The Overlooked Advantage of Starting a Company Later in Life

How old is too old to start a business? You’ve read the title of this article, so you already know that’s a trick question.

Colonel Sanders was 62 when he opened the first KFC franchise. Laura Ingalls Wilder had her first Little House novel published at 65. The more meaningful your life’s work is, the less likely it is to conform to a predictable timeline. Predictions are based on patterns, and the greatest achievements break patterns to offer the world something new.

This becomes easier if you’ve lived a rich and full life. Spending time in the world helps you recognize what problems still need solutions and how to take advantage of those opportunities. But you won’t always find them by looking directly.

Your best ideas can take decades to develop and come from unexpected twists of fate. Below, I’m going to share a few that ultimately helped me turn Roof Maxx into an eight-figure roof restoration company in my 50s.

Your most successful venture likely won’t be your first

A few lucky people might strike gold the first time they ever put a shovel in the ground, but most of us dig around for a while first. According to reporting from OCI Insights, 97% of founders have full-time work experience before they start their companies. Just 3% start without it.

I launched Roof Maxx at age 51, but it wasn’t my first company, and I wasn’t new to roofing. I’d been in the industry since my early 20s. So while it might be fair to call me a late bloomer in terms of starting a national brand, that’s actually not the whole picture.

Those early years as a roofer were difficult, but they helped me understand the industry from the inside. Getting up on rooftops to inspect them made me familiar with materials. Talking with individual homeowners helped me understand their needs — and the ways in which those needs weren’t being met by the rest of the industry.

Valuable lessons often come in unexpected forms

Little House on the Prairie became more than a series of successful novels. It blossomed into a media franchise that eventually included several television adaptations and even a Broadway musical. Today, it’s widely regarded as a cornerstone of Americana.

But Laura Ingalls Wilder faced years of rejection before the first novel in the series secured a publishing deal. Prior to that, she spent years writing for farming publications.

That probably seemed inauspicious at the time — but in retrospect, that experience clearly taught her how to write in the voice of the Midwest. Every experience can be a lesson on how to succeed if you’re open-minded enough and willing to apply what you’ve learned in different situations.

While it’s certainly less dramatic than the above, here’s an example from my career: Working with real homeowners had shown me they were being routinely underserved by the roofing industry. Most contractors weren’t offering a full range of services. They only wanted to do replacements, even for rooftops that didn’t need them.

So in my 30s, I started Roofer Success International (RSI): a peer-to-peer coaching program that educated contractors on how to run a business while also servicing the customer’s real needs, from inspections to repairs and maintenance.

RSI held live events and offered hands-on training. We showed roofers everything from how to answer phones and schedule appointments to what options they should offer customers and how to price them.

At this point, I didn’t even know that I was going to start Roof Maxx. But as it turned out, my experiences as a roofer and with RSI would both contribute to that company’s eventual success.

Experience is transferable (so get as much as you can)

Roof Maxx’s flagship product can help homeowners put off expensive replacements for years. It does this by restoring the flexibility and durability of their existing asphalt shingles, making them last longer.

You’ve probably already guessed my first point, which is that I never would have recognized the need for this kind of product if I hadn’t spent all those years in the business. But running RSI is actually a better example of how transferable business experience is.

I had started RSI to highlight a gap in the roofing industry, but it turned out I actually loved being an educator. Teaching let me magnify the influence I wanted to have on the industry. What I didn’t expect was that it would also show me the key to growing Roof Maxx consistently.

We eventually chose to expand Roof Maxx through a dealership model where we distributed our product exclusively to roofers who joined our network. This meant their success was our success. It also meant they needed in-depth knowledge about our product and how to sell it effectively.

The idea to build a dealer management platform would never have occurred to me if I hadn’t created RSI over a decade before. But because I had, it was the obvious solution.

Not only did developing our own online portal directly benefit the business by allowing us to share training resources and stay in contact with dealers, but it also created a dedicated virtual community where those dealers could share knowledge and best practices. The love of teaching I had discovered years ago turned out to be more than just a way to advocate for what I wanted to see in the industry. It became the growth lever that helped my brand thrive in all 50 states.

So don’t worry about starting your company late. For all you know, you’re already gaining the experience that could one day make your career.

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How old is too old to start a business? You’ve read the title of this article, so you already know that’s a trick question.

Colonel Sanders was 62 when he opened the first KFC franchise. Laura Ingalls Wilder had her first Little House novel published at 65. The more meaningful your life’s work is, the less likely it is to conform to a predictable timeline. Predictions are based on patterns, and the greatest achievements break patterns to offer the world something new.