For Serial Entrepreneurs, More Is Better

Serial Entrepreneur Janet Kraus
Credit: Larry Lawfer
Serial Entrepreneur Janet Kraus

Janet Kraus started developing her entrepreneurial skills at seven, when she loaded vegetables from the family garden onto her wagon to sell to neighbors — packing the smaller tomatoes into three-for-a-quarter lots and tying her mom’s ratatouille recipe to the jumbo zucchinis to make them more enticing.

James Currier, who grew up near a New Hampshire lake, showed similar instincts at six, starting a homegrown business to supply visiting fisherman with worms.

“I knew where they were. They were underneath the apple tree,” recalls Currier, who put up signs around the lake, offering worms for sale, and “made a lot of money doing that as a six-year-old, seven-year-old, eight-year-old.”

Kraus, 45, and Currier, 44, both grew up to be successful serial entrepreneurs, each co-founding and selling multi-million-dollar companies.

While they don’t all start as industrious tykes, serial entrepreneurs appear to share a number of characteristics, including creativity, salesmanship, independence, high energy, an affinity for people and a collaborative spirit. Nerves of steel seem to help, as does the example set by entrepreneurial parents. In many cases, serial entrepreneurs prefer starting businesses to expanding them or running them long-term.

“I think the most fundamental driving force is that they become constitutionally unemployable,” says Irv Grousbeck, consulting management professor at the Stanford Graduate School of Business. “They get out there and see the exhilaration of creating something. Their ideas are tested in the marketplace, not in a supervisor’s judgment.”

“Once they get in that environment, entrepreneurs don’t want to go back and work for someone else. They want to be self-employed because there’s so much freedom,” adds Grousbeck. Entrepreneurs can enjoy happy investors and customers and a board that loves them, hire good people and set the company’s culture, he says. “It’s a source of great pride for them.”

Currier, CEO of San Francisco-based Internet-business developer Ooga Labs, agrees. His company website displays a letter in which he discourages young engineers from taking a “cube job” withMicrosoftor Oracle or a “boring” financial company, encouraging them to head to the world of tech startups.

Currier has started several companies, including online self-assessment business Tickle, which he and his business partner sold to Monster Worldwide in 2004 for $110 million. Four years earlier, the same week the tech market started to crash, the company, which generated some of the Internet’s earliest “viral” content, received a $7 million in venture capital days before it would have missed payroll.

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“I think growing up in a household where your parents are making their own way in the world teaches you that you can make your own way in the world, and that the world is yours to shape ... that you can survive if the world goes badly and survive if the world goes well,” says Currier.

“There is ego, there is a drive to show others that you have succeeded and to get their admiration and to get their appreciation and, if you want to get real psychological, to get their love,” he says. “There’s a muse there where you are driven to create.”

Currier compares serial entrepreneurs to movie directors, who spend several years assembling a film and telling a story before moving to the next project.

Rod Drury
Rod Drury

New Zealander Rod Drury, 45, who spent much of his early career working in software development at Ernst & Young, ultimately transformed his teenage fascination with computer technology into a career as a serial entrepreneur.

He, too, has helped found several businesses, including software company Glazier Systems, sold for some $7 million in 1999, and e-mail intelligence concern AfterMail, sold to Quest Software for $15 million in 2006.

Drury believes his mix of technology, sales and people skills have served him well. And because New Zealand is a smaller market, he was able to take smaller steps, working his way to doing bigger deals in his late 30s and 40s.

“By that time you have so much so maturity, so much confidence,” says Drury, now a New Zealand Stock Exchange board member and CEO of online accounting portal Xero. He also recently helped found Pacific Fibre, which aims to build an underwater cable to connect Australia and New Zealand to the United States.

While he expects Xero to be his last CEO stint, he plans to keep his hand in the technology space as a board chairman and investor after leaving an operational capacity in a few years.

“I just love it, it’s so much sport. It’s just a huge amount of fun. I love meeting great people and building stuff and seeing it used around the world. It’s really intoxicating,” says Drury.

Making Things Happen

Excitement and a sense of making things happen seem to be two driving factors for serial entrepreneurs.

Kraus, a senior lecturer at Harvard Business School, has started and sold two businesses, including concierge service Circles, which Sodexo purchased in 2007. She now invests in startups and sits on the board of five early-stage companies.

Kraus said she realized in her 20s that she wanted to start her own business — with a partner — rather than stay in a consulting career as an employee. Deciding what type of service to offer, Kraus and her co-founder picked a customer they understood, “the time-starved, busy woman,” and in 1997 launched an online personal-assistant business.

“It was just really, really early,” by about five years, as consumers didn’t know how to reach the Internet much less how to use a credit card on it, says Kraus.

Her firm refocused on corporate customers who could offer the concierge services to employees or members. After Circles grew to a $50 million revenue business, Kraus realized she wasn’t sure she was the one to take it to $250 million.

“I sold that company and started another the next day, literally the next day,” says Kraus, who likes the startup phase. “It’s fun. “It’s electric, it’s like nothing else.”

But every serial must end — sooner or later.

Kraus, Currier and Drury — all in their mid-40s with young children — have either shifted or plan to move from CEO to director-investor roles.

“I've probably started six companies and currently I’m trying to run none of them," says Currier, who, in addition to Ooga Labs, is in charge of its startup health technology firm, Jiff Inc. "I'm trying to be a chairman of a lot of these right now. I'm running two and I'm looking for CEOs.”