Achievement-oriented people are given to depression both when they fail and when they succeed. If your identity is tied up in your work, then you feel bad about yourself when work isn't going well. That's obvious, and that's the message of this blog post. The implicit message is that you're depressed because you're not succeeding, so get your shit together and succeed and be happy like everyone else.
But then if you do succeed, you start to wonder, why did I just spend my youth in this masochistic, narcissistic path, and why the fuck am I not as happy as I was expecting, and is this really all there is in life. This is a classic "achiever in crisis." The problem is that you realize all along you've been doing things that OTHER people wanted -- that is, you've been doing things that make you valuable in society -- perfect summed up in the raison d'etre du jour, "making the world a better place." And nobody stopped you, because who can argue with making the world a better place? (Or being a doctor, or whatever.) But upon reflection, you quickly realize that this was in many ways easier than asking yourself what YOU wanted out of life. I.e. you've pushed aside your innate feelings and desires, whatever they may have been, and replaced them with the external motivation of achievement, under the rationale that you'd be able to "figure it out" after you had "made it".
Unfortunately achievers aren't really sure what they want "deep down" because achievement is inherently defined by society, and then after they've "made it" they freak out because they start to wonder if there even is a "deep down" or if they're just a highly educated donkey chasing a carrot.
If you talk to e.g. people who've gone through rigorous Ph.D. programs, you'll find a number of them were severely depressed after their defense. It was just kind of a let-down after such a long buildup, and then they started to wonder why they invested the entirety of their twenties into it and question whether that's really what they wanted their life to be. At least before the defense they could have something look forward to, and the various requirements provided a source of manic energy to propel the achiever forward.
Anyway I don't think the problem here is "not enough success," and I don't think the solution is having more coffee meetings. Founders need to take a hard look in the mirror and ask themselves why they're doing what they're doing and whether their depression is truly a function of their free cash flow or if there's a deeper dissonance between the founder's feelings and the expectations of society, i.e. the heroic mythology of the founder that Silicon Valley has been inculcating in susceptible teenagers for the last 20 years.
Just my 2c. I am not a founder just an observer and aspiring societal psychiatrist. If you want to learn more I highly recommend "The Wisdom of the Enneagram":
It looks a lot like astrological pseudoscientific trash but read it and see if things in it resonate with you.
Ok back to work.
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