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But then this analogy doesn’t hold… Has there ever been a startup in history where it’s break even everywhere? Investors don’t get their money back, customers (

by apgwoz 1y ago

But then this analogy doesn’t hold… Has there ever been a startup in history where it’s break even everywhere? Investors don’t get their money back, customers (hopefully!) are made whole, and the founders and employees are now out of a job and _perhaps_ didn’t get their final pay check depending on how bad it is.

tptacek 1y ago
Yeah, you're missing my point. Given most startups fail, the question isn't "at the end of the day do you still get a paycheck for your failed startup", it's "how much of your life did you burn on that failed startup". Since we're talking about a specific startup whose founders are participants here, I think we can do without the ghoulish stuff about them not making payroll or whatever; "winding down" implies they're failing in an orderly way.
- 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.

by apgwoz 1y ago

tptacek 1y ago

Yeah, you're missing my point. Given most startups fail, the question isn't "at the end of the day do you still get a paycheck for your failed startup", it's "how much of your life did you burn on that failed startup". Since we're talking about a specific startup whose founders are participants here, I think we can do without the ghoulish stuff about them not making payroll or whatever; "winding down" implies they're failing in an orderly way.

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.