Yes, me and my co-founder will be bootstrapping for at least the first year. But our plans are to become cash flow positive in 6 months. I can probably survive for 3-4 years with no job, my partner at least 1 year.
You have 3-4 years socked away and you're wringing your hands over this decision? I think the answer is no, you shouldn't. That kind of runway should make the decision an absolute no-brainer if you really want to strike out on your own.
I would assume he's taking any obligations he has into account when he says 3-4 years. It's not like anyone would say "I have 3-4 years, except when you take into account my mortgage, kids, student loans, eating, bills..."
No, I'm advocating being realistic about your tolerance for risk. If 3-4 years of runway isn't obviously long enough, then you probably don't have the stomach for a startup.
I had 3-4 years runway when I started and it wasn't obviously long enough (I remember hearing the exact same comment you just posted when I asked for advice). I ended up starting up, failing, and taking another job (still have 2-3 years runway left) and don't regret it at all.
People with 6-figure salaries and 3-4 years runway tend to be calculated risk takers. They don't jump in unless it looks like there's a decent probably of success. That doesn't mean they won't take any risks, just that they want the odds to be in their favor.
All that said, I'd say go for it. You can always get another job, and 3-4 years means you won't be in dire financial straights when you're looking. Starting your own company often uncovers other opportunities that wouldn't otherwise be there if you just sat in a secure day job, too.
Umm... you left your job, tried a startup that failed, and you still have 2-3 years of runway left. It's pretty obvious to me that you had a long enough runway.
I'm not saying this to be mean (plenty of startups fail), but your startup did fail. Your experience isn't exactly a knockout blow to the argument that anyone hesitating to jump in even though they have 3-4 years of runway might be too risk-averse to be successful with their own company.
Someone who has a failed startup is in a better position to give advice than someone who has not.
You seem quite willing to deem someone not ready or not in a position to give advice. Also, before you make a bold claim about someone's character it would be helpful if you read their previous comments.
It didn't really hurt my feelings. We're all (well, mostly) adults here; we can disagree without taking it personally.
I just thought it was kind of odd that you'd suggest someone might not have enough risk appetite for a startup, and then when someone else replies that most entrepreneurs take calculated risks, point out that they failed. Failure is a part of risk. All those folks who did take the risk of starting a startup...well, most of them failed. Does that make them unqualified to give startup advice? Kinda contradictory, given your original point.
I never said you were unqualified to give advice, and I wasn't trying to insult you for your startup's failure (of course failure is a part of risk). My original point was that risk-averse people probably won't have successful startups, and I didn't understand why you would hold up your failed startup up as evidence to the contrary.
Here's another bold opinion: if some jackass like me can persuade him not to do a startup by pointing out that startups aren't for the risk-averse, then he probably shouldn't be doing a startup.
Who's judging anyone? He asked if he should leave his job to do a startup, I said "probably not" based on the fact that he's hesitating even though he has a really long runway.
Okay, fine. I'm more concerned about people who have 3-4 years of runway and still aren't confident enough to jump into a startup without first consulting a website full of strangers. To each their own.
The above comment is inspiring to me - and I think epitomizes why Americans have been so wildly successful in the tech realm.
Up here in Canada... well, a very wise entrepreneur in Toronto once told me: "Up here they ask you how many times you've succeeded. Down there they ask you how many times you've failed", and I think there's truth to it.
In that case you are well placed to give it a shot. There are few certainties in life, but you are not in a bad position.
A few months ago I was in the same position as you, was procrastinating about quitting, and ended up getting made redundant as a complete suprise. Personally I haven't looked back. Nothing is guaranteed, you need to personally decide more which you will regret most: quitting now, taking the risk and going for it, or waiting till till later when the economy might be better, but then you're personal circumstances might have changed. At the end of the day - it has to be your decision, but if you do genuinely have 3-4 years of cash, then go for it!
If you're relying on external funding in the near future it might be hard.
If you've got the cash to fund it yourself, then there is a case that it's a great time to start a business.