Having bootstrapped my own business, my biggest issues were dealing with stress and 'the unknown'. I was unmarried at the time so I could handle the pay decrease and living without niceties.

Cash flow was always on my mind - if a client postponed payment, or flat out refused to pay for whatever reason (happened to me a few times, even from 'established' clients) I would be mentally overloaded trying to figure out how to get by for the month.

You go through such a roller coaster ride of emotion - There is no better feeling of joy and accomplishment than having a client sign a contract and pay with a nice check; there is no worse feeling than sitting at your desk, staring at the wall trying to figure out how you'll pay the bills for the month...

Anyhow, I would never trade the experience for anything, though I'm not sure if I could have handled it if I were married at the time; I would echo Dave's sentiment that bootstrapping is hard but also extremely rewarding. You'll come out a tougher SOB for it, thats for sure! ;)

I agree that the experience is worth it. I'm currently in it with a wife and 3 kids, and I wouldn't trade it for anything right now.

Good job pointing out the effect on your family. Bootstrapping is more than just a pay cut when your spouse and/or children will be affected as well. Discussing the potential risks with them is 100% necessary before taking a major leap.

So how many bootstrappers have spouses and families? Seems to me like the kind of risk that's easier to take for those who are younger and/or have fewer responsibilities.

Also, how many boostrappers make lifestyle changes months before they leave their day job for the uncertainty of boostrapping? I would imagine you'd want to have enough saved for 6 months of expenses (the general rule of thumb for anyone actually) and an idea of what your new life is really going to be like.

I'm not married yet, but live with my girlfriend, so it's a similar situation. She's OK with my trying to bootstrap it and also offered to help me with my share of the rent, if necessary, for a month or two. She doesn't make enough to support the two of us indefinitely, but it's helpful to have somebody else with more stable income. The other nice thing about having a spouse (that I can't cash in on yet since we're not married) is that you can use their health benefits, which will get you better coverage and save you money.

Having kids changes the equation altogether. If I had kids, there's no way I'd try what I'm doing now with as little safety net.

I mentioned it in another comment, and maybe it's not clear from my post, but I'm married (14 years) and have 3 kids (ages 8, 10, and 12). Being bootstrapped with a family like that probably requires more adjustments than for those who aren't married and don't have kids.

But you bring up a good point about prepping for those changes before you get into it. If you have the notion to start down that path, then making those adjustments ahead of time will help ease some of the "pain".

I'm not sure I understand the pay cut part. Why not start it up on the side and keep your regular job until it grows big enough to replace your existing salary? If it fails then you can just keep doing what you were doing before. Seems less risky and stressful than going all in on something you're unsure about.

Trying to get your startup going on the side while maintaining your current job is certainly an attractive option for many people. But the risk with that approach is that the startup never gets launched and off the ground. They tend to stall and stall and stall, all because they have that big safety net of their current job and salary. It can work, but not always.

I would also add: how well do you handle rejection and failure?

Good call. If you're not used to failing, and failing often, then this isn't for you.

Though on the other hand, how else do you learn?

Fair enough, but you can fail in something other than a bootstrapped startup and learn from it, all without risking your own personal stress, finances, etc.

If you're in a position to try starting your own company, you're already in a position of great privilege. Either do it, or don't do it, but don't complain.

That doesn't make sense. Is the African woman living in a straw hut starting her basked weaving business with a micro-financing loan for $50 in a position of great privilege? Is the unemployed construction worked who starts his own repair business in a position of great privilege? I mean I've tried to interpret your remark in several ways, but none of them make sense.

Anyway, listing the disadvantages of something isn't complaining, it's just being realistic.

Not sure if this was meant for me or not, but I hope I didn't come off as complaining in that post. I just wanted to make sure people thought about the personal side of things before diving into it. People tend to overlook the spouse's point of view, and I wanted to make sure I pointed that out.

I don't think it came off like that at all. I think you sounded realistic and pragmatic.

My spouse does add extra pressure, though not on purpose...it's just there. However, I'm permanently unemployable, so what else can I do? :)

As far as bootstrapped startups go I can say one thing -> they suck.

When you're in that spot where you don't really know which bill to pay this month and which can probably wait a little while longer, all the while you're asking the bank to extend the limit on your bank account and trying to look all "Yeah hey, I sure as fuck am making enough money to pay for this! Yeah!" ...

... it's not a fun place to be.

But on the other hand, it's a whole lot more fun than when I had a somewhat cushy job as a webdev doing repetitive mindnumbingly horrible things for an advertising agency.

I think there is another way to look at it -> Bootstrapping allows you to stay in control.

You get to decide how many financial sacrifices you take for your business. We do 3 days of contracting and spend another 3 days working on our product. Yes, this even includes one "free" day on a regular basis.

I don't even think it hurts our progress that much. Personally I couldn't focus on a business while not being able to pay my bills.

Being limited on time, but having a little extra cash has been a very good combination for us so far. We spend our time efficiently, and we can sometimes hire people to help us with stuff we're not good at.

Note: I live in a nice big place in Berlin paying most expenses for myself and my girlfriend (she is studying). Not fancy, but certainly not sacrificing anything either. (YMMV, especially in a more expensive city or with kids)

I hear ya. When you have to get your spouse to pay for simple items because you have to keep your servers running or giving i-o-u-s for Christmas, you really have to start considering if what you are doing is the right thing to do.

But, I wouldn't trade the experience of bootstrapping for anything in the world. It taught me frugalness and prioritization. It also brought me a hell of lot closer to my sig other.