Solo & Freelance
About the company
Tom Nakamura runs Startup, a one-person strategy consulting practice. Like most solo founders, he wore every hat in the business—including the one that dealt with receipts, expense tracking, and tax preparation.
The challenge
Tom had been running his consulting business for three years without a system for tracking expenses that actually worked. He tried spreadsheets, notes apps, and a folder of scanned receipts. Every approach fell apart within a few months.
Tax season meant spending two full weekends trying to piece together a year’s worth of expenses. The real cost wasn’t just time—Tom was missing deductions like client dinners, software subscriptions, and travel costs. His accountant estimated he was leaving $2,000–4,000 on the table every year.
“I’d start the year organized and by March it was chaos. Receipts in my email, some on my phone, some I’d just forgotten about entirely.”
Tom Nakamura, Founder, Startup
What Startup needed
Tom wasn’t looking for an enterprise tool. He needed something simple enough that he’d actually use it—and free enough that it made sense for a one-person business.
His requirements: capture receipts without friction, categorize them automatically, and produce something his accountant could use come tax season.
The solution
Tom signed up for Payflow’s free Starter plan and connected his bank account in under ten minutes. When he had a client dinner, he took a photo of the receipt on the spot. When a software subscription charged his card, Payflow captured it automatically.
When a client sent a reimbursable invoice, he forwarded the email to receipts@payflow.io and Payflow extracted everything—vendor, amount, date, category—in under three seconds. By tax season, every expense was already categorized and every receipt was attached.
“The forwarding thing was the game changer for me. I get so many receipts by email. Being able to just forward them and have everything extracted automatically meant I didn’t have to think about it.”
Tom Nakamura, Founder, Startup
The result
Tom’s first tax season with Payflow took one afternoon instead of two weekends. He exported a complete expense report, handed it to his accountant, and was done.
With every business expense properly captured and categorized, his accountant found $3,200 in legitimate deductions that had been missed in previous years—software, client entertainment, home office costs, and professional development expenses that had simply never been tracked. Tom has since referred three other consultants to Payflow.
“I made back the cost of upgrading to the paid plan in the first week of January. And that’s just the tax savings—I’m not even counting the time.”
Tom Nakamura, Founder, Startup
