Money To Burn: The Best Of Dotcom Era Advertising
Remember when a half-baked business plan, a 5-minute logo, and absolutely no revenue model besides “uhm, I dunno, sell ads, maybe?” got you millions in VC funding, a sweet Silicon (V)alley office, massive parties, and puzzled looks from everyone who wanted to know what the hell a “dotcom” was?
Mmm. The good old days. Until the bubble burst, of course, but between 1997 and early 2000, the Party Was On. Everyone got into the game. Actual entrepreneurs, fake entrepreneurs, Stanford MBAs and engineering students, caterers … the long tail was pretty damn long.
Advertising agencies got into the Good Times too.
Join me on a trip back to an era where a brand was only as good as how much cash they blew on a Super Bowl spot, a time where my Mom wondered what the hell that “period-see-oh-em” thing at the end of every commercial was, a time that my non-industry friends burned with jealousy but were able to point and laugh when things came to a crashing halt.
In no particular order…
We’ve decided to fire gerbils out of this cannon…
Thanks to the team at Cliff Freeman and Partners, when we finally discover that the gerbils are actually in charge, we may be in some trouble. This spot debuted in 1998. The gerbils were PISSED.
He’s got money coming out the wazoo.
Best. E*Trade. Spot. Ever. This still makes me giggle.
Well, we just wasted $2 million bucks.
Indeed you did. Wasn’t really funny then, not funny now. Note to current and future creatives – proudly joking about how much money you burned is probably not a brand-building concept. Also, while Hewlett-Packard started in a garage, I don’t think there were many monkeys present.
Don’t let anybody tell you it’s easy.
This one has a special place in my heart; I know from personal experience that herding cats is not easy.
Computer stuff explained.
A single-word domain name that makes the product self-explanatory. Enough cash for a Super Bowl spot. Approachable, friendly founders. But … it’s the SUPER BOWL! How much money was wasted on this local-spot-for-a-non-chain-restaurant-that-has-Senior-Tuesdays-every-week-esque shit?
Because pets can’t drive.
No dotcom spot round-up is complete without at least one mention of the pets.com sock puppet.
But we don’t know diddly about making ads.
No shit, guys. That’s why you hire experts.


























Technology Director @ Wieden+Kennedy. Founder / CEO @ Oakley+Partners. Former VP, Technology & Production @ EVB. Co- founder, Flavorpill Productions. Caffeine addict. Serial entrepreneur. Smartass.