Finding an Entrepreneurial Path

By Karen Guzman

In the spring of 2017, Matt Dittrich ’18 walked into a classroom at the Yale School of Management for a course with Professor A.J. Wasserstein, and the trajectory of his life changed.

“I sat down in A.J.’s very first class at Yale SOM,” recalls Dittrich. “The room was packed, and about a dozen students hovered outside the doorways. Those 80 minutes changed my life. I finally found my fit at Yale—and my calling as an entrepreneur.”

Dittrich’s calling was a route to entrepreneurship known as a search fund, and Wasserstein was the perfect teacher to show him the way.

Wasserstein, the Eugene F. Williams, Jr. Lecturer in the Practice of Management, stepped back from his own career as an entrepreneur, CEO, and search fund investor in 2017 to join the Yale SOM faculty. It was a time when student interest in startups was booming, and the school’s Program on Entrepreneurship was only a few years old.

Wasserstein brought real-world experience and an affinity for mentorship. In the classroom, he pushes students to tackle business opportunities and challenges as if they were entrepreneurs and CEOs. Students discuss case studies—Wasserstein has written dozens of them—and quiz their protagonists, who are periodic guest speakers.

His underlying message to students is simple, Wasserstein says: “Entrepreneurship is a marathon, not a sprint. It’s an endurance test, not necessarily an IQ test. The most important personal characteristic in an entrepreneur is grit.”

It’s a message that has stuck with Dittrich. “A.J.’s true magic comes from the passion and perseverance—the true definition of  ‘grit’—he demonstrates,” he says. “His behind-the-scenes mentorship, lesson planning, academic writing, and community building are what make him extraordinary. My front-row seat to his classroom performance and backstage pass to his practice have motivated me to become a better leader—and a better human being.”

Wasserstein has developed four courses at Yale SOM, all related to aspects of entrepreneurship. All of his courses use, build on, and apply the tools and concepts established in the Yale SOM core curriculum. Wasserstein’s popular Entrepreneurship through Acquisition is the introduction to search fund entrepreneurship that changed Dittrich’s path. In the search fund model, an aspiring CEO raises money through investors and purchases a company to lead.

“It’s a model that catapults you from classroom to CEO within a few years of completing an MBA,” Wasserstein says. “Since you’re buying a business, rather than starting one, you don’t have to have a brilliant idea. It also eliminates the hardest part of being an entrepreneur—the first mile.”

Dittrich launched his search fund, Blue Wood Capital, after graduating from Yale SOM. “A.J.’s mentorship inspired me,” he says. “Three years later, he’s still at the top of my iPhone contact list, and not just because his name starts with ‘A.’”

The course, Dittrich says, offered a deep-dive opportunity to fully explore the search fund model, its strategy, and how to enter the space. Dittrich went on to found the Yale Entrepreneurship through Acquisition Club. 

Wasserstein’s teaching and mentorship have staying power, according to Dittrich, because he pushes students to develop their set of values and leadership philosophy to guide their careers. “Values create a compass,” Dittrich says. “If you understand what matters most, you know what path to strike when life is full of uncertainty. Launching my company at the beginning of the COVID-19 pandemic, I can’t overemphasize how much this compass has empowered me.”

Wasserstein helped Ross Butler ’21 to jump start his own search fund career before he even graduated from Yale SOM. Butler took Wasserstein’s Entrepreneurship through Acquisition, and before the course’s end, he had purchased BPI Information Systems, a cornerstone of the I.T. industry in northeast Ohio.

“I view A.J. as both a professor and a mentor,” Butler says. “He has a unique ability to support while not shying away from hard truths. He was instrumental in my decision to pursue BPI while at SOM.”

Jennifer McFadden, associate director of entrepreneurial programs and lecturer in the practice of entrepreneurship, says Wasserstein approaches course development the same way he approached launching new ventures.

“He starts by taking a deep dive on a topic and immersing himself in the research,” McFadden says. “He then masterfully combines deep research and tactical advice to give students the practical experience they’ll need to succeed. He’s passionate about inspiring the next generation of leaders and gives so much of his time outside of the classroom to current students and alumni."

Helping students discover “their own voice and compass” is at the heart of teaching, Wasserstein says: “There is no single correct approach to entrepreneurship or leadership. Two students sitting next to each other can have wildly different styles, and both can be right.”

And there are many possible avenues for entrepreneurship. “Search funds are just another path that might resonate with a subset of aspiring entrepreneurs,” Wasserstein says. “My job is to show students lots of doors and let them decide which is the right door for them.”

Not all of them enter that door immediately. Michael Warady ’17, a joint-degree graduate of Yale SOM and the Yale School of the Environment, spent a few years working for a family investment office after graduation.

“After deciding to start my own company, one of my first conversations was with A.J.,” he says. Wasserstein’s insights and probing questions pushed Warady to examine his own plans and motives in a new and clarifying way. Today, he is president of the Sylmar Group, which seeks to acquire businesses in the water and wastewater sectors as a route to address growing water quality and availability issues.

“A.J.’s experiences are undoubtedly one of his greatest attributes, but it’s his humility in understanding that everyone has a different style and a different path that makes him a truly effective mentor,” Warady says.

Elizabeth Davidson ’20 took two of Wasserstein’s courses, served as a TA, and wrote multiple case notes and cases with him. Today, she’s an associate at the innovation consulting firm Innosight, but has an eye on an entrepreneurial future.

“In A.J.’s classes, representation matters,” Davidson says. “He exhibits a wide range of entrepreneurs, so that all students might be able to find themselves in one or two. This approach really helped drive home the point he ended every class with: You can do this!”

Davidson also credits Wasserstein for her solid grounding in corporate finance, learned through exposure to case studies and real-world problems.

“‘Do the math’ is a phrase A.J. repeated often, and it rings in my head frequently,” Davidson says. “Since I didn’t come to SOM with a quant background, I sometimes shied away from doing the quantitative analysis in groups or taking the time to do a quick discounted cash flow to better understand a company’s valuation. After A.J.’s classes, I felt confident that I could, and should, do the math.”

Before coming to Yale SOM, Wasserstein founded the records management company ArchivesOne and led Onesource Water, a bottle-less water service business. After selling Onesource Water, Wasserstein realized the time had come for his own career switch.

“Being an entrepreneur is a super gig,” he says. “It’s a complete reflection of your vision, values, and strategy. It’s a pretty amazing feeling to build something that is bigger than yourself that excels.” But he wanted to pursue an encore career that was more about service and helping others. And he discovered that teaching was his second calling.

“I love it,” Wasserstein says. “I get to read, write, research, and talk about topics I’m passionate about, and I’m surrounded by amazing students and faculty in an energizing community. It’s a dream opportunity.”

Wasserstein tells his students that anyone who’s willing can take on an entrepreneurial role. “Entrepreneurs aren’t anointed, selected, or ordained,” he says. “The only thing special about an entrepreneur is that they made a decision to take the first step in a long and ambiguous journey, and they’re willing to fail.”

One piece of advice that he offers to all aspiring entrepreneurs: choose a business with strong economic characteristics that underpin the industry, so you are tilting the odds in your favor. “I like to be in simple businesses that are enduringly profitable, and I don’t care what industry the business is in, as long as it is legal and ethical—and has fantastic economic characteristics. Of course, the business needs to be a fit for the entrepreneur, too.”

Wasserstein also encourages students to consider the scope of their entire lives. He encourages his own children to do the same in a book he wrote for them, What Matters Most: A Young Adult’s Roadmap to Life. A career—even as a highly successful entrepreneur—built at the expense of a fulfilling personal life is a formula for regret, Wasserstein says: “Being an entrepreneur isn’t everything. At Yale, I hope students discover their personal values, life goals, and career aspirations—and how they all fit together. After graduation, students need to know where they’re trying to go, and what success will look like for them to get there. That is part of educating leaders for business and society.”