Should money prevent me from starting a company

You can start to work on your idea on your free time, so that when your 5 yrs are up you have a company that you have been nurturing, and if you need to you can then see about using your vested options to help better fund your idea.

But, as was mentioned, this depends on what your current obligations are, and your current financial situation. If you need to work to pay bills then staying with this company may be your best bet, as it is equivalent to being paid $300+k/yr beyond your current salary.

Find a way to make your current job more challenging, perhaps, and you may want to think about why you get bored with corporate life, and why own ideas didn't pan out. Take some time to better understand your strengths/weaknesses/motivations before you make such a big decision.

I'm all for following the dream, but it sounds as though you have an opportunity to set yourself up for life here.

For me, it would depend on the schedule of those options and a very conservative view of the future stock price, but I would tend towards putting in a few more years and keeping your expenses low.

Being in your early 40s, mortgage paid, with a few million in the bank would give you a lot of options. You could then spend years on entrepreneurial vetures or even angel investment.

Would it be insane to stop living a life you cannot stand and risk it for a life you want? no, it isn't.

If you liked the corporate life, then leaving your job would make no sense. If you had family obligations that would require you to keep the job that would be another thing.

The real question is, why do you want to start another company... If you are doing it just for the money, then you are more likely to make money keeping your job. If you are doing that because being an entrepreneur is a part of who you are, then you would not deny it. If you can afford to follow your dreams, then you should do so.

Figure out if sticking it out for another five years is worth the fact that you will have a few more years worth of saving for the next dream you would want to peruse...

Whatever you choose to do, I wish you luck.

In my exprience, money always matters in some way.

Option one, You quit, start a company earn net 1,7 mil in 5 years
Option two, You stay start or support a side project and loose 1,7 mil in 5 years

In these two option you will just be the same place, comparing to alternative cost of your desition.

I definately take Option Two and I will have chance to spend 300k a year for my dream so I can focus on my product rather than trying to findind money and attracting talented people.

James has a great idea about working on your idea in your free time. That's how I got my jig off the ground.

My take is that you should amass as much savings as you can stand to help you realize your new company. Think of it as a game. The more you vest at your present job, the more runway you have for your new gig.

It's not insane to walk away to follow your dreams. I did it and it was the right thing for me (although, the amount of money was not nearly as much). For me, it came down to being able to create something I believed in and had some control over. I'm with you on the corporate overload thing -- not my deal at all. It's a deeply personal thing. No one can make that call except you.

If you are totally miserable at your present job, then quit. Nothing crushes the sprit nor the creative juices like drinking bad corporate coffee and listening to corporate buffoons.

If you stay and suffer with the corporate culture, what do you plan on doing with the money? In your current financial situation it doesn't sound like you really need the money. I wouldn't be so sure that a financial company that just went public will have a stock price that is a lock 5yrs from now.

What is your new venture? I think the viability of this business is the key since you are not comfortable in the corporate world.

The exercise I wrote up in my Part 1 http://answers.onstartups.com/questions/2070/how-to-become-more-of-a-risk-taker/5584#5584 answer would be a great tool to use with this decision.

For some people, quitting and just going for it is the right answer. For me, I preferred to work in my day job and then start my business part time before completely quitting.

Ultimately, it comes down to how much you really believe in, want to and are willing to pursue your new entrepreneurial venture.

Wish you the best.

One big lesson for start up leaders is the need to have more capital in hand than you think you'll need. I'm concerned that you might be heading down a path to leave a big chunk of current equity on the table in your pursuit of creating your own new business.

Is there any chance of creating a "best of both worlds" situation here? In other words, is there a way to preserve your current equity, change the things which are bothering you in the current role, and potentially have your current employer back your new venture?

First, sit down and write out exactly what you do not like about your current situation. Then, schedule some time with your manager to have an open discussion on your career options. Do NOT threaten to quit during this discussion - simply say "hey, there are lots of great things about being part of this team - but - I'm wondering how we could change these 2-3 things". Depending on how that goes and depending on your relationships, you may want to introduce the idea that you have a great new business idea and would like to pursue it and that you're willing to share some of the upside.

Even if they are not willing to change or open to backing you, I'd encourage you to stay to at least your next equity vesting date so that you walk away with as much funding as you can to help get your new venture off to a good start.

One cautionary note - you point out that you've tried multiple entrepreneurial ventures and that only one has been successful. So, you may have a great idea - but - execution and results count more. At a minimum, before you jump - make sure you fully understand exactly why each of the ventures which did not work failed and that you understand how to not make the same mistakes.

Good luck either way.

Doug - I am in a similar boat - I just quit from a role in the financial software market because of the usual issues in the corporate environment (I was employed by the firm that acquired my first business) - drop me a line if you want someone to bounce your ideas off confidentially - see my profile for contact details.