Scaling is on the minds of most bootstrappers at least some of the time; you have dreams, you're working hard on them, what happens when the inevitable wild success strikes you and your company? Surely you have given some consideration not just to how you would spend the piles of money you will be raking in but to how you will serve the demands of all those customers shoveling that money toward you?

Working with small businesses that are finding success lately has left me considering this question, at least with respect to website hosting providers. The fact is, it can be very difficult to find a vendor that can satisfy the needs of a boostrapping business as well as the massive success that business may eventually become.

The importance of doing so should not be under-rated, however. The traditional approach to scaling is to switch suppliers when demand exceeds the ability of the existing vendor to keep up, but this is complicated and inefficient in most circumstances and in the worst cases, can dramatically check the growth of your own company as time and energy is devoted to making the transition instead of into improving and marketing your own products.

Unfortunately, there are few vendors that are structured to serve both the low end and the high end of their lines adequately. In fact, many are proud of specializing. But with today's technologies and social networking capabilities, it may be a false choice they are making. Few entrepreneurs get into their respective businesses without some dream of success. Why would you fail to serve them when they are just starting out and gain their loyalty for the long term, and at the other end of the scale, why would you let them move on to someone else just when they are starting to gain their greatest success?

Maybe there is an opportunity there for some other bootstrapper to make a success out of!

If there is anything that bootstrappers like to do more than think about and talk about their own startup businesses, it is listening to other bootstrappers talking about their startup businesses.

So the new series of guest posts on Seattle's TechFlash technology news website called "Startup Confidential" should be right up your alley.

Following Seattle entrepreneurs Damon Cortesi and Aviel Ginsburg as they launch their own startup, the series promises to unveil many of the normally obscured process of making the sausage that goes into a new startup. Posts so far have covered such sticky subjects as determining equity distribution and dividing up project responsibilities with a limited but mutually dependent team. The posts are written by Damon and Aviel themselves, so you get all the raw content and emotion that comes from having real stakes involved; decisions to miss deadlines over personal lives are laid bare. These are trials that most entrepreneurs go through but few expose to the world.

It's easy to get distracted and dragged off track with all the minutiae and details that go along with starting up a business, even if you are not someone who is naturally inclined toward micro-management. There are just a lot of complications that come up, a lot of unexpected costs, and a lot of plans that don't pay off quite the way you hope and it's easy to get sucked into the loop of trying to manage all that cost and bother.

You can't entirely avoid some of the afflictions, but you can seek to minimize the impact and make your costs more predictable by making a greater use of stipends in your business than you might normally be comfortable with. This comes primarily out of experiences in dealing with employees and personal technology requirements, as discussed here; but it can apply equally to any number of other detail-oriented aspects of your business.

With technology, there has been an expectation created that the company will provide devices necessary to do the job, and that company or contracted IT resources will be used to support that technology. This often leads to a lot of disappointment among the staff, who get stuck with devices they don't necessarily like or want, and a lot of unexpected expenses, as the support costs go through the roof as people use and abuse stuff they don't like in the first place.

Both these problems can be addressed by the use of employee stipends to purchase and support items they will use in the course of business. With a properly structured business, you don't have to care what phone your employee uses, any more than you can what color Post Its they use. If that's the case, why involve yourself in the purchasing decision? Figure out what your reasonable annual expense is for those items, fork it over to the employees, and let them figure out the details themselves!

It's scary, but it provides extremely stable budgeting, and reduces a lot of pointless meetings and conversations that revolve around topics that really have nothing at all important to do with the focus of your business. Successful startups stay focused; don't sink yours with endless meetings about managing office supply expenses.

© alancleaver_2000


It's almost that time of year. I never was a Beatles fan, but you've probably heard the lyrics...

Let me tell you how it will be;

There's one for you, nineteen for me.

Should five per cent appear too small,

Be thankful I don't take it all.

I have it by Stevie Ray Vaughn. And he makes it sound even more cynical and depressing.

Taxes don't have to be that bad. But if you've moved recently from a staff position to being self-employed, you need to change the way you think about your taxes.

If you become a contingent worker, you'll need to rethink your taxes. For someone used to being on staff, "It's a mindset shift," says Eddie Gershman, a partner in Deloitte Tax's private client group. The common perception is that you'll pay more tax if you work for yourself, since you'll cover the employer portion of Social Security and Medicare taxes. While you will be on the hook for that self-employment tax, the tax advantages to working for yourself can soften the blow.

BusinessWeek looked at the issue recently and has a couple of tips that can make April 15 a little less painful. You shoudl read it.

Speaking of simple, one area that gets complicated quickly for many entrepreneurs is accounting. Although it's an entirely anecdotal observation, it seems to me that frequently the most successful entrepreneurs I work with are those who have the best heads for numbers. They know what their financial situation looks like and where their targets are to meet their corporate goals. Those who are less financially astute have to work harder to keep up, and they often end up complicating things more than is necessary to run smoothly in the important early days of their start-up.

The folks over at Less Everything asked their accountant to come up with an article for beginning business owners, and the seven tips he came up with are a fine start for anyone considering, or having just launched, a new business of their own.