I'm going to share a rare little bit of my personal history here in the hopes that I can help save you from some of the difficulty I went through. I'm going to talk about bootstrapping, and how you can do it better, right from the start.

When I left my last company about five years ago and was figuring out what I wanted to do next, I did what most bootstrap entrepreneurs do... I started the business and started trying to figure out how I was going to most immediately start generating income from the business. At the same time, I was trying to do some easier-to-obtain consulting in other areas to keep the cash flow going so that I could work on the main business.

Of course, the problem with that is that I was trying to market and build several different businesses, and the supplemental businesses weren't really setting up anything that was going to increase my ability to focus on the primary business. Thank goodness I had the foresight to sign up as an About.com Guide, but I kick myself for not doing more with it at the outset.

Why?

See, while I have an ongoing commitment here to produce new content, I also have a steady flow of income not from the new content I produce, but from the content I have already produced. I won't go too far into the details, but let's suffice it to say that if I had focused really heavily on this for three months -- produced about 100 articles -- I'd probably be making enough just from my passive income from older articles to more than cover all of my living expenses, even doing the same amount of work I'm doing now (this is a part-time gig -- I also do consulting, speaking and various other freelance writing).

Instead, I ended up chasing four businesses -- my book, related speaking/consulting, About.com and the other consulting I was chasing because it was easier (I was way ahead of the demand curve five years ago for my core business). Now, it's not that there's anything wrong with pursuing four different lines of business -- I'm a big advocate of multiple streams of income. The problem was that none of them were setting up any kind of passive income, at least not for a very long time.

Now what does this have to do with you and with bootstrapping?

Well, one of the most common reasons that bootstrap entrepreneurs shut down their businesses is cash flow problems. This is especially true for those who are married with children. Even if the business is making money overall, a few months with little or no income -- par for the course for startup businesses -- can pressure or force the entrepreneur to drop the business and go back to a traditional job to support the family. Or, they stubbornly keep saying, "Just one more month," as the bills keep getting farther and farther behind and the debt keeps adding up.

So what's the solution?

Create automated passive income before or as you're starting your business. It is possible to do this with your own products, but it's much faster and easier to do it in other ways. Here are a few ideas to consider, as well as some resources to help you explore further:

• Infoproducts - If you can crank out a decent e-book, fine, but by far the least time-consuming and most valuable content, if you're so inclined, is video tutorials. If you know how to do something with a particular program or online and can show others how to do it, you can make money with that. If you're up for the task, self-publishing a book is a little more time-consuming, but can also be a great credibility builder and promotional tool for your business in addition to the revenue it generates on its own. Just remember -- books are a business, and you have to approach it as such or else they can become just an expensive hobby.
• Affiliate marketing - You don't have to sell your own products - you can sell other people's products. There are generally two ways to do this. The first approach is to create a purely sales site - typically a fairly long single page that promotes the product - and then advertise it through some combination of pay-per-click advertising and free advertising. The second approach is to create a content site, typically either covering a particular industry or type of product, and usually containing product reviews. For details on how to do this with the most popular affiliate program on the web, check out How To How to Really Make Money on the Internet With an Amazon.com Affiliate Site.
• Social networking and social media - A growing number of social networking and social media sites are now paying members for content production, recruiting new members and even just general activity. If you enjoy blogging, you can get paid $5, $10, even $20 a post in some cases, or even earn a couple of hundred dollars a month for being an ongoing contributor. Other sites allow you to earn money from articles, photos and videos you produce. There are literally dozens of sites where you can make money online without spending a dime. The great thing about this is that if you're smart about it, you can actually get paid for doing things that promote your main business.
• Network marketing - That may surprise you to read, since the "failure" rate for network marketing is even higher than it is for entrepreneurship. But see, the thing is... it's extremely difficult and time-consuming to make a full-time income from network marketing. It's very easy, though, to make a few hundred extra dollars a month without spending a lot of time at it. Pick a network marketing opportunity that has a product you believe in and is a fairly simple sale and not a big-ticket item. Also, be sure that you treat it as a business and not just a hobby.

While making a living from some of these activities may sound appealing to some, most entrepreneurs I know have a dream - something bigger than just financial and time freedom. That's the reason to pursue this other stuff -- not instead of your dream business, but precisely so that when the cash flow crunch hits, as it almost certainly will, you can keep pursuing your dream business and still support yourself and your family.

Want to learn more? In addition to the various links scattered throughout above, here are a few more excellent resources on About.com and elsewhere on the web:

• Online Business Ideas - Membership sites, dropshipping, affiliate programs and more.
• Consultant's Crack the Billable Hour Ceiling - How to stop trading hours for dollars.
• Blogging Jobs - Make money blogging for others. Pick carefully and you build your reputation for your main business in the process.
• Monetizing Your Blog - Make money blogging for yourself.
• Real Estate Investing - Yes, there really is such a thing as "no money down", and you can make money investing in real estate without a lot of capital.
• Genius Types - Passive income strategies for artists and other creative types.
• Problogger - The premiere source for making money from blogging.
• Make Money Online: 100+ Tools and Resources - A big list from Mashable.
• 19 Ways to Make Social Sites Pay - A smaller list focused on social networking and social media.