I was born into a very comfortable lifestyle, courtesy of my father and grandfather. New Canaan, Connecticut was the bastion of "Old Money" and great Corporate-sponsored wealth...more FORTUNE 100 CEO's than anywhere in this country. To say that I was privileged is a significant understatement.
Of course, being the rebellious child that I was, my behavior continually exacerbated my dear parents and I left home permanently at the age of 17 when I entered into the U.S. Army as an Infantry Soldier. To my complete shock (as well as everyone else's, lol) I excelled in the Military, was Appointed to West Point, attended the United States Military Academy Preparatory School (USMAPS), won a 4 Year ROTC Scholarship (trading in my West Point Appointment) and attended the University of Virgina in Charlottesville, Virginia.
As a First Year student at UVa., I took a 4th Year course called "Entrepreneurship" at the venerable McIntire School of Commerce, aced the class and used my class-prepared business plan to launch my first "official" enterprise on Nantucket Island, Massachusetts. I made so much money (for me, 40 years ago in 1977) that I gave back the remainder (3 years) of my ROTC Scholarship and proceeded to make my fortune in the unlikely field of moped rentals at high-end resorts. I was a multi-millionaire by the age of 22.
Over the next nearly 40 years, I started an estimated 150 businesses, made and lost millions, married having two beautiful daughters, divorced and now have 7 spectacular grandchildren under the age of 3 (both daughters had twins). My married life consisted of making and spending more and more money and when I became divorced 22 years ago, my 3 beautiful homes (Nantucket, Sanibel Island and Boca Grande), exotic cars, businesses, properties and a lifestyle that commanded me to earn $50,000 per month to sustain....were completely gone.
Life should have started the process of simplification for me then but always the rebel, I dusted myself off and proceeded to accelerate my entrepreneurial fever pitch to build back what I had lost and then some. Never having finished my undergraduate degree at UVa., I nevertheless yearned to go to Harvard Business School and in the late 80s reached that goal by being the youngest attendee (29) ever selected (since 1972) in the Owner's and Presidents Management Program (OPM) at Harvard Business School. The same year I started at Harvard, a handful of we intrepid entrepreneurs (including Michael Dell) started the Young Entrepreneurs Organization (YEO), now the largest entrepreneurial organization on the planet. (www.eonetwork.org)
Even though the divorce wiped me out financially, I traveled out West (Arizona) to be near my two little girls and proceeded to re-build my lost empire. Starting off in a cramped bungalow I shared with two of my girlfriends...in 6 months, I was living in what was once Phoenix's largest home, a 1929-built mansion of 12,000' with a 3500' guest house, garages for 8 cars and sitting on the premier 1st hole of what had once been the venerable Phoenix Open for years. (see Linked In photo at top of my profile)
I taught my own version of entrepreneurship ("Ready, Fire, Aim") at ASU's Barrett Honors College as an Adjunct Faculty member, started multiple new ventures and even established the Country's 1st Accredited College of Entrepreneurship at Grand Canyon University...some 10 years ago now.
As an entrepreneur, you often fail more than you win so when I crashed and burned on my last Arizona venture, I headed to Ethiopia where I volunteered as the Entrepreneur-In-Residence for an international NGO and enjoyed a remarkable 6 months there. I may have even stayed if my VISA didn't run out and upon my return to the States, was seduced by the pure luxury of living here rather than in a Third World Nation, as nice as it was.
I moved first to California, then to Las Vegas and after starting yet another new venture in the luxury villa rental space (www.lv4less.com), creating an inventory of unused time and arbitraging the spread of cost vs revenue (I filed a Patent Pending on same), I took a partner and moved back East. I lived in New Hampshire and the Hamptons and when a potential new partner from San Diego beckoned me to visit him about a possible Joint Venture for the villa business...I came out West.
My potential new business partner lived in La Jolla, where I was staying...and as the negotiations stretched out...I simply stayed here. The Village of La Jolla has been my home for two years this Christmas and I can happily say that I have found my final home base. The original villa business has successfully morphed into a significant travel company (www.avia travelservices.com) and I happily started a handful of other businesses like www.hlcostseg.com, www.entcreditcard.com, www.cannabizinsiders.com etc.
Here is where the "Simple Life" comes to bear for me...no more mansions and fancy exotics and $50k per month overhead. I live in a simple place two blocks from the Pacific Ocean, walk everywhere and use Lyft or Uber when I need to. I recently visited with a very helpful Financial Planner and am busy establishing a "sinking fund and insurance policy" to pay for my 7 grandchildren' college educations....all reaching University-age at the same time... in 15 years or so.
My "office" is wherever I can use my laptop and Smartphone while sipping my lattes. I constantly meet new people and have found some rather unique ways to recruit young people to assist in my start-up launches. Life is very good and guess what(?) I do not need or even want the excessive overhead of my past life. I am content to "live simply and to simply live."
I can only hope that my message reaches my fellow entrepreneurs out there constantly struggling and striving for more...before they learn the hard way that life is a lot easier when you are satisfied by what is most important.