Ask HN: Should I quit my startup? | Hacker News Reader

Ask HN: Should I quit my startup?

4 pointsthrowaway_obv14 comments

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.

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?

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.

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.

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?

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.

This is a very natural, very common, place to end up in your role. And it's not uncommon for CEOs (and especially those without a hands-on tech role) to view product development purely as a cost center and to build out sales and marketing disproportionately (not least from the point of view of the engineering team).

15% with 4 year vesting sounds ok, if not great, for the situation you've described.

I agree with one of the earlier posters: you should produce a roadmap of what you believe needs to (not should, not could) be done and document the level of effort required to achieve that, in combination with the misc IT and operational work. Include in that roadmap the time required for recruiting and training the people you believe are required, both initially, and considering ongoing turnover.

Share that with your fellow co-founders / management team, and strive to get buy-in to the necessity of achieving the goals you outline. Depending on the context of the organisation, it might work to present this as a natural part of the growing maturity of the company? Sort of a "While it's been fine to two people in a corner thus far, we're reaching a point where that's holding us back, and here's a plan to take us to the next level".

In my experience, the sales team will be very supportive of anything that gets them more to sell: every extra feature, every refinement, etc, gives them another opportunity to grow the addressable market, or to satisfy another potential customer, etc. If you're able to get them involved and bought-in by getting some pre-presentation feedback on the roadmap, it might be worthwhile? You don't have to just sell this to the CEO: you need to have the rest of the organisation selling it to the CEO as well.

If your proposal is accepted, all is good, and in 12 months you can use that as negotiating leverage to get more equity :-)

If your proposal is not accepted, even in some inevitably cut-down form, what is then entirely implicit, with no threats or rashness or backing people into corners, is that it's kinda obvious that your personal point of view and the general company's point of view have diverged. And that's the time to start looking for a new opportunity.

Getting a new job in your situation is a whole other post, but if college is an option for you, now might be a good time? Otherwise, carry on in your current role but pay much more attention to networking: go to meetups, contribute to some open source, start blogging, build relationships with customers of the business, etc. It'll likely take 3 to 6 months to find a good new role, so set your expectations accordingly, and work every week towards that as a personal goal. You'll have to take time away from your current over-worked situation for this: but you need to prioritise yourself over the company, and this is the perfect way to start.

Best of luck!

I'll work on the roadmap idea for sure. Are there any resources I can refer to for this? I've not really done that kind of work before, so I don't know how best to go about it.

> If your proposal is not accepted, even in some inevitably cut-down form, what is then entirely implicit, with no threats or rashness or backing people into corners, is that it's kinda obvious that your personal point of view and the general company's point of view have diverged. And that's the time to start looking for a new opportunity.

I believe this is why you had put the emphasis on saying "I believe this _needs_ to be done".

College is not really an option for me in my current situation. Regardless of anything else that happens, I will start to focus a lot more on networking just so I don't get backed into a corner anytime I'm in a hard place.

I'm not aware of any resources to help with developing a roadmap. A web search might find something useful, but I don't know.

The basic idea is to project what will be needed for the business (new functions, expanded functions, some things might be no longer required) and then figure out how it would be technically best to deliver those, with some anticipation for further future changes.

Determining the business requirements is a whole job in itself. Look for upcoming regulatory changes (new federal or state or industry rules you'll need to adhere to), things that competitors are introducing that you don't yet support, and the kinds of things that customers will start to want once they begin using what you provide currently. This is where input from the sales team can be really useful. You'll likely also have some tech debt you will need to clean up, and maybe a couple of big hairy issues that are the root cause of a lot of your reported bugs? Maybe also there's some operational things that cost you a lot of time or effort that could be automated?

For each of these items, you need to rough out a plan of how to deliver it. Work out some sort of estimate of the effort required, and then balance that against the value to the business of getting it fixed.

That'll give you a priority list which ignores interdependencies, and product architecture. You then need to factor those in, and resort the list such that it will deliver pretty good business value in an order that's technically reasonable.

That's your roadmap.

You can also have branches of the roadmap which are determined by key business decisions: do we pursue this opportunity or not?

Ultimately, you can then present an order of work, and a level of resourcing needed to deliver it, and for each item you can explain why you think it's important and how it fits into the future strategy of the company.

The emphasis on "need" rather than "could" or "should" is that roadmaps tend to have a lot of wishful thinking, and blue sky ideas thrown at them, and that's largely a waste of time. Focus on just the things that are absolutely needed to get the customer base, and the revenue, and maintain an acceptable quality of service --- otherwise the whole exercise can be disregarded as a waste of scarce resources just by picking on the one little bit of future-proofing you slipped in there ...

For me, the self-discipline required to do the networking is extreme, but it's crucial that you build a network around you that gives you options if and when you decide to move on. That's especially true if you're not lucky enough to have a college degree, which can make more transactional job hunting difficult.

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

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?

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.

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.

Any ideas on where I might be able to find a mentor?

PM me.

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