Sit down and talk it out with them. While they may not be able to afford to keep you, it may be possible to work out a transition plan for them to get someone else in to fill your place.

If the company has been operating for 5 years and can't afford to pay you at least 75k in salary for all the stuff you're doing, then the company won't die because you leave, it's already dying. You'll just be putting the last nail in the coffin.

Keep in mind that you are in business as well. You've been operating at a loss essentially for several years. For what? Do you have a stake in the company? Didn't say that so I'd say no.

I'd have left 2 years ago. Even if they pitched in $150 a month in health-care costs, you're still losing a lot of money.

My Beliefs on startups, either gleaned or painfully learnt that I use to assess most anything:

• ACTIVITY VS. RESULTS: In startups, do not confuse activity with results. Do not confuse progress with results either.

• PROFIT IS BLOOD: Profitability and regular cashflow is the blood flow of your startup. Being able to survive is an accomplishment but a small one. Growth is the true goal.

• STARTUPS ARE ABOUT VALUE Every thought, action, person, feature, should be thought of in terms of value. Seems obvious, but we see the gap between user wants and what software delivers.

• EVERYONE SHOULD GIVE VALUE Everyone must contribute value that measurably and consistently brings results in a direction everyone wants to go. If someone isn't working as hard as you in their area they are not helping.

• 1+1 SHOULD ALWAYS EQUAL 11.: When involved with others, synergies must magnify greater than the sum of people. If you do not have a great advantage by coming together chances are things may fall under their own weight if things really take off.

• GET AND STAY ON THE SAME PAGE: People's priorities change. Ensure everyone can be committed to the same game plan (including R&D if that's where you're at) for the same amount of time and effort everyone is. Talk early, Talk often.

• HEALTH OF A BUSINESS IS THE # OF NEW CUSTOMERS: The health of a business can be quickly determined by the number, frequency and size of new customers + regular orders.

Complete speculation:

This sounds to me a case of you doing the majority of the work in the business. The idea could be bad, or the business skills you need around you (sales and marketing) to make this product successful simply aren't there with your Boss and his son.

Based on that, would you be okay to continue working here if there was growth and results happening at your current salary?

1) Are they doing this full time like you are? If not, how is a full time effort being delivered to sales and marketing to ensure success of your hard work?

2) If they are doing this full time and not getting results, you should take that into consideration.

3) It might be enough when you start having doubts. Unless there is something dramatic that is different, you will keep getting what you have been getting if everyone keeps doing what they have been doing. If you're in a situation where you love the project and it's not getting anywhere, maybe you can still enjoy it and take a lesser role.

4) If you decide to leave, explain to them that you care about them and the project. Clearly outline the needs (it doesn't seem to be just money) in your family that you don't want to try and extract from them to hurt them. Offer to keep developing for 4-6 months either full time, or gradually becoming part time to cross train the next guy. Only agree to do so with a very clear transition plan. You may want to use this time to get that 1/3rd of the company that you're owed, if you are owed it. Owning something of nothing is one thing, but if it takes off you do have sweat equity that should be recognized (even if it's profit sharing) if it has been agreed to.

5) Would they drop you if it was no longer financially viable for them? What kind of explanations would you be given if it happened?

All the best. It's brave to take a risk and you can always keep the positive lesson from anything.

Cry.

When it comes down to it, you're deciding between the welfare of your family or your boss' family. It sucks, but there's really only one way to come down on it.

I'd probably feel terrible about it, but I'd leave. My advice would be to talk to your employer about your feelings. Explain you'd really like to leave, but maybe offer to give them a lot of notice -- a few months, maybe -- while you find another job and they find someone to replace you (if they can). That way you can help train your replacement (fun!) and hopefully they can ease your workload a bit for the final few months. This will also mean they'll be more flexible about you going for job interviews.

You gotta take care of you.

If you want to stay, talk to the owner, tell him that if he can't pull more money for you, that you want voting shares in the company as a form of payment. (laywer blah blah)

If he balks, you need to be prepared to walk. This means that you should have one firm job offer in hand, so you need to start looking.

But you need to talk to him and let him know what's going on. Don't corner him and make him overreact. That could be bad. If you don't feel comfortable talking to him about it, he's a bad manager and you need to walk.

Essentially his business is failing and you're being dragged down alongside it.

If you want to be super nice: help him find and train a replacement, and send customers his way.

Ultimately, you need to take care of your wife and yourself.

Before I joined my current company I had an opportunity to join a startup that was in exactly the same phase you are currently in. 3 years in and hadn't moved past its two founding employees. I walked away from it and joined a startup that had been around just as long but had 65 employees when I joined it.

First of all, three years and zero growth are generally a very bad sign. Even in this economy, you should be able to hire more employees and grow your business at a faster rate. If you can't get capital via product/services revenue, investment, or loans in that amount of time, then its time to get out. The odds are that you have poor management or you're bankrolling a bad idea.

Find a replacement, offer to train him/her, and come up with your exit strategy.

I hate to say this, but in my opinion you need to scoot. I'd start looking immediately. Even in this economy, you should be able to find something new, but a startup is likely to have real issues for a few years, at least. Venture capital might be hard to come up with.

I know it's gotta be difficult, because you probably feel some ownership, but it's not your company. Staying there, if it does fail, will leave you without a job, trying to find new work.

As far as telling them before you find something new, that's a tough call. if they're strapped for cash, they're likely not going to be able to hire your replacement and keep the both of you going for any meaningful time. The fact is, though, it's business.

You have a family, and your family has to come first. I'd get yourself out of that mess and back with a reputable company, earning what you're worth and caring for your family.

While trying to look out for everyone's best interest is certainly admirable, your first loyalty needs to be to your family. Even if the money was good you would most likely would still be miserable which, speaking from experience, pretty much makes home life miserable. I think it's pretty much time to get out.

The first thing I would do before I ever open my mouth would be to get my resume together. You should have a ton of experience to draw from considering the fact that you are the only technical person in the company. Once I had this together I would just start applying for jobs whether it be directly with companies or through a recruiter. Personally I think finding a really good recruiter helps a lot.

Once you have some really good job leads or offers, that's when I would sit down with my employer and be honest. Don't get personal, but just explain exactly where your at. No one can argue with the fact that you are trying to the right thing for your family.

A few do's and don'ts:

• When talking to your current employer, don't make it a sob story. Let them know how much you really appreciate the opportunity they've provided for you, and that you just need something a little more stable.
• When you accept a new job offer Do let them know that you want to give your current company as much notice as possible to help with the transition.
• Don't try to use a job offer as leverage from your current company to make you a better offer. Personally I think that's kind of underhanded, and it sounds like they aren't in a position where they can do that anyway.
• When interviewing and they ask why you're leaving Don't make it about money, or anything other than the fact that you are looking for an opportunity to grow. If push comes to shove it is Ok to mention that you are looking for something more stable than where you are at currently, but always stay positive.
• Most importantly, pray about it.

If your concerned about your experience, don't be. Play up your positives. A really good cover letter I think goes a long way.

Best of luck!

You have to take care of your family FIRST! Don't wait until it's too late. Go look for a company that can afford you a health insurance. If something happens to you (God forbids), think of what would happen to your wife. Think about your goals and motivations...and think again!

Steps to take:

Step 1. If you and your wife are having a hard time making ends meet, then she should be working, regardless of whether you have kids or not.

Step 2. Get on your wife's health insurance plan. Can she get veteran's health insurance? You mentioned she was in the military. Try to explore this avenue.

Step 3. Set a deadline. Stress has a direct correlation to the gap that exists between what we want and what we don't have. It sounds like you are desiring stability and profitability. Sit down with your boss and explain that you are going to work until X date for X salary/benefit, and then Y date for Y salary/benefit as the scale progresses. Ask for what you feel is right and be firm about it. If it doesn't work, then there are plenty of companies out there looking to hire.

Good luck.

I think the best plan in these situations is to have exactly this conversation with your boss. You are not morally held to keeping the company going. It is important to decide between is this the job you want and with the benefits you need for you and your family's happiness.

In this situation, I like the honest approach of sitting down with your boss and saying this isnt working for me. I feel bad because I dont know that the company can survive without me but my family and I cant survive. Then you can ask him for how he thinks you should both proceed. You guys may decide to cut now or you may set a timeline that says if you dont have insurance/raise in 6 months you are walking.

If the company is so underfunded it cant even afford your salary, a good question is whether you think it has enough money to survive. It takes money to market, sell and create a successful company. Does the company have what it takes to succeed in a resonable timeframe and will you get compensated for the risk you are taking with your life and career trying to get it there? This has to be weighed against keeping the family happy.

You've been there 5 years, obviously things aren't going to change over the next 5. There's been no growth and with a major employee leaving (the other engineer) and with them not replacing him, you can say the company is shrinking.

The answer is simple: if you want health insurance and/or better pay you have to leave. You've been there too long and you're getting complacent with your job. Just leave, you'll be much happier. You should do your boss a favor and give him heads up that you will be leaving soon (assuming you're sure he won't can you ahead of time but if you are the only guy that's highly unlikely). You might considering working extra hours for him on the side to give yourself even more pay in the future on top of your new job.

I am all for loyalty and I think you've shown that, but the company needs to give him some back. Do not think of it as working for a person, but as working for an entity. If the company want to keep you then it should show that needs by taking care of a valuable employee (ie: paying you more, benefits) especially if you can easily find a better job. It sounds like you have committed a lot. If the other guy is committed (I don't know what he has already put in) then I would advise him to take out a loan to take care of you. If the company can't do that and has been 'on the verge' for 3 years.. then it is probably failing anyway.

Do not stay on to a something that is failing out of loyalty and do not stay on to a company that can't take care of you to your detriment. Companies succeed and die and this is normal. The only reason I would stay on is if you can see getting great reward for the cost. There is risk involved but it sounds like you are reaching the end of what you and the company can pay.

Being honest with yourself and others will pay off better than trying to hobble together something based on pure loyalty. Talk to your coworker/boss (not as a friend, but as a fellow employee of the company) and try to figure it out.

You need to walk off only if you have an offer from other company. Otherwise you will be jobless in the current economic scenario. Try freelancing, try yoga (I can dispatch some Yoga DVD's for you for free) to keep you in good health. Dont worry much about them. They will find another replacement. Remember nobody stays hungry. Else move to another country for some new experience, better savings and lower living costs.

It's a tough spot, though I believe that in the end your family matters most, especially if you have plans for children. I think that after five years, your Boss has to understand the point in life that you're in and your needs. I am also concerned about whether your current job would count for the experience.

Is there some way you can work for them part time and take a primary job with benefits elsewhere? They can maybe hire someone cheaper to do the lower-level mundance stuff, while you still do the stuff that takes experience and smarts.

Should you decide to stay or decide to go? There's lots of good advice here. What I'll say is if you would decide to stay, it needs to be because you feel like this business is actually going to succeed, not just because you feel the business is going to fail without you. From the details you've given, it sounds like the company/owner is not able or willing to accomplish what is needed in order for the business to succeed. I may be wrong. Only you can truly answer that.

And for one more piece of advice from someone who has been involved with a startup (and left), get your deal regarding the ownership **in writing**. No matter what, it sounds like from where you're at that a discussion of some sort with your boss is in order. If you decide to stay, part of that discussion has to be about getting your ownership in writing. It's not a slam against the owner or his son, its just how business is done.

From an ethical standpoint, I completely understand where you're coming from. Not 100% related, but I lived with a friend of mine for a few years, most of which she had no job to pay the rent. I kept her around because I "knew" that if I wasn't there for her, she would fall flat on her face. Truth is, I got taken advantage of, badly. I dished out so much money that it makes me sick to think about it. In the end, things never worked out and I'm the one left to clean up the mess.

The bottom line here is that you need to look out for yourself. While you may feel you have a commitment to the company, you have to look at it from a business standpoint. All CEO's need to know when to cut their losses and move on. It sounds to me like this company is doomed (or at least very likely). If you're willing, allow for a transitional period. Just make sure that you have a job lined up first and that both parties are agreeable to a reasonable transition (it sounds to me like two weeks will not work for you in this situation).

Good luck...

Realize that your boss is a bad business man. Get out now. It's not going to turn around, and the company has let its services be devalued. Leave. Today. Really.

Then cry, create a resume, get unemployment, and get a better job. YOU DESERVE IT!

I've been at several start ups and there are a few things they had in common.

• It always seemed like we were on the verge of something or on the verge of "making it".
• When the money finally did run out, the company took care of their number 1 and not mine.

When I was working for startups, my wife always had a stable job with good health insurance. It sucks that you feel like leaving them would leave them high and dry, but I'm pretty sure when they come to a decision that they have no money left, they will probably have no money left to pay you any severance, leaving you high and dry.

I'd look for another full time job, when you find it, let your current employer know that you are leaving and that you would be willing to transition someone new and consult for them at an hourly rate.

I worked for a start up, I learned several things there.

1. No matter how "nice" an owner seems, any start up owner is in it for profit (otherwise it would be a nonprofit). He will not hesitate to firesale the company(split up the assets and sell them piece by piece), if he can find a buyer (without regard to the employees). It's not evil, just good business. He will try to control expenses as much as possible by skimping on everything, including salaries, even when the company makes money. His goal is to get as much as he can from employees with as little money as possible.

2. Get it in writing. A "verbal" agreement to split the profit 3 ways is nothing. Generally speaking employees at a start up are paid less because they have a stake in the company. The idea is that your stake will compensate you for the low salary. If you work for a start up without some type of stake, that is a bad business decision on your part. The whole idea of a stake is to compensate you for your low salary, blood and sweat, etc... If an agreement isn't in writing it is worthless. He could make a fortune and give you nothing.

3. Start up owners are often over optimistic. There is usually a fast plan, a medium plan, and a slow plan. Often the business takes the slower plan that wasn't mentioned. Generally these plans promise the world, bonuses, pay increases, shares in the company, and some type of end game where the company is sold. if there is no business plan at all, that is a big red flag. If the plan changes, that is a red flag, but as long as each new plan makes some sense it may not be terrible. Sometimes plans change, you thought there was a market for something and there isn't, but during the process you make something else and find a market for that. Or you find the market for the product you are selling is different than you thought. But too many changes may be a red flag.

4. In your career you need to be in it for yourself. If a company fails to pay you what you are worth, and fails to rectify it then good-bye. If a company fails to provide insurance and other benefits you need, good-bye. If you are working 80 hours a week every week and need to see your wife more, good-bye. I can tell you now that you are severely underpaid. You have a family to support. I have a friend (who is a key employee at a start-up) and he keeps whining about the company's slow profits and that he is going to leave, and they keep giving him more shares. But he makes sure to get it in writing. Even so he is considering quitting once his shares vest this time. His idea is that someday they will sell the company and the extra shares will be worth something. But for a non key employee like me, I had no leverage for negotiating shares. They just found someone else to do the job (at market rate) and didn't have to give any shares to that person.

I worked for a start up and my biggest regret was not leaving sooner. Some of the guys were in it with huge stakes. But because I just got out of college they got me cheap (which the COO admitted he was shocked at the deal and if he knew he could get employees like me that cheap he wouldn't have hired the rest of the guys) and gave me a tiny share (a tiny fraction of a percentage). 1.5 years later I got a raise (10,000 more per year) and I was really happy. Then 2.0 years later I got a raise with everyone else (another 10,000 per year) and again I was happy. When I finally quit, they offered me 40,000 more to stay without blinking, that was their first offer (meaning negotiating they probably would have gone higher). I still left, and my other job had Offered me 20,000 more. But the reality is that you don't know what you are worth until you leave. And also, that your salary is based on your previous job. So by the start up underpaying you, you will be underpaid in your next job. They will base your salary on 48,000 and not the 75,000 or so that you should have been making. Also when searching for a job, they will wonder why you are underpaid, did you suck that badly? If you left at 75,000 (probably around what a 27 year old software developer with 5 years experience should make...if you a superstar the salary goes way up) you would now be starting at 75,000 so your next job would probably pay you at least 80,000 and for a really good move more (in this economy it will be hard). By leaving at 48,000 you will be lucky to get 55,000. Someone may realize you are really underpaid and offer you 70,000 (they may have to because the job may have a salary range and hiring you way under it in a big company may raise red flags) but finding someone is luck. And the economy is not going to help you there.

With a start up basically 3 things happen: 1. It runs out of money and fails (most common) 2. It limps along a lot slower than the owners imagined and they end up selling it for way less than the business plan 3. It is wildly successful, makes millions of dollars, or is sold for millions of dollars making everyone rich (most rare)

The one I worked for was #2. it is still limping along, and they are making more profit. But no one is selling the company anytime soon, even though it was formed in 2002 on a 4 year business plan.

if you have a normal job you work 40 hours a week and make market rate (sometimes 50 or 60 hours too but if your aren't making above market rate it's a bad deal).

if you work for a start up you work over 40 hours a week at a discount for shares. In the end if your shares are enough to compensate your salary for market rate and the extra time it is a bad economic decision on your part.

I understand that you are nice and want to do him a favor. But losing 5 years of income (assuming you started at 22) probably say 20,000 a year so 100,000 a year in income is more than a favor. A favor is let me give you $20 to help you get this. Let me give you $100 as a loan to help you out. Not let me give you $100,000, not have health insurance so if I get sick I will drown in medical bills, and not see my wife.

You shouldn't even be asking the question. It is obvious what the answer is. Quit IMMEDIATELY. I mean give time for a transition plan but no more than two months. In reality one month is probably more than enough. 6 months or a year transition plan is a no no.

I guess it depends on what you think the prospects for the company might be. Startups can indeed take a long time to get going, especially when running on a shoestring budget. But if you do stick it out I would definitely demand a stake in the company on top of whatever salary you get. It really sounds like you ARE the company at this point, so that wouldn't be an unreasonable demand.

Maybe sit down with them and talk about their business plan, and how they plan on going forward. Tell them you'd like to see the company grow, but you can't afford to continue the way it is, so there needs to be some real hope of improvement.

If you CAN manage to make something of the company, and it's a business that you believe in, you'll probably be happier in the long run than being just another corporate tool. But if there isn't much prospect of making it then you really have to move on and take care of #1.

Start looking around for jobs before you tell them that you plan on leaving, to protect yourself, but do give them as much warning as you can before leaving.

If I were in your situation, I'd have one more thing I'd want to resolve (if you haven't already), and that's to learn where the company really is, and what's the real remaining opportunity.

Get ahold of Geoffrey Moore's Inside the Tornado or a similar book and see if it helps you understand where the company really sits in the opportunity cycle. Perhaps you'll be able to talk it through with the owner and agree (on what would be based on what you learn). But see if you can at least maximize what you learn from this. Five years is a long time - I would think you are either on the cusp, or not. Also, if you know any wise investor-types, talk to them as well.

Working for two companies and neither can pay you a decent salary? You need to cut the cord man :)

I know everyone is telling you to run, but I caution you to take some time to think about it. What chance does a programmer have to own their company? You need to take an ownership of your company. You need to make the company work. If there are only 3 people in the company everyone is responsible for the success of the company. If you know how to make it work yell at your boss until he makes the changes or fires you. This is YOUR company, you built it from the ground up, if you take ownership you could have a chance at making it, if you walk away you are looking at working in another cubicle for another company for another 30 years.

First think about the viability of the company, not relationships. Is the company going to work? Can the software be sold? It has 1 client that must be paying 48k a year, that’s better than 99% of the start ups. Next figure out what needs to be done to make it work and work better. Decide if you are willing to do it. Then sit down with your boss and driving the company. On the other hand if you don't think it is viable you shouldn't be there.

On another note, get all compensation in writing soon. It is amazing how fast people forget the programmers when the money starts coming in.

I know you feel like this is an ethical dilemma, but at some point you have to look out for yourself. I was in a very similar situation. The decision wasn't personal. You have to be able to live with that fact. I know it's hard when you're at a small company because everything seems personal.

Been there, done that. Ultimately I was a key developer at a company at one point being the most senior programmer there and #1 knowledgable of all the systems. Pay was crap, benefits were null and they couldn't afford me.

I did try and stick it out for awhile, but ultimately I had to realize that my sanity wasn't worth it anymore. I was in college part-time at the time and wanted to go full time and finish my degree, this job wasn't very permissive of this with their time requirement. So eventually I had a chat with the boss, started transferring everything I knew to a new hire and over the course of 3 months phased myself out completely, no regrets either.

For what it was worth this was in 2000, and the .com bubble burst of late 2000-01 ultimately did them in. They wouldn't have had much longer to live anyway.

Just one more comment. Your quit should be also good for your boss and his son. They will have to finally find new jobs where they actually might earn more. Who knows, maybe your boss still runs the company because he feels responsible for you.

you know the company is going to hit it big as soon as you quit, right?

is there any reason the company can't provide the health insurance? If they were eligible for SBA then surely they're a legit company and can at least get something. Is there some kind of financial reason? I worked for a startup when I first graduated, their health plan was an HMO and it was so bad it wouldn't cover some very basic medical needs I have... my physical and mental health got so bad that I had to leave in the interest of my own well being. I realized that they had depended on me so I was kind of screwing them over, but remember this: NO job is worth your health (or your family's health). Maybe take some initiative by looking into healthcare plans for small businesses and provide your boss with that info. there's plenty of those plans out there, maybe it's just a matter of finding the right one.

In the words of my father, "you need to look after you and yours before someone else".

Sounds awful. Tell your boss you have to call it a day. If they are keen on continuing, offer them a decent notice period (3 months maybe, it might take 3 months to find an alternative position in this market anyway). Although you can't tell us much about the start-up (understandably), if they haven't 'made it' after 5 years then they are not going to make it in the currently economic climate and in the end, your boss and his son will probably be better off doing something else as well.

Help them find a replacement and look after yourself.

By the way two other observations.

1. "We've never had money for marketing, and though we were approved by the SBA for loan backing, no one will give us an SBA business loan so we can actually do marketing." If you don't market your product how do you expect to sell it. I don't think the company will hit it big when you leave. Basically on a start up usually sales/marketing come first at the expense of everything else. Unless you have customers the company is dead. Any money that came in should go to marketing.

2. You have a severe problem. Do you want a divorce? "I had to move out of town to help some of my friends in their business (which I now am on evenings and weekends... and no, they don't have money to pay me a salary at all =) )"

Now only are you working for one start up for little money, you are working for another start up for nothing. There is a difference between helping a friend and being taken advantage of. You have to learn to say NO. and don't screw around with your livelyhood. You need a good secure job to support you and your wife that provides benefits. Also if you are working during the week and on the weekend when are you seeing your wife? You're going to burn out quickly. Exactly how long do you think your wife is going to put up with never seeing you and having nothing to show for it?

I wouldn't be so harsh with you. But you are already working for a start up for little pay and now you are giving your time away to another for nothing. Your next job may be another start up for little pay to "help" someone out. And maybe you'll "help" other friends out on the side. You need to take control of your life man. And learn to say "NO". It is shorter than saying "YES".

Your priorities should be 1. family 2. other stuff relevant to you and your wife being happy and so forth .... .... much higher number than 2. Job

You said it yourself you can't afford health insurance. What happens if one of you gets in a car crash or needs surgery (sometimes reproductive issues with woman start to show up in their 20's like endometroisis, fibroids, etc. and surgery may be required...not saying it is guaranteed but even if there is a 1% chance you can't afford it). If you're going to work on the weekends, it should be to provide for your family where your start up doesn't. Hell even working at Walmart would be better than what you are doing now with your spare time on the weekends, at least they pay. Even rentacoder's dirt cheap India rates would be better than nothing.

This question has been well answered but I wanted to make a general high level comment:

Don't stay at a failing start-up for more than a year. Get your 1 year of stock and move on.

Now, in this case, you don't even have a stock plan--it's not a real start-up. Find a new job, hopefully one where you can work with other people and grow. I would say that having spent the first 5 years of your career working alone has been a big disservice to you and ideally you could find a place to work that can make up for it.