Startup founders on the lessons they learned from military life

Founders come in all shapes and sizes—and, in some cases, stars and stripes.

In 2022, veterans were the majority owners of more than 1.6 million firms employing nearly 3.2 million workers, according to the US Small Business Administration’s Office of Advocacy. Veterans also make up 4.3% of business owners in the US.

For founders coming from the disciplined and highly regulated world of the military, the transition into entrepreneurship can feel both freeing and disorienting. Going from taking orders to building a company from scratch means trading established systems and clear hierarchies for ambiguity, fast decisions, and constant uncertainty. While that environment can create new opportunities, adapting to the unstructured chaos of startup life doesn’t always come naturally to people trained inside institutions built on structure and tradition.

Across interviews and emails, Founder Brew discussed how the military experience translates into founder life, with four founders who are also US Military veterans:

• John Doyle, founder and CEO of secure mobile carrier Cape, was a special forces sergeant in the US Army before spending a decade at Palantir.
• Kimberly Shenk, co-founder and CEO of Novi, a former captain in the Air Force, is a graduate of the Air Force Academy and served as a senior data analyst.
• Adam Hunter, founder and CEO of InPress, was a staff sergeant in the Air Force and served from 2011 to 2017.
• Daniel Castillo, founder of Ghost AI Systems and CEO of production company Media Geeks a former Marine Corps corporal

Interviews were conducted separately and have been edited for length and clarity.

Veteran founders share the hardest part of leaving military life behind for founder life

John Doyle: In the military, there is a lot of structure, a very clear hierarchy, and often a book that literally tells you how to do your job.

What is amazing about a startup is none of that exists. Monday morning, you check into a WeWork and now you’ve just got a company and a couple bucks in the bank. There’s nothing else. You don’t even have an email address for yourself. So you get to write the entire thing from scratch. That is fun and motivating, but can also be really disorienting.

Kimberly Shenk: When you’re in the military, you are all there in a group of people that subscribe to the notion of service before self. The whole concept is you’re serving a greater mission than yourself.

Moving into business and founding a company—yes, you ideally want to work for a company that has a really strong mission and that you’re going out and doing something really important for the world, but that idea of service before self is not like all-encompassing of your entire life.

Adam Hunter: Can I say not having 30 days of PTO anymore? Kidding. Sort of. The real answer is stability. Air Force life, at least in the role I had, was demanding but predictable. You had a schedule. You had time for hobbies. You were required to work out. You worked with mostly the same people for years at a time.

The founder life is the complete opposite. PTO? I don't know what that is anymore. Nine to five? I’m writing this at 8:20 p.m. Working out? With what time? It’s the same sense of duty I felt in uniform, just applied very differently.

Shenk: The other [transition] is more fundamental. I remember my first job out of the military, I was a marketing data scientist for Sports Authority, and learning about business was really challenging. There are many different dynamics.

In the military, of course, you have a budget, but you’re managing to a budget, not to a growth metric. You’re not trying to hit a revenue metric. There’s nothing like that. There’s no business component of it…Coming out of and doing that from a founder perspective, and learning about those concepts in business, was really eye-opening and challenging for lots of folks that transition out of the military.

What veterans have to unlearn in startup culture

Daniel Castillo: When Media Geekz first started growing, we were partnering up with an agency…And then we saw how the agency operated versus how we operate. In the Marines, you go as fast as possible, break it and fix it. The agency we were working with was more like NASA. You launched a rocket perfectly the first time…... Starlink or not—Starlink, SpaceX, and NASA operate completely differently. One is, when it’s a very slow, precise process. The other one’s blowing up rockets and risking everything all the time until it works. We operated that way.

Even for Ghost AI, I’m shipping a new product every single day.

Doyle: In the military, you really rely on your training. The quote is “under pressure we don’t rise to the level of our expectations, we fall to the level of our training.” That is completely true, and it runs through so much of how you approach the work of soldiering.

There really isn’t a meaningful way to prepare or train for starting a company. There is plenty of pressure and stress, but there is no playbook and no way to “practice,” so you are just constantly hoping to rise to the level of your expectations.

Hunter: To some extent, the directness. In the military, when you say you're going to do something, you do it. Full stop…If you miss a deadline without a good reason, it's your ass. I carried that mindset straight into being an entrepreneur, and it can land with...mixed reception, which is fair.

Early on at InPress, I had to learn that telling a developer or a senior hire the same thing the same way I’d tell a junior airman is often not how you get their best work…Startup teams are small, which means every person on it is a domain expert I’m depending on. They didn’t sign an oath. They have other options. My job isn’t to enforce the standard; it’s to communicate it in a way that earns buy-in, and makes them feel a sense of ownership for it.

On the military lessons that still shape how they build

Shenk: I would say the biggest, most important one is the concept of service. That’s why I joined to begin with, like serving something larger than myself. It is still very important, because now I think about it, building a company, you’re serving your customer, you’re serving your stakeholders, you’re serving your employees, and so that is extremely important in that concept of like what it means to serve a mission and bring that to your customers and your employees and everyone day in and day out.

I’ve talked about this in building the company, but the way that the military operates, it’s called an OODA loop. It’s basically “observe, orient, decide, act,” and it’s a continuous loop. The discipline around that is you’re constantly observing your situation that you’re in, you’re orienting what you’re doing to that situation, you’re making decisions based on that, and then you’re acting, and then you’re observing the results of those actions. You’re constantly making that framework happen as fast as possible.

The things you bring from the military with you when building a startup and making decisions to grow a company

Doyle: Pain tolerance. You have to be willing to stay in it and persevere, even when every internal voice and signal is telling you to give up. When I went through the Special Forces training pipeline, by far the most common reason people washed out was they quit. It wasn’t that they couldn’t do enough pull-ups or whatever, they just decided they were done and they quit.

The only way a startup can fail is if you run out of money or quit. And if you’ve got high enough pain tolerance to not quit, then you just have to keep an eye on your burn rate and you’re all set.

Castillo: The biggest thing is speed. I want things to be high-quality and fast all the time. I feel like I quietly break everything in my own private thing, and then once the clients come in, everything’s so well architected, so well built, that I can do it fast. so I can do an intake for a client in 20 minutes, where another founder might take four or five hours because they didn’t build those systems and templates that the Marines taught me.

When military training influences business decisions

Hunter: There was this guiding principle in the Air Force that they always repeated: “Integrity first.” I’ve always said I’d rather watch InPress go under than sacrifice our moral fortitude and the mission that inspired the creation of this company.

Last year, we had an interaction with a VC that I think put that to the test. We were deep in due diligence with an investor I thought was fully bought into what we were building: verified, factual journalism, no algorithmic echo chambers, mental veggies instead of junk food. Right before we expected to close, they pushed back on our content standards…They were demonstrating a lack of integrity in that they were willing to apply pressure to push us away from the core of our mission before the deal was even closed. It told me everything I needed to know about what would happen after the money hit the account. I ended the conversations and told them it wasn’t a fit.

Doyle: I remember staying late at the office with my colleague and founding engineer David Dunn early on for one of our first maintenance windows. There was absolutely nothing I could do to help, it was a purely “David” task. But my NCO roots wouldn’t allow me to violate the buddy system and leave him solo, so instead I went to the liquor store, got the fixins to make us both Manhattans, and stayed until it was done (though I did nap on the couch for part of it).

Shenk: You make bets as a company, and you’ll make investments in things. The first thing that you learn in the military is you make investments, you do something, and if it's not working, you have to make tough and quick decisions to iterate again…sometimes those might be people decisions.

There was a point in time earlier in Novi’s career where we…thought we were going to build out a part of the organization, and we hired against it and very quickly thereafter realized it was not going to turn out. We ended up having to let that entire part of the bet of the organization go…It’s emotionally hard. It’s difficult to admit also to a company that you made a bet and it didn’t pan out. But from an organizational perspective, and the thing I also learned in the military is, that’s also the challenge of being a leader.