Jake Wood Was Once a Warrior, Then a Nonprofit Leader. Now He’s an Entrepreneur.

Steven Spielberg

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 gun 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.

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