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Ask HN: Should I quit my startup?

I'm a cofounder of a startup where I've been working for the past 2 years. I was a late addition to the team to get some technical chops on board (Company running for 1yr before me). After I was brought in, I've coded the entire product from scratch, learning a lot along the way, and while that has taught me a lot that I otherwise might not have learnt, we never seem to have the budget to hire another developer, and I'm feeling quite overburdened. Over time, I've noticed my level of enthusiasm and happiness go down, and I've become generally irritable. I'm a product guy at heart, and my CEO is an operations-loving guy who keeps throwing around buzzwords. He's grown the sales team over the last two years while neglecting the product team. It's an army of sales people selling a product built by 2 people sitting in a crummy faraway corner of the office, and that doesn't feel right to me. Now would be a good time to mention that the second person (designer & another cofounder) is leaving soon, and part of the reason (after other personal reasons) is that their potential was never realized here due to lack of product focus. I've tried to win the CEO over so that he would support the product with the recognition and resources it needs, and largely I've been successful, but it is a lot of effort when he's built the company with an operations-first mindset, and I don't know if it's worth it. I've fantasized about quitting a lot of times, and what's held me back has been the fact that there is no one else here that could fill my shoes and the entire tech platform might collapse without me keeping it up, and that I don't know what I could work on after this. I should also mention that I'm currently 20, I dropped out of school, and this has been my first real job. I also think I am quite highly skilled for my age.

pinouchon 8y ago
Is the product deserving more engineer attention (I suspect it does, but you should still carefully consider the question because that could be how the CEO thinks). And if so, do you think you have done everything you can to convince the CEO, and allow more resources towards the product ? I would try to speak openly to the CEO about the fact that you are considering quitting. Also, what about equity/options/vesting?
- throwaway_obv 8y ago
  Yes, I think the product could be better with more than 1 engineer working on it. Currently I have to support our app, landing pages, office IT, do sysadmin stuff, and automate things for the operations team, and my attention is fractured between these different hats. I've done everything in my power to convince the CEO, and I've managed to get a budget that would be about 70% of what is market rate - but the CEO has put additional demands on that, like extra working hours, which would be a dealbreaker for most decent candidates. My CEO says I should hire someone and train them if I find the budget limiting. How would you approach the CEO about this topic? I have a 15% stake, with 4 year vesting. I do think my equity is on the lower-end of things. It started out at 5 and I negotiated it up to this number, so I don't think I have any more scope there.
  - pinouchon 8y ago
    I think your argument would be better if you don't just say "the product would be better with more people working on it", but also say how you plan to recruit them, what you need to do that, and how velocity would increase. If you can show that you have thought it out and you can manage the product side of things, it shows that you are serious about growing the product team, not just randomly throwing capricious (and costly) demands. Regarding the possibility of quitting, I think it's better to warn the CEO early about that, than making a decision and suddenly tell him that you are leaving. If you were the CEO, how would you want your coder/product guy to behave? Then behave like that.
    - throwaway_obv 8y ago
      Thanks, I'll work on the points you've mentioned before talking to the CEO. Should I tell the CEO that I _might_ be leaving when I'm not completely sure (maybe he agrees to the above and things can be worked out), or wait until I've made a decision to give them a notice?
      - __d 8y ago
        I would say: Don't tell. It will probably be felt as a threat (do what I want or I'll make you hurt), and no-one likes to be threatened.
dylanhassinger 8y ago
its time to renegotiate your role, or leave. think of it like refinancing a mortgage. set up a meeting a present a roadmap forward that would make you happy. put yourself in the real co-founder role and get what you want. may include more equity, a plan to grow the team, different office layout, whatever u need. offer him this roadmap forward, or you will leave (1 month notice would be honorable). if you leave you will find better opportunities and more pay, guaranteed. you have a proven track record and good attitude
- throwaway_obv 8y ago
  That sounds like a good idea. Couldn't the I will leave if you don't do this part sound like a threat and sour the relationship?
  - mindhash 8y ago
    You could keep a certain timeline to see if things are transitioning. Important to have a conversation about product focus and what would it mean for the company. Write a few bullet points so the ceo knows serious Ness of this discussion. After your meeting you will know if you want to stick around. Try to convince ceo at least 3 times before you call it quits.
raarts 8y ago
Find a mentor. Sometime with more experience often can give you insights that are valuable and helpful. Or your thoughts will just keep running around in circles and you won't get any further.
- throwaway_obv 8y ago
  Any ideas on where I might be able to find a mentor?
  - raarts 8y ago
    PM me.

pinouchon 8y ago

Is the product deserving more engineer attention (I suspect it does, but you should still carefully consider the question because that could be how the CEO thinks). And if so, do you think you have done everything you can to convince the CEO, and allow more resources towards the product ? I would try to speak openly to the CEO about the fact that you are considering quitting. Also, what about equity/options/vesting?

throwaway_obv 8y ago
Yes, I think the product could be better with more than 1 engineer working on it. Currently I have to support our app, landing pages, office IT, do sysadmin stuff, and automate things for the operations team, and my attention is fractured between these different hats. I've done everything in my power to convince the CEO, and I've managed to get a budget that would be about 70% of what is market rate - but the CEO has put additional demands on that, like extra working hours, which would be a dealbreaker for most decent candidates. My CEO says I should hire someone and train them if I find the budget limiting. How would you approach the CEO about this topic? I have a 15% stake, with 4 year vesting. I do think my equity is on the lower-end of things. It started out at 5 and I negotiated it up to this number, so I don't think I have any more scope there.
- pinouchon 8y ago
  I think your argument would be better if you don't just say "the product would be better with more people working on it", but also say how you plan to recruit them, what you need to do that, and how velocity would increase. If you can show that you have thought it out and you can manage the product side of things, it shows that you are serious about growing the product team, not just randomly throwing capricious (and costly) demands. Regarding the possibility of quitting, I think it's better to warn the CEO early about that, than making a decision and suddenly tell him that you are leaving. If you were the CEO, how would you want your coder/product guy to behave? Then behave like that.
  - throwaway_obv 8y ago
    Thanks, I'll work on the points you've mentioned before talking to the CEO. Should I tell the CEO that I _might_ be leaving when I'm not completely sure (maybe he agrees to the above and things can be worked out), or wait until I've made a decision to give them a notice?
    - __d 8y ago
      I would say: Don't tell. It will probably be felt as a threat (do what I want or I'll make you hurt), and no-one likes to be threatened.

dylanhassinger 8y ago

its time to renegotiate your role, or leave. think of it like refinancing a mortgage. set up a meeting a present a roadmap forward that would make you happy. put yourself in the real co-founder role and get what you want. may include more equity, a plan to grow the team, different office layout, whatever u need. offer him this roadmap forward, or you will leave (1 month notice would be honorable). if you leave you will find better opportunities and more pay, guaranteed. you have a proven track record and good attitude

throwaway_obv 8y ago
That sounds like a good idea. Couldn't the I will leave if you don't do this part sound like a threat and sour the relationship?
- mindhash 8y ago
  You could keep a certain timeline to see if things are transitioning. Important to have a conversation about product focus and what would it mean for the company. Write a few bullet points so the ceo knows serious Ness of this discussion. After your meeting you will know if you want to stick around. Try to convince ceo at least 3 times before you call it quits.

raarts 8y ago

Find a mentor. Sometime with more experience often can give you insights that are valuable and helpful. Or your thoughts will just keep running around in circles and you won't get any further.

throwaway_obv 8y ago
Any ideas on where I might be able to find a mentor?
- raarts 8y ago
  PM me.