What my time in Special Ops taught me about leadership

Mach49ers come from all walks of life. But Gary Clarke 's story? That's something else.

In honor of Veterans Day, we're proud to bring you Gary's five hard-won leadership lessons from his nine years in the US Army.

The time to start is now. Enjoy.

By Elke Boogert , Mach49 Managing Editor

What my time in Special Ops taught me about leadership

By Gary Clarke, CFO-in-Residence and Head of Venture Economics & Finance

When I run into something tough, sometimes I jokingly say, “Hey, at least I'm not laying in a ditch dressed up like a tree being shot at.” Here are five hard-won lessons from my nine years in the United States Army.?

First things first: there’s no secret sauce.?

For me, finding success, whether in the Army, in corporate, or with startups, is just getting up early and putting in the work. I have also built up a toolbox of skills over the years, which I can turn to and apply. For example, as I mentioned in the intro, I know I can put things into perspective. That, along with discipline, accountability, and responsibility for your actions, helped me professionally – and personally.?

In 1994, as a commercial pilot, I joined the U.S. Army. I went straight into Special Operations, where I stayed until 2003. For nine years, I worked with foreign internal defense and unconventional warfare units, implementing national security objectives.?

Why am I sharing this? Because working in startups, corporations, or the Army is not too different. While the stakes are different, the pressure was familiar to me.

Oddly enough, sometimes corporate life can be just as tough as the military.

In the army, we dealt with a lot ambiguity and very fluid situations. You’re juggling the dynamics of clients, teams, and project outcomes in business. The stressors are often different, but people count on you in much the same way.?

So, here are the five key lessons I take with me every day, from special operations to leading teams?

Plan for things to go wrong

My military experience shaped my leadership philosophy, one that emphasizes adaptability, teamwork, and a sense of humor – even in tough times. In Special Ops, we always planned for things to go wrong. That flexibility was key then, and it’s key in the startup world too. You can have the best financial models, lay out the best go-to-market strategy, and hire the best possible team, but everything changes as soon as you hit the market. No battle plan survives first contact. In the startup world, no marketing plan or business plan survives first contact either.?

Staying calm under pressure

One thing that has always stuck with me is the importance of keeping a calm head. In the military, we were trained to slow things down and stay calm when everything around us was falling apart. That skill has come in handy more times than I can count — though I'll admit, there are still days when I have to remind myself of that lesson, and I let myself down. Whether in the military or the corporate world, plans rarely go as expected. I remember to stay calm under pressure, even when everything feels like it’s falling apart.?

Mentor, and be mentored

Having mentored many veterans transitioning to civilian careers, I know how tough that shift can be. Veterans often struggle with the different expectations in the civilian world. That’s why it’s so important to find someone who can guide you through it. For those making that transition, I encourage seeking out environments where your skills can shine, whether that’s in a defense contractor setting or, for the adventurous, a startup.

Trust your team

As a leader, my approach is all about empowering my team. In Special Ops, decisions were pushed down to the lowest competent level, and I carry that with me in business. Tell your team what needs to be done. Then trust them to apply their skills, giving them autonomy and the accountability to be responsible for the outcome.?

Keep it fun

Especially when things were chaotic, we’d start meetings with a joke, just to lighten the mood. That sense of humor and team trust helped us navigate challenging moments. My time in Special Ops was full of camaraderie and humor, and while today I most often work remote, it's always good to have fun and be there for someone when they need that.??

Today, I help corporate ventures navigate how to strategically manage opportunities, identify and mitigate risks, and allocate capital. But I also strive to keep learning. Every day, there are different markets, revenue models, different people, new challenges, and so on. But every time, I find myself going back to that adaptability and the rest of the “toolbox” that I’ve built up over the years.?

We’re publishing Gary’s article in honor of Veterans Day, which is a federal holiday in the U.S. on Monday, November 11. Mach49 is grateful for his service, and all veterans around the world.?

GARY CLARKE is a serial C-suite executive with over 30 years of startup operating experience. For Mach49, he serves as the CFO In Residence, working on business models, strategy and finance.?

Gary began his career as a commercial pilot, then served in Army Special Operations. Having transitioned from active to reserve duty at the dawn of the browser wars, Gary then found himself shaping the commercial internet at some of the definitive companies of the era, including Spry, Netscape Communications, USinternetworking, Amazon, and WolframAlpha. Gary led VC and family office-backed startups in advanced materials, biotechnology, PEM fuel cells, and enterprise SaaS through multiple stages and exits.

Gary graduated from the US Army JFK Special Warfare School and holds a BS in sociology from the College of Charleston as well as a PMD from Harvard Business School. He is an FAA-licensed commercial pilot, with an MEIIL rating.

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