Once a Warrior, Then a Nonprofit Leader, Now an Entrepreneur

Jake Wood was a few months out of the Marine Corps in 2010 when a catastrophic earthquake hit Haiti. On the spur of the moment, he and a few other veterans headed to Port-au-Prince and started looking for ways to help. With no organization and no supply chain, it was a haphazard response. “The only thing we got right is that none of us died,” he said.

But amid the chaos, they were still able to provide aid, offer lifesaving care and find a sense of meaning outside the military.

Upon returning home, Mr. Wood realized he had stumbled on a massive need, and also had found an underutilized asset that could help solve the problem.

“Disasters are increasing in frequency and severity, so it’s a growth industry, as sad as that is,” he said. “And our underutilized asset was very apparent. It was the three million men and women who served overseas in Iraq and Afghanistan.”

Later that year, Mr. Wood co-founded Team Rubicon, and he never looked back. A decade on, Team Rubicon has deployed to more than 700 disasters around the world, has put tens of thousands of veterans to work and has struck partnerships with big brands like Under Armour and T-Mobile.

This year, Mr. Wood stepped down as C.E.O. of Team Rubicon and founded Groundswell, a company that is aiming to democratize corporate philanthropy by giving employees individual accounts with which to make charitable contribution.

This interview was condensed and edited for clarity.

Was there a moment in your childhood that you still come back to today when you think about your work and what you’re doing in the world?

My family moved to Europe when I was 6 or 7, and my parents took me to a Nazi concentration camp called Mauthausenin northern Austria. When you’re that age, you don’t really understand what evil is outside of a cartoon depiction of it. But that really put it in perspective.

There were photos of the liberation of the camp, which was really inspiring, to see these American guys who had fought across Europe and managed to save these survivors. That moment taught me about good and evil.

Was that part of the reason you joined the Marines?

I think it inspired me as a young boy to think about serving in the military. I would speak to recruiters who came to the cafeteria, and I began my applications to the military academies. And then I hit a growth spurt and became good at football.

I started getting recruited my junior year of high school, and I narrowed down my top choices to Stanford and Wisconsin. And the moment I stepped on campus at Wisconsin, the program resonated with me. These guys, they work hard. The culture there was incredible. And at Stanford, the coach was like a Zen Buddhist. The offensive line coach didn’t believe in yelling at players. I’m like, “How do you coach like that?”

I don’t know many people who turned down Stanford for Wisconsin.

I’ve never been a believer in pedigree, and it’s something that I say all the time when I’m recruiting people. If you went to Stanford, that’s cool. I don’t have anything against you. But you’re not going to get a leg up with me based off of your pedigree.

You eventually joined the military, though.

9/11 happened my freshman year. I was getting breakfast before going to the stadium for practice, and I immediately thought, “Am I doing the right thing? Am I in the right place?” As I sat there I get the call from my dad, and he says to me, “Don’t think about it. You are not dropping out and enlisting.” He knew what was going through my head.

I didn’t for the next four years, but I maintained an intense interest in what was happening, first in Afghanistan and then in Iraq. Then Pat Tillman was killed right before my senior year, and I said, “Enough is enough.” I played my last game on Jan. 1, 2005, and enlisted within a month.

What did the training you received from the military give you that you didn’t already have before you went over there?

I was a unique enlisted marine. I was older than most, because I’d been through college. I had been a college athlete, so I just had a different mind-set and mentality than a kid who is, like, 18 years old coming in. And I had the physical training and the discipline and was used to getting yelled at.

One thing that changed between college and when I went overseas was a level of confidence. I did not have a successful college football career. I was frequently dislocating my shoulders. So I never broke the starting lineup and spent my entire time backing up the starter. When I went to the Marine Corps, I excelled. There is a level of confidence all Marines kind of get. We’re kind of known for being a little cocksure.

Do you think that being somewhat older when you joined the service helped you deal with your experiences?

I didn’t see combat until I was 24, and your mind is fundamentally different at 24 than it is at 18. But the other way I was extraordinarily blessed was the family that I came home to. My time in the service gave me an understanding of just how blessed I am. I came from a loving household — two parents, great sisters — and I returned to that same family.

Some of the guys I served with came from poor backgrounds, marginalized backgrounds, and they returned to those homes when they came back. So they come from a dysfunctional setting, go to war and go home to a dysfunctional setting.

The exposure that I received to those less fortunate than me has given me a perspective on the world and our country that a lot of people that come from the same privilege I did just can’t see. They refuse to accept it. And I have no choice but to accept it because it’s been in my face.

Understand the Taliban Takeover in Afghanistan

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Who are the Taliban? The Taliban arose in 1994 amid the turmoil that came after the withdrawal of Soviet forces from Afghanistan in 1989. They used brutal public punishments, including floggings, amputations and mass executions, to enforce their rules. Here’s more on their origin story and their record as rulers.

Who are the Taliban leaders? These are the top leaders of the Taliban, men who have spent years on the run, in hiding, in jail and dodging American drones. Little is known about them or how they plan to govern, including whether they will be as tolerant as they claim to be. One spokesman told The Times that the group wanted to forget its past, but that there would be some restrictions.

How did the Taliban gain control? See how the Taliban retook power in Afghanistan in a few months, and read about how their strategy enabled them to do so.

What happens to the women of Afghanistan? The last time the Taliban were in power, they barred women and girls from taking most jobs or going to school. Afghan women have made many gains since the Taliban were toppled, but now they fear that ground may be lost. Taliban officials are trying to reassure women that things will be different, but there are signs that, at least in some areas, they have begun to reimpose the old order.

What does their victory mean for terrorist groups? The United States invaded Afghanistan 20 years ago in response to terrorism, and many worry that Al Qaeda and other radical groups will again find safe haven there. On Aug. 26, deadly explosions outside Afghanistan’s main airport claimed by the Islamic State demonstrated that terrorists remain a threat.

How will this affect future U.S. policy in the region? Washington and the Taliban may spend years pulled between cooperation and conflict. Some of the key issues at hand include: how to cooperate against a mutual enemy, the Islamic State branch in the region, known as ISIS-K, and whether the U.S. should release $9.4 billion in Afghan government currency reserves that are frozen in the country.

When you think about your tours in Iraq and Afghanistan, are there moments that taught you about what it means to be a part of a team and to be a leader?

The first firefight that I was ever in, about three or four weeks into my first tour in Iraq. This is 2007 during the surge. It’s the deadliest year of the war, and we’re in the triangle of death, right in Anbar province. We’d been bombed, blown up on the roads a couple of times prior to this moment. One of my squad mates was already killed in a roadside bomb. So we’ve seen some action, but we haven’t been in like a real knock-down, drag-out gunfight. And one morning we get ambushed. One of my buddies is shot through the throat early in the fight. And this big gunfight ensues. There’s about 40 of us, and I don’t know how many of the bad guys were there.

I led Marines across an open field, 150 yards, machine gunfire fire pouring in, because we had to reconnect with the rest of the platoon and evacuate this casualty. How did any of us muster the courage to do that?

It’s obvious that there was this love. Nobody hesitated for a moment to run across the field because Nathan was bleeding out. But love isn’t actually what directly leads to courage. Love actually creates this sense of safety for each of us. The safety was psychological and emotional.

People always find it weird to hear a Marine talking about psychological safety because it seems like such a kind of a woke, liberal sentiment. But it’s real. The five of us that were running across a field knew that if we got hit, there’d be 30 Marines lined up to take their turn to run out and get us. We felt relatively safe in that moment. The best leaders create a sense of safety in the team that they lead. And I think that that’s really what unlocks innovation and the drive to do more.

How did Team Rubicon get started?

Oct. 24, 2009, was my last day of service. I immediately applied to a handful of business schools. January comes around and I get a rejection letter from Stanford, which pisses me off. And a couple days later, the Haiti earthquake happens. I felt inclined to do something, so we went to Haiti, and we thought that our experience as military veterans would help us to be effective down there. We treated hundreds, if not thousands of patients. Some of them would not be alive today if we hadn’t been there. It was just postapocalyptic. But our military training made us very adept at navigating a post-disaster situation. So we came back and we just didn’t stop.

You talked about love and the safety that it creates. What does that look like inside a nonprofit organization or a company?

Empathy is core to leading with love — understanding your people and having compassion for who they are, what they’ve experienced, what about their life has brought them to that moment in time when they’re following you and putting their financial livelihoods in your hands.

You’re not just treating them as a tool to be used as a means to an end, but truly investing in their future, even if it’s not with your organization.

Why did you leave Team Rubicon to start Groundswell?

Throughout the last decade I’ve often asked myself the question, “Am I an entrepreneur at heart and will I want to do another start-up?” Because I’ve broken like five teeth from stress grinding. Being an entrepreneur is not an old man’s game. Eventually I settled on the fact that I still wanted to start something again.

One of the things that delayed my decision to step back as C.E.O. was that I was scared that I would never have the opportunity to have as much impact as I did at Team Rubicon. I didn’t want to be an entrepreneur again if it meant, like, shipping cat food faster.

Finally I had this idea for Groundswell, and it immediately scratched the itch. The impact that we might be able to have over the next decade building this company could be transformative.

Having served in Afghanistan, what were your feelings this summer when we withdrew so quickly?

It was extremely hurtful to see us leave in the manner that we did. I’ve long known we lost the nation-building war. But to pull our pants down on the way out and get embarrassed on the world stage was just deeply hurtful. I wanted us to lose in peace. Instead, we lost in such spectacular and embarrassing fashion. The whole thing to me was a microcosm of how the war had been managed. It was just sad.

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