Looks like I have to play bad cop here. I appreciate the openness, but as a potential customer... not so much. Because while sentences like this are kind of inspiring:

  Instead, let’s give ourselves permission to fail.
  ...
  And you know what? It’s okay if we’re not. If Keen busts, we’ll all find new grand adventures. 

As a (no longer) potential customer, they clash harshly with this one:

  In last week’s outage, we had our first major data loss in over 12 months.

Because you know what? When I trust you with my money and my company's data, I don't want those precious assets to be with someone who's been given permission to fail. I really do want it to be someone who tells the troops this: "Let’s double-down, work through the weekend, push through the issues, get ‘er done, rally!"

The issue to me is public declarations vs private thoughts.

There is absolutely nothing wrong with waking up covered in flop sweat, wondering if you're destroyed your business and the job situations of people you genuinely like and appreciate.

However, I've found that a good part of leadership is, in fact, shutting the hell up when "routine" bad things are happening because too much openness can stress out employees. By "routine" I mean pretty much anything other than the certain death of the company, at which time they deserve reasonably early notice).