Love, e-company style

(Business 2.0 Magazine) -- For Ben and Mena Trott, there was never any doubt about which of them would be the voice of their startup. After all, she was the one who strode into the Baskin-Robbins in Petaluma, Calif., where he was working and asked him to the senior prom. "He was the valedictorian, and I was the class clown," Mena recalls.

It was the beginning of a productive - and profitable - partnership. The high school sweethearts went on to found Six Apart, which makes one of the most popular blogging tools on the Internet, attracting more than 40 million unique visitors each month.

Ben & Mena Trott, Six Apart - The high school sweethearts founded a company that offers popular blogging tools including LiveJournal, Movable Type, TypePad and Vox.

Xochi & Michael Birch, Bebo - They took a chance on each other after meeting in a British pub. Six startups later, they've created one of the top 10 social networks in the United States.

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The Web, it turns out, is filled with companies run by married couples. Most of them are tiny mom-and-pop operations destined to stay that way. But several have blossomed into hit websites with millions of users and all the attendant pressures and complications.

For example, Bebo, the giant social-networking site with 35 million registered users, is run by two serial entrepreneurs who met in college. Nerve, one of the first online magazines, was co-founded by CEO Rufus Griscom and is now run by him and his wife, Alisa Volkman, the vice president for sales. The founders of Flickr, the No. 1 spot on the Net for sharing photographs (sold to Yahoo for a rumored $30 million), had to mortgage their house to keep their fledgling website going.

Running a thriving business is hard work. Staying married may be even harder. So how do these couples do it? Having weathered the entrepreneurial storms and made both their companies and their marriages work, the husbands and wives behind Bebo, Flickr, Nerve, and Six Apart were kind enough to share the secrets of their success.

Ben and Mena Trott have been together since they were 17, so you might assume they're inseparable. Over time, however, they discovered that one key to running a husband-and-wife business is spending plenty of time apart.

For the first years of Six Apart, the couple worked out of their spare bedroom, five feet from each other. But working with your spouse has its own special pitfalls. "For the first four years of our marriage, we had not been apart for more than five hours at a time," Mena says.

Then one day Mena didn't feel like going to a Fiery Furnaces concert that Ben wanted to attend. And soon after, she traveled by herself to a SuperNova conference in Washington, D.C. They found that they enjoyed their time apart - individually, they had strengths they lacked when joined at the hip. Today the co-founders have separate offices and rarely share responsibilities. Mena has become the company's most visible spokesperson, while Ben focuses on behind-the-scenes product development.

This has its drawbacks, as Ben has learned. "Occasionally our employees are surprised," he says. "They don't immediately realize that we don't always have the same opinions." But the two are now as comfortable with their separateness as they once were with being inseparable. "It allows us to miss each other," Mena says. "It's when you don't miss the other person that things get dangerous in a marriage." In a business partnership too.

When Stewart Butterfield first met Caterina Fake, he didn't propose marriage. He proposed that they start a company together. She was an inveterate overachiever, and perhaps he sensed that this was the way to her heart. They did eventually get married, in June 2001, and achieve business success, but the journey wasn't easy.

December 2003 was especially tough. The company they were running at the time, Ludicorp, which was trying to develop a multiplayer online program called Game Neverending, was struggling. Back-end development was six months behind schedule, and they were short on both money and time. They had enough cash to try one last thing before they went under. Making matters worse, Butterfield had the flu and spent a night struggling to hold down food.

The next morning he had a wild idea. They would use their remaining money to go in a totally new direction - a photo-sharing website. That's how Flickr was born. And although they had to take out a second mortgage on their home in Vancouver, British Columbia, to keep the company alive - "We literally bet the house," Fake says - it was worth it. They sold the company to Yahoo (Charts, Fortune 500) less than 18 months later for a rumored $30 million.

"I've seen many, many relationships fall apart because one of the partners is in a startup and is giving it most of their time and attention," Fake says today. "It's hard for the other partner to compete with something so all-consuming." But there are rewards, she says, both financial and emotional. "There's nothing like sharing an intense, life-changing experience with someone to bring you closer. Late nights, early mornings, laughter, terror, white-knuckle meetings with people you desperately need to give you money, getting your first check from a paying user - how can you beat it?" she says.

Sometimes the second company is the one that makes it. And sometimes it's the second relationship that survives. Ten years ago Rufus Griscom started Nerve Media, now a thriving online magazine business, with then-girlfriend Genevieve Field in an apartment with about 500 square feet of floor space. "One advantage of co-founding a company with your girlfriend is that it's an incredibly efficient use of real estate," Griscom says. "We got a lot of value out of that little space." The pair's edgy smart-smut site, Nerve.com, survived the early shakeout days of Web publishing. Their relationship did not.

But, by his own admission, Griscom is a slow learner. In 2001, while he was dating Alisa Volkman, he and his team hired her on spec to sell film rights to some of the stories that were appearing on Nerve. Volkman was later brought on to pump up the site's ad revenue. The couple married in 2004 and had their first child in 2005. He's still CEO of Nerve, while she is the vice president for sales at Nerve Media. In December the pair launched Babble.com, a hipster parenting site that is on track to be profitable this month.

Despite this muddle of personal and professional, Griscom now has strict rules about separating the two - a lesson he learned the hard way. "In the early days, we didn't have much of a business, so we were eager to sell the story of Genevieve and me," he says. "But now there is a successful business, so we focus on that." At work, he and Volkman try to keep their relationship low-key. "It's in the elevator ride up to our offices that a transformation occurs," Griscom says. "We start the ride as a couple and end it as business associates."

Michael and Xochi Birch also lived through times when quarters were close and the future uncertain. They met as college students in a British pub. Now, two children and six startups later, they've learned that the key to both business and marriage is to trust their instincts.

When the pair launched social-networking site Bebo in 2005, it was their sixth startup together; previous efforts included Birthday Alarm, an e-mail service they started in the United Kingdom, and Ringo, a social-networking site that they ended up selling to Tickle.com.

While they were making the transition from the United Kingdom to the United States, the couple lived briefly in Xochi's parents' house in Pittsburg, Calif., along with 10 other family members, sharing a bedroom with their two kids. "At one point I had a server delivered at the house," Michael recalls. "The deliveryman was very distrustful and checked my ID. He had a hard time leaving that box with me."

The travails and uncertainties didn't discourage the two from taking risks. If anything, it gave them confidence in their ability to plot a path and change course as necessary. Bebo, for example, first launched as a Flickr-type photo-sharing site in January 2005. "A month after launch, we had 6 million users," Michael says. "But we realized that this was not the site we had intended to launch. We were interested in helping to create new communities. Six months later we relaunched as a social network."

Their course correction proved to be the right move. From their base of 6 million users, they began growing pageviews at 10 percent per week. Now they have more than 35 million registered users. They also moved out of that bedroom and bought a house in July 2004 after looking at it only once. Like their relationship, it was love at first sight.