I first learned about What's Next? in 2006 when it offered me what I thought at the time would be my next job. I was working as an editor at a national men's magazine and, having survived several regime changes that had put all but a handful of my peers out on the street, I liked the symmetry of joining a magazine devoted to helping people like me figure out their second acts. What's Next asked me to just hold off giving notice until it finalized the contract with the major media company that had agreed to pony up the $4 million (on top of the $750,000 it had already raised) that would bankroll the venture. "Don't worry, it's just a formality," they said.

When the deal fell apart, I was disappointed, but not as disappointed as the three veteran former publishing industry executives who had devoted the previous 24 months of their life to getting the project off the ground. One of whom, it turned out, was my neighbor.
That's how I got to be friends with Mark Gleason, or as I came to think of him, my karmic professional-life alter ego. For the next several years, as he and his partner Jeremy Koch continued to try to figure out a way to launch What's Next?, every time Mark got an actual paying job in our increasingly infirm and decrepit industry, I'd lose mine, and vice versa. It was as if the industry was just too physically far-gone to employ us at the same time.

Then last fall it gurgled up one final sputum of layoffs and closures, and we both lost our jobs. As our wives headed off to work, now we spent our days scheming over various ephemeral consulting gigs and our efforts to resuscitate our respective media ventures -- two suburban dudes with several-hundred-thousand-dollar mortgages and $10,000+ a year in property taxes (his are actually $15,000), still trying to figure out what's next.

Then a few weeks ago, Mark called with some good new news: "You should check out the site. We went live today." Sure enough, three years after we first talked about it, there it was. Cool.

"After the market crashed in September, there just seemed to be more need for this than ever," Mark explained. "When we originally conceived of it, we thought of the audience as Baby Boomers, people in their 40s, 50s and 60s, who had made a decent amount of money with big companies in the '80s and '90s and were now looking for more fun or fulfilling ways to spend the second half of their careers. But now a lot of those people need to find new careers, particularly since a lot of the jobs that have been lost, especially in fields like finance and media and real estate, are probably never coming back. So we saw a real opportunity and we developed a business plan and decided to get something out there quicker."

The site, started with $100,000 in seed capital, is a more modest enterprise than what we used to talk about, with a solid core of sound, useful meat-and-potatoes advice and resources. There's a section called Careers 2.0, for example, with instructive stories of inspiring second acts, like the realtor who opened her own detective agency, or the high-powered New York couple who relocated to Park City to run the museum there and start a management-consulting business out of their house, or the banker who bought a small-town zoo. There are also places to purchase detailed guides to navigating specific career changes (the first PDF for sale is on becoming a teacher), buy downloadable self-assessment tests and search for career coaches and financial planners in your area.

Any thought to publishing a print magazine, obviously, has long been abandoned. "Do we wish we had that $750,000 we spent on direct-mailing and focus groups? Sure, but we don't waste a lot of time crying over that," says Mark. "We did learn a lot about the market in that time."

One thing they learned is that trying to build a site with millions of visitors that can generate significant revenue from display advertising is definitely not the way to go. "The web has become too crowded and the ad rates are too low." What can work is creating a smaller more targeted audience, and selling them stuff, and charging for listings by services that need to reach your specific audience.

"We charge $20 a month per listing for the career coaches and financial advisors," Mark told me. "That doesn't sound like a lot, but we're confident that within five years, we'll have 7,000 to 10,000 listings on the site. The same goes for the guides and tests. We only have one PDF on the site now, but by the end of next year we should have 100 and be selling several thousand a month."

I pulled out the calculator. Those numbers aren't Google, but they're impressive enough. Again, very meat-and-potatoes, or the sort of approach you might expect after five years of having your more expansive ideas puffed up, burst, inflated again and vaporized by what passes for so much of the entrepreneurial environment these days.

Which doesn't mean it will work, or work in time to help Mark out of his latest predicament. He and his partner are now out beating the bushes again, trying to raise enough capital to start drawing salaries and hire a staff. Meanwhile, two weeks ago Mark's wife got laid off from her job as a marketing executive for a developer of luxury resort properties. So now they've gone from a one-income household with a several-hundred-thousand dollar mortgage and $15,000 a year in property taxes to a no-income household, which, in my experience, is even less sustainable than one-.

"We'd like to think she'll find something soon," he said. "But then I look at some of my neighbors who've been out of work for a year. So we'll see."

Fortunately, he says, his partner Jeremy has committed to continue devoting full-time to What's Next, even if the funding fails to materialize as quickly as they hope -- "and I'm looking at reinventing myself and maybe leaving the media business altogether." In particular, he's begun exploring leveraging his experience as the president of our town's school board to hook on with one of the dozens of more entrepreneurial education initiatives and private-sector firms like Teach For America that have popped up in recent years.

"On the site we make a big point of encouraging people to look at areas that they're passionate about," Mark said, "but that also have growth potential. And education clearly has that. Obama is pouring billions into it." It could be what's next.


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