I recognize the irony. The reason it's ironic is because it's doomed to fail. You cannot raise money in order to lessen the influence of money. If this campaign does anything, it will simply invite opposing groups to raise more money in order to elect anti-campaign finance reform candidates.
What's important isn't a success or failure (in Lessig's "trial" election cycle or in 2016). I think his point is: people care enough about campaign finance reform to help raise $5m in a month.
If candidates knew this was something their constituents cared about, they might actually run on it.
Who cares if Lessig fails. We're finally talking about campaign finance.