Yeah, his journey is incredibly, incredibly lucky. One of the first employees at Pinterest, then raised money for Gumroad when he was still a teenager, then when Gumroad didn't grow fast enough (Not even failed!) he was basically gifted it by his investors.
A reality 99.9% of us can only dream of, and I've always found his writing/tweeting a bit distasteful because of it. Lottery winner telling you how to pick a ticket kind of vibe.
When you say lifestyle business, what do you mean? Is it a self employed kind of job/business where he will be broke if he doesn’t show up everyday? Or more like he will do very well and have a good lifestyle but not have big fuck you money?
He could be making millions in a respectable way but not with enough out-of-control growth to move the needle for some billionaires, who then look down their nose at him with the attitude that he should get a life and get some style.
The latter. When people say "lifestyle business", they typically mean a business that can comfortably sustain the owners' lifestyle, but is never going to grow significantly.
If the VCs are willing to write off their shares then it’s surprising or unfortunate that it doesn’t happen more often. Maybe more companies could scale down and salvage something from the ruins with the right incentive.
It kind of screws over everyone except yourself though.
VCs gave you money for a VC business, you get to turn it into a "lifestyle business" with no or little obligation to them anymore.
Your employees joined what they thought was a growing startup, then you lay them off after they built the product because there's no need for them anymore since you're not trying for hypergrowth.
What's worse, it might provide other incentives. If you know that you can always negotiate a soft landing, you're not as maniacally driven towards that unicorn status, which is required to make VC economics work.
Failing a VC-funded startup is an expected outcome (statistically). What difference does it make whether the founder ended with nothing (the typical scenario) vs. a lifestyle business? VCs get nothing either way.
VCs aren't screwed because they already accounted for the risk of failure. That's kind of their job.
Target smashes damaged goods instead of selling them at a discount so employees or customers don't purposefully cosmetically damage things they want to buy.
If the failure state of a business is "the founder can buy it for pennies and try to make something of it", then why wouldn't all lifestyle businesses pitch themselves as VC-backed growth businesses and then use up all that money and settle as a lifestyle business?
but this piece at least didn't really come across to me as preachy or anything. Just sort of describing how it happened. No idea if it's all accurate, but at least sounded reasonably honest and plausible.
A reality 99.9% of us can only dream of, and I've always found his writing/tweeting a bit distasteful because of it. Lottery winner telling you how to pick a ticket kind of vibe.