Meet Trenton Wisecup of Arrow Roofing Services, LLC

Today we’d like to introduce you to Trenton Wisecup.

Hi Trenton, so excited to have you with us today. What can you tell us about your story?
Born into Section 8 housing, where rent was just $20 a month, Trenton Wisecup didn’t grow up with advantages—he built them. No college degree. No handouts. Just grit, relentless drive, and the courage to take risks when others played it safe. At 19, he jumped into door-to-door sales for one of the biggest storm roofing companies in the U.S. and didn’t just get by—he took over. In his first year, he became the #1 sales producer, pulling in six figures and proving that hustle beats experience every time.
By 21, he went all in on himself. Instead of playing it safe, he launched his own roofing company, and within a year, it was doing seven figures. By 22, he was a self-made millionaire.
Since then, he’s generated over eight figures in sales, built and led teams of 50+ reps, and helped countless others transform their closing rates, income, and mindset.
In 2022, he was officially ranked the #1 Roofing Door Knocker in the nation, winning the National Knocking League and proving why he’s one of the best closers in the game. His personal record? Over seven figures in a single month.
But Trenton doesn’t just build businesses—he builds people. Whether it’s recruiting top talent, training elite sales teams, or creating new systems that help businesses dominate, he’s obsessed with helping others win and unlocking their full potential.
His company is now ranked in the top 1% of all roofing businesses in the USA, but he’s just getting started.
At 28, based in Michigan, he continues to scale, innovate, and push others forward.
While others fear risk, he runs toward it. While most make excuses, he makes impact. While many hesitate, he takes massive action.
If you’re looking to master the art of closing, scale your business, and develop the kind of mindset that makes you unstoppable, Trenton is the guy you want in your corner.
Because in his world, there’s no ceiling—only the next level.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Pouring my heart into my work has often felt like running a marathon with more hurdles than finish lines. The early days were a crash course in sales and service, where missteps taught me more than any training manual could. I clashed with difficult clients, wrestled with recruiting challenges, and endured sleepless nights over cash flow, collections, and the headaches of broken processes. Losing friends and even navigating legal expenses; left bruises, but each painful lesson built a layer of resilience. Through it all, my Will, Endurance, & Mindset became unbreakable 3 chord rope. Growing up I watched the Disney movie “Meet the Robinsons,” I found a funny sense of strength in its message. The Robinson family’s motto, “Keep Moving Forward,” and their willingness to celebrate failures as stepping stones mirrored my own story. Like young inventor Lewis, I learned that setbacks are often the greatest teachers, and by embracing them, staying optimistic, and believing in tomorrow, even the toughest moments can explode into greatness.

We’ve been impressed with Arrow Roofing Services, LLC, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
As a 29‑year‑old family man; married to my beautiful wife and raising two kids, I’m driven to build something lasting and meaningful for both my clients and my family. At Arrow Roofing Services, my youth and depth of experience in sales, insurance, and retail allow me to innovate with technology and Ai, positioning us as a future‑focused roofer in an ever‑changing environment. Using the best and most modern approaches with our clients. We’re most proud that our team earned the top roofing door knocker title as NKL champions in 2022 and again in 2025, and that Arrow Roofing Services has been recognized as a GAF Master Elite contractor, placing us among the top 1% of roofers nationwide. As one of only five contractors in Michigan offering GAF Timberline Solar and the very first to install it in the state in April 2024, we’ve set a new standard for renewable roofing. These achievements, along with my recognition on Forbes and the success of my bestselling book “Flip the Script – Negotiating with Tactical Empathy” co‑authored with Chris Voss, underscore our commitment to excellence and innovation.

What was your favorite childhood memory?
Growing up, our Christmas mornings were usually quiet affairs where the birth of Christ and the warmth of family mattered more than the few gifts under the tree. One year, when I was about six years old, I had been captivated by a knight Lego set I’d seen at Big Lots, but given our poverty it felt like an impossible dream. On this Christmas morning my parents handed me wrapped box and when the plastic armor of tiny knights emerged from the paper, I was stunned into silence. Tears welled up as I realized they had somehow scraped together enough to give me the one thing I’d wanted so bad. In that moment, the toy became a symbol of how hard they were willing to work to bring joy into our lives.

Pricing:

• 0% interest options available
• $117/month roof payments

Contact Info:

• Website: https://www.arrowroofingservicesllc.com/
• Instagram: https://www.instagram.com/trenton.wisecup
• Other: https://www.instagram.com/arrowroofingservices