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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




Unwarranted perspective from someone who is not a founder, but works with and has a lot of respect for them

I think the common thread between the two blogs is context and detail are important. I kind of think “Founder mode” is just doing your own diligence on your decisions rather than trusting heuristics or outside third parties. The “HR lawyers” or the “professional managers” are probably not nearly as tied to the company as the founder, and therefore unwilling to wade into the details and rely on such heuristics or “playbooks” for decision making or advice giving.

Tim does raise a salient point though in that finance functions are often overlooked or under invested, and siloed division. The whole company probably does not need to know the daily cash balance of the company, but team members should maybe think a bit more carefully about relative rates of return on their invested time or money, and “finance” is a good framework for doing just that. The best CFOs (or people more generally) look for that context (and help others do so too), so they can understand intuitively the impacts of potential decisions. Meanwhile, the professional managers run away from the detail and prefer to rely on playbooks and heuristics like the Conjoined Triangles of Success.

I don’t think it always has to be that way though, you just need people to care enough to wade into the depths of detail and care as if they were a founder.


Well, compromise is the hypotenuse of the conjoined triangles of success!


The main takeaway of this piece is to be wary of the principal-agent problem but hey everyone already knew that, right? RIGHT?


I find myself thinking more and more that Bryan Cantrill, despite him highly disliking Elon Musk, seems to agree with him regularly on many things including things such a this.




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