging mistakes, and fostering an environment where micro-contributions are valued as much as major milestones.

In a world dominated by knowledge work, Kurt’s story is a refreshing reminder of the importance of balance and tangible, hands-on pursuits in personal and professional growth.


You can find Kurt Uhlir at the below links

In the interview, Kurt shares

  • “I formed two LLCs at 14, not realizing I was starting a path where I’d learn I’m really good at operations and systems thinking.”
  • “Being part of 60+ acquisitions taught me valuable lessons, sometimes as an investor, sometimes buying, sometimes selling, but always in technology.”
  • “Stepping out of a three-year role with the largest real estate company that didn’t exist 15 years ago was my second hypergrowth experience.”
  • “I started my first business at 13—a lawn care service. Selling was easy; finding others who could understand the business, not so much.”
  • “My dad’s wisdom about taxes was the catalyst for forming an LLC at 14. He watched, shepherded me through, but the problem became my responsibility to solve.”
  • “Leadership, to me, is letting people fail. Not everyone likes it, but it’s a crucial aspect of cultivating growth and innovation.”
  • “Cold calling is my sales mantra. Founders should spend time on it, seeking to understand potential clients and not outsourcing that crucial initial interaction.”
  • “Sales success comes from believing your product isn’t always the best fit. I’ll tell you if we’re not the right match, even if you want to write a check.”
  • “Scaling is my passion. Going zero to one is what founders do, and I love advising and helping in that phase, but day-to-day scaling is my sweet spot.”
  • “Healthy confrontation, strong opinions held loosely, and a bias towards action – traits I seek in my team to foster transparency, growth, and a thriving culture.”