Eleven of my favorite business bootstrapping tips

I created my very first personal financial spreadsheet in 1998 when I landed my first “real job”. My money mentality might not be right for everyone, but it helped me pay for grad school without a cent of student loans, eventually quit my job and launch two businesses.

I’m not swimming in cash by any stretch of the imagination, but we pay our credit cards off every single month and my family lives completely debt-free with the exception of our mortgage. I didn’t get into this position because of any debt-rescue or lump sum winnings. I got here by bootstrapping as much as possible and living a minimalist lifestyle, which, thankfully my husband is on board with.

The list below contains some of my favorite penny-pinching and bootstrapping tips for both business and personal life.

11 Favorite Business Bootstrapping Tips

Eleven secret bootstrapping lifesavers:

1) Do you really need it?
I read a Guy Kawasaki book a few years ago called “The Art Of The Start“. I still remember one very important lesson from the book (I’m paraphrasing):

…If you feel like you need something in your business, don’t buy it. Wait a few days or maybe even a week. If you still feel like you need it, buy it. If you don’t, you’ll be glad you waited.”

2) Plan for spending
For a lifestyle business–one that grows organically and exists to pay the salary of its owner, along with perhaps an employee or two–all spending can be planned for. Six months of a salary can be saved before a new team member is hired. Extra earnings can be worked for and then saved before a computer is purchased. Expenses can be planned for and saved for in advance.

3) Costs can be defrayed
Every so often–say every six months–expenses can be examined and investigated to uncover an opportunity for savings. Are there any expenses that aren’t being used as heavily as they once were? Is there any equipment not being used that can be sold on ebay? Opportunities to cut expenses help defray the impact of future costs.

4) If you can’t afford it now, wait till you can
Why purchase something that you cannot afford? If the money doesn’t exist to pay for it by the time the credit card or monthly bill arrives, why buy it in the first place? Plan the intended purchase out and wait to pull the trigger until you can afford it.

5) Get paid upfront
This is my favorite tip for a number of reasons.

Imagine being a bill collector for a living. What a crappy job, right? So why would you ever want to do that in your own business? Examine your contract and figure out how to not do work unless you’re paid in advance. This allows you to only focus on work that a client is actually going to pay you for. Ever prep for a job only to find out the client never intended to pay? Ever edit a bunch of images only to find the client never followed through on the order?

Never again.

6) Reduce the clutter
Sometimes it feels good to buy things and play with new stuff. But if it’s adding to an already existing pile of clutter, remove the clutter, first. There might even be something hidden within that pile of stuff you totally forgot about.

7) Research “free”
Are there free options that are just as good? Or, would a free option work for now until you outgrow it?

I had a hard time justifying the cost of QuickBooks as soon as I found out that Wave (waveapps.com) offered basic accounting functionality for free. In fact, Wave’s features are probably plenty for the first few years of business for most solo-preneurs.

8) Pay for a year upfront
Many tools, such as my email marketing software called Get Response (getresponse.com – affiliate link), offer annual subscription prices that are discounted more than the monthly amount.

When you know you’re going to use something for at least a year, go for the annual price if it will save you some expense.

9) Use annual renewals as a reminder to re-evaluate
Whenever I know an annual renewal of something is coming, it’s a reminder to look at the tool against other options out there and ensure I’m subscribing to the best option based on how my business needs may have changed since the initial sign-up date. With monthly fees, it’s more difficult to remember to do this.

10) Plan for rainy days
Rarely do creative businesses display consistent, anticipated month-over-month revenue growth. Whether your business has seasonality impacts or unexplainable slumps, it’s smart to stick cash away. I’m a money hoarder, so I tend to save everything and plan for an apocalypse. You may wish to be a little freer with your cash and sock away 25% of net profit for emergencies.

11) Just because they call doesn’t mean it’s right
People trying to offer you stuff bet on your lack of planning. If your expenses aren’t planned for, impulse purchases are welcomed because it’s how you operate normally. Advertising reps and product makers know this.

As soon as you start planning for your expenses, you’ll be confident offering a resounding “no thanks” for every shiny new object waved in your direction. And if it’s a shiny object that you really think will help your business grow or perform better? Simply plan for the expense.

A bonus tip: remember the longview
Admittedly, I struggle with this one. Sometimes I have financial panic attacks. And sometimes (okay most times) this anxiety is completely irrational and unfounded. These kinds of attacks typically happen after a lull of five or more days without a new client inquiry. Suddenly, I’ve gone from just fine to “I’m closing up shop oh no what do I do holy mackerel how did this happen” mode.

At these times, I have to remember the distant horizon and what I’m working toward in the long run. Suddenly, five days seems eternally insignificant. Rather than throwing in the towel and walking off in a huff, I try to feel gratitude for the quiet. You know just as well as I do that when things get busy you crave a few of those quiet days. Even if you can’t predict them, you might as well enjoy them when they appear.

Follow me on Twitter and share your favorite bootstrapping tip with me there. I’d love to learn some new ones. Money hoarders, unite!


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  1. says

    You’re so right about getting paid up front. Another related problem is the “friends and family” discount, when people want to hire you just because they know you, so they assume that you’ll work for them for free or really cheap. It’s especially problematic when they want to hire you to do a type of photography you don’t normally do or deliver products you don’t normally sell.

    • says

      Hey Karen! Yea, I agree. I’ve been impressed that most of the friends and family that have asked me to help them with photography have been respectful of my time, fees, and other requirements I have for my business.

      How do you handle saying “no” when someone crosses a line you mentioned above?


      • says

        Aack, I forgot to check the “notify me of follow-up comments” box! My apologies for such a late reply.

        If it’s a type of photography I don’t normally do (or used to do but don’t anymore), I usually tell them that nicely and refer them to another photographer or two. Sometimes I consider making an exception, and in that case I quote them a fee that feels right to me. If they’re just looking for a deal, they drop out. Once in a while, someone will get offended that I won’t work for them cheaply. The way I see it is this: when I patronize friends for their services, I’m happy to pay them their going rate, because I understand that they set their prices where they need to be to make a living. So I deserve that same respect.

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