From Special Ops to Startup Founder: How Military Service Prepared Me for Success in Tech

From Special Ops to Startup Founder: How Military Service Prepared Me for Success in Tech

I was up early one Tuesday morning. I was a junior in high school and preferred sleeping in, but high school football was my life at the time, and we were going to review tape from the previous Friday’s game. Like the others around me, I pulled my hoodie over my head and tried to snooze for a few minutes before coach Lewis showed up. 

Suddenly, the door slammed open and a fellow teammate came in like a bat out of hell, screaming, “A plane flew into the Twin Towers!” 

Groggily, we ignored him, not knowing that life from that moment on would be different. 

The rest of the day passed in a blur of news anchors opining and asking more questions than they could answer, along with replays of the towers falling. 

At the time, I had no clue who or what had caused this, but I knew I couldn’t just sit by and watch. Before too long, it became clear that al Qaeda was behind the attack, and I decided I would enlist in the Army. Thanks to encouragement from my best friend, I landed on trying to become a Ranger. I knew that Rangers were a part of the special operations community, and that making it through the gauntlet of selection was not guaranteed, but I felt the pull, and knew that I had to follow it.

Shortly after I made my decision, I told my parents that I was going to join, and they could not have been more caught off guard. Sure, my dad had been in the Air Force, his dad had been in the Navy, and my great grandfather had been in WWII, but I didn’t seem like the type who was driven to join the military. I was a pudgy kid who loathed discomfort. Not quite the archetype for a commando.

But the switch had been flipped, so to speak. I met with a recruiter and started researching what it would take to become a Ranger. First of all, I had to be able to run. Much to my dismay, having played lineman my entire football career, I started running long-distance for the first time in my life. Fortunately, the Ranger standards were very clear: 5 miles in under 40 minutes, 2 miles in under 14:30. I also knew I’d have to meet the other standards of pushups, situps, pullups, etc. Beyond that, I'd also have to manage discomfort. And not just physically — I had to have determination and be comfortable in ambiguous situations. I can’t count the number of pushups I did while I waited for basic training, but having that clear goal gave me purpose, and direction. My family and friends couldn’t believe the transformation.

Two months after graduating from high school, I found myself stepping off of a bus in Columbus, GA, at two in the morning. A waft of humid, sticky, non-conditioned air smacked me in the face. It was 85 degrees, and it smelled like a damp rag. I was full of doubt and drenched with sweat. As a kid from a small logging town in the foothills of Oregon, I felt like Dorothy in the land of Oz.

But I adapted. 

Through basic training, I found my footing. I was eager to become an infantryman — to take the fight to Bin Laden. We craved news from the outside world, but only got snippets here and there. After basic training, I moved on to jump school, then selection for the Rangers. I was becoming stronger and more confident, and a healthy dose of cockiness came with that. 

After I passed selection for the Rangers, I was stationed at 2nd Ranger Battalion in Ft. Lewis, WA, just three hours from my hometown. My family was excited to have me so close, but of course also nervous, seeing how the war was progressing. At this point, the invasion of Iraq, and the war overall, was not going well.

Just thirty days after being sent to my unit, I was deployed to Afghanistan. My first day in that country happened to coincide with my 19th birthday.

Late that night, we loaded the helicopters and flew out to the border region between Afghanistan and Pakistan. Our goal was to catch drug dealers and Taliban leaders who were funneling weapons and support to al Qaeda. We ran missions every night and trained during the day. The fear I experienced during this period was not of an improvised explosive device or AK-47 ruining my day, but of letting down my squad. In particular, I feared letting my team down.

Fortunately for me, my team leader didn’t give me the chance. He taught me everything about Rangering: Slow is smooth, smooth is fast; how to clear rooms and handle detainees; how to build a breaching charge.

He also taught me how to suffer. I’ve never tried to quantify how many pushups I did while I served in the Rangers, but it must have been in the tens or hundreds of thousands. Every infraction was a reason to get used to doing flutter kicks, lunges, or mountain climbers. Let’s say you left a piece of equipment behind, or you were dragging your feet, or you didn’t have an extra set of batteries. It didn’t matter what it was —  Ranger team leaders were always looking for an opportunity to “smoke you until your eyes bleed,” because the consequences of mistakes were real. This wasn’t a video game. I had to keep up, or they’d kick me the hell out of there.

After my first deployment, I attended Ranger school, followed by three subsequent trips to Iraq. I took part in hundreds of missions, capturing high-value targets, as well as some of the worst people on the planet. I learned to fast-rope out of a helicopter and plug a sucking chest wound. Navigating by starlight using just a map and compass became second nature, as did leading teammates.

My confidence soared. I was achieving my goal of becoming a combat-tested Ranger.

As I transitioned out of military life back to the civilian world, I carried the lessons I had learned through the brutal training and endless missions I had conducted. The discipline and rigor I had developed while serving were instrumental when I transitioned to college life.

My adjustment to civilian life wasn’t without its challenges, though. I found it difficult to connect with other students at the university I attended. Through no fault of their own, their backgrounds did not align with mine. Despite being only 22, I had been to war, and I didn’t have patience for the things college students tend to do.

The first day of freshman year was a real wake-up call. I was seated and ready to go at 7:55 for an 8 AM class because, in the Rangers, “If you’re not five minutes early, you’re five minutes late.” Ten minutes after class started, another kid walked in. Eighteen, still in his pajamas and slippers, and he couldn’t have cared less about being late. My blood boiled as I thought about how hard I had worked to have the opportunity to attend college, and seeing this person act so nonchalantly was difficult for me.

It was particularly hard for me to recognize that not everyone likes waking up for early classes, and that most of these students, who I now called my peers, hadn’t developed the habits ingrained in me by my basic training instructors, Ranger cadre, or team leader. Over time, my expectations of others changed, but as a non-traditional student, I initially found it difficult to find “my people.”

I raced through college as quickly as I could, not taking summers off. I loaded my schedule with as many courses as I was allowed, because I naively thought that life started once I got out of college. Instead of slowing down to appreciate the opportunities I had while studying, I kept rushing to the next thing. When graduation was pending, I considered going to law school, and considered becoming a scuba instructor in Thailand, but ultimately I went the safe route: I took a job with a Fortune 500 company. I was a management trainee at a company that offered corporate apparel. I was literally sorting dirty laundry from hotels and restaurants. Most days I had to wear a suit, I didn’t have any friends, and I was getting fat. I was miserable.

Then I bumped into someone who told me offhand that, “You should be in business development.” I hadn’t a clue what “business development” was, but I took his advice and started looking for jobs, ultimately landing one at a venture-backed startup in Palo Alto, CA 

I had studied Entrepreneurship in college and wanted to work at a startup. The idea of working on cutting-edge tech was enticing. This was 2010. Facebook, LinkedIn, and all of Silicon Valley were all the rage.

Right away, I learned that business development was really code for something else: sales.

I was prospecting, emailing, and cold-calling people all across the country, trying to set meetings for the Sales Reps I was supporting. The company was small, with somewhere around 40 people, but everyone was fun, energetic, and very smart. I felt a little out of place again. I had used the military to pay for a college degree at the University of Oregon. These kids had perfect SAT scores and attended schools like Harvard, Stanford, and Berkeley. I’d never even taken the SATs. I felt like an imposter.

What I found I loved most about the role was improving processes. I did what I could to streamline, simplify, and improve how I operated. I loved to find ways of increasing our email open and response rates, and I enjoyed looking for unique ways to boost productivity. 

Because of my propensity for optimizing, I was moved into a management role. At the time, there were only a handful of people on the team, but my job was to hire, onboard, and develop recent graduates so they could help support Sales Reps. I would train them on how to prospect, do outreach, and use the systems we’d built. Before I knew it, the company had grown to 250 people, and I was managing 70 of them.

The folks I developed became the pipeline for talent in the organization. I was constantly filling a leaky bucket as other team leaders poached the team members I hired and mentored, moving them into closing Sales roles, Account Managers, Marketers, Finance, etc. Despite the leaky bucket situation, I was proud to have built out an engine that supported the company through both talent and sales opportunities.

Eventually, the team grew so large that management decided to restructure the Sales organization, which meant they didn’t need me to lead that team anymore.

In response, I was “offered” a role as Director of Operations, which meant I’d be the person managing all of our systems, specifically Salesforce. Salesforce was the Customer Relationship Manager (CRM) we used to track everything in the business. Not just leads, accounts, and deals, but also product features, invoices, and marketing campaigns. I was meeting with leaders in every function of the business, getting a taste of what their problems were and how to solve them. Because I had been there since the company was small, I had context for why we did things the way we did, as well as the struggles reps faced.

Ignore the fact that I had no experience with how to code, how to architect a database, or really how APIs even worked. I was given an enormous amount of autonomy to solve whatever problems felt important, and I loved that freedom.

I also enjoyed meeting with the stakeholders, hearing what their must-have’s, want-to-have’s, and like-to-have’s were, and then pulling the levers to actually solve the business problems behind them. I thrived on having an iterative process that gave me constant feedback.

One common problem in any system touched by Sales teams is data cleanliness. It’s difficult to keep any database up to date, but it’s particularly difficult when the people who use it loathe doing data entry. So the data decays, and the database gets stale. Early on, I was tasked with cleaning up all of our Account records. I need to clean up addresses, websites, LinkedIn profiles, etc. on 250k records.

When I first exported the list from the database, I tried to open the file in Excel and my computer crashed. What the hell was I supposed to do? I couldn’t even open the file, much less clean anything up. A friend suggested that if I knew how to code, I could use a programming language called Python to do the trick. I didn’t know what Python was, much less how you get it to solve the problem I was facing. I ended up taking some introductory coding classes and fell in love with the programming language. Python allowed me to not just manipulate files, but to interact with data providers and work in a much more efficient way.

I started to spend more and more time programming, building tools that made my job more efficient, and began considering a career as a software developer. 

One day, I walked into a leadership meeting, and the feeling in the room was tense. I could tell something was off. Our VP of Sales, my counterpart running the Sales team, was out. A new guy was in.

Not long after that meeting, I got a personal email from the VP of Sales who’d been canned. He had just started a new job, and their Salesforce org was a hot mess. He asked if I could help him set up his instance just the way I’d set it up at my current company.

Not even knowing how much to charge, I told him, “Sure thing!” and bid the project at $50/hr. He signed a slapped-together contract, and we were off to the races.

By day I ran operations for a 400-person startup, by night I architected Salesforce at his new company. Most of what I was building was relatively simple, but because the system was brand new and there were no other stakeholders, things got done more quickly. It was a relief not having to deal with the headaches and dependencies of a system bogged down by several years of changing operations.

Just weeks into this project, I received another email. It was from the same VP of Sales, introducing me to some of his friends who were running into the same problems and needed my help. Feeling more confident, I bid $75/hr, and they didn’t blink.

This carried on for months, and I made a deal with myself: If I got five customers, I would quit my day job.

I had always dreamed of being my own boss. Having studied entrepreneurship, my goal was always to start my own business. Soon enough, I had those five customers paying me each month, but I also had a 401k, health insurance, stability, and a baby on the way. So, I broke that promise to myself and kept doing what I was doing: Operations Director by day, freelance Salesforce contractor by night.

When my first daughter was born, I had the opportunity to take three months of paternity leave. It wasn’t long into that break that I found myself with a lot of free time on my hands. With no ability to breastfeed, I mostly hovered around my wife, who in turn encouraged me to work on my budding consulting practice.

By the time my leave wrapped up, I had grown my book of business to the point that the income I was generating on my “side hustle” was roughly the same as the day job I would have to go back to.

On my first day back, I found myself in charge of cleaning up a large, complicated mess that was created while I was out. Certain decisions were made without consulting me, but now, it was on me to fix the resulting problems. The straw that broke the camel's back was learning that the new head of Sales (hired while I was out, no less), went ahead and purchased a massively complex product for the company's SFDC setup, and also went ahead and hired a consulting firm to implement it, despite me being the product owner — I was tired of the consequences of other folks’ poor decisions falling on my lap. Right then, I decided that I was going to take a bet on myself and strike out on my own, full-time. 

Shortly after this, I put in notice, giving my company three months to find a replacement. By the time that three months had passed, they hadn’t found anyone. My boss asked if I would be able to help them continue managing their Salesforce org once I transitioned out of the company. Luckily for him, it just so happened that I already had a business in place that could support them.

From that point on, I never looked back. The first few days of each month were usually stressful, as I didn't know whether I would have any business coming. But my time in the Rangers taught me to focus my attention on the things I could control, so that’s what I did. I put my head down and did training, wrote blog posts, did podcasts — anything that moved the business forward. Ultimately though, I'd breathe a huge sigh of relief when the phone eventually did ring.

I was a full-fledged entrepreneur, on the cusp of founding what would eventually become Kicksaw. I’ve written more about that part of my journey in this essay, which I encourage you to read, especially if you have any dreams of being your own boss. 

My journey from special ops to startup founder isn’t one that I could’ve predicted, but it’s one that has taught me many lessons along the way. From how to get comfortable being uncomfortable, to how to lead, follow, and set the example for others to follow, military service was instrumental in preparing me for my current path.

My biggest takeaway, though, is that you have to trust your gut. A good friend once gave me some great advice that summed this up perfectly: "Advice is what you ask for when you already know the answer but wish that you didn't."

Whether your gut drives you to become an Army Ranger, an entrepreneur (or both), or something else entirely, my advice for you is that you listen to it.

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