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Before creating the world's most comprehensive list of videogame cheats, Mahalo CEO Jason Calacanis worked at AOL under then-CEO Jon Miller. Calacanis joined AOL only after it bought Weblogs Inc. from him for $25 million and since Miller led that acquisition, eventually invested in Mahalo and now sits on the company's board, Calacanis is naturally a little biased in his feelings toward Miller, whom Calacanis considers a mentor. Still, when we heard talk of Miller as a contender to be Yahoo's next CEO, we figured Calacanis's opinions would at least be entertainingly biased. Our email exchange:

Vallewag: What would you think of Jon Miller going to Yahoo?


Jon Miller would be amazing for Yahoo because he is extremely good at building display advertising businesses and buying young startups. Remember, when they let him go he was coming off back to back 40%+ gain quarters in advertising revenue—second only to Google (and well ahead of Yahoo). His biggest strength at AOL—in my mind—was buying promising startups and giving them tons of support, no red tape, and breathing room. Yahoo needs new blood and a focus on display advertising, with Ross [Levinsohn, former CEO of Fox Interactive and Miller's partner at VC firm Velocity Interactive] at his side you would have a very potent operator and M&A team.

Yahoo's best strategy right now is probably to build display advertising while buying and growing promising startups. Yahoo needs growth, Jon and Ross are growth guys (i.e. MySpace,, Weblogs, Inc, etc). As a bonus you have hundreds of VP/SVP/EVP level executives out there who are loyal to Jon and Ross, so you might see a talent influx with them at the helm, and talent wins.

Valleywag: You think he'd take the job?


  • Pro: It is the most challenging job in the space second to AOL
  • Pro: Having reinvented AOL this would be cake walk/much more pleasant.
  • Push: It would require a move from East to West coast—which is both a + and -
  • Pro: It would be a great way to show the folks at [Time Warner] who's the man

I'd say if he gets the call he would most likely take it... big opps like this come along once every 5-10 years.