Investors aside, did anyone make money here?
Either way, I’m glad that they are continuing to exist. Chef was onto something with Habitat and (especially) InSpec.
The risk is that one of the later investors had a ratchet or something that would allow them to claim more of the proceeds in a sale. You can't just take $220M cash, subtract $105M in funding and pass that to the founders and employees. The preferred shares were probably "participating" meaning they get a portion of the common.
Here's an example of a ratchet: https://www.forbes.com/sites/petercohan/2015/11/07/unicorn-s...
Founded in 2008, that's 105M for some fraction (maybe a majority) of the equity... minus fees / taxes / legal costs, that's a pretty lousy investment, especially compared to market returns over this timeframe.