My Story

My parents split when I was five. Me and my sister were raised by our single mother in  Wisconsin, who worked multiple jobs to make ends meet. My first job, when I was ten, was helping her deliver the Star Tribune newspaper out of our rickety old Mazda. We’d get up at 4:00 a.m. because the car took about thirty minutes to heat up. Half the time, it still didn’t. She’d always make her tea with two teabags. I always thought that was standard until I moved to England for a couple years in my early thirties. 

Back then, kids had to buy lunch tickets to get their meals. I remember one time, while waiting in line to get mine, I turned to the other kids and said, 'Watch this—I bet I can get mine for free.’ They were stunned when I actually pulled it off. When I got older, they were less impressed. 

One year, my mom was so embarrassed when the PTA gave her a care package full of clothes because all my jeans had holes, but this was more because I cut ‘em myself to emulate the hair spray rock bands, like Poison and Motley Crue, that I loved so much :) Around that time, I remember asking my mom, “Are we poor?” To which she replied, “Nope, we’re rich in love.” Sounds kinda cheesy maybe, but that has always stuck with me. 

My second job was at fourteen, helping my dad roof houses in the South during the summers. It was back-breaking work in the Georgia heat, and my dad, a Vietnam vet and former drill sergeant, was no easy boss. He finally let up on me one day, after I nearly passed out on top of the roof. 

Each morning, before heading to the job site, we’d stop by Home Depot to hire one or two undocumented workers for the day. My heart would absolutely drop on those mornings when we showed up a little late and the lot was empty. I remember one day tearing off shingles with a short, hunched-over man in his 50s who looked more like 60+. He worked circles around me. Looking at his frail, sunburnt body, I couldn’t understand how he did it. I’d take five water breaks in one hour. He took none.

For lunch we’d all sit out by the van eating Burger King while my dad tried out his broken Spanish. Dad would tell me, “A lot of the guys don’t even buy ‘em lunch. I usually give ‘em a good tip too.” And I believe it—every time we brought them food, they looked surprised. And though they were always very quiet and kept their head down, I remember seeing big smiles whenever dad butchered his Spanish. 

I can’t help but wonder why anyone would disparage these kind-hearted souls, doing the work that many Americans would never consider. When I think of them, I’m reminded of my mom once telling me about a time she ran into a Jamaican man living on the street. She thought he might’ve been an angel (kinda crazy, I know lol), and said to me, “you never know…” But I really do believe that how we treat those facing hardships in life might be small tests from above, or rather, opportunities.

When I got back to Wisconsin, I’d tell my friends about all these adventures and how fun it was staying with my Dad on the camp grounds all summer. They’d laugh and call me “trailer trash”, which I thought was not only mean but inaccurate: we stayed in a camper. But I guess that just doesn’t have the same gravitas without the alliteration ;) 

Throughout high school I worked full-time—first as a dishwasher, then as a cook. I’d help out with bills and paid for my own braces, but I didn’t mind working; in fact, I loved it. Sophomore year, after getting my driver’s license, I started skipping school a lot, along with drinking and smoking weed. My grades nose-dived to full F’s, and it wasn’t long before I found myself in a pre-expulsion hearing. It was seeing my mom cry in front of the administration at that meeting that made me realize I had to make a change. So, I moved down to Georgia for my senior year of high school. 

Adjusting to the South was tough, but with no friends, no time (I had to take full night school), and an Army drill Sergeant on my ass, I managed to graduate on time. With a 2.4 GPA and no money, college was off the table, so I enlisted in the Navy. I chose the Navy ‘cause of their Nuclear program and ‘cause the Army sucks: Go Navy! ;)

The Nuclear program was a great deal: you get paid to go to school, earn college credits, and serve your country. Although I was rejected twice at first, it was because of this program—and a Senior Chief career counselor who cared—that I was finally accepted to the Naval Academy Preparatory School (NAPS) in Newport, Rhode Island. I’d go on to Annapolis where I boxed on the club team and earned my BS in Quantitative Economics. 

In 2006, I moved to Virginia Beach and served on the USS Gunston Hall as a Surface Warfare Officer. From there, I went to minesweepers before transferring to my shore command at Navy Information Operations Command at Ft. Meade, right across from our treasured spy agency, the National Security Agency (NSA). After my contract was up, I transition to the Ready Reserves so as to attend college at the University of Oxford where I earned my MBA.  

I made Lieutenant Commander before transferring to the Inactive Ready Reserve to pursue my own startup ventures. Over six years, I launched three companies, investing everything I had into each. All of them failed. The last one—a charity-based dating app—was valued at $3 million before COVID-19 hit. One silver lining: I met my wonderful wife, Erin, and we moved in together just before the pandemic. 

With my savings gone and my third startup derailed, I took a lucrative job with Amazon Web Services (AWS), selling cloud technologies. But instead of feeling secure, I felt numb. The money was good—but I wasn’t. So I walked away for a year to make art, ask hard questions, and see if I could unlearn the version of success I’d been chasing.

During that year, I started building a crazy mailbox I call the Ruborg Cube (a mix between Rubik’s and Borg—I’m a huge Star Trek fan), which took me a year to complete. You can see it here. The idea behind it took root while we were living in a high-rise apartment in Chicago, before the pandemic. I was perplexed by the nature of modern-day society: How all these little self-contained family units could live just inches away from each other, yet us all be total strangers. And how inefficient it all seemed—maybe we could share a blender or microwave or something. Or how practical it could be if we helped each other out with childcare, for example.

When the pandemic hit, that feeling of isolation became even more pronounced. I was working from home, so to save money, we moved back to our house here in Virginia Beach. I had also hoped that maybe we could find our community in a more suburb-style area. Not much changed though as I continued to interface with the world mostly through a computer screen. Even after the pandemic, society felt sluggish in returning to normal.

So, I started thinking, 'What could I do to signal to my neighbors that I’m open to being approached?' That’s when I built this crazy mailbox. And it’s working—people ask me about it all the time, and I love that it’s helping me meet my community.

During that year off, however, I racked up a lot of debt. After all, you can only be off the hamster wheel for so long. Times were tough, so we took on three tenants, and since debt collectors were draining my bank account, I started storing their rent payments in CashApp instead. I had $3,050 saved up when hackers—where from, I’ll never know—drained it completely. The way CashApp treated me—so rude and dismissive (they later lost a class action lawsuit against them)—added even greater insult to injury. I was so infuriated and depressed after getting off the phone with them that I chugged half a pint of vodka, ran into our bedroom, and painted on the wall, in big purple letters with my brushes: “Protect the Poor.” It’s not so much that I considered myself “poor”; as it was the realization: so this is how they treat people? Those words stayed up for a year before we finally repainted the wall, but their imprint remains.

A lot has changed since then, and I’ve really found my groove. I’m now in my second year of teaching and it’s been a real blessing. I work for a private company that outsources teachers to public schools wherever they’re needed most. Last year I helped teach sixth and seventh grade math, this year I’m supporting general education in fifth. The kids are beautiful little devils, but I’ll save more on that for another day…

This is my story. I cringe at how much I talk about money, but right now, the story of America is about money. Yes, it’s also about power and corruption, opportunity and justice—but really, they’re all the same.

“Learn to do right; seek justice. Defend the oppressed. Take up the cause of the fatherless; plead the case of the widow.” — Isaiah 1:17