Our business’s 25th anniversary is coming up. 25 years. It was about this time of year that I was very deep into drafting the business plan, preparing for our launch in January. Since I don’t have a time machine, this is not a letter to myself, but it is the first 10 things that come to mind that I’d like to share with new entrepreneurs trying to bootstrap their business.

1. Business Planning for Clarity

When I first started, I wrote an 80-page business plan. It was detailed, and while it scared off potential partners who weren’t aligned with my vision, it also clarified everyone’s intentions. Some wanted a hobby or extra cash; I wanted to build a business to be our primary income source. That clarity ensured I only worked with people who shared my vision. Whether your plan is one page or 80, use it to align your team and make sure everyone’s on the same page. For small businesses today, I prefer shorter, more actionable plans—one or two pages. However, if you’re bringing on partners, don’t shy away from a detailed plan to ensure alignment from the outset.

2. Always Keep Selling

A business without inbound cash cannot survive. By 2001, we had picked up several new clients, we were busy. So I hesitated to sell, fearing we couldn’t handle the workload. That mistake caused cash flow issues for months. Always maintain a healthy sales pipeline at all stages—prospecting, nurturing, and closing. Don’t let your pipeline go stale, and don’t take your foot off the gas. Keep selling.

3. Customer Spread

Avoid letting one customer be the majority of your income. My target was usually less than 8% of gross annual sales attributed to any single customer. After a big sale, I would be out of balance and so my focus the next month or 2 was to earn new accounts to keep the right ratio. The smaller the number is potentially the less profitable per dollar as you might have more overhead to service the larger base of customers. I’m talking to those who want to build a long lasting sustainable business. This way, losing one customer will not end your business. I’ve watched many web design companies pick up one or two customers and that was the primary source of their annual revenue. When those customers went elsewhere or out of business, so marketing firm followed.  I’m also not arguing for smaller customers. Figure out your average order and then figure out how many you need to manage the risk of one leaving and now you have some new targets to reach.

4. Embrace the Simple Life

Bootstrap financing often means focusing on the essentials. Think about the Amish or Quakers and their philosophy of simplicity—what do you minimally need to keep your commitments to employees, business partners, and clients? Resist the constant pull to acquire more tools or resources. This mindset will ensure you stay lean while fulfilling all your obligations.

5. Audit & Remove

Subscription services can silently drain resources. When decision-making is appropriately distributed among employees, it’s easy to lose track of what’s necessary. Schedule quarterly audits to evaluate your expenses. Keep what’s essential and cancel the rest, even temporarily. A disciplined approach to financial housekeeping helps you stay in control. I apply the food safety rule of “when in doubt, throw it out”. Stay thin. 

6. Avoid Debt Whenever Possible

Debt-free with cash reserves is a powerful position for any business. While debt is sometimes unavoidable—such as zero-interest loans or other favorable terms—it can be a slippery slope. My mistakes taught me the weight of being debt-laden versus the freedom of being debt-free. Build a cash buffer, and if you must borrow, ensure the returns outweigh the costs.

7. Pick and Stick to a Money System

There are many financial systems out there, each with valuable lessons. However, hopping between them can create confusion. Pick one system, like Mike Michalowicz’s Profit First, and commit to it. Follow it rigorously before making modifications to suit your business. Consistency breeds results.

8. Track Your Progress

You can’t improve what you don’t measure. Whether you track progress using profit and loss statements, bank balances, or month-over-month sales comparisons, find a system that motivates you. Personally, I’ve found looking at sales numbers compared to the same month in the prior year to be a great motivator—even when I’ve missed the mark. Choose a metric, track it consistently, and watch your performance improve.

9. Pre-Fund Payroll

One of the biggest stresses for small business owners is meeting payroll. I’ve been there. Avoid this by creating a separate payroll account and funding it in advance. Even saving 0.25% of revenue can eventually replace reliance on a line of credit. Start small, and gradually build a buffer that ensures your employees are paid without stress.

I have a business contact and good friend, who once said to me, “If you haven’t pulled over to the side of the road, and got sick over the guardrail, because of the worry of the upcoming payroll, then you haven’t owned a small business”. I chuckled because I understood that stress. Early on, I sold my own possessions to pull in cash to make payroll. Have a separate payroll account and fund it in advance, even if little by little. 

10. Prepare for Lynchpin Scenarios

Every business has critical processes or people whose absence could create chaos. Early in my business, cash flow depended on new accounts monthly. When illness left me unable to sell for weeks, we pivoted to a recurring services model, significantly improving our value to clients. Identify your potential “lynchpins” and develop contingency plans. Use your rainy-day fund to bridge gaps and reduce dependence on these critical elements.

Starting a business is a journey filled with decisions, risks, and learning curves. These ten ideas come from my own experiences over the past 25 years—some learned the hard way, others through the wisdom shared by those who came before me. Not every piece of advice will fit every business, and that’s okay. One mentor once told me, “Take what serves you and leave the rest.” Whether your goal is to build a sustainable legacy or create a springboard for future opportunities, I hope these insights offer clarity and direction as you forge your own path. Bootstrap boldly, and remember: every small step forward is still progress. Good luck!