My two cents 1. If money is very pressing, you should save up enough until it isn't. Spending all your saving is obviously going to induce a lot of stress. Be

My two cents 1. If money is very pressing, you should save up enough until it isn't. Spending all your saving is obviously going to induce a lot of stress. Better yet - spend other peoples money. That means raising money, but you'd be surprised how many angle investors or startup programs there are out there, that are willing to seed you with (relatively small amounts of) money. The catch here is that they typically want a very solid business and marketing plan, and will probably turn down typical cookie-cutter ideas (marketplace, social network, etc.). 2. Yes, it's hard to do when bootstrapping yourself,but hire people to do the marketing and sales. These things can and will make or break early startups and businesses. Let's take he music venue analogy: Imagine that you want to build the best concert venue in town. You've poured your hard-owned money into it, along with blood, sweat and tears. Finally the venue is finished - but there's a problem: No one knows about it. You figure it will pretty much sell itself, and hire in some artists to perform there - but have done zero advertisement or marketing. Concert comes and goes, but no-one showed up - because no-one knew about the concert. Bands and artists still want their money, same goes with utilities and what not. Point is - if you can't do the sales or marketing yourself, you need to hire someone to do it for you. You're just throwing money into a black hole and getting nothing in return, because potential clients don't even know you exist. If you can't afford someone - anyone - to do that for you, then you probably don't have enough funds to begin with. edit: It just seems like your biggest troubles stems from the fact that you (seemingly, or due to anxiety) hate sales and marketing yourself, and that your product/segment may have been quite a tough to succeed in.