One of the first lessons I got from my father was when he told me “if you are not in trouble, you are not accomplishing anything.” This may seem strange advice for a young child to go break the rules, but it turns out that breaking the rules has been a long Tupper family tradition. My grandfather was a “rum runner” during prohibition, smuggling booze across the Canadian-New York border. And my grandmother smuggled herself over that same border, never asking permission to enter the United States, nor ever filing out any paperwork during her 60 years of life in the good old USA.

And my father, while studying in the seminary to become a priest, made a B-line from the realm of religious mythology to an evidence-based career as a university biology professor. He asked critical questions and got fantastical answers, so he packed his bags and went in a different direction than the one being offered by the Catholic Church.

And for me, it wasn’t long after he shared with me his life advice that I was caught in a church with a Sharpie, drawing mustaches on the large oil paintings of former bishops hanging on the walls. During high school and college, I embraced those who couldn’t or wouldn’t fit in and follow the rules. I abandoned my comfortable station in the social hierarchy, and slummed it with the freaks, fags and punks. I jumped in with two feet, and never looked back.

All of this personal background is relevant to you, the reader, because I am not unique, nor alone, in learning that going rogue, and causing trouble can reap huge rewards in a wide range of life’s experiences.

And today, as many of you are leaving the service, it is important to recognize how your veteran skillsets and experiences make you very much the ‘punk rock disruptor’ in the private business sector. You have been imbued with unique attitudes and approaches to accomplishing your business missions, and you have the potential of being the Apex-predator of the private sector. The audacity and fortitude you learned in executing combat missions. The tireless spirit of running 24-hour operations fueled by nothing more than dip and coffee. You executed missions in austere Mad Max conditions, while they worked in air-conditioned high-rise offices.

You are the potential usurper of safe and comfortable business models and theories. And it doesn’t matter if you don’t feel punk rock, or you never looked punk rock, because whether you like it or not, you left the service of Uncle Sam and entered the private sector with all the tools and attitude to be a punk rock sleeper agent, ready to raise hell with a confidence and stamina tested under fire.

If this is starting to sound like just another motivational speech, then you aren’t grasping the importance of what I am saying.

Embrace your inner rogue. Too many gods of war leave military service, put on a tie, and become sheep trying their best to fit into a milk toast private sector environment. I’m here to tell you that going rogue and thinking in a punk rock manner is something customers, markets, and yes even established business bosses WANT.

In my twenty years with Uncle Sam (most in the RC), I never stopped pushing the envelope when I saw the potential of my soldiers being suffocated by wet blanket policies.  I ignored SOPs, and engaged in spirited (and sometimes insubordinate) debates with commanders. When I was wrong, I learned from the lesson, and came back twice as strong the next time.  And when I was right, I didn’t brag or boast, I just let the win speak for itself.

Sure I got a reputation as a trouble maker, and the nickname “Crusader”, and some ass chewings, and even some sore feelings when friendships dissolved over my methods and practices as a result. But I gained the respect of many of my peers and higher ups, who saw that my rebellious ways were rooted in a desire to improve the organization, not destroy it.

Simply put, a rogue streak can be an accelerant to career success and progression. I accomplished things in my career that to this day defy explanation. I was hand selected to take over a rifle company in my Infantry Battalion, even though I was a Medical Service Corps Officer. I remember the awkward day when the Old Man called me to his office. “Lieutenant Tupper, you arrived here, and the Medical Platoon was ate-up. You got it squared away. The training you are doing….(he paused) is irregular (he paused again), but it got the morale of the platoon up, and it’s an impressive turn around for what was a dysfunctional section before you arrived.”

I felt the need to remind the Old Man that I had zero Infantry training nor experience. I was immediately cut off. “Lieutenant, the current crop of leaders in that Company are all Fort Benning trained and MOS qualified, and they are failing miserably. Frankly the Company is out of fucking control. The unit needs a radical make over, and I think you are the one who can do it.”

The fact that this posting of a medical MOS soldier into a combat arms slot **may** have violated a wide range of Army regulations, as well as some little thing called the Geneva Convention, had me excited AF.

I spent about 18 months in command of this rifle company, followed by a yearlong OEF deployment as an Infantry mentor to an Afghan National Army Infantry Company. During this tour, I had my share of gunfights, shot some bad guys, and never lost a man on a mission under my command. When all was said and done, I was awarded the branch of Infantry, and the CIB, yet I never spent a day receiving any formal Infantry diplomas or schooling. Go figure.

Like myself, many of you reading this are now in the post-military phase of your career. It is important to remember that the private sector is even more vulnerable and exploitable to attacks from a rogue mindset.

My quick vignette of this rogue approach from my private sector experience should also help drive this message home. My main business focus today is as a landlord to about 500 university students who live in my properties. While most student landlords approach their job as defenders of their properties against the unwashed youthful hordes, I built my business model on defending, embracing, and supporting student culture and pastimes. I built stages in my attics and basements for their weekend music parties, and put up thousands in annual bar tabs for my tenants. I fund student organizations and community groups who share the same attitude of supporting art and culture and youthful exuberance.

I served on a wide range of boards and committees at the University and in the community, and when the “grown ups” decry the late-night parties and loud music, I am the first to call out their hypocrisy, knowing full well they also partied in their college days, and they turned out just fine.My day to day business operations also buck conventional standards. I ignore professional accountants and advertising agents and consultants, and instead hire my student tenants to do much of the same work for me. They bring new innovative ideas and attitudes that are free of the chains of established business culture. They get valuable real-world work experience to pad their resumes, while I get first crack at new ideas and models. I strengthen my bonds and connections in the student community, and my bottom line benefits because students will happily work for a fraction of what the professionals charge.

This has the secondary effect of a minimal advertising budget (students’ word of mouth fuels my rentals, not paid advertising), as well as a higher degree of respect between landlord and tenant, which tamps down on normal student destructive outbursts and damages to my houses.

If you question whether this approach is really good for my business, the fact is all my houses are rented out a full year in advance, and I’ve never had a vacancy in my twenty plus year business history speaks for itself. While my traditional landlord competitors are regularly in court, being sued by tenants or suing tenants for missing rent or damages or lease violations, I have a jaw dropping, twenty year streak of NEVER having set foot in court for any landlord-tenant dispute. I’ve had over 10,000 tenants, and not once has a disagreement arose to the level of court involvement.

In closing, the message here is simple. The punk rock, rogue approach to life is one that can reap many rewards, especially in place many of you are venturing into for the first time; the private sector. Our marketplace is filled with examples of rogues and punks and nerds destroying established business models, and reaping huge rewards. You don’t need to have a mohawk to kick ass in this regard. You can be a rural kid from Kansas who has lived a conservative, rule-following life to date. But when you leave military service, armed with some very real and very potent rogue skills and tools, you should recognize this and embrace the potential to kick open doors and make your mark in the business community.

Ben Tupper
Ben started his 20-year career as an enlisted medic and ended as an Infantry Officer. The zenith of his misadventures and maladies was a tour with an Embedded Training Team (ETT) in Afghanistan, where he earned his military badges and bobbles, but also cut his teeth as a writer and author. You can find his offerings and appearances on NPR, BBC, Slate, PBS, Fox, or read the long-form of his experiences in his first book Greetings From Afghanistan- Send More Ammo. You may find him checking in on his bar The Beer Belly Deli and Pub in Syracuse NY, where he will happily buy you a round.