A Massachusetts roofing contractor has been sentenced to prison for concealing $1.6 million in income from the Internal Revenue Service.

On Aug. 12, U.S. District Court Judge Brian E. Murphy sentenced Jake Miller to one year and one day in prison, to be followed by one year of supervised release. He was also ordered to pay restitution in the amount of $449,329. The sentencing follows Miller pleading guilty to tax evasion in February 2025.

Miller, 42, owned and operated Kostas Roofing, a commercial and residential roofing business in Natick, Mass., conducting business under the alias Paul Kostas, according to the District of Massachusetts U.S. Attorney's Office. Between 2013 and 2021, he cashed his customers' checks and deposited the proceeds into his personal bank accounts. The transactions went undetected due to the name discrepancy.

The IRS states Miller received at least $1.6 million from his roofing business from 2013 to 2021 but did not file income tax returns for any of these years. As a result, he evaded paying income taxes of nearly $450,000.

The charge of tax evasion provides for a sentence of up to five years in prison, three years of supervised release and a fine of up to $250,000 or twice the gross gain or loss, whichever is greater. Sentences are imposed by a federal district court judge based upon the U.S. Sentencing Guidelines and statutes which govern the determination of a sentence in a criminal case.

Ethical Behavior

Aside from the obvious advice of not following in Miller's footsteps and cashing checks into a personal account under a pseudonym, roofing contractors should take the proper steps to ensure they're on the IRS' good side. Not only does it keep them out of any legal trouble, they remain trustworthy in the eyes of their customers.

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Bookkeeping and financial advisory company JTC CPA says it's essential to create detailed records of each transaction, whether the revenue is coming from installations, repairs or maintenance. Include information like the customer's name, project details, invoiced amount and payment terms.

"When you receive payments from your clients, it’s crucial to handle them promptly and accurately. Recording payments accurately in your bookkeeping software ensures that your financial records reflect the true state of your cash flow," the company says on its website.

The company says by staying on top of invoicing, managing outstanding payments and promptly recording and depositing received funds, contractors can optimize cash flow, working capital, and ensure financial stability. Regular internal audits and diligent bookkeeping can protect contractors against inadvertent errors and deter willful evasion. 

Industry and government advisers encourage contractors to minimize cash dealings, adopt digital payment platforms and engage third‑party payroll services.

Thea Dudley, CEO of Pocket Protectors, says payment portals help alleviate multiple collection issues that could lead to unintended consequences. If a contractor hasn’t already adopted one, they should research the portals available to find one that works for them.

“If you have not bit the bullet and gotten an online payment portal, eliminate the post office as much as you can,” she said. “The best thing you can do is find a way to do it online. And there’s so many options.”