Entrepreneurship is a lot like a combat deployment—you never quite know what’s coming next, but you adapt, you overcome, and you push forward.

Recently, I had the opportunity to sit down with Dog Tag Bakery’s Class 21 fellows—veterans, military spouses, and caregivers taking on the challenge of starting and running businesses of their own. Dog Tag Bakery has been a part of my journey from the beginning. They were Compass Coffee’s first customer, and over the past 11 years, our partnership has grown in ways I never could have imagined when I first started roasting coffee.

Our discussion covered everything from pitching investors to competing with Starbucks to the brutal reality that work-life balance is mostly a myth for founders. The questions were sharp, the insights were real, and the energy in the room reminded me why I love talking to fellow entrepreneurs—especially those with a military background.

"How did you go from being a Marine to running a coffee company?"

If you had told me in 2011, while I was leading a Marine infantry platoon in Afghanistan, that I’d be running a coffee company with 22 locations, a state-of-the-art coffee roastery, and a growing ecommerce business, I probably would have laughed.

Back then, coffee was just a bitter necessity to stay awake. It was black, burned, and barely drinkable. But when I transitioned out of the military, I wanted to do something totally different. I didn’t know anything about coffee or business, but I figured I could learn.

The original idea was simple: make real good coffee. I had no plans to build a factory, hire a corporate team, or go national. But like any good mission, the plan evolved. Dog Tag Bakery was one of the first places to serve our coffee, and that small step eventually led to partnerships with restaurants, hotels, and grocery stores.

"How did you grow so fast?"

Short answer? We listened to customers.

Long answer? We listened, adapted, and weren’t afraid to admit when we were dead wrong.

When we first opened Compass Coffee, we had a clear vision: serve amazing light roast coffee and introduce customers to its complexity. We were passionate about the nuanced flavors, the floral notes, the bright acidity. But there was one problem—most of our customers didn’t want light roast coffee. They wanted medium and dark roasts.

We had two choices: stick to our vision and struggle or adjust and grow. We adjusted.

Then there was the food. We thought biscuits would be a hit. Turns out, people wanted croissants. We adapted.

We thought gluten-free would be huge. It wasn’t. We cut it.

These weren’t just minor adjustments. Every decision was a test, a lesson, and a step toward understanding our customers better. And it wasn’t just about what we served—it was about how we operated. When we first started, we thought people wanted gourmet, single-origin coffee experiences. But a lot of people just wanted a reliably great cup, served fast.

That shaped how we designed our cafes.

That shaped how we trained our baristas.

That shaped how we built our supply chain.

We made Compass faster, more consistent, and more adaptable. There’s no magic formula for growth, but the businesses that succeed are the ones that are willing to listen, iterate, and evolve.

"Should I take on investors, or should I bootstrap?"

Depends on how much you like answering texts from investors at 10 PM.

At Compass, we do have investors—mainly successful businesspeople from the D.C. area. They bring experience and guidance, but they also bring expectations. Investors want updates. They want to know their money is being put to good use. And sometimes, they’ll text me if they have a bad customer experience.

That’s the trade-off. Investors can provide the capital and expertise to help you scale, but they also come with expectations. They want to see returns, which means pressure to grow fast and hit specific milestones. If you take outside money, you need to be crystal clear on what you’re signing up for—and whether you’re comfortable giving up some control in exchange for growth.

For veterans starting a business, I always recommend something built on personal reputation—photography, consulting, landscaping. Low capital, low risk, and total control. No investors, no overhead, just you and the work.

Starting small with a home-based or service-oriented business is the best way to get your feet wet in entrepreneurship. A plumbing or moving business doesn’t need a storefront or a huge upfront investment. You can learn as you go, refine your process, and build a customer base without taking on massive debt.

Another key advantage? These businesses let you adapt fast—no long leases, no big loans, no red tape. If something isn’t working, you pivot. And as a veteran, you already have the skills to make it work. Leadership, problem-solving, resilience—everything that made you effective in the military applies directly to entrepreneurship. Deliver great work, be reliable, and word-of-mouth will do the rest. The key is to start. The only way to learn business is to run one.

"Can you compete with Starbucks?"

Absolutely. And we like going head-to-head.

A lot of people assume that competing with a giant like Starbucks means obsessing over everything they do. That’s a mistake. You have to know the landscape, study your competition, and understand the industry—but you can’t let their strategy dictate yours.

It’s like Sun Tzu in The Art of War:

"If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle."

I know what Starbucks is doing, and I think about it. But I don’t spend my time trying to copy them or react to their moves. They’re a massive corporation—slow-moving, less adaptable, focused on efficiency at scale. Compass is the opposite. We move fast, we’re scrappy, and we provide better coffee and better customer service. That’s where we win.

At the same time, our biggest competitor isn’t Starbucks. It’s ourselves. The real challenge is staying focused on what we do best—making people’s days better, one cup at a time. That’s where our energy goes.

As an entrepreneur, your time and energy should go into making your business the best it can be. The key to competing—whether it’s against Starbucks or anyone else—isn’t trying to be them. It’s knowing exactly who you are, delivering real value to your customers, and executing better every single day. That’s how we compete.

"How do I pitch my business to investors?"

Be yourself. Be confident. And don’t overcomplicate it.

People get so obsessed with making the perfect pitch deck that they psych themselves out. Investors don’t just invest in ideas—they invest in people.

At the end of the day, if you can explain what you do in a few clear sentences and why it matters, that’s a solid pitch. Investors want to back people who believe in what they’re doing. If you’re authentic and you’ve done the work, that confidence will come through.

I also tell people: Prepare, but don’t try to be perfect. Investors can tell when you’re over-rehearsed. Just like in the military, the best leaders are the ones who can speak with conviction without sounding scripted.

"What was the hardest moment in Compass Coffee’s history?"

Easy. COVID.

One week. That’s all it took for our business to drop by 85%. Overnight, downtown D.C. shut down. Office workers disappeared. Seven of our 14 locations were in downtown, and they went from thriving to barely surviving.

We had two options: accept defeat or do what the Marine Corps teaches you—improvise, adapt, overcome.

The first question we asked ourselves was: What do people need right now?

We had a coffee roastery with a simple syrup bottling line, and suddenly, people weren’t looking for coffee—they needed hand sanitizer. So we pivoted. Fast.

What are we good at? Supply chain, branding, R&D, and moving quickly. Within two months, we had transformed part of our operation into a full-scale hand sanitizer production line. It generated enough cash to keep us in business and gave us time to think about our next move.

Then we asked ourselves: People are stuck at home. They still love coffee. How do we get it to them without making them leave the house?

That led to our next pivot: single-serve coffee. We became obsessed with making the best Nespresso-compatible capsule. We sourced the best materials, tested every detail, and took a process that would normally take a year and crammed it into two to three months. We took a big risk, bought the machine, did all the R&D, and figured it out.

Then we launched our ready-to-drink Cold Brew On Tap and expanded our e-commerce business so people could get Compass Coffee delivered straight to their doors.

It was a brutal time, but it forced us to innovate in ways we never would have otherwise. We didn’t just survive—we came out stronger, with an entirely new product line that still fuels our business today.

Failure isn’t the opposite of success—it’s part of it. Every business owner will face gut-wrenching moments. The key is learning, adjusting, and moving forward.

"Can you actually have work-life balance as a business owner?"

If you want a comfortable 40-hour workweek, don’t start a business.

People love the idea of entrepreneurship—the freedom, the excitement, the potential rewards. What they don’t always see is the cost. When we opened Compass, I was unlocking the doors at 5 AM, roasting coffee in the afternoon, and doing the books at night. I didn’t have much of a social life. My relationships suffered. I missed weddings, birthdays, vacations. That’s the reality of the early years.

The real question isn’t whether work-life balance is possible—it’s what kind of business you’re trying to build. If you want to start a high-growth, capital-intensive company, your business will take over your life. That’s just the nature of the game. But if you’re building a lifestyle business—say, a solo consulting practice or a wedding photography company—you can design it to fit your priorities.

It also depends on your stage in life. I have a one-year-old now, and that changes things. Early on, the business was like my child—it required all my time and energy. Now, I’m still involved every day, but I’ve built a team that allows me to step away when needed. That took years.

So, is work-life balance possible? Sure—but not at the start. If you want to build something great, you have to be all in. The key is to love what you do so much that the work doesn’t feel like work. Because for the first few years, it will consume you.

"What’s the best advice for a veteran starting a business?"

The best thing the military teaches you is how to adapt and lead under uncertainty. That skillset is invaluable in business.

Veterans already have an edge in entrepreneurship. Leadership, problem-solving, resilience—these are all skills you honed in the military, and they apply directly to running a business. Entrepreneurship is a constant battle between risk and reward. The key is knowing how much risk you’re willing to take, how hard you’re willing to work, and what success looks like for you.

Taking on investors or raising a lot of money sounds exciting, but statistically, 90% of businesses don’t make it past year two. That doesn’t mean you shouldn’t take the shot—it just means you need to be honest with yourself about risk. Some ideas can become billion-dollar companies, but the chances of that happening are slim. The better question to ask is: What do you really want? How much risk are you willing to take?

If your goal is to build something that lasts, focus on businesses where you have a competitive advantage, where you can control the process, and where your reputation is your greatest asset. Start small, iterate quickly, and focus on delivering value to customers. That’s how you create something sustainable.

For veterans just getting started, I always suggest service-based businesses that require little capital—consulting, photography, landscaping, construction, personal training. These are businesses where you control your own destiny, don’t need outside investors, and can start making money right away. The biggest risk for new business owners is overhead—leases, payroll, debt. Keep it simple at the start.

Conclusion

Entrepreneurship is never easy. It’s unpredictable, demanding, and full of challenges you can’t always prepare for—much like the military. But if there’s one thing veterans know how to do, it’s adapt.

The lessons we learn in service—leadership, discipline, resilience, and problem-solving under pressure—are exactly what it takes to succeed in business. The difference is that in the military, the mission is given to you. In entrepreneurship, you have to define it for yourself.

For the fellows in Dog Tag Bakery Class 21, this is the start of something new. Whether it’s launching a small business, building a brand, or simply exploring what’s next, the key is to take action. Listen, iterate, and keep moving forward.

It was an honor to be part of the conversation. I have no doubt that the businesses, ideas, and careers these founders build will be just as impactful as their service. I can’t wait to see what they do next.