Before the economic crash, many Americans over age 50 were telling pollsters they intended to start businesses rather than retire after finishing their primary careers. Now, the ranks of would-be entrepreneurs are swelling out of necessity as the recession pushes more people into premature early retirement.

How are 50-plus entrepreneurs faring in the current tough economy, and what valuable lessons are they learning? I spoke recently with two very different types of midlife entrepreneurs who got their start before the crash. One raised venture capital to launch an online venture; the other started a sole proprietorship that develops educational books and multimedia about career and life transitions.

Their stories illustrate the diverse ways baby boomers are transitioning to midlife entrepreneurship. This week, we’ll focus on the experience of Robin Wolaner, the founder of TBD.com; next week, we’ll hear from Steve Vernon, founder of Rest-of-Life Communications.

Wolaner actually isn’t new to start-ups. Her first big splash came in 1987 when she started Parenting magazine–just as huge numbers of Baby Boomers were busy having babies of their own. She later sold the magazine to Time Inc., where she continued to work on magazine success stories like Martha Stewart Living and Sunset Magazine.

Two years ago, she launched TBD.com, a social networking site for boomers. The name is short for “to be determined”–a reference to Wolaner’s belief that baby boomers are embarking on new adventures in life.

TeeBeeDee is a place where members can do what Wolaner calls “purposeful networking”–comparing notes, getting ideas and inspiration. Although plenty of boomers are joining Facebook, Wolaner says that’s about “managing the relationships you already have.” TBD, by contrast, is for “meeting new people and sharing passions about what’s going on in your life now.”

Wolaner, 55, was inspired to start TBD by her own challenging life transition experiences. She’d taken some time off from fulltime work to spend more time with her young children and to write a book about her experiences as a woman in corporate management, called “Naked in the Boardroom: A CEO Bares Her Secrets So You Can Transform Your Career” (Fireside, 2006).

But after a divorce and a bout with breast cancer, Wolaner found herself asking how she wanted to spend the next part of her life, and that led her back to her love of doing start-ups.

TBD launched well ahead of the economic downturn, with initial start-up capital of $4.8 million. And while it has enjoyed robust growth in traffic, Wolaner’s plans to raise new funds to grow the business have stalled, so the company has been tightening its belt. “We had planned to raise money in 2008–and 2009 is worse, so we’re trying to get to self-sufficiency from what we raised, with a small team,” she said. “It’s a lot harder than I thought it would be, but I don’t know anyone whose business is easy this year.”

Wolaner hears often from TBD members interested in starting their own businesses. “People need to find a way to create meaningful work for themselves in this horrible economy,” she says. “I think people are finding that they can get by on less than they thought they could, which you need to do when you start up, no matter what. There are financial sacrifices you need to make, and in this environment it’s a lot easier to take the leap.”

Despite the recession, she sees plenty of plusses to starting up in the current economy. “It’s a good time to buy anything you need–your dollars go further, the available talent pool is deeper. ”

However, with the tough climate for fund-raising, no one should expect venture capital to come flooding through the door for unproven operations. She advises entrepreneurs to bootstrap their ventures wherever possible. “Venture capitalists are very scared, so you need to start it first and demonstrate traction before you can attract capital.”

Wolaner recalls using her own credit cards to start Parenting–probably not a wise funding strategy in today’s shaky banking and lending climate. You should also avoid tapping into retirement funds if at all possible.

It’s also critical to take the time to identify a business niche where you’re confident demand will exist. Pursuing your passion is great, but also give some thought to trends in the economy and where the government is focusing its economic stimulus efforts. Some of the best current bets: education, the new green economy, health care and just about anything related to aging.

Next week: Steve Vernon.

Tags | entrepreneurs, start-up