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I got your point (after the Free Parking clarification). (To be clear, my comment wasn’t on Double specifically. No clue how strapped for cash they are while w

by apgwoz 1y ago

I got your point (after the Free Parking clarification). (To be clear, my comment wasn’t on Double specifically. No clue how strapped for cash they are while winding down. They seem to be doing right be people (paying fees and such), and that’s great.) Finally, maybe it’s unintentional, but you seem to be implying that “it’s not worth burning your life on a failed startup,” which seems like a bad take. If you spend 5 years on a startup that shows promise but ultimately doesn’t pan out, is that always worse than spending 6 months on a startup that fails fast? First, this would be wildly hard to prove, and second, there are obviously counter examples.

tptacek 1y ago
Yes. If you spend 5 years on a promising startup that fails, that is strictly worse than spending 6 months on a promising startup that fails.
- apgwoz 1y ago
  LOL. Completely disagree. In that 5 years, I’ve identified a shit ton of stuff that works, doesn’t work, and made relationships along the way. I’d bet money on the founder of the 5 yr startup being successful over the 6 months founder.
  - tptacek 1y ago
    You do that stuff in every job. Meanwhile, people with careers in startups do multiple startups. You get a finite number of them. You are literally better off working at somebody else's successful startup than you are spending 5 years on a doomed startup. The most valuable asset you have is time.
    - apgwoz 1y ago
      Both of us are arguing based on feelings and intuition, so this is going no where. If you can cite a study then so be it. I think what we can both agree on is that it is pretty obvious that prior startup experience is key to the next startup being successful.
      - tptacek 1y ago
        I really don't think I need to cite a study that 5 years of time is a lot to give up on a company that goes nowhere. It happens! It's normal! And very painful. Which is why getting to a decisive resolution in 6 months is often a gift. You will make more money, and probably work on equivalently interesting problems, working any other job than at a startup you cofounded that limps for years before winding down. It's really hard to see what upside you're finding here. I don't say this often, but this isn't a place I see leaving at "reasonable disagreement".
        apgwoz 1y ago
        > I really don't think I need to cite a study that 5 years of time is a lot to give up on a company that goes nowhere. I think your problem is that you have one definition of success for a startup and that’s to become a unicorn. > working any other job than at a startup you cofounded that limps for years before winding down. Not everyone starts a startup to become a billionaire, and not everyone seeks to _make more money_. But aside from that, the way you’re going to _make more money_ in another job is by working at a large company that can pay you more money. That large company has lots of people and lots of jobs that are specialized… because? Lots of people are there to do them. If I work on a team in a large company, I very likely have a narrow focus and I am not “solving interesting problems” on average.
        tptacek 1y ago
        You keep saying stuff like this, but I'm asking a simple question. How have you personally benefited from spending years at a startup that failed, so much so that you were better off at the doomed startup than in any other place in the industry? I'm looking for some kind of relatable experience.
        apgwoz 1y ago
        You haven’t asked a question before now… I’ve worked at a few “unsuccessful,” but long term startups. Bought, but kind of for parts. The 2 yo startup I closed down was the most enjoyable and most rewarding from a learning perspective. The longer term, but unsuccessful, ones were also enjoyable and great learning experiences. The two larger company experiences had me much more pigeonholed, even as a principal engineer / architect, and exposed me to far less of the important aspects of running a company or product, generally, but I made money. Often it was not enjoyable, and certainly leadership did not always enjoy my questioning of their actions and decisions.

by apgwoz 1y ago

tptacek 1y ago

Yes. If you spend 5 years on a promising startup that fails, that is strictly worse than spending 6 months on a promising startup that fails.

apgwoz 1y ago
LOL. Completely disagree. In that 5 years, I’ve identified a shit ton of stuff that works, doesn’t work, and made relationships along the way. I’d bet money on the founder of the 5 yr startup being successful over the 6 months founder.
- tptacek 1y ago
  You do that stuff in every job. Meanwhile, people with careers in startups do multiple startups. You get a finite number of them. You are literally better off working at somebody else's successful startup than you are spending 5 years on a doomed startup. The most valuable asset you have is time.
  - apgwoz 1y ago
    Both of us are arguing based on feelings and intuition, so this is going no where. If you can cite a study then so be it. I think what we can both agree on is that it is pretty obvious that prior startup experience is key to the next startup being successful.
    - tptacek 1y ago
      I really don't think I need to cite a study that 5 years of time is a lot to give up on a company that goes nowhere. It happens! It's normal! And very painful. Which is why getting to a decisive resolution in 6 months is often a gift. You will make more money, and probably work on equivalently interesting problems, working any other job than at a startup you cofounded that limps for years before winding down. It's really hard to see what upside you're finding here. I don't say this often, but this isn't a place I see leaving at "reasonable disagreement".
      - apgwoz 1y ago
        > I really don't think I need to cite a study that 5 years of time is a lot to give up on a company that goes nowhere. I think your problem is that you have one definition of success for a startup and that’s to become a unicorn. > working any other job than at a startup you cofounded that limps for years before winding down. Not everyone starts a startup to become a billionaire, and not everyone seeks to _make more money_. But aside from that, the way you’re going to _make more money_ in another job is by working at a large company that can pay you more money. That large company has lots of people and lots of jobs that are specialized… because? Lots of people are there to do them. If I work on a team in a large company, I very likely have a narrow focus and I am not “solving interesting problems” on average.
        tptacek 1y ago
        You keep saying stuff like this, but I'm asking a simple question. How have you personally benefited from spending years at a startup that failed, so much so that you were better off at the doomed startup than in any other place in the industry? I'm looking for some kind of relatable experience.
        apgwoz 1y ago
        You haven’t asked a question before now… I’ve worked at a few “unsuccessful,” but long term startups. Bought, but kind of for parts. The 2 yo startup I closed down was the most enjoyable and most rewarding from a learning perspective. The longer term, but unsuccessful, ones were also enjoyable and great learning experiences. The two larger company experiences had me much more pigeonholed, even as a principal engineer / architect, and exposed me to far less of the important aspects of running a company or product, generally, but I made money. Often it was not enjoyable, and certainly leadership did not always enjoy my questioning of their actions and decisions.