That blog post could be a metaphor for 42floors foray into the brokerage market - the guy in the suit being 42floors:
"it’s totally fine to ask someone before you come into the office what appropriate dress means" = it's totally fine to understand the market before deciding to enter it
"He was failing the go-out-for-a-beer test and he didn’t even know it" = they just failed the go-into-a-new-market-beyond-your-means-test
Maybe Jason Freedman's lack of humility in the past led him to the idea that led to these lay-offs, and hopefully he now has some humility and focuses on the business not how much of a cliché he can make his startup.
I remember back in the nineties when tech company culture was a reaction against the stuffy, seemingly irrational dress codes of older companies. The refrain used to be "we want people who can get the job done, who cares if they wear a tee shirt and jeans instead of a suit and tie?"
Perhaps we're going full circle and the people who want to tell their employees how to dress are back in charge. But now instead of getting a choice between a button-down shirt in white and one in light blue, the choice is between a tee with a funny picture on it and one with a vendor logo on it :)
"it’s totally fine to ask someone before you come into the office what appropriate dress means" = it's totally fine to understand the market before deciding to enter it
"He was failing the go-out-for-a-beer test and he didn’t even know it" = they just failed the go-into-a-new-market-beyond-your-means-test
Maybe Jason Freedman's lack of humility in the past led him to the idea that led to these lay-offs, and hopefully he now has some humility and focuses on the business not how much of a cliché he can make his startup.