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@Velocio
There were two bits of his pitch which impressed me, and both related to understanding his market and the challenge.
The company with the largest share of this market (offering desks ad-hoc) is Regus with their business lounge model. They have only 6% of the market. That's the biggest... the market is massively fragmented with no clear leader.
Their biggest competitor: Starbucks.
And that's when I was sold. He's right, when you have a few hours to kill between meetings, it's wifi you seek out, a place to rest your bag and grab a seat whilst you try to fit in a couple of hours work.
The problems with Starbucks though is the need to consume to justify the space, security of your possessions (especially inner-city), keeping the seat (if you need to go to the loo), the noise and distractions (if you're trying to work and need to make phone calls).
And that's basically where I went from being "Nah, that won't work", to "You know, he may have a chance... so long as he gets the location and the convenience is there, he might just crack it".
Understanding the problem you're trying to solve and the market is the first thing. And I actually think he gets that bit. The bigger high risk question is more whether he is the one that can actually make it work by getting landlords on board to put their empty space to good use.