Jacob Wijnberg

Former U.S. Army Green Beret Jacob Wijnberg applied to Stanford GSB after high-stakes deployments in Eastern Europe and Syria, intending to launch a career as a venture capitalist and bring sustainable investment to countries emerging from instability and crisis. However, his experiences abroad made him realize he could also have an impact at home.

“I’ve actually turned my eye to the problems facing American cities,” says Wijnberg, a Dartmouth undergrad who ended his Army career as deputy director of a special forces company assigned to deploy quickly for some of the country’s most sensitive military operations. “What energized me when I was in Syria, and what energizes me about the problems in U.S. cities, is the opportunity to have a direct and tangible effect on people’s lives.”

After spending a decade on overseas projects such as improving irrigation for Syrian farmers and making war-torn areas secure for kids to attend school, he recognized the opportunities in the United States. “There’s a lot of opportunity in our own backyard, especially post-Covid as cities adapt and serve their citizens in the 21st century. It’s going to require people willing to roll up their sleeves at the ground level, and it’s going to require businesses to invest in our cities again to make them the engine of growth that they have been for most of this country’s history.”

What was your most memorable deployment with the Army?

It was definitely my last Syria deployment in 2020. Geopolitically, at that time, there was a lot going on. The year started with tension with Iran, and we deployed under all the COVID uncertainty and protocols. We were dealing with this big open-ended question of what comes next. I was in charge of an area roughly the size of Rhode Island with about 1.6 million people. As the senior U.S. military person on the ground, I had to do everything you expect Green Berets and Rangers to do, all the way through working with the State Department and NGOs, to working with local governments on how to actually function. I didn’t sleep much.

How’d you adjust to being a full-time student again after that?

It was difficult. You’re coming out of a situation where everything is clearly laid out for you, career progression is written down with a menu of options, you know your scope of responsibility, and there’s also this great sense that, even on the dullest day, the mission is still gigantic. As a student, you face an infinite number of choices about what to do with your time and the rest of your life. That’s something a lot of veterans have to work through. Stanford GSB does a good job of telling you you can do anything you put your mind to, but the hard part is figuring out what to decide on.

You still want to bring “sustainable investment” to places in turmoil, now including American cities. What does that phrase mean to you?

The worst thing that can happen to a community is when people give up on trying to start businesses. You end up with a doom loop where the best and brightest take their talents elsewhere, and it’s hard to recover from that. In places like Syria there’s a fundamental issue of access to credit and lending. It’s difficult to get a business off the ground if you can’t get access to credit or startup capital. So you end up with a narrowing of goals that holds communities back and makes people susceptible to extremism and conflict.

Were there any helpful mentors during your military career?

In Syria, I had a chief warrant officer and team sergeant that I had a special relationship with. I was responsible for final decisions, but I leaned heavily on them to think through difficult tactical and strategic decisions and navigate the burden of command. They had the benefit of decades of experience, of seeing people before me make mistakes. When leadership works well in the military, you agree in public and disagree in private. The three of us did that very well.

What about them do you want to emulate?

They both have an element of groundedness. There’s so much being thrown at you all the time, and it’s hard to parse what matters and what doesn’t. It’s like juggling a bunch of balls, and some are made of glass, and some are made of rubber. People like them can help you figure out which balls are rubber and which ones are glass.

Any similarities between what you learned in the Army and what you’re learning at GSB?

I’m just wrapping up a class called I’m Just a Bill taught by instructor Keith Hennessey, who served for decades on the Hill and in the Bush White House. It’s a 10-week-long mock-Congress simulation. The biggest similarity to what I learned in military training is conflict resolution. GSB does an excellent job of bringing people into situations where there’s inevitably going to be some degree of interpersonal conflict. Sometimes you need to confront it head-on in order to have an honest discussion to resolve it.

Did the Army teach those soft skills the same way as GSB?

The Special Forces qualification course included role-playing with retired Green Berets, and I remember thinking during that course, “This scene seems so contrived, and there’s no way this would possibly happen in real life.” After I graduated from Dartmouth, I deployed to Syria and found myself having almost word-for-word those same conversations in Arabic that I had in the course. I realized the value of the role-play experiences. And now that I’m at Stanford, some of the best courses are the ones with an opportunity for role play.

Any other GSB experiences that were particularly influential?

Hennessey also teaches Fiscal Policy, which was his wheelhouse for decades in Washington. He forces students to articulate and defend their beliefs. It’s too easy in society and even academia to make claims about what you believe without any further probing. But Keith really wants his students to understand why they believe what they believe. He’s helped clarify my own thinking on a bunch of issues, and he’s given me the tools to further investigate my own beliefs and clearly articulate them to other people.

You’ve described the opportunity to lead as “humbling.” How so?

When I entered the military, I was hopeful and probably a little cocky that I knew all the answers to the test. That’s never true, and you hope you make the best decision with the information you have available. Humility comes from recognizing that you’ll never have all the information you need, and that you need to be comfortable with the uncertainty of the outcome. I also realized I needed to listen more to what people around me are saying, and be prepared for my expectations to differ from reality.

What kinds of events have you planned as a leader of the GSB Veterans Club?

The accomplishments I’m proudest of are the Veteran’s Retreat, the fireside chat with Gen. James Mattis, and the monthly socials.

What advice would you give to veterans thinking about Stanford GSB?

There’s a lot unique to being a veteran at Stanford and the GSB that isn’t always communicated when vets first land here. How to think through my career? How do I network? How do I translate my military skills to the civilian job market? We’re here to help mentor and guide the first-years through whatever questions they may have. During the Veterans’ Retreat, GSB lecturers Scott Brady and Robert Siegel drove home the point that while veterans may not have the same finance and accounting skills coming into GSB as those from banking, private equity, or consulting, we do have skills that make us immensely marketable after graduation.

You’re a jazz fan. Pick the one album you’d want if you could only keep one.

Idle Moments by Grant Green. I’ve been listening to that album and song for 20 years. I can put it on any time I feel like things are spinning out of control. It has a way of re-centering me and putting me at ease.

Photos by Elena Zhukova