Ask HN: Considering leaving my job at a startup? What should I consider?

The best time to take risks is when you don't have any responsibilities, so in that sense, you're at the right time of your life to do this. On the other hand, if you're good at starting things but not finishing them, then why not make a pledge to yourself before you strike out on your own: Get an MVP version of your new business up and going first.

If you don't try, you'll never have the possibility for success. But stack the odds in your favour first.

This post, also currently on the HN front page, seems relevant: https://news.ycombinator.com/item?id=8779799

If you lack the motivation to work on your project after work and you typically lose steam after a few months, I think leaving a steady job would be the worst thing you could do. The cited obstacles seem more like excuses than things legitimately standing in your way. Get excited about something, then take the plunge.

Six months may feel like a long time right now, but it really is not. I would stay at the current position, get the equity (not matter how small). Use this time to prepare your startup, getting a startup making revenue is a lot more than just coding. You can start to educate yourself about how to best set up a company, talk to potential customers (email or phone). If you think this is not very interesting to do then I suggest not starting a company at all.

If you still feel the same after this time then take the plunge.

Reference: Worked with a lot of startups.

If you can do it, take some time off and see if you can take a small project from inception to completion. It's harder than it seems, especially as a solo person, but you'll learn a lot from it. Spend some time trying to get users to learn about marketing and sales. Even if you don't succeed, those skills (full product life-cycle, marketing and sales) become very marketable resume points.

I'm also of the opinion that it's good to spend some time in the trenches at a big tech company to better appreciate the differences between small startups and mega-corps (and if you can something in between). It's one thing to read about it and get an idea, it's another thing to experience it and understand better what the pros/cons of each environment are. If you end up at another growing startup, this experience will better help you understand what's happening to the organization as it grows. Too many founders end up with growing organization and don't understand what a big shop looks like or how it functions and end up dragging the potential of the company down around them.

Both of those experiences can become very valuable to any future career direction you choose: small startup, on your own, big software house. If you're missing one or two of those, it's hard to say you have a complete picture.

Alternately, 6 months is really not a lot of time to learn and observe. Startups always go through lots of rapid changes, but seeing some of those through to completion (or stagnation) can be very informative. You're young enough that another year or so there won't kill you and won't prevent you from pursuing anything you want after that. Only you'll have more perspective and experience to work off of.

I was in a similar position few months ago, getting bored doing the same thing again and again. I could have changed jobs for a better pay and profile but it would not have been a significant improvement in work quality. Also the job was intense so I would end up thinking about the startup all the time with no time left for personal projects. I have decided to take a break of couple of years to learn new stuff I have already made a list of, experiment with some personal projects I always wanted to create and figure out what I would like to do later. Just ensure that you have a fair bit of runway so that if any of your projects get serious you can pursue it to end.

Not sure if this is your first 6 months in the working world or not. I'm guessing that it is. I'm not trying to discourage you from leaving, but I wanted to offer some perspective.

If your startup is indeed rapidly growing, I think it is invaluable to see the growth first hand. Only a fraction of startups really see true rapid growth. Having that first hand experience will give you some perspective when hopefully, one day, your startup experiences that growth. Additionally, when interviewing at the "big hot startups", I think it's a major plus to have seen that growth somewhere else. But be honest with yourself if it's real, rapid growth, and not just some vanity metrics.

Secondly, I share some concerns that if you're burned out after your workday now, that quitting to do your own thing is going to be better. However, I can certainly empathize and understand that it is possible, but harder, to build a product part time at night. To hedge your risk, you should find that idea that you're really excited about, commit to getting an MVP and some traction to prove to yourself that you have an idea, and then quit.

While doing so, keep your responsibilities and cost of living structure low. Don't sign a new bigger apartment while you're getting a salary. Also, I'm not sure if you've thought about how long you can live without a salary. Do you need to supplement your ramen profitable startup with any extra income (contracting or otherwise?) If that's necessary, you'll need to spend time getting work and doing the work. I personally dislike contract/consulting work. I could never mental hack my way into feeling ownership of it. I've learned I'd rather work at a product company and work on something on the side, than do a startup "full time" while part time consulting to cover bills. Your preferences may be different.

Remember that startups are really hard. I've been through it to an acquihire, and I've had friends that were acquired for tens of million of dollars. And when I talk to them, I'm reminded that even though they're doing well, it's really hard. I absolutely think it's worth it if you're willing to bet on yourself.

Feeling like you've hit a ceiling at work and that you're only learning from yourself, sometimes can be fixed. Talk to your manager. Let them know. Maybe there's more responsibility for you. If you strike out on your own, guess who you'll have to learn from. Just you again. While joining a large community of people working on their own startup is fun, it's also lonely. No one cares about your startup more than you.

I was in the same situation as yours 6 months back. I left my job and persuaded my desire to startup. Turns out it takes more than being great at coding to build a startup. I'd to learn Marketing, Pitching, Emailing etc. skills in my journey which I never thought about before starting up whereas, I thought building a good product would cover that part. So, I'm not scaring you away from starting up but I'm just saying that you should consider these points as well in your decision making process.

I've gathered few questions and important points which I would ask/tell myself before starting up again. Here are they:

1) Do you have a co-founder which can leverage your skills?

2) Have you zero down on an idea and did your market research?

3) How confident are you about the target market?

4) Do you have a execution plan or Goto market strategy?

* Market first, product later

* Ideas are worthless unless they're executed really well.

Thanks,

Rather than advice, how about some tasks?

1) Make an investor pitch deck for your idea. What questions will investors ask? Where is your idea strong? Where is it weak? What's the market size? Who are your competitors? What are they doing wrong?

2) Make a business plan. What do you need to succeed and why? Who pays you and why? What are the risks involved? What are your exits and pivots?

3) Make a one-page sales cutsheet. How can you convince someone to part with their money by handing them a single page of paper? What will they like? What won't they like?

If you are making and saving a lot of money, I'd recommend to stay put (unless you can do immediately better somewhere else).

You have a lifetime in front of you. The opportunity to make an unusually high salary might not always be there. But a stack of cash might help in a lot of ways later on.

Disregard this advice if you have groundbreaking idea and the capabilities to carry it out. (Not to be nasty, but rather realistic), you probably don't. Sit down and have a good honest heart to heart with yourself about this.

Don't go away from something. Go towards something.

If you leave the job, you should also leave the Bay Area and go somewhere you can afford to live while trying out your own ideas, as you'll give yourself 2x - 3x the runway.

A job at a fast growing startup is worth a lot. It's an amazing way to take on a lot of responsibility quickly. You should be learning a lot.

My recommendation would be to keep daydreaming about doing your own startup, but don't quit until:

- you have the killer idea

- you keep obsessing about your idea

- you have talked to 10 people about your idea face to face

- three of those 10 people told you to quit unequivocally

Based on what you have said, I think that you may want to try to change your position at the company. If the company is growing quickly then there are probably positions in the company that will exist soon or were just made that can provide you with very useful skills and knowledge. You may be able to do other things during the day instead of coding, which will probably reduce the amount that your work is taxing you, allowing you to work on side projects more. You may not want to move into a role with responsibilities that aren't programming but as others have said the knowledge and experience you gain during growth is crucial to success, which you will learn even if the company doesn't execute well. It will also help you know what qualities you would like in a co-founder,if you want one, or how you should approach starting something of your own.

One of my friend was in the similar situation, I managed to convince her not to quit, so she got a developer to build the MVP and test the market. The idea didn't workout but she had her job and got promoted to much better positions.

So hiring someone to develop the MVP is an option you might consider.

If it's only six months, stick around for the equity and the opportunity to be a part of the team as it scales up. That's invaluable experience. If you can manage it, put the pieces in place to get your idea off the ground by the time the summer rolls around.

Good luck!

If you're sick of it, find a new job. If you start something of your own, try going freelance first. It's far easier to sell and you can cut your teeth there. Definitely don't sink yourself into a startup that hasn't gotten any traction. You have to seriously tell yourself this will be your life for the next 10 years or so.

Unless right now one of your apps has like 400 followers/likes and not even an alpha to test, don't do it. But once you do, go nuts!

If you're really serious about starting something on your own, you can do nothing better than stay exactly where you are. You are getting first-hand experience with the challenges a growing company faces. You have a real opportunity to learn how this process works, you should be thrilled at the chance to see it through to the end.

Everything gets easier when you can point to a win on your resume. From finding a great co-founder, getting yourself into the accelerator du-jour, or luring early investors. More importantly you'll actually have a good jumping off point for your future.

There is a big gulf between building a product and building a viable business. If your goal is the latter you need to embrace the opportunity you have to learn. It's an invaluable experience.

There's a lot of fantastic advice here from people much more experienced than me, but I will just say having done a couple startups myself and continuing to be in the startup "industry" as well that they're all right... So to echo all of them in summary:

1.) Stay for the equity and for the experience of watching a truly growing startup grow - most startups never grow in any significant way, they just die

2.) If you're burned out now after 8 hour days, wait until you're doing 14 hour days to survive with your startup... if you can't find the energy to do it at night (or your social life is more important to you), you're possibly not cut out for running your own startup

3.) Startups are much much more than coding (unfortunately)

With all of that said I wish you the best of luck as I also left my first job out of college (Edit: realized this is not necessarily your first job out of college (or that you went to college) but leaving this here none the less) after less than a year to pursue other things (in my case a masters program) and I understand how the first job is not necessarily the right job.

I'm in a slightly similar situation. Just that I'm in my final semester sitting for placements. But I don't really want to join a company or work for someone else's startup right away.

I'm actively looking for good ideas and people to start up with. While I'm not very experienced developer, I'm indeed capable of working on an MVP for testing out an idea, and taking things from there, if it all works out fine.

I would love to hear from you and see if we can make something out of this. You can support me a bit while MVP development, and if it looks promising, you can quit your job and we can completely concentrate on this thing.

TL;DR: it doesn't sound like you should jump ship.

Everyday I feel like I want to leave to start something of my own.

This is a normal impulse, but until you're getting a solid signal that you can start something of your own, and without taking onerous financial risk, don't take it too seriously. It's "freshman wants to drop out and write a novel" syndrome. Everyone goes through it, and we survive. You'd be weird if you didn't have this impulse on occasion.

Size up your current situation for whether you're getting the mentorship and resources and connections that'll make you be able to be a founder for real, and preferably without severe financial risk. If you are, great. (I'm guessing that you're not there yet, but a good startup will put you on the path.) If you're not, find a way to change your job as it currently is, in order to make it so. This may mean befriending people in upper management (a skill worth learning) or furtively re-focusing your efforts toward networking and career growth (also a skill worth learning) or something else.

If you're considered to be a valued contributor, then see if the founders will introduce you to investors on a casual, social basis. Yes, it's a political risk to ask, but this kind of political risk is insignificant in comparison to the risk involved in starting your own project.

I am always so exhausted after writing code for 8-9 hours a day that I definitely don't want to come home after commuting for 45 minutes (plus I like having somewhat of a social life).

If that 8-9 hours of work is advancing your career, it's not wasted. If it's not, then start slacking a bit (once you've established a solid reputation based on your first months, you can) and direct your focus toward building contacts and advancing your technical knowledge-- that is, work hard on the parts of the job (as you define it) that advance your career and slack on the stupid shit that doesn't.

I feel like I will enjoy it more.

That's "grass is greener" syndrome. If you're a natural entrepreneur (and it's OK if you're not; they're only ~1% of the population, and people who are not that can still be great entrepreneurs) then you'd enjoy bootstrapping, even though you'd have no money most of the time and most people (including almost all of the VC-funded entrepreneurs) would find it exhausting and miserable, and would rather give up some autonomy for a stable income. (The trait of the natural entrepreneur is an outlier stance on the rich-versus-king spectrum.) It's completely OK if you're not a natural entrepreneur; I'm certainly not. That just means that you're going to want to work for someone else and learn on their risk and dime, for at least 5-10 years, before you're confident enough to go out on your own.

If you're not a natural entrepreneur, though, you're not going to start a business unless you have funding already delivered (and, by the way, that's probably the right strategy for most). If you're going to try to raise a seed round with no connections, forget "enjoyment". The odds are against you, and fundraising if you're not part of the in-crowd (and it sounds like you're not, because that's 0.1% of the Valley, and it sounds like you're under 25, and you're in an employee role at a startup) is fucking miserable. People have been driven to suicide by the fundraising process. It is that fucking bad. Of course, if you run into a business co-founder who comes with the resources in-hand... that problem goes away. Then again, you're also likely to be #2 at best. It depends on you whether that's OK.

Plus, I feel I'm really only learning from myself at the startup.

You're ~22. Unless it's a shit-house, you're not the best and most experienced programmer there. Find someone you can learn from and star...

you work only 8-9 hours a day and have just a 45 minute commute and you're whining about it? For someone in their twenties that makes no sense to me. I'm twice as old as you, work longer hours than you, have a longer commute and manage to raise a daughter and contribute to my github projects when she's asleep. I'm no better than anyone, my point is that you sound so whiny and entitled. If you don't like your job then change it, but you definitely don't sound like someone who would do very well going out alone.

you work only 8-9 hours a day and have just a 45 minute commute and you're whining about it? For someone in their twenties that makes no sense to me. I'm twice as old as you, work longer hours than you, have a longer commute and manage to raise a daughter and contribute to my github projects when she's asleep. I'm no better than anyone, my point is that you sound so whiny and entitled. If you don't like your job then change it, but you definitely don't sound like someone who would do very well going out alone.

"The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man." --George Bernard Shaw

I was in your shoes just over a year ago and decided to go with starting my own startup. I thought having started two startups prior with some success would make it easy but I was wrong.

The reality is that the default of any state of any startup is failure. You probably won't understand the magnitude of the problems you'll face until you see them directly. At this point, your ideas are just ideas and you should work on validating them.

There's a lot of ways to go about doing this and it'll really depend on the market you're chasing. It's likely that a combination of customer interviews and sales will let you gauge which of your ideas have promise and which won't. Something that really helped me was thinking about questions VCs ask when they're evaluating a startup. What's your unfair advantage? Why hasn't this worked before and why will it work now? These questions are incredibly important even if you're not interested in raising venture. There's a lot of books and literature on the web so I won't get into this deeply.

You probably noticed that I didn't say writing code. Sometimes writing code is how you should be validating your idea but most of the time it isn't. You should get in that mindset. However, when you need to write code there's a few ways to get over that commute drain:

1.) Wake up earlier and put some time in before you start your day.

2.) Live closer to your job. It'll alleviate a lot of the problems of coming home and not wanting to do more more work.

3.) Write code on the weekends instead.

Also, whatever you do, don't do it alone. I did it alone for the first time and it's awful. Your job is a great place to find future cofounders or employees. Do hackathons with them on the weekends. Tell them your ideas. See what they excited about.

A year later, I'm doing some consulting on the side to pay the bills and getting into a pivot that's finally moving the needle. Even though most of this year was a total failure, I couldn't be happier and I'm glad I did what I did. Feel free to shoot me an email at jr.sunny at gmail dot com if you have any questions or need any help.

Read Running Lean and other related books. They will help you create a project that gets traction before you write any code. Customers before Code prevents project burnout you describe.

Also, start networking. It can take 6-18months (or more) to find your confounders.

While getting paid its a good time to ramp up CustDev and Lean skill sets