“I observed water damage being done to houses, which led me to my first gutter job: installing plastic gutters for a customer," Cobb reminisces about his entry into the industry. That same day, he spotted someone running installing seamless gutters across the street, and an opportunity dawned on him. From around 1987 through 1994, he began to outsource gutter installations while running a painting company, managing to secure a couple of jobs each week.

"In 1995, I purchased my first gutter machine," Cobb shares. And the decision changed his life. Tony's gutter company generated around $350,000 in revenue its first year. 

As he delved deeper into the industry, Cobb realized the pivotal role systems played in running a business. Running a gutter company wasn't just about gutters...it was also about the operations of the company, the logistics of it, and its management. Hence the name of his business: All Gutter Systems. The name is not just about the design or layout of gutters; it's about the systemic approach with which Tony has meticulously built his company. His goal was to build a systemized gutter company that could operate without him directly involved in everyday operations. Why? Well, so he could take more vacations.

It worked.

By 1998, Tony was able to take a month-long vacation and climb Mt. Denali in Alaska. While he was away, the company had its most profitable month yet. But he wasn’t done. Tony had a clear goal in mind: he wanted to sell the gutter company for a million dollars within ten years. He accomplished that in just nine years and ten months. 

But triumph was closely followed by personal adversity. The sale of his company triggered a divorce, leaving him with next to nothing. The company he painstakingly built from the ground up nearly faced destruction within two years under new, less motivated ownership.

Tony often refers to this as the darkest days of his life. Not only had he lost his marriage, his wife had also taken the children.

Undeterred, Cobb regained control, purchased the company back, and set about rebuilding his gutter empire.

The second coming of All Gutter Systems was even stronger. Not only did Cobb get the company back on the right track within a week of regaining control, he also introduced his Under Deck Oasis product. This new venture turned out to be a game-changer, growing to be more than two and a half times the size of the original gutter company.

Over the years, Tony reconnected with his children and involved them in the business; even taking them on many of his legendary vacations nationally and overseas.

When asked about what inspires him in his work as a gutter professional, Cobb's eyes light up. "It's the pleasure I derive from watching other people improve their lives, thanks to a well-paying job. It's a joy to see them afford a nice house, a good car, and even start a family while securing their future, all within the gutter industry."

To Tony Cobb, the keys to success in the gutter market – or any market for that matter – are simple. Identify the need, find the right niche, and understand what’s important to the customer. His mantra? "If you can offer a solution, you can always make a good living, provided you are willing to put in the work." For Tony, whether it's on a mountain peak or in the gutter industry, the journey is all about balance, resilience, and the relentless drive to push forward.

Tony’s latest venture, the Rain Gutter Association (the RGA), is intended to push the industry forward by developing standards, certifications, advocacy, and membership benefits for the gutter community.