One of the most challenging aspects of being in a startup is finding money. Being in a startup doing something that hasn’t quite been done before makes it even tougher. “What exactly does your company do?” Um, well, uh, we generate content for Web sites. We run a Web site about books. We do RSS feeds on book news, blogs, etc. We’re kind of a newsroom for hire. Then you get that sideways look. Then we mention MSN and Random House as clients and they say, “Oh.” But landing that startup money, that’s not easy. You need to articulate your vision for the company, then find the right match for an investor. It’s like finding a kidney donor. Matching blood type alone won’t do it.

Wearing more than one hat in a small operation has its own challenges: balancing the sales end of things with making the widgets — in our case developing content for our site and for clients. And sales requires two oars in the water: One oar is prospecting, the other is servicing clients/building the widgets. If you don’t have both oars working, pretty soon you’re just spinning in place.

Diane Evans, “the boss,” was just in a meeting with a prospective angel investor. We should know by tomorrow when we can eat again (I exaggerate, but not much).

By the way, the rest of our mighty crew is Rick Rubright as the skipper and evil sales dude, yours Truly as Gilligan, Mike Needs as the Professor.

For many would-be entrpreneurs, one of the more distasteful things involved in a startup is fundraising, or dialing for dollars. Unless you hit the lottery (one in 20 million chance) or a sugar daddy/mama comes through (not likely), you’re gonna need to raise funds. And as you do that, figure for a year’s worth of labor, lawyers, accountants (assuming you’re not one yourself, and we’re not), office space (maybe), supplies, labor/salaries (maybe) — add all that up, then triple it, and you’re getting close to a realistic startup cost. Have a concrete business plan, in writing, and be prepared to revise it. A lot. Thank God for modern software. 30 years ago that rewrite meant spending untold hours hunched over the IBM or Smith-Corona typewriter, clack-clack-clacking away. Now, you just boot up your laptop and delete and insert. What could be more fun than that?

And so, with business plan and 30-second pitch ready to go, start dialing. Ask for money and ask for referrals.

Diane Evans, “the boss,” has been dialing for dollars for something like two years. She’s at it again today. She enlisted my wife to assist. It’s hilarious, they carry on like sisters. Through trial and error, Diane’s gotten really good at pitching. And we’ve made some amazing connections. I’ve made some small contributions, getting our foot in the door at the Cleveland Clinic and a connection with world’s most connected guy, Daniel Moneypenny. If you don’t know Daniel Moneypenny, you don’t know squat. Cuz he said so.

Prospecting leads to meetings and, sometimes, a deal. It all takes a lot of time and stomach-churning moments. But when it works, it is awesome.

One success story: MSN.com. More on that later (above).