Sasha Novakovich (MBA ’99) was in her second year at HBS when she and classmate Tracy Lawrence got the idea for what would become GetConnected, a company that processes voice, data, and video services transactions for retailers. Despite some ups and downs, it thrived. Eight years later, a competitor acquired the company’s technology and Novak-ovich was back at HBS, this time as an Entrepreneur-in-Residence (EiR). “My primary charter was to help students who were interested in starting businesses upon graduation,” says Novakovich, who served as an EiR from 2007 to 2008. “But going back to school in that capacity was rejuvenating for me as well. Suddenly I was in a situation where I could really think about different kinds of business problems and potential opportunities because I wasn’t constrained by my own operating reality. It was a great way to give back to an institution that afforded me so many opportunities.” (The EiR position is unpaid.)

Novakovich also researched and wrote a case with HBS faculty Mike Roberts and Bill Sahlman and offered a four-part “how-to” series for students interested in the nitty-gritty details of starting a new venture. “Nothing I did felt like work,” she says. “It was so different from being an operator and having a product, deadlines, and customers.”

Now in its sixth year, the Entrepreneur-in-Residence program invites accomplished entrepreneurs to the HBS campus for a year to collaborate with faculty and advise students who have the start-up itch. This year, for the first time, the program expands to four individuals whose lives and experiences show what different roads the entrepreneurial journey can take.

“Students are hungry for the kind of perspective they can get from people who have one or both feet in the world of entrepreneurship,” says Senior Lecturer Mike Roberts, who also serves as executive director of the Arthur Rock Center for Entrepreneurship. “As much as our faculty is connected to practice, students still see us in the role of evaluator. They feel freer to confess to nonfaculty their ignorance and fears about starting a business .”

Todd Krasnow (MBA ’83), an EiR from 2006 to 2007, describes the year as “all the fun of being on the HBS faculty without the heavy lifting.” He held brown-bag lunches, sat in on classes, and coauthored a case with Roberts and Sahlman on financing Zoots, the dry-cleaning service he cofounded in 1998. He also advised a number of student teams competing in the HBS Business Plan Contest, an event he judged in previous years. “It made me feel good that three of the four finalists that year, including the winning team, came to me for feedback,” he says, “and that the plans they submitted were quite a bit different from what they first showed me.” A member of Staples’ original management team, Krasnow is currently a domain expert in marketing at Highland Capital Partners, a Boston-based venture capital firm.

I spoke to this year’s EiRs as they were settling in — too early to assess how things were going but not too soon to tap into their collective insights on launching a new venture. Private or nonprofit sector, up market or down, the observations that follow highlight the many approaches to what it means to be a successful entrepreneur in today’s marketplace.

Bussgang

All illustrations by Joe Ciardiello

Jeffrey Bussgang (MBA ’95) is collaborating with faculty member Noam Wasserman on a case to be taught in Wasserman’s elective course Founders’ Dilemmas: Money and Power in Entrepreneurial Ventures. Targeted at future entrepreneurs, the class considers early decisions that have important long-term consequences for founders and their ventures, particularly the issue of whether to cede company control for financial gain. “Rich versus King is a very familiar paradigm for me,” says Bussgang, an early hire at Open Market and cofounder of Upromise, an online college savings vehicle acquired by Sallie Mae in 2006. Now a general partner at Flybridge Capital Partners, Bussgang represents the firm on the boards of BzzAgent, ClickSquared, DataXu, digitalArbor, Mall Networks, Simple Tuition, and Transpera, among other new ventures. An avid baseball fan and father of three young children, Bussgang also writes a blog, Seeing Both Sides, that offers venture capital perspectives from a former entrepreneur.

When I graduated from HBS in 1995, the market was pretty desolate. There wasn’t a lot of start-up activity. Shortly after that, we had a huge boom. Compared to that time, things are more normalized and sane. We’re seeing more experienced, repeat entrepreneurs who have created valuable companies and been through the IPO cycle and the M&A cycle.

I think entrepreneurship and innovation are still strong. The contraction in the venture capital market doesn’t shake my confidence in the industry and its potential to work with entrepreneurs to create massively exciting and valuable companies. There’s just as much entrepreneurial energy out there as there ever has been. If anything, it’s accelerated. You see it at HBS, where more and more students want to start new businesses.

When you’re running a company, it’s a very lonely job. If you’re at a venture capital firm, you can share all the ups and downs with your partners and collaborate in a way that’s very fun and unique.

Being an entrepreneur is an extreme, emotional roller-coaster ride. I don’t miss the extreme lows, but I miss the adrenaline of the extreme highs.

In choosing a business plan to fund, I look for a unique perspective on an enormous market opportunity. By that I mean a great team with an advantage — a unique angle, set of relationships, or intellectual property, for example — that sees something that others don’t see. You have to be convinced that three other people with the same idea in Silicon Valley or Bangalore, India, would not be able to out-execute this team.

Passion, tenacity, and a magnet-like ability to draw talent, supporters, and partners are all key attributes of being a successful entrepreneur.

There are huge, huge market areas right now that are suffering from great dislocation and transition, and for which technology innovation has an opportunity to create tremendous value. Health care, the Internet economy, financial services, and energy technology are all very interesting areas for start-ups.

My advice on work-life balance is to first have a clear and detailed contract with your spouse as to what expectations they have of you and what expectations you have of them. Compartmentalize and set boundaries. Don’t be afraid to say no. Don’t be afraid to unplug.

Decker

Susan Decker (MBA ’86) came straight to HBS from Tufts University, where she majored in economics and computer science. As an analyst at Donaldson, Lufkin & Jenrette, Decker covered Yahoo!, a company she would join as CFO in 2000 before serving as its president from June 2007 to April 2009. The mother of three school-age children, Decker is on the boards of Berkshire Hathaway, Costco, and Intel. “The EiR program seemed like a good fit, in that it’s an advisory role that keeps me focused on an institution I care about while also allowing a bit more time flexibility than I could have when I was running Yahoo!’s operations,” Decker says. She will devote part of her EiR year to helping with the MBA Silicon Valley Immersion Experience Program (IXP) in January and collaborating with faculty on cases related to entrepreneurial management.

My summer jobs in college involved programming computers. One year I worked for a subsidiary of General Electric, specializing in the creation of a fourth-generation programming language. It helped pay for school, and I enjoyed the discipline. It also taught me early on that you can often add more value quickly and have a greater impact as a specialist than as a generalist.

One of the themes we talked about a lot at Yahoo! is fast failure. You want to create a culture that encourages taking risks and trying new things. If they don’t work out or fail, which many of them will, you want to do that quickly, so you can regroup and go on to the next new idea or product or opportunity within the organization.

I was at back-to-school night for my first grader a little while ago. The teacher said that they’re trying to encourage the kids not to fear failure by having a mistake jar in the classroom. Every time someone makes a mistake, they put a little note in the jar about it. And when it’s full, everybody celebrates. I thought that was great.

In every musical composition, there are notes and pauses. And the pauses are as important as the notes in the production of the entire piece. Now that I’m in a pause, I realize how much I really wanted and needed it. If the right opportunity came along sometime in the next few years, and it worked with my life, I’d love to do it. But I’m not spending any time thinking about it now. The thing I feel so blessed to have is time to spend in the moment.

A lot of the industries that are going through major reorganization or collapse were probably headed there in five to ten years anyway. It’s a difficult transition, but it’s exciting in the sense that this economic recession is forcing transitions faster, quickly crystallizing areas where there may be real opportunities on the one hand and exposing areas that will never be competitive on the other.

The pool of capital may be more limited. But I’m not sure that’s a bad thing. The VC industry went through a phase where it expanded enormously in capital and attracted professionals who were very deal-oriented. Now it seems to be retrenching, returning to its roots.

When the water is highest in the river, you can’t see the rocks. Right now you can see the rocks. There’s more clarity on which areas are not likely to be competitive and which will be important places to spend time.

Sharpe

As the protagonist of a popular case in the required curriculum course The Entrepreneurial Manager Jim Sharpe (MBA ’76) is looking forward to stepping off the page to advise students who may be pondering some of the same questions he considered when he made the decision as an up-and-coming employee of General Electric to pursue his long-term goal of buying and managing his own company. Sharpe, who hired his wife, Debby Stein Sharpe (MBA ’81), as CFO, sold Extrusion Technology (an aluminum extrusion fabricator) to a private equity firm in December 2008. In 21 years, the company’s annual revenues grew from $4 million to $32 million. Sharpe will be attending and contributing to Entrepreneurial Management in a Turnaround Environment, an elective course cotaught by faculty members Paul Marshall and Bruce Harreld.

Not everyone is cut out to be an entrepreneur. It’s lonely, it’s risky, and it doesn’t always work. There are compromises and disappointments. For some people, the level of uncertainty is not a good thing.

I didn’t have a great idea or start something new that I thought up on my own. It was an existing business that we radically changed over the years. In a manufacturing-related business, change is a constant renewal process.

I was surprised when Kent Bowen approached me about doing a case. We were just a small manufacturer. I didn’t think what I did would be relevant in the classroom. But there were actually quite a few students interested in the practical decisions and trade-offs around leaving a career in a large corporation to buy and run a business, as well as the questions of working with your spouse and maintaining a balance between traveling and having time for family.

“Entrepreneurial,” for me, meant running my own company. It wasn’t a start-up that required intense, all-encompassing energy 24 hours every day, which made it possible for me to achieve some level of work-life balance. But I had to be willing to live with not seeing as many customers, or maybe not moving into as many markets. At one point I had to make a decision about buying a competitor. Debby and I talked. The kids were three and five years old at the time, and we were thinking of adopting a third. We decided that we didn’t really need to do the acquisition and expanded our family instead.

It was far more challenging to get out of the business than it was to buy and run it. I thought it was difficult to spend a year looking for a business to buy when I had no money, and people didn’t really want to talk to me. But it took around ten years to sell it, which is a very long exit strategy. We could have found somebody to liquidate the business and take it off our hands, but that wouldn’t have been best for our employees or our customers. It just took that amount of time to do it right.

The downturn in the economy has been helpful for entrepreneurship. It’s caused a lot of individuals to think about controlling their own destiny. More people will think about striking out on their own, whether they’re a hairstylist, a carpenter, or an MBA.

My priorities today are significantly different than they were thirty years ago. After I left HBS, I was very focused on developing my skills, learning new things, and surviving in a big corporation. In other words, it was a lot about me doing stuff for me. Now I’m more outward-focused and more interested in helping other people and giving back what I’ve learned.

Walker

The former chairman and CEO of CCMP Capital, the $12 billion successor to JPMorgan Partners’ global private equity group, Jeffrey Walker (MBA ’81) has spent years doing headline-making deals. Now, as chairman of Millennium Promise (MP), he helps lead an organization with the vision of ending extreme poverty worldwide by 2025. Despite this shift, Walker sees more similarities than differences between his careers in the private and nonprofit sectors. He traces his current work to his earliest involvement as a member of his local board of education; since then, he’s served as chairman of the JPMorgan Chase Foundation and sat on the boards of the Big Apple Circus and many other organizations. In 1999 he founded NPower, a nonprofit that provides back-office technology support to other nonprofits. At HBS, Walker will assist Professor Lou Wells in organizing the Rwanda IXP; he’ll also collaborate on a case about New York City’s Robin Hood Foundation with Associate Professor Alnoor Ebrahim and work with Professor Dutch Leonard on developing cases on the topic of “active philanthropy.”

I’ve always loved taking an active role in growth enterprises. Working on companies like JetBlue and Office Depot was fun, interesting, and fulfilling. Now I feel like I’m back in those early days but on the nonprofit side, helping organizations reach the next level of professionalism, growth, and access to funding. It wasn’t a startling, night-and-day change from the private to the nonprofit sector; it was more a normal, evolutionary process.

Any successful organization starts with people with a gleam in their eye, who can get passionate and excited about an idea or concept. Being able to share that vision is an important part of any nonprofit and for-profit strategy. Then you can go back and see if it has the potential to be scalable, if it’s going to have sufficient impact, if the management team is solid, and if there’s an appropriate measurement system.

The vision of Millennium Promise is simple: to end extreme poverty worldwide by 2025. The organization was founded by Columbia University’s Jeffrey Sachs and philanthropist Raymond Chambers. They believe that innovation requires building an organization that’s separate from larger, more bureaucratic, and historically stable entities. I’d always thought that Africa was the next generation’s problem — that it was just too tough. But the more I looked at MP’s Millennium Villages initiative, the more similarities I saw to what we did in the private sector in raising funds and funneling them to smaller incubators.

Villages are the foundation of change. The idea behind Millennium Villages is to bring a holistic approach to development, targeting agriculture, education, health, and infrastructure. We’re leveraging the knowledge and expertise of local clusters of experts and raising funds so that we can support eighty test villages across ten countries and measure our results in each of those key intervention areas.

We raised about $130 million from 64 angel investors in our first round of funding and have been on the ground for four years. Since then we’ve lowered malaria by 85 percent, increased the number of eligible children attending school by 25 percent, and boosted agricultural output by two to four times, depending on the area. Now we’re talking to the UN, the World Bank, USAID, and others about scaling the village program to a countrywide level.

A continuing theme runs through my interests and priorities, whether it’s the early days of Office Depot and JetBlue to what I’m doing now at MP, working with someone like Jeffrey Sachs, who wants to literally save the world and thinks he knows how to do just that. It’s a classic entrepreneurial belief — that I know the answer. I love working with those kinds of characters.

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