Interview With a Roofer: Michael Kalish on Trust, Staying Power, and Building Roofs That Last
Interview With a Roofer: Michael Kalish on Trust, Staying Power, and Building Roofs That Last
Ask Michael Kalish what his role is at Freetail Roofing and you are not going to get a particularly impressive title. His answer is simply, “Owner and janitor.” That probably tells you something about him before the interview even gets started.
Michael has spent 33 years working in roofing, construction, and the trades, but roofing was not exactly the childhood dream. He graduated from high school a year early and went straight into building houses as a framing carpenter. By 18, though, he already knew one thing: “I knew I wanted to be the boss.”
So he spent much of his twenties learning. He worked in different trades, picked up experience wherever he could, and roofing was one of the things he regularly did. It did not become the main thing until 2008, when the economy had crashed and Williamson County was hit by a major hailstorm. From there, the transition into full-time roofing happened naturally.
More than three decades after entering the trades, a normal day for Michael now involves considerably less standing in one place. He works with the Freetail office to coordinate jobs, performs quality-control checks, spends plenty of time on the phone, and drives. A lot. “I put 50,000 to 60,000 miles a year on my truck,” he said.
Fortunately, there are tacos involved. His road lunch of choice is about as complicated as you would expect from a Central Texas roofer: tacos. The soundtrack might be classic country or Motown, although true crime and theology podcasts are also in the rotation.
A Roof Is a Bigger Deal When It Is Your Roof
After doing something for 33 years, it would be pretty easy to forget what the experience feels like for someone doing it for the first time. Michael tries not to.
A homeowner may replace a roof once or twice in a lifetime. For the roofing company, Tuesday morning might simply be another scheduled project. For the homeowner, there are strangers walking around their property, thousands of dollars involved, insurance paperwork they may not understand, and the sound of an entire roofing crew working directly above their head.
“It’s a very big expense that is disruptive and noisy,” Michael said. “It can be unnerving to have to sit back and trust someone else’s team to get it all right for you.” That is why he believes a roofing company owes customers more than shingles and labor. They need advice, education, and guidance throughout the process.
Sometimes that guidance should result in a new roof. Sometimes it should not. Asked what honesty looks like in the roofing business, Michael’s answer was simple: “Telling someone that they don’t need a new roof if they only need repairs.”
That attitude is tied closely to something he learned much earlier in life. “Trust can take time to build and one wrong instant to lose. Treat it accordingly.”
In a smaller community, that matters even more. Michael has lived in Texas his entire life. He was born in Dallas, spent portions of his childhood in Alvin and Midland, moved to Austin at 13, and has called Liberty Hill home since 1994. His description of small-town business is only one sentence, but it may be one of the best explanations for why reputation matters so much around here: “You can’t hide from the people if you’ve wronged them.”
Eventually, you are going to see each other again.
“There’s a Piece of Me Keeping That Place Together”
For Michael, doing a roofing job right means thinking beyond whether the roof looks good when the trucks leave. It means building something meant to last instead of something that will need to be replaced again before it should.
His favorite roofing moments actually come later. “When it’s storming at night and I’m able to enjoy the rainstorms while knowing that my clients can do the same.” That may be one of the strange rewards of spending your life in roofing. You begin looking at buildings differently.
When Michael drives past a home Freetail has roofed, he often has the same thought: “There’s a piece of me keeping that place together.”
That responsibility does not change based on the size of the house. As Michael puts it, “Your home is a sacred place whether it’s a mansion on the lake or a mobile home.” That perspective becomes particularly important when customers are vulnerable. He remembers young families trying to understand their first insurance claim and elderly homeowners who may be especially vulnerable to scams. Those are the situations where roofing stops being primarily about materials. Someone is counting on you.
Staying Power
Michael does not romanticize the business. Roofing is physically demanding. Texas summers are brutal. Storm seasons can be chaotic. Insurance payments can drag out for months after the company has already paid the expenses associated with a project.
And sometimes you make mistakes.
Michael still remembers one particularly memorable lesson: “We tore off the wrong roof one time.” The scheduling procedures improved significantly after that.
But he believes the difference between someone who simply does roofing and someone who takes pride in it is ultimately staying power. “This is a tough business on so many levels,” he said. “If you just do it for the money only, then it will chew you up and spit you out.”
What keeps him going is remembering where the work eventually leads. “You’ve got to begin with the end in mind. You can’t get to that end if you quit.” And the “end” is not just a completed roof.
Freetail’s work supports the families of the people doing it. Michael described it this way: “Every nail, every drop of sweat is diapers, groceries, and the lights on at home.” That perspective changes the meaning of the work. A roofing project is a customer’s home on one side of the equation and someone else’s livelihood on the other.
Michael talks about his own family with the same pride. Outside of work, the thing he is proudest of is his family: his wife, eight children, and granddaughter. He names his wife as the biggest influence on the kind of person and worker he tries to be.
She also apparently knows exactly how to improve a rough workday. Asked about one small thing that makes a difficult day better, Michael’s answer was, “My wife calling me handsome.” Thirty-three years in the trades and apparently the fundamentals remain undefeated.
Someone You Can Count On
Michael says roofing has taught him that he needs God’s help, that he can do hard things, and that he can keep moving forward even when he does not feel like it. It has also given him an appreciation for the relationships built along the way.
There are customers who are genuinely happy to see the Freetail crew around town. There is a core team that has shared years of hard work together. Michael describes that group as loyal, while quickly adding that the loyalty goes both directions.
When asked what reputation he hopes to have with customers, he chose three words: dependable, trustworthy, and knowledgeable. With his team, he described it a little differently. “I want them to know you can count on me like that old lighthouse.”
And if someone had to describe him as a worker in a single sentence, Michael hopes it would be this: “That guy is steady.”
After 33 years, thousands of miles, plenty of roofs, at least one house that definitely was not supposed to be torn off, and a whole lot of Texas weather, that may be the reputation Michael values most. At the end of the day, he wants people to know one thing: they can count on him.