Ask HN: How do you know when to quit your startup? | Hacker News Reader

Ask HN: How do you know when to quit your startup?

77 pointszxcvvcxz48 comments

Another interesting question might be: what factors have caused you to quit your startup before (that you co-founded), and do you think it was the right decision?

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I quit when it stopped being fun. It had gone public and there were a couple of hundred employees. I was in the office on New Year's Day, celebrating the fact that I had been into work every day that year. I was flying somewhere twice a week, and spent all my time talking to lawyers, bankers, accountants and brokers. Customers only when they were threatening lawsuits. Conflict with another cofounder didn't help. My father's passing was one more message.

I started as a creative person, programming. I realized I had to go back to that to be happy. So I typed an email to my cofounders on the spot. Three days later, I was out of there.

I was fortunate to remain good friends with most of my cofounders and key employees. I've had a blast in the succeeding years - making a better income most years and getting to do things I enjoy. Having time for a great wife and kids makes it even better.

It was the best decision I ever made.

I've had a blast in the succeeding years - making a better income most years and getting to do things I enjoy

Are you saying that you co-founded a startup that went public, grew to a couple of hundred employees, and it wasn't a financial windfall for you? I'm honestly curious if you're willing to provide more details.

I think he's talking about salary, which tends to go up when you're not a major shareholder. They have to motivate you to stay with a higher base pay/bonuses, when they can't trust you to stay because you care for the company.

Think of a Balance Sheet vs. Profit and Loss. Yes, I had a good base of assets after I left. But after that, I wanted to make sure I made more than I spent. Too many founders get lucky and blow it all. Think about sustainability.

Doing what you want, having no employees, and generating enough income for all your fun is a worthy goal!

For me, two decades without making money was probably too conservative, YMMV. My heart started going out of my shareware business in the early 2000s when it became more about keeping up with Apple's frequent changes and API deprecation than making games. Technology cycles in the 90s lasted maybe 3-5 years but today that's shrunk to maybe 1 year or even 6 months. So I have abandoned the notion of sustainability in my development, and instead try to focus on fundamentals, basically paring down my plan to the point where I could imagine working on it half asleep or having never seen it before. Because I know that in just a year or two, it will be harder to resurrect the code than just rewrite it in whatever wizbang methodology comes along. Case in point: Node.js, Swift, Rust, Go, Unity, etc etc etc. Basically it’s become easier to wait for an API to arrive than write one yourself. That was a bitter pill for me to swallow as a back end developer.

The other big deal breaker for me was loss of autonomy. When the code begins to rot (as it always does) then someone has to go in and renovate it. Since I was the hacker, that task generally fell on my shoulders. It got to the point where the entirety of my time was spent on damage control. I had initially enjoyed that kind of work, but once it became an expectation, I lost my passion for it.

So the most important lesson I learned is that if you are being compelled to perform work by others, rather than governing your own fate, it’s time to leave:

https://www.youtube.com/watch?v=UQrPVmcgJJk

It's funny that code rot is so inevitable. Some people think that the code just needs to be written and designed very well to avoid technical debt. But it always rots in some way. Even if the code is never changed or amended and no new complexity added, it rots because api's, platforms and basically the tech that surrounds and it relies on changes.

>it rots because api's, platforms and basically the tech that surrounds and it relies on changes.

The whole point of standards is for that not to happen

I don't agree with that statement. Standards are there to make development easier via an agreed upon "standard" way of doing things. Code rot has nothing to do with that. Things change all the time. No amount of standards stops change. Your code is rotting the second you're "done" with it, simply because everything else around it is still moving. Just accept that and learn to write code that is easily testable so that you can make your changes as necessary and have some confidence that you haven't broken anything in the process. Trying to write rot-free code is pointless. Trying to write code that is easy to update and repair is a worthwhile goal.

No. An FTP client written in 1987 works today because of standards. I meam standards that define how the application interacts with other applications and input.

That approach works for free command-line tools written for technology specialists.

But not if you are trying to make money with an app for the "general public", for example on the mobile app stores or oldschool shareware. Keeping it working is not enough, it must keep up with the latest trends in design and APIs that become available for extra features.

The old APIs and design guidelines could be a perfectly precise standard that still works - but it's the old standard when users expect new ones.

Code rot is a whole lot less inevitable if you choose to write your code in certain ways and pick the technology you use very carefully.

A lot of it has to do with not using the popular whiz-bang junk of the day.

When you're asking yourself whether it's time to draw a line and move on, you know exactly when the time for doing it was: a year ago.

I've never heard anyone say that they felt they quit their startup too soon. I've heard many (myself included) complain that they stuck it out way too long.

There's plenty of other ideas out there. Don't waste your years on something that's not a clear winner.

I almost quit my startup too soon.

In February 2009, I quit my job to go full time on my startup in anticipation of closing an angel round. The next week, the financing fell through.

For the next six months, I was teetering on the edge of ramen profitable - with very little ramen and very little revenue growth. I seriously considered quitting, and in retrospect, there was really no compelling evidence indicating that I shouldn't quit.

Today, my company is doing quite well - we are 100% bootstrapped, profitable, high seven figures of revenue, 34 employees, and good continued growth prospects.

Looking back on 2009, I still feel like I should have quit at that point; I got lucky by sticking it out. I got lucky because I found it easier to muster the courage to keep trying than muster the courage to walk away.

I almost quit too soon, and every day I feel incredibly lucky that I didn't.

Thanks for sticking with InQuicker! It's a great product!

I've regretted leaving a startup at the time I did. I was miserable, but probably could've stuck in there for 10 months if I'd seen the liquidity event that was coming.

In my experience, most early founders don't quit because they're discouraged by lack of traction. That's why advisors and investors quit.

Founders quit because of a difference of opinion around product vision and because relationships are just plain broken. One of my colleagues put it this way, "If you look at the people around you and feel sad because you're helping people you hate (who you used to like) win, that's when you need to quit."

I quit my startup too soon. After being gone for a month I realized that I had made a huge mistake. Thankfully one email that hinted I wanted to come back had me back in the office the next day.

One of my ex-coworkers didn't like working at a specific startup and didn't think they'd be profitable, so he ended up moving to another. However, had he remained with that startup for a few more years, he would've made over $15 million in stock options. Yeah, he's a little sour on that lol

Perhaps you can follow a basic rational investing principle: If, knowing what you know now, would you invest at the current stage/valuation? If no, dump it. If yes, buy more.

Read this book: http://www.amazon.com/Dip-Extraordinary-Benefits-Knowing-Sti...

It helped me make the decision when i was struggling with my startup. The problem with mindlessly persisting is you are not aware of what you're doing. You need to step back and think about why you're staying in. After that if you still want to go on, you should. Otherwise, no.

+1 thanks for the recommendation. I just bought it as an audio book.

I am more or less retired. I still help a few consulting customers occasionally, but it am dedicating my energies to a few tech projects that I view as long shots. I hope this book puts me in the right frame of mind to make good decisions on where best to apply myself.

When you figure out why it's a bad idea. That way you ensure you've actually learned something from the experiment, and it gives you closure.

After we failed to get into YC, my partner quit when he got a salary offer that was too good to refuse.

The distance between now and that offer within the startup was too long to imagine based upon how successful we had been independently.

It was always about odds. 10:1 at 10x with us, or 1:1 at 1x with them.

His girlfriend had a lot to say on the matter. She needed a home.

I wish his quitting never happened, but I was powerless to stop it. And I can't blame him, though I wouldn't have made the same choice had the circumstances been reversed, I understand why he did.

When they stop paying you. Seriously, don't waste your time hoping for the best.

*Worked for two startups that couldn't make payroll. CEOs promised money was around the corner so I kept working. The money never came.

Were you a cofounder, though? Sounds like you were an employee.

Not everyone is the CEO/CTO of a startup.

Question specifies that, though.

The question specifies co-founder. It doesn't specify CEO/CTO.

Funny you say that, these startups actually wanted me to be referred to as a cofounder even though I wasn't. They actually leveraged that title to make me sacrifice salary and work much harder than I should have (i.e. many all-nighters). When I found out funding was running out and I was only being paid enough to cover rent I had to leave.

The questions specifically asks for co-founders, not employees.

There can be a lot of dangerous signs around money, and your mileage may vary on when it's okay or not. Prior to leaving I was OK, if wary, with 'Em so X can't make rent this month, is it OK if we take 500 euro from your salary so he can use it to pay rent? We'll get it back to you.' Of course that really meant 'We are not going to pay you as much any more, good luck getting it back'.

I wanted to post a similar question.

My brief history : co-founder of 3 "start-ups". One totally disappeared. The second one managed to get off the ground and pay the founders basic salary, but not beyond that. It's now in slow decline. I'm still involved just enough to collect the little salary I can from it. 3rd one is running for a couple of years, and feels like heading in the right direction, but it still seems some time before it can even pay basic salary to the founding team. Unless the hockey-stick growth suddenly hits.

None of those startups look like the kind that would make an 'exit' or get investment. More like a lifestyle-business. Which means shares are pretty meaningless and are unlikely to ever be. But a good reason to stick around is some level of independence and hopefully an ok salary some day (but that's not given).

Any tips to help find the right direction?

I shutdown my startup of two years a few months back. We were full time and bootstrapped, minus a few thousand from an accelerator program. We shut down when our money started running low and the third pivot didn't come together the way we hoped. We felt like we were finally heading in the right direction, but theres was still a lot to do before we could see some initial traction. Some could argue that if we kept at it at a few more months or raised some money maybe we could have had a better perspective. But we were adamant on not raising money and pivoting was getting old. In some ways it did feel a little premature. But I don't know how many times we could say "just 3 more months" before it was meaningless.

It takes a long time to build a successful business and maybe two years wasn't enough time. But over time we became less excited about the vision and the space started to get very crowded. We spent two weeks evaluating all of our options and outs before we decided it was over. It was a sad day when we finally decided to close shop, but my co-founder and I both seemed to be on the same page. I don't know if theres an exact right time to shutdown. For us it just felt right.

I was considering writing something about this but wasn't sure if there was an audience. Startups are a gung-ho never-say-die world where quitting is very much frowned upon but the reality can be tough. You can face a lot of forgivable difficulties (I once had to entirely rewrite our backend over the course of a weekend because the CTO had written it in a language 2/3rds of the tech team didn't use, we repeatedly delayed MVP launch for reasons that wouldn't have stopped feedback).

You can get over all of these, work around them and try and make sure the same mistake doesn't happen twice, but the breaking point is really when you stop trusting your co-founders. At that point there really is no other choice. Since leaving and getting distance, lamenting with others, not having followup matters resolved professionally etc I've seen that it was the best decision I could have made.

For me it was when I ran out of savings, sold all my stocks, ran out of that money, and still didn't have a shipped product. My cofounders are still going at it, and I wish them all the best, but we spent the critical months of our startup designing and redesigning a thing without ever getting user feedback.

For all the other folks out there at Google or other largish companies, who are considering quitting and forming a startup: Don't do it until you have at least once seen a project through from conception to launch.

Redesigning without feedback is so painful to experience, can completely understand.

Two times, I've split.

First: when it was clear my co-founder and I no longer got along well and she wanted to take the product / business in a direction I wasn't excited about.

Second: when I realized all of my extremely hard work rebooting the company only amounted to a possible merger being executed behind my back with "promises" for more / better ownership (#1 mistake on my part was taking promises and not being firm about contract boundaries).

If you are a co-founder, and you are being side-lined, and you have no recourse to get back into the driving seat, it is time to go. This can happen if the other founder secured the funds and has the support from the board.

Your only reason to be a founder/co-founder is to be on the driving seat - otherwise why bother with all the downsides of being in a startup?

In my case, there were so many things suggesting that we quit that I'm surprised we didn't sooner: http://blog.paulbiggar.com/archive/why-we-shut-newstilt-down...

Startup = Growth[1]. If you can't find growth, pivot or quit it.

[1] http://www.paulgraham.com/growth.html

From my experience two years is a reasonable time for a startup to find a viable business model. If it hasn't by then, you really should quit

I would suggest reading Ryan Carson's blog. there's a good post with the same title as your post. hope it's helpful.

http://ryancarson.com/post/25041202750/when-to-kill-your-sta...

It depends on how do you think of your startup. Is it a occasional lose, or a inevitable lose. Does it still have its Creativity?

Take a look at Startups Anonymous, it's a nice little forum for founders - they answer these questions honestly.

When you're stuck with a loser, it's time to stop.

Never surrender!

this is terrible advice

Agreed. I'll quit when I draw my last breath. If I quit before then, I might as well do everything in my power to hasten the "draw my last breath" bit.

Everybody fights, nobody quits! Never surrender!

That said, a tactical withdrawal is acceptable. MacArthur left the Philippines, but he didn't quit.

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