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bcantrill · 2024-09-01 · Original thread
This is a good piece in that there is absolutely truth to it -- but it's also a bit dangerously non-specific in that it potentially leaves founders with the notion that whatever they happen to think is tautologically correct. To supplement this piece, I would make three specific recommendations that I think tack into the same themes (namely: mistakes founders make -- including trusting the wrong people at the wrong times), but with quite a bit more detail.

First, Tim O'Reilly wrote a superlative piece in 2013, "How I Failed."[0] I cannot recommend this piece highly enough, and it had enormous impact on me as a founder. Its message is quite a bit more complicated than the Graham piece: there are times to stand your ground and resist conventional wisdom (HR in O'Reilly's piece), and there are times when expert practitioners of that conventional wisdom will save your bacon (the CFO in O'Reilly's piece). And the truth is more complicated still in that O'Reilly's specifics may or may not be the ones that a founder needs to apply to their own situation.

Second -- and I recommend this whenever anyone mentions Jobs -- is Randall Stross's "Steve Jobs and the NeXT Big Thing"[1], a history of NeXT written at Jobs' darkest hour. An extraordinary book that will leave you with a much more nuanced view of Jobs: not only in terms of his strengths (definitely those!) and his weaknesses (here in spades!) but especially the way that the NeXT experience surely informed Jobs's (much more successful) return to Apple. (It is a galling failure of the Issacson biography that he spends so little time on NeXT.) Selfishly, I would also recommend our Oxide and Friends discussion of the book.[2]

Third (and finally): a very common specific mistake that technical founders make is how they build out a go-to-market team. This isn't discussed nearly enough, and I was on a podcast episode of Software Misadventures ("Ditching the Rules to Build a Team that Lasts"[3]) with my own co-founder (who came up on the go-to-market side) in which he elaborates on this mistake -- and how founders can avoid it.

[0] https://www.oreilly.com/radar/how-i-failed/

[1] https://www.goodreads.com/en/book/show/226316

[2] https://oxide-and-friends.transistor.fm/episodes/next-object...

[3] https://softwaremisadventures.com/p/oxide-ditching-the-rules