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How 15 Years of Almost Failing Helped Me Find Success

by Brand Post
September 29, 2025
in Business
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How 15 Years of Almost Failing Helped Me Find Success
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Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

  • Perception is only reality until money’s involved.
  • Don’t go with the flow if you want your business to grow.
  • You can only seize the moment if you’re ready when it comes.

You might assume that great business ideas are immediately successful. But that just isn’t true. People don’t magically recognize the value of a product or service. You have to present it to them in the right way, at the right time. To complicate things even further, you’re not always going to know when that right time is, or what approach will be most effective when it comes.

That means you’re going to do a lot of trial and error before things finally click. And until then, all those repeated attempts to get your business off the ground are going to feel a lot like failure.

The scariest part? There’s no bulletproof method for telling the difference between a struggling business that’s about to go belly-up and one that’s about to take off. But there are lessons you can take from the time you spend struggling that will make it more likely to pay off in the long run.

I spent 15 years barely keeping my head above water in the roofing industry before I managed to turn Roof Maxx into a national dealer network for residential roof restoration treatments. Here are some of the most difficult — and valuable — lessons that almost losing my shirt taught me during those challenging times.

Related: Overnight Success is a Lie — Here’s How Failing 22 Times Taught Me the Reality of Success

Perception is only reality until money’s involved

Every founder knows it’s in their best interest to present a successful image of their company. Success is both a powerful magnet and a potent weapon: It draws investors and potential customers in while keeping competitors in check. But just because a business looks successful doesn’t necessarily mean it is.

For 25 years, my brother Todd and I ran a family roofing business that became a household name in our town of Columbus, Ohio. For at least 15 of those years, we appeared to be wildly successful. The truth is that we found ourselves on the verge of bankruptcy twice during that period.

Political consultant Lee Atwater famously coined the phrase, “Perception is reality” — but that’s only true when you aren’t dealing with finite, measurable resources. If you were on the outside looking in, your perception would have been that Todd and I were printing money. In reality, we were hemorrhaging it. And since we knew we couldn’t afford to keep doing that forever, we understood that the business model would have to change. We just didn’t know how yet.

Don’t go with the flow if you want your business to grow

The low-risk thing to do in residential roofing at the time was to sell roof replacements. Actually, it still is — roofing contractors haven’t focused on repairs since the mid-1980s, when I was brand new to the industry. The years since then have seen most roofers in North America move towards pushing complete replacements to maximize profits. That means recommending total tear-offs and brand new shingles, even if the customer only needs routine maintenance.

As you can imagine, this was a popular strategy with roofers, but not with customers. It’s like having the insurance company declare your entire car a write-off after a minor accident.

Todd and I were never comfortable with that approach. We knew success lay in solving this problem for our customers, not contributing to it. The company we had back then was called Feazel Roofing, and we focused on providing tune-up packages for homeowners. This was practically unheard of outside the commercial sector, but we believed we were filling a vital niche the rest of the industry was ignoring.

After fine-tuning our maintenance program offerings, we made Feazel Roofing a highly profitable business over the following 10 years before ultimately selling the company. Our profits and referrals grew simply because we were focusing on the best interests of the customer.

The fact that we nearly went bankrupt twice might lead you to believe that we were wrong. But as it turned out, our instinct was correct. Our moment was coming; it just hadn’t arrived yet. Which brings us to the final and most important lesson from this time in my career.

Related: 10 Lessons About Failure That Every Entrepreneur Needs to Know

You can only seize the moment if you’re ready when it comes

Before discovering the Roof Maxx product, Todd and I had no intention of starting a national business. We believed in what we were doing, but didn’t see an opportunity to expand. Our plan was to sell our roofing business and go into a kind of semi-retirement, probably continuing with residential roof restorations on a local level.

As it turned out, that put us in an ideal position to pivot when we came across the Roof Maxx product — an eco-friendly plant-based solution that can extend the lifespan of asphalt shingles for years by simply being sprayed onto them and absorbed over the course of a few hours. It represented an opportunity to accomplish everything we wanted to do with our business, but it also came as a product we knew we could get the country’s homeowners excited about.

We sold the business as planned, but instead of retiring, we poured everything we had into this new venture. We also structured the company as an independent dealer network instead of opening and operating our own new locations, which allowed us to scale rapidly.

Today, Roof Maxx is one of the world’s largest virtual home improvement companies. We provide the product and training resources for our dealers — they apply it to rooftops all over North America and give homeowners an alternative to costly roof replacements.

It never would have been possible if we hadn’t learned anything through those difficult early years. Stay honest about your setbacks, stick to your principles and be ready to move when your moment arrives. You’ll be able to take advantage of the opportunities that are coming your way as well.

Related: When My Startup Failed, I Was Hopeless and Left in Tears. Here Are the Lessons That Helped Me Restart and Launch Three Successful Companies.

Key Takeaways

  • Perception is only reality until money’s involved.
  • Don’t go with the flow if you want your business to grow.
  • You can only seize the moment if you’re ready when it comes.

You might assume that great business ideas are immediately successful. But that just isn’t true. People don’t magically recognize the value of a product or service. You have to present it to them in the right way, at the right time. To complicate things even further, you’re not always going to know when that right time is, or what approach will be most effective when it comes.

That means you’re going to do a lot of trial and error before things finally click. And until then, all those repeated attempts to get your business off the ground are going to feel a lot like failure.

The scariest part? There’s no bulletproof method for telling the difference between a struggling business that’s about to go belly-up and one that’s about to take off. But there are lessons you can take from the time you spend struggling that will make it more likely to pay off in the long run.



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Tags: EntrepreneursFailingFailureFindGrowth StrategiesHelpedLessonsSetbacksSuccessSuccess StrategiesYears

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