[yowlingcat]

I think it's okay to want the freedom, outsized reward and even the status of being a successful founder, with all the risks attached. I think it's also fine to want the benefits and stability of being an materially comfortable employee in tech with a good career progression. They are different paths and different strokes work for different folks.

But I think it's fair to say you have to pick a lane. You can't have your cake and eat it too. If you haven't succeeded as a founder, it rings ironic to proclaim "4 year vesting with 1 year cliff is just simulating what FAANGs were doing 10 years ago but out of touch tech wannabes are imagining is normal now" or that "we only took non-dilutive capital, nothing that converts to shares - people need to use their imagination."

Do you think it's fair for someone would to ask whether if you were really serious about succeeding as a founder, you should've invested a little less imagination into the capitalization strategy and a little more imagination towards identifying the ideal customer problem to be solved? After all, it's not like there's any dearth of founders who have built successful businesses with the standard VC backed approach. Especially those who were facing bear markets for what they were building.

Lord knows VC could use some competition. The issue I've observed is that everything else (except bootstrapping for very specific kinds of businesses) is purely worse for a founder who isn't already independently wealthy, which is ultimately just a different kind of bootstrapping.

I'd love to be proven wrong if there is, empirically, an alternative.

[yieldcrv]

so you find these ad hominems in my post history to be relevant because they were interesting to you, but then the idea of actually being passionate about being on the coding side is too incongruent with what you think someone that achieved large numbers would do, calling into question that exposure and experience

okay

following my business successes - which can include passing through profits outright, and or exits - I’ve done “thought leadership” and advisory to other companies, I’ve travelled around Europe for extended periods of time half way doing advisory but mostly living out a dream I wanted and enjoyed, I’ve formed funds and managed capital with great legal counsel, fund administrators, the works. I’ve had periods of illiquidity, even periods where liabilities were greater than assets, right now I like to get paid to do nextjs, and rust, and a couple other stacks.

turns out, you don't have to pick a lane. people take the linkedin and resume I choose to show at face value, which only shows IC roles and an Engineering Manager role.

[yowlingcat]

Well, there's only so much time I can spend on the internet convincing someone with an oversized sense of their own success that they're doing it wrong, so I'll try to be brief and I wish you all the best after this interaction.

If we're being frank, if the idea of picking a lane is doing something well, by choosing both lanes, you've actually chosen neither lane.

1. You are clearly not independently wealthy enough to have to never work again; otherwise you wouldn't care about "subsidized health insurance / contribute to an HSA" (both of which are things that the independently wealthy couldn't care less about), so either you are a) making up achieving outsized exits as a financier and you never actually achieved it, or b) worse, you made the outsized exit, became independently wealthy, and due to fiscal irresponsibility lost your position of independent wealth

2. You clearly aren't in a stable career position at a company with a long tenure steadily moving upward seeing as how you ended up having to take a job at a company with incompetent leadership that ultimately ended up firing you for making ultimately a reasonable suggestion

If anything, I think you have proven my point which is that you very much do need to pick a lane. There's the old saying that "startups don't die of starvation, they die because of indigestion" owing to the common and real risk of overly broad scope and dilution of focus. I think that same warning applies equally to careers -- your dilution in long-term focus may have played a role in you not achieving the success you might otherwise have been able to achieve. But I can't tell you for sure. Only you will be able to figure out that answer. And in order to figure out that answer, you have to be willing to be honest with yourself.

Best of luck.