Ask HN: Considering quitting my day job to work on my startups

As soon as I saw the word "startups" -- plural -- I thought "he's doomed". However, while the popular wisdom is to focus soley on one thing, one startup, I often find that leads to imbalance. Perhaps having two ventures is a good thing.

What I'm doing right now is a 5-6 hours/day job for the bills and working on my projects the rest of the day. Balances out pretty well -- I get physically tired from work and get some social interaction/out of the house/out of my own head. And the rest of my time -- and all of my headspace -- is free to write and code.

But, to get back to you, it sounds to me like you really would rather be working on your projects.

Here's what I'd suggest -- you don't want to leave your boss in the lurch, and you still need some money -- so why not just talk to your boss about working reduced hours, say half-time, so you can help them and have more time for your startups?

Good suggestion. Perhaps you need to hang around to help the new programmer for a couple of months to ensure a smooth handover?

Exactly. That part was implied, I just forgot to say it. ;)

Here's my advice regarding sorting out #1 vs #2. The question in my mind is how much each factor is. When I quit my day job, the social pressures/burning bridges aspect of it was a part of my reluctance. But, of course, more financial instability was another.

In the end, I asked myself "if I could snap my fingers, and tomorrow be out of my day job, without having to go through the social awkwardness of quitting, etc.... Would I do it?" My answer was an instant "yes". That showed me that any threat of the financial instability was not a real concern, but just an excuse for me not wanting to burn bridges.

After that, I was entirely confident in my decision to quit.

This is really good advice. I'm worried about not only what my coworkers and bosses will think and what that will do to our friendship, but also what my parents will think. If those weren't an issues I'm pretty sure I would quit without hesitation. The money is an issue, but ultimately I'm confident I'd be able to find a job if it were clear neither of my start ups were going to work out.

well, the next question question is will you regret not doing this in 10 year's time? I know it's a cliche to say you only live once, but you really need to think about it in those terms. I didn't want to look back and regret not taking the opportunity. Is this is just-now opportunity? Will this opportunity be there down the line?

I had similar concerns about family and co-workers. In the end, everyone at work was very nice about it and my family was surprisingly supportive.

I chose to quit my full time job for the benefit of my own startup, the difference was I hated the company that I was working for and I hated the job... In your case I would suggest to look into a part time deal. It seems like you have a good rapport with your employer and u have the integrity and the dignity to realize what is fair and such... See, if u can reduce your involvement with your employer to say 30%.. Just a thought. Good Luck!

I've considered this, but I'm not sure how they would respond. If I'm open and tell them I'm not 100% committed to my work there, I'm not sure they'd still want me to work there anyway. I think I have to be prepared for the worst case if I even bring up part time with them.

I understand. You are gunning for either all or nothing... I just wanted to point out that perhaps u can strike an in between option.. which might benefit all at the end and make it a win-win given the circumstances.

One thing you may want to consider is proposing a part-time arrangement with an agreement to end employment permanently at some date. This is, of course, assuming you are willing to quit the job for good. However, this has been working out quite well for me as it affords me significantly more time to work on my startup while removing the need to hide intentions at the day job.

>but it's still a large gamble.

I know it seems like a big gamble room your current vantage point, but it really isn't. You are an entrepreneurial developer in a tech economy where that skill set is at a premium (at least in startup hubs like the bay area). It seems like the worst case scenario is that you end up getting a job at another startup if your projects don't work out.

Good luck!

The only pushback is that you are risking your savings on this, so it's still a big decision (maybe not gamble exactly, depending on how you look at it). There's always opportunity cost at risk.

However, I know I personally work best when I focus on one thing, or at most two. Seems like you have too much on your plate, so I would recommend cutting something as soon as you reasonably can.

Either get your head back in the game, or quit. You aren't doing your employer -any- favors by taking his money when your productivity has "dropped to almost nothing".

You aren't doing your employer -any- favors

Normally I'd agree but in this specific case it sounded like he's the only developer. Being around just so fires can be quickly put out and so that you can transfer knowledge when the new hire arrives is definitely worth something to the employer.

There are actually three other developers so it wouldn't be the end of the word for them, so to speak.

A good friend of mine told me that, the minute I start affecting my personal brand and reputation negatively at a job, I need to start thinking about what to do next. The worst thing is to leave on a low note than a high note.

If you think leaving the job is inevitable, then you should start preparing for that - i.e. work hard, because the last memories in their minds will be the ones that stick the most.

I've been through this, and I have an open invitation to return to an old job because of it. For now I've left it all and I'm building my own company. Just make sure you understand your costs, and make sure you have health insurance. Don't buy into all the crap about - i'm young, i'll just buy the cheapest insurance on the market. The insurance is for the things you don't expect. Not being able to eat or pay rent are small problems, but neither can bankrupt you. Medical costs can. My buddy broke his leg on a mountain; fortunately he has insurance, but if he didn't the costs would have bankrupted him. He's a young and healthy guy otherwise

Also, people start their own companies with far less than 1 year of savings. You'll find, even if you have 5 years of runway, the prospect of jumping the safety of your paycheck is going to be terrifying. Once you do it though, you'll stop thinking about it very quickly. Look at it differently - 1 year of runway may force you to work harder than ever; you know, necessity is the mother of all invention.

How much is decent health insurance these days for someone young, in good shape, and with no existing conditions?

I pay $105 in California from Anthem Blue Cross with a $3500 deductible. After the deductible, everything's covered... basically, i do my best to stay healthy, but worst comes to worst, $3500 will be the least of my worries.

#2 suggests you may be underpaid. I'd go to your boss privately and tell him you've thinking about leaving to do a startup because you don't feel challenged at work, and this is hurting your productivity and interest in the job. All of this is true, you're just afraid to say it because of an innate desire for conflict avoidance.

Be honest with the people around you about what you want (part of this means thinking it through yourself...). In a worst case scenario you lose your job. But if you're really ambivalent about leaving, giving notice like this should alleviate any guilt over quitting and being honest should keep you on better terms with people than the alternative. And you never know. Perhaps your boss will give you a raise or otherwise help solve your motivation problems.

Money really isn't the issue nor is it the lack of a challenging project. I have two start ups that are up and running and have paying customers. I started the two start ups because the opportunity to do so was too good to pass up. It wasn't because I was unfulfilled at my day job. The reason I'm not giving 100% is because I'm just more interested in my start ups now and running them takes more time and cognitive capacity than I can commit in a 24 hour period.

I was going to give some other advice, but, given that you have a year of runway, AND partners, AND revenue... what are you waiting for? Seriously? Do you have children and/or others who really depend on your income?

My other thoughts:

It strikes me as odd that there are two threads on this theme at once...

I'd recommend going part time (if you really don't want to quit), as another poster did, if they'll let you (my company did). My company also seemed to be in the same position as yours at #2, but when I left, it seemed pretty amiable - and when I came back a year later, they had no room for me.

It's quite possible that the hiring department is incompetent. Anyway, that is not your concern. Especially if you're not productive there; taking their money for nothing isn't that big of a favor to them.

1.) Are either of the startups making any money now? Are there good prospects for either of them to start making money soon? Do you have any other financial obligations?

If there are good financial prospects for one or both startups, and you can live for a year on your savings, and you have no other financial obligations, I don't see why you wouldn't take the plunge. Even if the startups don't work out, you will probably have substantially increased your skillset in a year.

2.) On the one hand, you shouldn't screw your current employer. On the other hand, if they can't find a developer after several months of trying, that's their problem, not yours.

Try to make the transition as smooth as possible for them, but don't stay just because they can't hire.

1) Both start ups are making money now. And my only financial obligations are rent + utilities + food and misc stuff.

One is B2B and the other is B2C. The B2B obviously has a smaller market but the ARPU is fairly high. If it continues to grow the way it's growing it should be able to support me soon. The B2C has a much larger market but the ARPU is much lower. I'm having a harder time getting traction with that one but haven't done any marketing. If things go well, it has a lot of potential to make a lot of money. If both are successful, they should more than be able to support me.

2) I feel like I'll be screwing my employer either way. If I don't quit or go part time, I'll be wasting their time and money. If I leave, and they can't find a replacement, they'll be down a developer for who knows how long.

If your start up is your dream - go for it!

You are much better of then most entrepreneurs: the projects are up and running and are making some money. A lot of people quit their jobs and then get started. And a year of runway is even better!

But I agree to the other comments that you should focus on one of the projects which can really become big.

Re 2: recruit your replacement yourself. Maybe you fins somebody even here in HN?

Sure. Job post here: http://www.photoshelter.com/about/index/jobs/engineer-php

1) If you use up all those savings and things don't work out and you have to go back to getting a regular job, would you feel good or bad about having done the whole thing? If good, go for it.

I should also mention that I have a partner in each of my start ups. So, if I drop one or both of the start ups, I'll be screwing them over as well.

No doubt, get out of there. One year's runway is plenty and you are not doing your current employer any favor's by lingering.

Okay ... I'll bite. What are your startups?

http://www.sproutvideo.com

http://www.physicalfix.com

I am really digging the idea of charging $1 for the trial. Care to share how it's effected the quality and quantity of trial users?

This is actually an idea I took from my current employer. We did this from the beginning so we don't really have numbers on how it effected our signups. The real motivator behind was mitigating our costs. The previous company I worked for was a video hosting company and there were lots of issues with abuse. Lots of people would sign up for free accounts, upload full tv shows or movies and post them on popular sites for illegal tv or movie watching. We'd delete these accounts as quickly as we could, but the second we did that, they would just open another. The cost of storing, encoding and streaming those videos to get a few paying users was something we didn't want risk. I can tell you that the majority of users who have signed up for a trial have yet to cancel their account. So, I don't know if we're getting less signups, but I have a feeling the quality is higher.

So, just to follow up... I quit today.

Just do it.

I would ask to start working part-time and quit if they won't let you.

I'd second this, especially as a temporary measure.

You'll of course have to be prepared to be fired outright, but odds are if you offer to stay on a while and help them hire and train a replacement, they'll take you up on it and you'll leave with all your social karma intact - which means you may be able to come back later if your startups go belly-up.

Social karma has real value that way, it's worth some effort to maintain.

Are you single and do you have kids?