[jstandard]

Agree the essay was a great read. I didn't see anything to suggest the OP missed that fact so much as had a reaction to a specific part of the essay and wished to discuss it.

Being a part of the SV startup ecosystem myself, I also see the term "lifestyle business" used as a soft-perjorative for "not ambitious enough".

[graeme]

That's exactly how OP was using it though, with full awareness. OP's mindset at the time was "I failed: I meant to start a billion dollar business, and I only have a crummy lifestyle business"

They now have come around and appreciate their success. Their use of "lifestyle business" was chosen to convey their own negative attitude at the time.

The comment I replied to totally missed that the author wasn't critcizing their own business! They just felt badly about it a few years ago. See the part of the comment where they praise gumroad.

A more self aware comment would have merely decried the prevailing VC attitude that led the founder to feel bad. Instead the commentor seems to think the founder needs cheering up and convincing.

[jstandard]

I see your point. The admonishment to Sahil at the end to "stop using" the term "lifestyle business" does seem to miss Sahil's self-awareness of the internal conflict between knowing about the misuse of the term and yet still allowing it to affect him at one point in time.

It's refreshing to see this perspective from founders. It's a story not often told and does well to characterize the grinding rollercoaster of hard decisions you won't easily find in the sea of "A-co raised $40mm!" press releases.