The Medicare enrollment event at the Richmond Public Library’s main branch on Hull Street was winding down on a Thursday afternoon in late February when I noticed Corey Kirby standing near the exit, holding a folded flyer and looking like a man who had walked into the wrong room. He was wearing a gray Henley with a faint grease stain near the cuff, and he had the particular stillness of someone trying very hard not to look worried.
I was there covering the event for American Relief — specifically, the question of how many working-age adults stumble into Medicare information sessions because they’re desperate for any kind of financial footing and don’t know where else to start. Corey Kirby, it turned out, was one of them. He was 53. Medicare was still 12 years away. But he’d seen the event listed on the library’s bulletin board and thought, maybe someone in there can help.
I introduced myself. He shook my hand with the kind of firm grip that comes from 23 years of working on engines. Within ten minutes, he was telling me about his shop.
A Business Built on Loyalty — and a Lease That Changed Everything
Corey Kirby has owned Kirby Auto Service, a four-bay shop off Midlothian Turnpike in Richmond, since 2018. Before that, he spent 15 years as a line mechanic at a dealership — good steady work, he said, until the dealership restructured and cut a third of its service staff. Rather than look for another employer, he scraped together $22,000 in savings, signed a commercial lease, and opened his own place.
For the first few years, the shop did well enough. Gross revenue in 2022 hit roughly $131,000. He had two part-time employees, a loyal base of customers who came back for every oil change and brake job, and a lease at $1,850 per month that he described as manageable.
Then the numbers started moving in the wrong direction. Gross revenue fell to approximately $114,000 in 2023, and then to around $97,000 in 2025. He attributed some of it to inflation squeezing his customers’ discretionary spending, some to a newer national chain that opened nearby, and some to the simple reality that running a one-man show means every sick day is a lost day of revenue.
The lease renewal notice arrived in November 2025. His landlord was raising the monthly rate from $1,850 to $2,405 — a 30 percent increase, effective January 1, 2026. Corey told me he sat in his truck in the parking lot for nearly 20 minutes after reading it before he could go back inside and face the rest of the workday.
He also lives with a roommate in a rented house about four miles from the shop — a cost-sharing arrangement he adopted specifically because his personal expenses needed to stay low while the business stabilized. His 2025 net business income, after operating expenses, came out to roughly $41,000. That’s the number his accountant had been working with for the last two tax seasons.
The Tax Returns He Filed Every Year — and What Was Missing From Them
Corey had been filing his taxes with the same local accountant since he opened the shop. He paid the fee, signed the forms, and moved on. He had no reason to question the process — it seemed professional, and he had no basis for comparison.
When I asked him how involved he was in reviewing what was actually on those returns, he laughed with the kind of quiet embarrassment that told me everything.
After our initial conversation at the library, I connected Corey with a volunteer at a Volunteer Income Tax Assistance (VITA) site — a free IRS-sponsored program that provides certified tax preparation for individuals generally earning under $67,000. The VITA volunteer, a retired CPA named Marcus who runs sessions out of a church on Semmes Avenue, agreed to review Corey’s prior two years of returns.
What Marcus found was not fraud or error, exactly. It was omission — the slow, expensive kind that compounds over years without anyone raising a flag.
Total additional deductions Marcus identified across these categories: approximately $11,000 to $13,000. On a net income of $41,000, and depending on Corey’s effective federal tax rate, the estimated additional tax savings ranged from roughly $2,400 to $3,100. For a man whose rent had just increased by $555 a month, that number was not abstract.
Finding Help in an Unexpected Place
The process of untangling two years of underclaimed deductions was not instant or painless. Marcus spent two sessions with Corey over three weeks — one reviewing the prior returns, one preparing amended documentation for 2024 and projecting forward into the 2025 filing.
Corey told me the hardest part wasn’t the paperwork. It was accepting that he had needed help and hadn’t known how to ask for it — or even that help of this specific kind existed at all.
He also looked into whether his shop qualified for any Virginia-specific small business relief programs. The SBA’s Richmond District Office provides access to microloans and technical assistance through local partner organizations, and the Virginia Small Business Development Center network offers free consulting for business owners evaluating their financial position. Corey attended one session in March 2026 and said it was the first time in two years he’d talked to someone who didn’t immediately try to sell him something.
He hasn’t taken on any new debt. He’s still cautious about the microloan route — not opposed, just watching the numbers for another quarter before committing. His priority right now is the amended return and making sure the 2025 filing is structured correctly from the start.
Where Things Stand Now
When I last spoke with Corey in mid-March 2026, he had filed an amended 2024 return and was two weeks from submitting his 2025 taxes with the full suite of deductions properly documented. The projected refund for 2024 was approximately $1,900 — not a windfall, but meaningful. The 2025 filing was on track to reduce his tax liability by roughly $2,600 compared to what it would have been under his previous approach.
The shop is still under pressure. Revenue hasn’t recovered. The rent is still $2,405 a month. He told me he’s considered whether to renew again in 2027, or find a smaller space and scale back to two bays. Nothing is settled.
What stayed with me after our conversations was not the dollar amounts — though they matter — but the specific shape of the problem Corey represents. He is not someone who made reckless decisions. He opened a business. He paid his taxes. He signed what his accountant told him to sign. And for years, the system processed his filings without ever surfacing the full picture of what he was entitled to claim.
That’s not a dramatic failure. It’s a quiet one. The kind that doesn’t announce itself until a lease renewal letter lands in your mailbox and suddenly you’re running the math in a parking lot, trying to figure out if the thing you built can survive another year.
Corey Kirby is still figuring that out. But he’s doing it with better numbers than he had in February.
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