International Insights: Kris Singleton

   Photo courtesy of Paul VanHelden

 Photo courtesy of Paul VanHelden

I've known Kris Singleton for over 10 years and am honored to call him friend. Kris has been schooling me in life for a long time. Kris is all about family and has had the opportunity to travel all over the world.

Kris is incredibly smart and surprises me with the insight he has on so many different subjects. Kris has been my sounding board to many projects and advice in general.

Kris can tell a story. If you ever have the fortunate opportunity to listen to him in person, you'll be in for a treat.


Name:  Kris E. Singleton, Sr.

Originally From: Nantucket, MA

Currently In: Tucson, AZ

Occupation: Senior Executive - Defense Contracting, Investor, Veteran


Increase Freedom (IF) - Tell me about yourself:

Kris Singleton - I began my career in the U.S. Army, working across several disciplines in tactical and strategic capacities.  After nearly a decade on Active Duty, I transitioned out of the military and began my path to Wealth, Health and Happiness.  I currently serve as a senior executive for a small Defense Contracting firm, own two small businesses and am in the early stages of building my personal real estate portfolio.


IF - What’s the most fun you’ve ever had?

Kris - The most fun I’ve ever had was spread across the three years I lived in Germany.  As a young enlisted man, I didn’t have many responsibilities that extended past the duty day, so my nights and weekends were full of cuisine of various cultures, impromptu international outings and a variety of alcoholic adventures.  I think the value of actually living abroad during the early adult years is immeasurable and I would encourage parents of young children to begin traveling them as early as possible.


IF - What’s the last movie you saw?

Kris - The Accountant.  Awesome!


IF - What’s the one activity or hobby would you do all the time if money didn’t exist?

Kris - Traveling (First Class of course) to any location with history, deluxe accommodations and fishing or golf.


IF - What do you think about when you’re in the shower?

Kris - My net worth, inspirational talks I’ll have with my son when he’s older, and Accounts Receivable.


IF - What’s your biggest life goal?

Kris - Build a Personal/Professional portfolio, that continually adds to my wealth, health and happiness, regardless of my location or attention, and is worth gifting to my son.


IF - Name your top 3 Bucketlist items:

1. Have something monumentally positive named after me, without asking for it.

2. Ride a bull.

3. Write a book that people not only read, but love!


IF - You win two plane tickets to go anywhere in the world, where do you go and who do you take?

Kris - I would take my son to Turkey.  I meant it when I said it’s important to travel your children early on.  I cannot think of many places with such a high concentration of cultural, religious, and natural treasures, that are not limited to just one demographic.  Plus the food is awesome!


IF - What’s something almost no one knows about you?

Kris - I am deathly allergic to cats!


IF - You’re stranded on an island and you don’t know if you’ll get rescued. You find a box with 2 books in it, what two books do you hope to find in the package and why?

Kris - A book on desert island survival and a book of crosswords (have to keep the mind sharp).


IF - Describe your perfect day, from the moment you wake up to the moment you fall asleep:

Kris - I don’t share this one.  Not that it’s too personal; it’s still a work-in-progress and right now I’m enjoying it too much to share.


IF - What’s your favorite travel memory?

Kris - Either Lane Belone’s first trip to ACK with me (3 hours in security at Heathrow, fake IDs, Jaegermeister girls, Lip Synch Battles, and Coronas on Nobadeer Beach) or Pat Consadine’s bachelor party (MA - CT - RI, a stripper named Diamond, Four Locos, Stoli Orange and blacking out only to win $2,000 from $10 in Roulette.) [IF: Indeed this was one of my favorite trips. Nonstop fun as a young fellow. Wouldn't trade those memories for anything...]


IF - What food dish would you travel for?

Kris - I would travel all the way to Boston, MA for some good Roti from Ali’s.


IF - Favorite travel accessory: 

KrisDowny Wrinkle Release.  It really works!


IF - What was your favorite song when you were 16?

Kris - That was a good year…but, “I’m sorry Ms. Jackson, Oooh”. [IF: Classic song!]


IF - What was going on in your head when you chose your occupation?

Kris - I can figure that out.


IF - You find a magic lamp, what are your first 2 wishes?

1. More wishes…just kidding, we all remember Aladdin, it doesn’t work like that. To live in my current body, with absolute health and wellness, until the age of 100.

2. The power of mind control.


IF - What’s something funny that you almost peed your pants?

Kris - A colleague of mine, Mike LaVallee, told me a joke in D.C. last week about a golf ball and a sand wedge.  Call him and he’ll tell you, his number is….just kidding, Mike.


IF - When traveling, what do you miss the most from home?

Kris - Sleep.


IF - If you could be any animal, what would it be and why?

Kris - A Triple Crown Thoroughbred. Good looking, young, fame and glory, massages every day and the stud fees. “You mean I get paid to…” [IF: Hahaha]


IF - What is your favorite travel app?

Kris - Expensify.


IF - What is the best life advice you would like to share with people?

Kris - Drink more in bars.  The vast majority of meaningful and powerful connections I’ve made as a professional or as a man, have been forged or fortified atop the stools of a tavern.


IF - What is the best travel advice you would like to share with people?

Kris - Build in an extra day on both sides of the flights if you can.  It seems excessive (four days), but if you have a day off to pack and run around town to find those travel-sized toiletries, plus a day to get acclimated and maybe sightsee, you’ll feel much more prepared to do whatever you’re in town for.  Then, on the other end of the trip, give yourself a flex day to see that museum you missed, or fit in one more meeting, or just recover from Nelson’s heavy hand at The Occidental. The last day, when I get home, I usually tackle laundry/dry cleaning, catch up on all of the emails I pushed off for when I got home and try to get reacquainted with the time zone (sleep).


IF - What world problem would you like solved right now?

Kris - Safety for the common folk.  All the people that wish to do harm to one another should go to Antarctica and duke it out. Leave all the normal people out of it you whack jobs!

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