Graham Dessert (Battle Tested)

Graham Dessert is the author of Battle Tested: 7 Lessons from My Company’s Bankruptcy, which gives readers an inside look at what led to the dissolution of Roofing101, a national roofing company that had been in business for twelve years before ultimately going under. 

Born in Colorado to a military father, Dessert lived in several different cities throughout his childhood.

“We moved every two to three years when I was growing up,” Dessert shares, before adding that the family later settled in Kansas City on a more permanent basis.

After high school, Dessert stayed in Missouri and attended the University of St. Mary, and even though his time as a Spire didn’t teach him much about the business world, the experience still had a profound impact on him.  

“My time there didn’t necessarily provide any value for my business future, but it did benefit me as a man,” Dessert says.  

“I took some amazing courses with some great professors. I also had an opportunity to play college football, meet great coaches, and cultivate relationships with other fantastic people.”

Upon graduating from college, Dessert immediately began working in the construction industry, and a few years later he started Roofing101, a roofing company that served the Greater Kansas City area, as well as Denver.

For years the company thrived off Dessert’s efforts, but eventually Dessert began to explore strategies which would allow him to scale Roofing101.

This led to him hiring a few sales reps, plus a production manager, the aim being to sell more roofs, generate more income, and create more opportunities for everyone associated with the roofing company.

“I started to steadily grow,” Dessert says of what happened next.

“And instead of being an owner-operator who was doing $1-2 million per year, I now could get to the next level.”

From there, Dessert continued to scale the business, and soon he had more sales reps and administrative employees, but Dessert says that expanding the business wasn’t solely about bringing in more revenue.

“Every decision I made was executed with the idea of personal growth in mind,” he explains.

Soon, Roofing101 had expanded outside the Kansas City and Denver markets, moving west into other major hubs with an unparalleled ferocity.

For Dessert, the rapid ascension was mesmerizing, but not everyone at Roofing101 exhibited the same drive or interest in building the roofing company into a national entity. 

“I assumed that the people who helped me start the business would be there down the road, and that they wanted to be part of a growing organization,” Dessert admits.

“With that in mind, there were no backup plans, and I did not have contingencies in place for if members of my original team left or became complacent.”

This would become problematic for Roofing101, in that no matter how much Dessert was willing to undertake in order to facilitate his company’s meteoric rise, he ultimately didn’t have the supporting cast around him who could help bring his vision to fruition.

“A healthy organization is internally building and fostering the next wave of leaders, but I was caught in a position where I did not have the next leader in place when I needed one,” Dessert says.

That lack of structural integrity within the company that Dessert is referring to could be considered the primary catalyst for the downfall of Roofing101, a company that after twelve years in business could no longer sustain itself, leading Dessert to file bankruptcy and cut short his business’ once promising future.

“It was devastating,” Dessert says of the company’s disintegration.

“And very humbling. People do not have bankruptcy on their vision board. It’s not something that we planned for, and at no point in my business career had I failed. Everything I had undertaken prior to that point had succeeded, and so when I made the decision to try to scale on a national level, I didn’t think things would be any different.”

Dessert adds that when the company was forced to close its doors, the internal anguish was just as painful as the new reality he was suddenly presented with.

“It was like a part of me had died when the business shut down,” he mentions.

“I had to go through a lot of grieving. I went to counseling and worked with pastors at my church to overcome it.”

Moreover, Dessert specifically recalls the day all his business’ trucks were repossessed.

By then his family had been living in San Diego, and he vividly remembers the pain of seeing the company vehicles he had accumulated being taken away.

For as agonizing as that sequence was, Dessert still found the courage to turn the event into a positive experience by snapping a photo of the vehicles being repossessed, the idea being to capture a time in his life that he would one day look back on and be grateful for.  

“I wanted to remember that moment. As the trucks were being taken away and I took that photo, I realized that everything that was happening, all the emotions and worry, were just temporary,” Dessert says.

“But the photo also serves as a constant reminder of reality, and the things that can happen in business.”

As time elapsed, Dessert gained perspective, and peace, and soon he found himself writing about the experience, even though the self-reflection brought about an immense amount of torment.

“It wasn’t something that I initially wanted to do,” he says of authoring Battle Tested.

“Writing a book like the one I wrote is me showing everyone my mess, and at first I didn’t want to go through the hard work of reflecting on why things went south because sometimes it’s hard to look in the mirror.”

But Dessert did indeed forge onward, using his creative talents as a means of introspection, resulting in him taking ownership and accountability for what happened with Roofing101, despite the fact that a litany of variables were out of his control.

“By doing this [writing Battle Tested], I learned that it’s important for people to dig deep and ask themselves how they contributed to failure,” Dessert says.

“I could easily point the finger at someone else or blame the circumstances that were out of my control, but that wouldn’t help, and I believe more people, not just in the roofing industry, but in general, need to understand how they contribute to their successes and their failures.”

Assuming responsibility is something that many struggle with, but it’s imperative if an individual wants to see real change in their life.

It’s this exact principle that Dessert abides by, and he’s now using his past experiences and current philosophies to consult other roofing business owners who have been afflicted with hardship, or simply want to avoid the potential pitfalls that may await if they don’t modify their business plan.

“I want to help roofing contractors and ensure that they don’t go through the same things and make the same mistakes that I did,” Dessert lists as the primary reason for why he got into consulting.

“So what I focus on with my clients is building the necessary structure and processes they need so that they can grow healthily and steadily.”

Adopting this approach hasn’t been easy for some of the roofing contractors Dessert has worked with, but constructing a viable long-term roofing company never has been a painless endeavor, which is why Dessert is routinely advising his clients to persevere through their current turmoil.

“People are stronger than they realize. If they put some effort and elbow grease into their business, they can solve whatever is currently plaguing them,” Dessert emphasizes.

“For context, the reason that I encourage my clients to grind through their financial problems is because bankruptcy is not something that you want to do. With bankruptcy comes a tag, and you are flagged for five to seven years. That label doesn’t make doing future business any easier, and that’s why bankruptcy should only be considered as a last resort.”

For his clients who aren’t in a financial bind, yet seemingly still struggling with the hardship that comes with being a roofing business owner, Dessert offers an alternative solution.

“Come up with an exit strategy. I don’t want to say that life is short, but time is limited. You only have so many minutes, and you shouldn’t spend those minutes doing something that you are not passionate about,” Dessert insists.  

“Sell the business and use the funds to start something that you’re more passionate about because what happens is when you jump into things that you’re passionate about, and that you’re good at, you will find creative ways to make money doing the things you enjoy.”

Beyond his consulting services, Dessert has contemplated an array of new business ventures.

He is still undecided how he will proceed in the months ahead, but one thing is certain:

Dessert is committed to evolving.

In fact, the Kansas City native will soon return to Greece, where five years ago he and a group of men did a race from Sparta to Thermopylae.

“We retraced the steps of King Leonidas and the 300 Spartans. We were the first group in the history of the world to do that,” Dessert reveals.

This time around, when Dessert returns, he will no longer be the same man he was back when Roofing101 was still in operation, his perspective more calloused, but he is just as ready to see how another physical challenge can elevate him as a man.

Says Dessert:

“That journey in itself is a leadership building event, and I’m excited to see what comes of it.” QS


Today’s post is sponsored by Business411!

A bit about Business411:

Elizabeth Calzadilla and her team help roofing contractors across the country increase their revenue and develop their businesses by offering specialized branding, marketing, and consultation services.

If you’re in the roofing and/or home service industry and are looking to level up your business, then click this link or scan the QR code below to get in touch with them today! 


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