True Story: I broke one relationship, and missed another because of my startup, is it worth it? [closed]

First off, I don't know whether I should dispense relationship advice.

Second, we only have a few lines from your perspective to go on. Everything what I say below may be false. Really. Don't take this for more than it is, it's just cheap advice given for free on an Internet forum, without knowing the deep details of your situation.

Note that at that point of time I didn't even ask her to support me, either financially, emotionally, and I didn't ask her to share my stress, work load and troubles.

I'm going out on a limb here, and extrapolating from what I have seen from myself, and from male entrepreneurial / programming friends:

This to me sounds like you took an often seen male approach, and assumed that your partner would get stress from sharing in the specifics of your startup; the agony, the fear of no income, the customers sending you negative emails, etc.

In my personal experience, most good women get stress from emotional absence in the relationship, not from the specifics of your job situation. Women often feel problems get smaller from sharing them in the relationship, whereas men sometimes feel sharing problems means burdening the woman with issues that aren't hers to carry, and hence don't share their burdens/fears/sorrows. And that's exactly the wrong and damaging thing to do.

Is it possible -- and again, I don't know -- that your relationship was troubled by your unwillingness to show your woman what you were actually doing and what you were secretly scared to death of, and not your long hours?

I got this strong feeling that if I openly pursued her, I could easily won her over. [..] the cost of pursuing a girl might not be very high but the cost of maintaining a relationship is.

Look, again, I don't know I'm just guessing. But the above sounds like a classic case of not being ready for the next relationship, and thus not sending the right signals to her.

What's the point of earning all the money in the world, and having no life?

I can't say, as I have never tried having tonnes of money. But as a good guess from my current vantage point, trading love away for financial success will never ever be worth it. At the same time, it feels to me as if you're selling yourself a little short. It sounds as if you attracted two good women within a short time frame; so clearly you have something going for you that is desired by the opposite sex. Good luck on the next one!!

Sad Guy - some thoughts - hope they're helpful.

1. Relationships are inherently risky things - although your situation significantly increases the risk, the things that have happened to you could have happened to someone in a steady normal job. Look at this way - better to find out about someone's tendencies towards infidelity early than 10 years down the line. If you are hoping to find a life-partner, you are going to have to risk getting hurt; there's no way around that.

2. If you have entrepreneurial blood, you are never going to be happy in a regular job working ultimately for someone else's benefit. So you're kinda stuck with running your business(es) and trying to work out how to get your life back. Having a couple of years of high intensity is okay (and some would say inevitable) but you need to see a light at the end of the tunnel. Getting to the point where you can share some of the work with a business partner or employee is something to aim for - if there are two of you, you can operate with a bit of give-and-take in the business. (For the record, I wished I had spent more time with my young kids after the first couple of years of my first business, but I let it carry on being non-stop for nearly 5 years - it's a wonder my marriage survived).

3. You've should be pleased that you've come to the realisation that there's more to life than money and business at this stage. I think it took me 10 years and countless misssed family opportunities to get to that place - opportunities I'll never get back. Use this as an opportunity to work out what you really want out of life and then go about achieving it. Seems like you want to find a partner - I suggest you make that a personal goal with a timescale attached to it, but recognise that (as a man) you can't do two things at once. Focus on getting the business to be more self-sufficient in the immediate term so you can devote more time to courting, etc, in maybe a year's time. Just don't lose sight of the fact that we each don't know how much time we have on this earth, and as Jeremy notes, nobody wishes they'd spent more time with their money.

Hope you managed to work through things. Good luck.

Every entrepreneur I've known has experienced the tension between the demands of a start-up and the rest of your life and relationships. And, as the saying goes, nobody on their death bed wishes they'd spent more time with their money.

One of my strategies is to be disciplined about how I manage the demands of those crazy periods when it's all piling up. I extend my core day into earlier and earlier morning - and protect evenings as long as I can. That way I know I can give time to others without worrying that I'm taking it from work. And those around know that sometimes, I'm with them because I value time with them, even if all they get is the worn-out bit of me that's left after a hard day.

Then, whether what I'm working on is successful or sinks without trace, the time comes when I hit the evening still fresh - and because I've stuck to the habit of spending time with people I'm close to, it doesn't feel like I'm pushing my way back into a social life I've forgotten!

When I read your question, it sounds more like two different stories to me. You seems to make a link between them. But that's just an impression.

Now about your question if it worth it:

NO

I believe that a great entrepreneur don't choose between good family & friend relationships and his venture. He chooses both and put priority on the first. Always.

Never drag your baggage from one relationship into another. Your new girlfriend is not your old girlfriend. Being cautious over you new girlfriend because of something your old girlfriend did is not a good way to move the relationship forward.

Also, it's admirable that you are so devoted to your work, but remember to stick your head out from the trenches every once in a while otherwise you'll miss what's going on.

Best of luck moving forward.