Creating the Founders’ Dilemmas Course

If Noam Wasserman's entrepreneurship elective were a start-up company, investors would be delighted with its growth.

When the Harvard Business School professor first offered his Founders' Dilemmas course in 2009, a mere 42 second-year MBA students signed up. Two years later, the School is offering four sections of the course, with 68 students in each section. Some 170 more students were wait-listed.

The course's popularity is a reflection of its universal nature—it addresses quandaries that virtually all entrepreneurs will face when trying to realize the dream of starting a company, no matter how viable the dream.

“We tackle the problems that are faced by almost any founder no matter what industry they are in, no matter what country they are in, and no matter what time frame they are in-boom or bust.”

"We tackle the problems that are faced by almost any founder no matter what industry they are in, no matter what country they are in, and no matter what time frame they are in—boom or bust," Wasserman says. "We help them to plan for the hidden minuses and the unexpected bumps."

Wasserman teaches two sections of the course, while Senior Lecturer Ginger Graham teaches the other two. They divide the course into four parts, the first three of which address timeless entrepreneurial dilemmas: deciding when to found a company, building the founding team, and dealing with investors. The last leg of the course highlights those rare founders who have achieved the entrepreneurial ideal of attaining financial success without having to give up the reins of the company.

When To Found

About 4 to 5 percent of MBA students at HBS decide to leap into entrepreneurship immediately upon graduation, or even before graduation, according to Wasserman. But "the data suggests that somewhere between 40 and 50 percent will be founding a company within a decade of getting out of here," he says.

Part one of Founders' Dilemmas helps students to figure out whether it makes sense to wait a while before launching a start-up, taking into account issues that single-minded young dreamers might not otherwise consider—including their personal lives. Early in the course, the professor essentially plays a foil to the blindly enthusiastic entrepreneur by taking on the role of a concerned spouse: "Look at the loans you have that are coming out of business school!" "I'm still in school, and I'm not bringing in a paycheck yet!" "We have two kids! You should wait until they are out of the house!"

"Even if the market is crying out for you to solve a particular problem, if this personal side is not there, it could mean the end of that market opportunity or of a critical personal relationship," Wasserman says.

In this section of the course, students study cases that deal with both early- and late-career founders. First they consider the case of HBS student Humphrey Chen (MBA '96), who struggles with the pre-graduation decision of whether to launch a start-up with a classmate or accept a cushy offer from a top-tier consulting firm. Next, they look at Barry Nalls, who describes lessons learned from starting his own telecommunications start-up, MASERGY, after working at GTE for more than two decades; in retrospect, Nalls wishes he had taken the entrepreneurial plunge sooner.

Students also study the case of major league All-Star pitcher Curt Schilling, who, as his pitching career winds down, decides to switch gears by founding a video-game company called 38 Studios. (Data suggests that a surprisingly high percentage of founders do switch to industries much different from the one in which they have the most work experience.) Schilling visits the class to discuss how his transition from one industry to another forced him to question and adust his knowledge of how organizations work, how to motivate employees, and how to finance growth.

Building The Team—finance And Founders

In the second part of the course, students consider the questions they'll face after making the key choice not to run the company alone: Who should the cofounder(s) be? Is it a good idea to bring in my best friend, or is that the worst thing I could do? How are we going to split up the roles? Which one of us will become the CEO? How are we going to split the equity among us?

"Each fork in the road brings us to a bunch more cofounder dilemmas, and as you're going down each of these paths you're running into new issues," Wasserman says.

This part includes case discussions of HBS graduate Vivek Khuller (MBA '99), who persuades classmates to cofound with him the electronic-ticketing company Smartix; Genevieve Thiers, who decides to bring in her boyfriend to help her build the caregiver marketplace Sittercity—and then has to deal with the big risks introduced by that decision; and Jim Triandiflou, founder and CEO of Ockham Technologies, who worries about losing control of the company as he and his cofounder consider various financing offers. By engaging in a real-life exercise as members of a three-founder team, students also get to experience firsthand the raw emotions of negotiating equity splits with their cofounders.

Beyond The Team—investors And Successors

Part three of the course is about "looking to outside investors once you've gone as far as you can with spending your own money, or tapping Dad and Aunt Sally for money."

Here, students study the differences between angel investors and venture capitalists. More importantly, they consider the often soul-wrenching reality that accepting outside funding means ceding some control, not to mention the risk of getting ousted from the company entirely. "It means realizing that investors take seats on the board and looking at how this may change the dynamics of the team, including the possibility of a new CEO," Wasserman says.

They discuss the case of Wily Technology, in which the founder is asked to step down as chairman of the board before the new CEO takes over. They also consider the viewpoint of the non-founding CEO via the case of Les Trachtman, CEO of Webpiont, as the founder tries to pressure Trachtman to leave the company by threatening to resign himself. And they study the case of Blogger and Twitter cofounder Evan Williams, who struggles with the challenge of steering his second startup, Odeo, without having board support for his decisions.

Achieving The Entrepreneurial Ideal

"Each of these entrepreneurs has had to give up something that really matters to them—a trade-off between something that's important to them and something that's really important to them," Wasserman says. "But at the end of the course we look at founders who were able to grow something valuable and also remain CEO of it—those rare ducks."

Still, even long-term entrepreneurial success requires an eventual exit strategy, as in the case of Nantucket Nectars, founded in the late 1980s and sold to Cadbury Schweppes in 2002. Students study the issues that founders Tom Scott and Tom First had to consider when negotiating the sale.

And even the most successful entrepreneurs deal with occasional self-doubt. Students in the course also look at the case of Brian Scudamore—who dropped out of high school to start the successful junk removal company The Rubbish Boys (now 1-800-GOT-JUNK), —as he reconsiders his decision to pursue franchising as a growth option.

"We look at the founders who were able to get to that Promised Land…and how they're different from the founders we looked at in the beginning of the course," Wasserman says.

In the end, the course is about self-reflection and foresight. (Wasserman explores these ideas further in an upcoming book, Founding Dilemmas, which will be published in late 2011 or early 2012.)

"Understanding one's self is a key thing we're trying to accomplish, so students can then look back at the class and realize, 'When I'm that person, in that position, I should not be making that left-fork decision, I should be making the right-fork decision,' " Wasserman says. "It's about choices….My research has shown that teams of friends and family cofounders have a higher tendency to blow up than teams of prior coworkers, but that doesn't mean you should never found with friends and family. It means that if you have decided that this is the best way to go, there are ways to set things up to decrease the risk of a blowup."

For more information about the challenges of entrepreneurship, please see Noam Wasserman's "Founder Frustrations" blog.