Casey Gerald

Bio

"If you want to understand the entrepreneur, study the juvenile delinquent. The delinquent is saying with his actions, 'This sucks. I'm going to do my own thing."
– Yvon Chouinard

When Casey Gerald is asked about his entrepreneurial philosophy, he mentions the quote from Chouinard, the iconoclastic rock climber and founder of Patagonia. Rather than a focus on the wealth creation and empire building that drives most entrepreneurs, Gerald, the co-founder and CEO of MBAs Across America, is motivated more by the opportunity to change a chaotic world. And given his tumultuous backstory, Gerald has stubbornly clung to the idea that fixing things that are broken is a path worth taking.

To that end, MBAs Across America is an organization formed by Gerald and three Harvard Business School (HBS) classmates in order to send MBA students out across the country to offer free assistance and guidance to small business owners. By helping these businesses both tactically and strategically, the goal is to have an impact by taking the learning from inside the hallowed halls of business schools out to those who could really use the guidance and insight. Getting funding for this innovative enterprise wasn’t easy but Casey and his team refused to throw in the towel. Eventually, with support from HBS alumni like venture philanthropist Arthur Reimers, who wrote a check for $50,000, and an infusion of capital from such outlets as the Rock Accelerator, MBAs Across America became an actual organization.

“I have looked at HBS as a secret garden,” Gerald said. “If you dig under the rocks a bit, if you look behind the bushes, if you have that extra five minute conversation with somebody, the most magical things can happen because of this place.”

In its first two summers, MBAs Across America sent out teams from business schools such as Stanford, Columbia, Babson and UCal Berkeley, traveling more than 40,000 miles into 28 cities and towns to work with 50 entrepreneurs across the heart of America.

“We have three measures of success,” Gerald said. “First, is it transformational for MBAs? The answer is yes. Second, are we providing deep and lasting impacts on entrepreneurs? The answer is yes. And third, are we telling stories that can pierce the culture? And the answer is yes.” Going into its third cohort, the program has already seen a 150 percent increase in applications from 30 of the top business schools in the country.

Gerald believes in slow growth with a focus on quality rather than numbers. “The idea this year is to get better, not bigger,” he said. “A lot of what we are doing is figuring out what scale looks like in a collaborative way.”

The vision is more than a bit radical. According to Gerald, the organization will launch an initiative called MBAsx2020 in July, 2015 which effectively writes its obituary. On July 4th, 2020, if all goes according to plan, MBAs Across America will cease to exist. “We’re going to self-destruct the organization,” Gerald said.

The goal is ambitious. Rather than think of success as having 35,000 MBAs participate in the MBAs Across America program, a better outcome is for the business schools themselves to offer this type of opportunity for the local entrepreneurial community. In that way, they can help to create a generation of business leaders who are a central force for progress in the world. To that end, Gerald believes, every business school ought to offer an experience like this without the need of an outside organization to set things in motion. “How can we codify this experience and make it modular enough so that it can go viral?” he said. “How do we help create a country where every entrepreneur in every community has the resources they need to draw from?”

By stamping an end date on the mission, Gerald is hopeful that he can bring a wide array of stakeholders to the table, working in collaborative fashion, “to build a movement, to answer these questions, and not perpetuate our organization.”

You obviously see the world differently than a lot of people. What led to this world-view?

I was raised in a neighborhood called Oak Cliff in Dallas by a collection of extraordinary witnesses in the community, including my grandmother. My parents were sort of out of my life by the time I was in middle school, which was a typical experience for a kid in my neighborhood and neighborhoods like it across the country. I wound up being recruited to play football at Yale, which was a totally life-altering exercise for a kid like me. No kid from my high school had ever gone to a place like that, but it seemed to matter so much to the folks in my community. I’d go to church and the old ladies would be crying. People stopped me in the store, “Oh, you’re that kid going to Yale.” I thought, `If it means so much to them, it must be a good thing to do.’

You were a four-year starter at defensive back at Yale but you were also a great student. And yet, you had some jarring experiences there.

I was a finalist for a Rhodes Scholarship and on the day of my last Harvard-Yale game, we not only lost that game at Harvard Stadium, but I went into the locker room after the game and got the news that I had lost the Rhodes. It was the first time I had failed in a major way. I went from being a celebrated scholar-athlete to a two-time loser. You couldn’t hide from this thing.

How did you rebound from that?

I got an email from Rick Levin, the president of Yale at the time. He said `Casey, I know you must be very disappointed today, but I just wanted to welcome you to the club of failed Rhodes Scholar finalists.’ And he listed all these amazing people who had gone on to be very successful from this failure. It was a critical lesson for me; a really liberating experience of failing in something that you deeply believed in and put your heart into.

You considered becoming a lawyer but eventually decided against that. What drew you to HBS?

Here I was, this poor country bumpkin from Texas and people always say that money can’t buy you happiness. But growing up, my friends and I knew that most of the reasons we were unhappy were because we didn’t have any money. So this idea that you could go and actually provide a life for yourself and your family was extraordinary. I wound up working as an intern at Lehman Brothers in the summer of 2008. My first day, they fired 3000 people. To be there in the thick of things as the whole world was falling apart was an extraordinary education. At the same time, I was being educated about the fact that just making a good paycheck wasn’t going to come anywhere near the kind of meaning that I needed in my life.

What do you mean?

I had this question that had always been in the back of mind: Why me? Why am I the one who made it? Why am I the one who got a chance? So the paycheck priority seemed to ring a little hollow. I had gone to a lecture at Yale Law School during my junior year and the speaker said, `If you wanted to change the world in the 20th century, you had to go to law school. But in the 21st century, if you want to change the world, go to business school.’ It made so much sense to me. After working on policy in the Obama Administration and seeing the rampant cynicism that crept up so quickly, it was heartbreaking. So many of us had our political hearts broken in those years. So after going through all this Sturm und Drang, it was time to come to HBS. I needed a reset.

How did your HBS experience impact your outlook?

I hear this often and it’s shocking, but people feel more themselves at Harvard Business School than in any other place they’ve ever been. And that was really true for me. The people I found at HBS—friends, section mates, classmates—are not just friends, they’ve really become family. The intellectual element—I don’t want to call it the academic element because I spent far more time talking to professors than I did reading cases—was being faced with a situation or a challenge that you have little or no prior knowledge about, with imperfect information and extreme time and resource constraints. You’ve got to develop a way to think through an approach to solve this challenge. You’ve got to figure out very succinctly a way to articulate that approach and defend your approach against 90 other people who might fundamentally disagree with you. That was extremely important for me.

How did this impact you as an entrepreneur?

If you consider the exercise of building a company, of trying to build a movement, of being a leader in a time of chaos, the experience of going through Harvard Business School was extremely critical to developing those abilities. If you think of the Yvon Chouinard quote, it helped me become a secure juvenile delinquent. MBAs Across America wouldn’t exist without Harvard Business School.