I didn't know how to do fancy

How I got my dog on Craigslist, and other adventures.

This weekend will mark 25 years since a big milestone at Craigslist: the date on which founder Craig Newmark first registered the domain name, craigslist.org.

Up until that time, for two years, Craigslist had simply been ... an email newsletter that founder Craig Newmark sent to people. (See! I was only 25 years too late!)

Now it reportedly does $1 billion a year in ads—mostly the $25 and $50 fees that people who want to advertise jobs and houses have to pay. For most people, however, it's free.

I first met Newmark in 2011 when I was writing for the military newspaper Stars & Stripes, and he was putting up serious money for veteran causes.

But I didn't realize then just how financially successful he'd been until I saw more recent reports on his philanthropy: $1 million to the progressive magazine Mother Jones, $20 million to the journalism program at CUNY, millions for other journalism, veterans, and election protection organizations.

(One published estimate, based on a bit of forensic analysis in Forbes, puts him at well over $1 billion.)

Most of his stake is still in Craigslist, which is just as reclusive, but which analysts think has a 75 to 85 percent profit margin. That means it's an extraordinary cash cow.

To put it all in perspective, and appreciate just how different Newmark is compared to all of the other billionaire tech entrepreneurs floating around Silicon Valley and the Bay Area, you need remember two points

First, Craigslist is basically bootstrapped, and that it wasn't originally supposed to be a company.

And second, consider what life was like in 1995, when that first email went out:

• Jeff Bezos had just moved to Seattle. He hadn't launched Amazon yet.

• Mark Zuckerberg was in 5th grade. Monica Lewinsky hadn't even become a White House intern.

• The #1 song in America was "Gangsta's Paradise" by Coolio.

• There was no PayPal. If you won an auction on eBay, you had to mail a check.

Newmark had no idea that the site could ever be so successful at first. And why would he?

He says its spare, old-fashioned design was mainly a result of his own limitations as a designer back when the whole thing launched. ("I didn't know how to do fancy," he once said.)

Perhaps most amazing is that when he did start to see the potential, he took an honest personal inventory and decided that he wasn't the best person to lead the company he'd created.

He recruited and hired Jim Buckmaster in 2000, and let him take over as CEO.

"I was able, to some extent, to divorce my ego from my CEO role. And I'd had a lot of lessons," Newmark said in an interview. "I'd seen micromanagement be a big problem in the tech industry. I just saw lots of situations where people screwed up by interfering with people who could do the job."

Anyway, I love coming across these odd little digital notes to history, like the Internet receipt showing when Newmark first registered the domain.

It was so long ago that you might not even have had to pay for it—at the very least, you could claim a domain and promise to pay via check later.

And in that spirit, allow me to list my best Craigslist transactions over the years:

• The 1987 Volvo I bought for $375 cash one night, after I'd worked late in Virginia and realized it would take probably 2 hours to take the Metro home, and here was this car for sale a block from my office.

• My dog, Lily, whose owner told me she was a lab-beagle mix but was obviously mostly pit bull. She was with me for about 7 years. I ultimately learned I was her fifth human, and I took her on a reunion tour to see all the previous people. I've toyed with writing a short book about this forever.

• An amazing, cheap, 4-bedroom apartment in Jersey City, NJ, about a baseball throw from the PATH train to NYC, with a giant backyard and enormous ceilings. It was so cheap because the landlord hadn't bothered to post any photos in his Craigslist ad, and because it had no photos I assumed it was probably a scam. But I had time to go by and look, and my wife and I lived there for three years.

Thanks Craig. Not a bad list, indeed.

(Low power mode ends soon! But not quite yet. Maybe another day or two. Reminder, we’ll be skipping the “7 other things” we normally run. But I invite you to share links to things you think your fellow readers would appreciate or enjoy in the comments.)