Double Impact: Entrepreneurs Prove that Life is Too Short for Just One Career

On May 30, Philip James ’05 wrote an e-mail to his team at Lot18, the wine e-commerce site he founded in 2010 that has since raised more than $44 million from investors.

“Starting in June, I’ll be riding my motorcycle around the world in order to raise money for Wine to Water, a charity that supports water projects in 15 countries,” James wrote. “I’ll visit some of the most desolate and destitute areas of the world to raise awareness for and assist in providing the aid these places require.”

By the time he hit the road on June 10, James had already raised enough money to fund 22 water filters in Uganda, which will provide clean water to more than 500 people for up to 10 years — “a great start, but a long way to go,” says James, who is documenting his journey and soliciting donations on his blog.

Not everyone shares James’s appetite for adventure. (He’s been known to convince venture capitalists of his tenacity by telling them about his climb up Mount Everest.) But James is one of many alumni who is driving change in more than one industry or sector, using one track record of success to inform another. Here, get to know — and get inspired by — three of them.

Two Fast Tracks

Deborah Jackson ’80 has always considered herself an entrepreneur — even when she joined Goldman Sachs straight out of business school. She started on a Monday and by Thursday she was in Memphis, TN, working on the firm’s largest healthcare transaction. “You had to hit the ground running,” says Jackson, who worked for Goldman for 10 years. “I spent most of my time on the road, on my own, figuring out what needed to be done and making that happen.”

That entrepreneurial drive led Jackson to found a boutique investment firm and then launch the healthcare technology and Internet practice at Shattuck Hammond Partners in the mid-1990s. Working with many doctors and developers who were starting companies, Jackson helped them bring innovative products to market — including the first software that transferred medical claims from doctors’ offices to public insurance companies.

But more than 20 years of nonstop travel and trade shows left Jackson depleted. “Sometimes when you’re working that intensely for that long, you need to create some distance and reassess,” she says. She spent a few years exploring areas that had always interested her — organic gardening, day trading, serving on nonprofit boards, learning about and investing in early-stage companies, and coaching women who had founded tech companies.

“I really enjoyed helping them with their business plans,” says Jackson, who also became an active member of Golden Seeds, a group of angel investors focused on women entrepreneurs. “My investment banking career gave me the ability to understand credit and financial projections, whether it’s an early-stage company or my own start-up.”

It became clear to Jackson that what she really cared about was helping women launch companies — and investing in those companies. In 2011 she cofounded Women Innovate Mobile (WIM), the first start-up accelerator designed for women-founded companies in mobile technology. “I think of it as mentorship on steroids,” says Jackson. Once accepted into the program, participants receive seed funding, business support, and access to a network of mentors, funders, and advisors. WIM receives an equity stake in each company.

Despite the enormous growth of women-owned companies over the past decade, their success stories, says Jackson, often fly under the radar. A recent report from American Express Open found that between 1997 and 2013, the number of women-owned businesses grew at 1.5 times the national average. But “there is so much commentary that women aren’t in tech, that women don’t take risks,” says Jackson. “I felt there needed to be a dedicated site and voice championing women’s innovations and accomplishments.”

Last fall, Jackson launched Plumalley.co, an e-commerce site supporting women entrepreneurs. To be featured on the site, “we have to think that the woman, her product, and her company are amazing,” says Jackson. In its first 10 months, Plum Alley profiled more than 50 entrepreneurs and was featured in the New York Times, Vogue, and Forbes.

Fast Company included Jackson in its 2012 League of Extraordinary Women, and in June, Forbes selected her from more than 1,000 nominees for its inaugural “40 Women Over 40 to Watch” list.

“Week by week, you can see what we’ve built,” says Jackson. The site offers a digital database of female investors, a map of female founders, and original infographics illustrating important trends related to female entrepreneurs and investors. Plum Alley also recently introduced a crowdfunding platform where founders can raise money for specific projects.

“There isn’t a week that I don’t go home on Friday thinking, ‘How did we do that?’” says Jackson. “It’s astonishing to me.”

Moving Up and Over

Peggi Einhorn ’80 never forgot the advice she received from the treasurer of the Metropolitan Museum of Art when she was an intern there the summer after she graduated from college. “She told me that you shouldn’t be afraid of moving between the private and public sectors,” says Einhorn. “That really resonated with me.”

Today Einhorn could be featured in a case study on exactly that sort of career agility. After various roles in arts administration, she climbed up the global finance ladder before serving as treasurer and CFO of the Robert Wood Johnson Foundation (RWJF), the country’s largest healthcare philanthropy. Since assuming that role in 2004, she likes to tell people she hasn’t had a single bad day. “Every day we talk about driving social change,” says Einhorn. “How different is that from driving shareholder value?”

Back when she graduated from Columbia, Einhorn never imagined she’d spend 24 years not only driving shareholder value at a global bank, but moving up through senior roles in business planning, investor relations, corporate treasury, and financial operations, ultimately surviving two mergers and serving as a senior vice president. Her entry into banking was fortuitous: her father introduced her to his friend Neale Godfrey, who happened to be a rising star in the industry. (She went on to become president of the First Women’s Bank in New York.) “Neale was vibrant and vivacious, and she was charting a path for women,” says Einhorn.

Inspired by Godfrey and by the industry’s international clientele — Einhorn had lived overseas and spoke Italian — she joined Chase Manhattan Bank in 1980. Along the way she frequently served as a mentor to other women and played an active role in the bank’s internal women’s groups. Another mentor and colleague, Dina Dublon, was the first female CFO of the corporation. “She was a real trailblazer for women and an inspiration to us all,” says Einhorn.

It was following the bank’s merger with Chemical Bank that Einhorn bolstered her nonprofit credentials. She applied for and received a David Rockefeller Fellowship from the New York City Partnership, joining 12 other executives for workshops on all aspects of city government. She also stepped up her “parallel career” as a board member of the Brooklyn Children’s Museum, serving as chairman during an $80 million expansion.

When a fellow board member talked to Einhorn about the CFO position at RWJF in 2004, the timing was right: the bank was on the verge of another merger, and Einhorn was retirement-eligible.

At RWJF, a big part of Einhorn’s job is advising the president and board about meeting the foundation’s annual 5 percent IRS payment requirement, which includes helping to set spending levels and tracking progress against them. With $9.5 billion in assets, the foundation is required to give away approximately $450 million each year. Einhorn sees her key objective as “ensuring that the foundation spends its money fast enough (to comply with the requirement) and spends it well.” To that end, among the first things she did was develop a robust modeling and forecast system. She also raised the quality of communications with the board. “Both were second nature to me because of the approach to analysis at the bank and the emphasis on simple and consistent messaging.”

Three years ago, when the foundation launched its Impact Capital Initiative, a $100 million allocation to make program-related investments, Einhorn had a funny sense of déjà vu: “This is work that is very financially oriented: transactions with credit that require an assessment of risk. So at one point in my career I was analyzing borrowers on the commercial side, and now I have the opportunity to take those skills and use them directly on loans that are part of social missions. How cool is that?”

Going Rogue

It’s hard to find someone who has played as big a role steering the wine industry into the digital age as Philip James ’05.

With Snooth, the site he founded about a year after he graduated from Columbia, James created the world’s largest online wine community, with millions of price listings and wine reviews. The site has more than 1.5 million monthly visitors — more than any other wine website — and also powers wine recommendations on Epicurious.com and myRecipes.com.

With Lot18, which launched in 2010, James gave consumers direct access to hard-to-find wines that are typically crowded out of the market by big brands. A Gilt Group for wine, Lot18 selects wines from around the world that are available on the site for a limited time. Once you plug in your zip code, Lot18 will determine which wines can be shipped to you legally — “navigating an incredibly complicated infrastructure of state regulations,” says James. In less than two years, Lot18 enabled members to purchase more than one million bottles from over 500 wineries around the world.

Although Lot18 has supported water charities throughout its history, James found himself personally drawn to Wine to Water when he read a memoir by its founder, Doc Hendley, a few years ago. “Wine is the ultimate luxury good, but there are billions of people struggling to find clean water, who can’t even conceive of such an indulgence,” says James, who is funding his expedition himself and giving 100 percent of the money raised to Wine to Water.

During his journey, James will cross more than 50 countries. Over the summer he rode across the United States, flew to South Korea, and took a ferry to eastern Russia. After crossing Siberia and Mongolia, he fell off his bike in Kazakhstan and broke his collarbone. Two surgeries later — one in Kazakhstan and another in the UK — he was back on the road. He crossed Turkey and is now travelling across Europe before he embarks on the most arduous part of the trip — the circumnavigation of Africa. There he’ll visit several of Wine to Water’s projects and “trust his life” to the same filters that they use.

Wine to Water began in 2004 as a series of wine tastings to raise awareness and support for the global water crisis. According to the World Health Organization, more than 3.4 million people die each year from water-, sanitation-, and hygiene-related causes. Ninety-nine percent of these deaths occur in the developing world. Wine to Water works to provide clean water and sanitation in 15 countries, including Cambodia, Ethiopia, Haiti, India, Sudan, and Uganda.

To follow James on his journey, visit his blog at wineandwater.org. “I’ve been most fulfilled seeing the impact of giving back to those so much less fortunate than we all are,” James wrote there. “Please know that as little as 10 cents can provide clean water to one person for a year. It’s easy to make a difference, and I hope that in this way you can share in the excitement of this journey.”