Entrepreneurs have to be ambidextrous. Take me. Lately, I've had to double as director of marketing (I'm normally president of zipRealty.com) because we launched our real estate Web site before we managed to fill the position. It's harder than it looks -- especially when you're also trying frantically to salvage the very thing you're planning to advertise. How do I know? Hear the saga of our first ad placement to promote our Aug. 29 site launch.

Advertising can be a black hole. Done badly or placed wrong, it's a waste of money. We had ruled out television right off because of the production time and cost. We figured the other media would be open to us. Not exactly. Getting a radio ad proved relatively complex, too. As for billboards -- one vendor said he had a great space on Highway 101 near Silicon Valley -- just $240,000 for six months. And I thought TV was pricey! That left newspapers. We researched the subject carefully and discovered what anyone who has looked for housing in the U.S. in the past 75 years knows -- home buyers look first at the Sunday real estate sections. Thus we decided to invest our advertising pennies there. This seemed an easy task. Call the newspapers, tell them what you want, they print it and send you a bill. Of course, nothing in life is that easy.

We thought it was reasonable to know the cost first. Alas, you can't get that information on the phone. First, each newspaper sends a glossy folder outlining its virtues over other media and providing demographic information. (Nice, but I need costs.) After a little digging, you find a rate chart. Now complete confusion sets in. Each paper has its own special rate schedule tied to different plans. Prices depend on the section, the date of the ad, and how much you advertise in the paper. Some bill by column inch. (What is a column inch?) Others by line. (Ever tried converting column inches to lines?) Others make you give them money up front, which you draw down as you use ad space. You can add colored bags, inserts, or sticky notes for specific ZIP codes. The sky's the limit -- and before you know it your bill is up there, too.

Being MBAs, we knew what to do. Create a spreadsheet. That, at least, let us compare apples to apples so the ad design phase could begin. We made it a team effort. The design group that had done our stationery and business cards mocked up a few ads and ran them by the entire company -- and their families -- at one of our Family Dinner Nights. After a month of trial and error, we had our ads, a signed contract, and an agreement on where to run them. All we needed was to call the papers. A warning, fellow entrepreneurs: You could have a heart-stopping moment if you don't heed those deadlines. Luckily, we got our stuff in on time.

Finally, on the 29th, we bought all the papers we could to check placement (and to see our ads, of course). Two out of three looked right. The third paper put us on page A6. We had nobody to blame but ourselves, because it turned out we had mistakenly asked for that slot two weeks earlier. Not perfect -- but pretty good, considering that while this was happening, we weren't even sure we were going to have a site to trumpet. Imagine. Newspapers full of ads, and no product. We made it across the tightrope again. See you in two weeks.

Scott Kucirek is president and co-founder of zipRealty.com, an online real estate brokerage. The company's Internet site and online real estate agents let people complete the entire purchase or sale of a house via the Web. The company's Web site is www.zipRealty.com, and you can E-mail Scott at Scott@zipRealty.com.