July 16, 2018

An Eye-opening Interview with J. Kale Flagg

J. Kale Flagg

J. Kale Flagg

A native of beautiful Honolulu, Hawaii, J. Kale Flagg dreamed of being a successful businessman since he was a child. J. Kale Flagg’s life and career have taken him all around the globe. From childhood travels thru France, England, Morocco, Cyprus, Israel, Turkey and Greece; to college at Yale University to jobs on Wall Street to working under the bright lights of Las Vegas, J. Kale Flagg has seen and done it all. His outstanding track record in business and his success in his personal and family lives make J. Kale Flagg a true inspiration to anyone seeking to accomplish their own dreams and goals. Recently, Interviewing Experts had the opportunity to spend a few moments talking with J. Kale Flagg about his formula for success.

Interviewing Experts: Why do you think that many people get stuck in their daily lives?

J. Kale Flagg: A lot of people simply do the exact same thing every day, and then they wonder why nothing is changing in their lives. I’ve heard insanity defined as doing the same thing time and time again and expecting new results – I call that a blueprint for failure.

Interviewing Experts: How does that translate into the business world?

J. Kale Flagg: I look at my sales team and employees and I ask them why every person in the world isn’t happy, or why most people aren’t doing their dream jobs. The answer I get is that they want to accomplish those things, but they don’t think they can. There’s an invisible barrier for most people.

Interviewing Experts: How can people break through that barrier?

J. Kale Flagg: Effort. Just go for it! I haven’t met anyone who put forth the tremendous effort it takes to succeed who didn’t end up achieving his or her dream. Sure, success comes easier for some, but at the end of the day, it is getting started followed by consistent pure hard work that separates the mediocre life from the life you dream of.

Interviewing Experts: Why do you think people are afraid to try?

J. Kale Flagg: It’s a fear of failure. It’s a fear of what other people will think or say. Sometimes it’s even a fear of success. For many people, success is an unknown because they’ve never been there before. And fear of the unknown drives people to stay in their comfort zones.

Interviewing Experts: How would you best describe this fear?

J. Kale Flagg: Think of a boat that has been floating in the same spot of water for years. There are better spots all around it, but starting the boat up also starts waves. It makes the ride uncomfortable, and just like in life, that makes many people resistant to moving or making changes.

Interviewing Experts: What is it about “making waves” that scares people?

J. Kale Flagg: Think about it—if you’ve been stuck in a rut for years, your friends and family know you as that person. They may not want you to change. But when you get on a path toward success, you may become a different person, and often times, there is resistance from those who are closest to us.

Interviewing Experts: What sort of parting advice do you wish to leave us with?

J. Kale Flagg: Don’t be afraid of change. Don’t be afraid of hard work. And don’t be afraid to make a few waves. But perhaps most importantly, don’t be afraid of failure—just keep moving, taking action, and striving ahead. In time, your efforts will pay off.


Growing up on the Island of Oahu, Hawaiian native J. Kale Flagg always knew he was destined for a professional career. What he didn’t foresee was that it would be in sales and marketing and eventually real estate. As a General Partner in American Redevelopment Fund, J. Kale Flagg is a respected business leader and well-known driving force behind some of the nation’s best real estate investments – even in a down market.
Early in his career, degree in Economics and Political Sciences from Yale University in hand, J. Kale Flagg worked in the financial markets of Wall Street as a consultant. He eventually tired of the repetitiveness and urban lifestyle and set out to find a new area of interest. What he found was an opportunity to harness a hidden talent – sales. Using a natural ability to teach, J. Kale Flagg created marketing strategies that would catapult both established and start up distribution firms to unparalleled success.
As his need for more challenging prospects grew, J. Kale Flagg expanded his professional portfolio. Today he plays a major role in Stable Development and Array Asset Management, both globally recognized businesses.
J. Kale Flagg is married with four children and resides in Reno, Nevada.

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