Alumnus Advises to “Fail Fast, Fail Often and Remain Humble.”

1.11.2024 Alumni News, Article, MBA
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Jackson Prentice (JD ‘07, MBA ’07), chief portfolio officer and executive vice president at Carr, speaks with Ashley Rogers, director of acquisitions for Residential Capital Partners and School of Business Alumni Council member, about his lifelong quest for knowledge and how it was nurtured at Wake Forest.

Ashley: Could you provide some thoughts on your early background and how that experience led you to attend Wake Forest?

Jackson: I grew up in the DC area and attended college in New England at Bowdoin College. Post graduation, I headed to California to thaw out a bit (and chase the surf dream) while thinking about where I wanted to focus the next phase of my education. My thoughts began to crystallize around the dream of attending law school. As I was doing my homework on potential schools, I recognized that I wanted to entertain schools in the Southeast. I had family in North Carolina and had vacationed in the Outer Banks for years. And, as I started looking at schools and programs, it dawned on me that adding one additional year of school would allow me to earn a joint JD/MBA degree. I appreciated the smaller school feel of Wake Forest. Ultimately, my decision was a combination of many factors, but my family’s heritage in North Carolina and the familiarity of family having attended ACC schools made Wake Forest very appealing.

Ashley: How has the JD/MBA degree shaped your career?

Jackson: In college I majored in philosophy and economics. I used both sides of the brain and really enjoyed both subjects. I knew I wanted to go to law school, and I thought doing a joint program would be a good fit for me. Looking back almost 20 years ago today, I can see it really helped me in my profession. How we were taught to think and analyze in law school is different from how we were taught in business school, and vice versa. There is a running joke that most attorneys are math phobic! Having a pedigree in both law and business helped me become a better businessperson.

I practiced law for six years at Troutman Sanders, and that proved to be a big differentiator as I transitioned over to a business role. I approach business issues differently than my peers who do not have a legal background. Whether it is how you analyze or digest information or how you approach risk mitigation, it’s a layered way of thinking about situational analysis. Regardless of the fact I am not a practicing lawyer, that thought process is ingrained in me. The JD/MBA degree has been advantageous for me in real estate because a lot of my profession is focused on negotiations. Whether it’s leases, JV agreements or broader strategic issues, using both competencies accelerated my career over the past decade.

Ashley: You have had a significant career in real estate, even dating back to your days in the legal profession. What sparked your interest in the real estate sector?

Jackson: My father and my grandfather were both in real estate, so I was always around it. However, my first passion was sports, as I played basketball through college. Once the NBA dream faded, I started focusing on academics and began to think more about real estate as a vocation. Once I started graduate school, I interned for a local real estate developer and then was a summer associate at Troutman Sanders, where I rotated through all the practices from litigation to real estate and everything in between. The transactional nature of real estate resonated with me – what we build and do, you can see and touch.

My current role is based in DC, but I have had the opportunity to expand into multiple markets and transform cityscapes all over the country, including Boston and Austin. At Carr we recently completed One Congress in Boston, which is a one-million square foot office tower in the heart of the city. Obviously, it takes a huge team to deliver one of these transformative projects, but I personally take a great deal of pride in playing a small part in our developments. When I drive around town with my son, he’ll say, “Hey Dad, there’s one of your buildings.” (Of course, every building that he sees he believes is one of our buildings!) Real estate is a relationship business with tight knit networks where your integrity and trust go a long way.

Ashley: What aspects of your current role do you treasure the most, and what aspects do you find the most challenging?

Jackson: In my current role as head of our portfolio, I am effectively overseeing our operating platform. We have several strong, diverse operating teams, many of which report to me. I sit in a unique position to be in the center of the transactional flow; I wear a lot of hats, which keeps the job interesting, fluid, and of course, sometimes stressful!

In my experience, managing people is probably the hardest part of the job. However, it can be the most rewarding as well. I have been given the opportunity to evolve as a leader in the company, which involves mentoring and growing some of our younger talent. As I gain more experience, I enjoy sharing wisdom with younger professionals, and watching them grow over time is validation of why I got into the industry. Twenty years ago, I did not understand the importance of the people component and how important it is to any business.

Ashley: What personal or professional skill do you feel is the most vital to succeeding/thriving in the corporate environment?

Jackson: It starts with a baseline of high integrity – do what you say and say what you do. Especially in real estate because when you’re transacting, people remember your integrity. I think once you’ve established that reputation, things yield themselves to you. At the end of the day, your actions speak louder than your words. When you are in a senior role, your people want to know you are in the trenches with them and that you support and empower them. The other skill that I believe is critical is the ability to multitask in a constructive manner, which I perfected while a student at Wake Forest. The ability to juggle a lot at once, absorb large amounts of information quickly, synthesize it, and then communicate it to an audience effectively is transformative.

Ashley: If you could go back to graduation day at Wake Forest, what messages would you give your younger self?

Jackson: I think “slow down” would certainly be one of the first things I would tell myself. Take the necessary time to learn about teammates and be more thoughtful about what makes them tick and how to get them engaged. This can help in building a sense of team and community. Also, I have learned that the way that I approach something may not necessarily be the same way that someone else does. Taking the time to understand different perspectives is important so as not to alienate people; this builds trust, which takes you a lot farther as a team than going it alone. Also, be aware it’s a team effort, no matter what you’re doing in the corporate world. Team building takes time and takes effort – a lot of effort. Lastly, appreciate where you are, how you got there, and the things that are happening around you. Life is moving so quickly that taking time when you hit a summit or a plateau and appreciating it before you move on is advice that I try to live by every day. Without that, you don’t have a real sense of what you have achieved.

Ashley: What is your favorite Wake Forest memory or experience?

Jackson: My relationships with classmates, as well as professors, created lasting memories. Attending graduate school at a private university in a relatively small city was unique, and the Southern hospitality made it a very warm experience. In general, graduate school runs at a frantic pace, so having faculty and staff support was critical. Many of my classmates remain good friends to this day!

Ashley: What’s your favorite professional trend, and what’s your best advice for continuously improving?

Jackson: To be a sponge and absorb as much information as you can get is critical. I am an early riser, where I check-in daily with The Wall Street Journal, The Washington Post for local and national information, and LinkedIn. I think it is important to take in content from different outlets with different perspectives so you can see all the different angles. As for continuous improvement, it comes down to humility. It’s important to understand that you don’t know everything and that you’re going to make mistakes every day. Fail fast, fail often and remain humble. If you do those things, remain hungry, and you’re willing to absorb, then you’ve got a leg up as you try to grow your career.