Jake started his roofing company with nothing but grit, a pickup truck, and his old crew from his previous job. The first year was a blur—phone ringing nonstop, jobs lined up, cash rolling in. However, by year two, cracks were beginning to show. Money always seemed “good on paper,” but somehow there was never enough to pay his crew on time. He would bid on a few jobs just to keep the team busy, forgetting to factor in rising shingle costs and the true cost of labor. When rain slowed things down, invoices piled up, but bills still came due.

After tax season hit, Jake learned the hard way that the IRS expected its cut before the insurance company finally paid for that big hail job he finished months earlier. He scrambled to pull receipts together, but many had vanished. And with no system in place, he didn’t know which jobs banked profits and which bled him dry. Instead of growing, Jake started to fall behind on payroll, vendor bills, and sleep. The stress left him second-guessing whether he had made the right move starting his own business.

Jake’s story is all too real. It’s not a lack of hard work—it’s the chaos, the lack of planning, and flying blind with the numbers that drives so many good roofers out of business before their company ever gets off the ground.

Jake’s turning point came when he decided to stop flying blind and called Profit Wise for help. Instead of just scraping together receipts and hoping for the best, Jake worked one-on-one with an advisor from Profit Wise who understood the challenges roofing companies face every season.