How Structure and Discipline Catapulted a Michigan Entrepreneur from Door Knocker to Roofing Titan.

In the competitive realm of roofing, where storms and challenges are as unpredictable as the weather, Trenton Wisecup stands out as a trailblazer. The founder and owner of Arrow Roofing, Wisecup has not only weathered the storms but has soared to unprecedented heights in the industry, bringing his business from $20 to over $20 million in just six years. His journey, marked by a unique blend of entrepreneurial acumen, structural discipline, and a relentless pursuit of excellence, has not only earned Arrow Roofing its place as one of the leading players in the roofing industry, but Wisecup’s tale of success also serves as a paragon of tremendous inspiration for aspiring entrepreneurs.

Building Success from the Ground Up: A Journey of Entrepreneurial Grit

Trenton Wisecup‘s entrepreneurial journey began at a very young age with ventures like lemonade stands and odd jobs. However, soon after graduating from high school, he joined one of the nation’s premier restoration roofers in 2015 at the tender age of 19 and thus started his journey in the storm roofing industry.

The turning point came when he took a leap by traveling alone to Texas in the aftermath of a significant hailstorm and ended up producing over $2M in sales. Hungry for more, he subsequently acquired a license as an insurance adjuster, playing a crucial role in the aftermath of hurricanes Mathew, Harvey, and Irma.

Armed with savings and experience in two important and large industries, Wisecup finally founded Arrow Roofing in March 2017. A hands-on leader, he initially handled sales and even participated in roof installations all by himself. This hands-on approach provided invaluable insights into every facet of the industry. Despite facing challenges like rejection from suppliers, banks, credit unions, and more, Wisecup secured a $10,000 credit line from SRS Distribution which proved to be a pivotal moment in his journey. He continued to soar since then, scaling Arrow’s revenue to an impressive $1.2 million within just a year, and eventually surpassing $5 million in 2022.

Discipline in the Storm: A Commitment to Excellence

Arrow Roofing‘s response to challenges has been a testament to Wisecup’s discipline and strategic thinking. Since its inception, the company has successfully restored over 1500 homes for Michigan residents, solidifying its position as a trusted name in the roofing business. Wisecup’s commitment to excellence brought it an A+ BBB rating along with a stellar reputation with 5-star Google reviews. 

Wisecup’s high energy, resilience, and consistent drive for superior performance is contagious – he built the same culture in all the members of his company. In order to deliver more precise and specialized roofing solutions to his clients, he along with his team attained Haag certification, making them all high-level hail damage specialists trained by forensic engineers. This also allows the company to offer expert-level advanced insurance system development for each client.

Series of Accolades for Arrow Roofing as well as Wisecup

Wisecup’s dual expertise in roofing and insurance ensured a unique approach for Arrow Roofing where they could pre-qualify projects for insurance claims, setting it ahead of most in the industry, and leading to swift growth. In 2022, Trenton and his team at Arrow Roofing achieved the unthinkable, clinching victory in the National Knocking League (NKL). Their prowess as the #1 Roofing door knockers in the USA marked a pivotal moment, showcasing Trenton’s ability to lead a team to unparalleled success in the competitive roofing landscape. Arrow’s ascent to the top echelons is further underscored by their coveted status as GAF Master Elite Contractors, a distinction awarded to the top 2% of residential roofers in America. 

Wisecup’s leadership extends beyond the confines of Arrow Roofing. He also serves as the captain-coach for 20+ roofing business owners in D2Dexpert, an association of industry leaders, underscoring his influence and recognition in the roofing community. His affiliation with the National Roofing Contractor Association (NRCA) further solidifies Arrow Roofing’s standing in the industry.

Vision for Tomorrow: Inspiring Growth in the Industry

In a span of just six years, Arrow Roofing has scaled remarkable heights, achieving over 8 figures in gross revenue. Even an earth-shattering pandemic like COVID couldn’t pull Wisecup back, thanks to his structured methods of operations and strong leadership. 

Yet, Wisecup believes this is only the beginning of Arrow Roofing’s success story. He plans to scale the company to even greater heights and move much further ahead than the $20 million revenue mark in the coming year. Looking ahead, he envisions Arrow Roofing to be a platform for both personal and professional development, creating a space where individuals can excel and positively impact others in the industry.