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Lucky for Vox Media CEO Jim Bankoff, business is good. For a somewhat new media company, it has several successful branches — the Verge, Eater, Curbed, SB Nation. While Bankoff once held a high ranking position at a legacy Web company (AOL), he seems content working with a newer, fresher brand.

But what if he weren’t at Vox, where would he rather be? Tonight, Sarah Lacy, at PandoMonthly in New York, asked whose shoes he’d rather be in, Tim Armstrong’s or Marissa Mayer’s. His response, which he pondered for a few seconds with wide unblinking eyes, was Mayer’s.

Bankoff himself is an alum of the former AOL empire, and back in those days, he worked as EVP of programming and products. He witnessed firsthand the difficult impasse of bridging old Web 1.0 companies to the landscape of broadband internet and websites post dot com crash.

Companies whose business was premised on a dialup ISP business plan invariably saw troubles. “Once a brand starts to decline, particularly for structural issues like a dialup ISP business, [it] is a very hard, if not impossible, thing to turn around,” he said. For AOL, the dialup infrastructure it championed was being eclipsed by an ever evolving business, and faster speeds, thanks to broadband.

So, in Bankoff’s estimation, AOL’s problems aren’t necessarily Armstrong’s fault. “I think AOL struggles fundamentally,” he said diplomatically.

He points to a perfect storm of business problems. There was the moving away from dialup, the AOL-Time Warner fiasco that almost bankrupted the two, and the $850 million boondoggle known as Bebo. These predate Armstrong and represented “over a billion dollars in blown capital,” Bankoff said. And, as he told Lacy, it’s hard for companies to respond after undergoing from the worst merger in history then blowing a billion bucks.

For Armstrong, “this is just that hand that [he’s] been dealt.” At the same time, though, Armstrong bet (and lost big) on Patch. Another hit to the company’s bottom line.

Mayer, on the other hand, had similar but less catastrophic problems at Yahoo. Yes, it was an early web company adapting to the new New Media, but she didn’t have to deal with a catastrophic merger and initial blown capital. And it definitely wasn’t built on a dying business structure. Between the two, Mayer was dealt the better hand.

“Marissa is doing a lot of innovative things to set Yahoo on a new growth course,” Bankoff said. So, he’d choose her stilettos over Armstrong’s Nike’s.

At the same time, Vox is probably a better bet of the three. And Bankoff, I’m sure, agrees.