How I’d Build My Small Business If I Had to Start Over in 2026

If I were starting a small business today, there are certainly things I’d do differently — but there are plenty of decisions I’d make the same way. Experience teaches lessons you just can’t learn in business school, and I’ve spent 20 years building a company that has grown sustainably, profitably and resiliently. If I had to start over, here are the lessons I wouldn’t leave behind.

Validate demand before you build anything

One of the biggest mistakes I see fellow entrepreneurs make is falling in love with an idea before confirming that anyone actually needs it. Unfortunately, starting a business simply because entrepreneurship sounds exciting isn’t enough. Before investing any serious time or money, your very first step should be to make sure you’re solving a problem someone actually wants solved.

My software company didn’t start as a business plan — it started as a problem. 20 years ago, I was working full-time at a growing internet service provider, and I had simultaneously started investing in rental properties and managing them myself. Balancing this alongside a young family became unsustainable, and I found myself frustrated by the lack of tools available to help me streamline everyday tasks like accounting, maintenance requests and lease renewals. So I built my own tool to solve the problem.

That tool wasn’t created to become a company, but I knew there must be other independent landlords like me facing the same challenges. I shared the software for free, and soon, hundreds of users were relying on the platform and requesting new features. I hadn’t spent a dime on marketing, advertising or any other customer acquisition. This early adoption validated demand and gave me the push to leave the security of my career and jump full-time into building my business.

Many founders build in isolation, spending months perfecting a product before realizing there isn’t a real market for it. The smarter approach: Test demand early and often. Talk to potential customers, share early versions, and let people try what you’re building — even if it isn’t perfect. Demand is the strongest signal an entrepreneur can get. If people are already asking for your solution — or better yet, willing to pay for it — you’re on the right path.

Keep your team lean for longer

Cliches exist for a reason, and I’m a firm believer that slow and steady wins. I ran my business as a side hustle for multiple years before even considering hiring another employee. When I launched, I managed everything myself, from coding to support to marketing. When I couldn’t keep up with the feature requests and support inquiries overflowing my personal inbox, I decided it was time to add another team member.

To this day, we operate with an intentionally lean team of top performers. I’ve never made a new hire without crunching the numbers to ensure our profits could cover the role’s salary and then some, and that the position would deliver measurable value. Slow, deliberate hiring has kept us agile, profitable and sustainable. Expanding your team before revenue can support it creates risk, complexity and pressure, and it can erode any hope of company culture. Lean teams force founders to prioritize high-impact work, build efficiency into operations and ensure every hire moves the business forward.

When everyone carries meaningful responsibility, collaboration is stronger, communication is simpler and ownership is shared. In my experience, slow and strategic hiring has preserved our independence, protected our cash flow, fostered an award-winning company culture and ensured sustained double-digit revenue growth for two decades — and counting.

Stay profitable from day one

Profitability is a mindset. Maintaining independent ownership has given me the freedom to keep financial discipline front and center — every dollar spent creates measurable value, and every revenue dollar covers its cost and fuels future growth. I launched my business with a single $400 expense and continue to turn down outside investment and acquisition offers. But this discipline meant several years of strategically running the business myself with lean operations.

Staying profitable is less about cutting corners and more about making intentional choices. Every expense — hiring, new features, marketing campaigns — is evaluated through the lens of impact and value for our customers. Once you start to generate real profit, use it to reinvest in your team, product innovation and customer experience. Profitability protects independence and allows you to focus on what truly matters to your customers without compromising your vision or values. Instead of looking at profit as the end goal, treat it as the foundation that lets you build a company that lasts, delivers value and makes a real difference.

Build strategically — don’t chase every trend

It’s easy to get distracted by the newest technology or latest trendy feature. I learned this lesson the hard way many years ago while trying to build an integration with a new technology partner. The developer we worked with wanted to use a flashy new approach that seemed exciting at first, but turned out to be a nightmare to troubleshoot. It consumed months of our team’s time, and when the developer left, the tool ultimately failed because it was written in a code language our team didn’t understand.

I quickly learned that strategic development is about prioritizing the features, integrations and enhancements that create lasting value for our customers, employees and the business. Now, every tool we build, every new feature we release and every partnership we pursue is measured against whether it solves real problems for our customers. Purpose-driven product decisions might not make headlines, but they build trust, loyalty and sustainable growth.

Focus on building something that lasts. The exciting part of entrepreneurship isn’t just looking back at what you’ve built so far — it’s looking ahead to what comes next. I’m energized by the opportunity to keep learning, adapting and leaving a mark on our industry for years to come.

If I were starting a small business today, there are certainly things I’d do differently — but there are plenty of decisions I’d make the same way. Experience teaches lessons you just can’t learn in business school, and I’ve spent 20 years building a company that has grown sustainably, profitably and resiliently. If I had to start over, here are the lessons I wouldn’t leave behind.

Validate demand before you build anything

One of the biggest mistakes I see fellow entrepreneurs make is falling in love with an idea before confirming that anyone actually needs it. Unfortunately, starting a business simply because entrepreneurship sounds exciting isn’t enough. Before investing any serious time or money, your very first step should be to make sure you’re solving a problem someone actually wants solved.

My software company didn’t start as a business plan — it started as a problem. 20 years ago, I was working full-time at a growing internet service provider, and I had simultaneously started investing in rental properties and managing them myself. Balancing this alongside a young family became unsustainable, and I found myself frustrated by the lack of tools available to help me streamline everyday tasks like accounting, maintenance requests and lease renewals. So I built my own tool to solve the problem.