Our tax bill was shocking. We went from having a refund to owing a significant amount of money.

How did their taxes get complicated?

For years, their taxes were the easy kind. Both worked W-2 jobs, filed with simple tax software, and got a refund every spring. Then Greg grew his video work into a real side business, and Rebecca opened her own therapy practice, seeing teens and adults across California and Florida. The 1099 income started coming in, and the refund disappeared.

In its place came a bill, and every filing season turned into a bad surprise. Worse, no one could tell them why. Every deduction came with another question: Is this actually deductible? Where does it go? And what proof do we need if we get audited?

As soon as we transitioned to having the side business and my full time job that's when our taxes got pretty rough.

What did they try first?

At first they tried to muscle through it themselves. Rebecca figured that if she could get through grad school and open a business, she could handle her own taxes. They tracked expenses in notebooks, in a half-built Google Sheet, and in what they came to call the “haunting manila folder,” a growing envelope of receipts they'd dump in all year and then frantically sort every March.

So they hired a CPA. Communication was the biggest problem. Questions went unanswered, or answers took weeks. Rebecca felt like a number instead of a person. In the end, the relationship amounted to a blank spreadsheet, a prompt to sign up for QuickBooks, and “we'll see you in March.”

Why didn't tax software fit?

TurboTax and H&R Block's free tiers asked about real estate and inventory, things that had nothing to do with a video business or a therapy practice, and every answer led to three more questions. The “free” option kept upcharging as the return got more complex.

One year Rebecca accidentally entered her income twice. The warning was easy to click past, and she filed with an error. The further their taxes drifted from a simple W-2, the less guidance there was.

What does their tax setup look like now?

Keeper was the first thing that felt built for them. They dropped in their forms, connected their bank, and the picture came together on its own. Recurring costs now get marked as deductions automatically: Google Workspace, Psychology Today, professional memberships and licensing, their electronic health-record software. Rebecca set the rules once and hasn't touched them since.

It also surfaces write-offs they'd never have counted, like a dinner with a former colleague where the conversation turned to a project they wanted to build together. Rebecca had filed it in her head as dinner with a friend.

Keeper is changing the way we behave. We're getting excited and trying to call out possible purchases that Keeper might catch for us - and often times it does!

Licensed in two states, Rebecca wasn't sure whether she needed to track her income separately for California and Florida. Keeper's chat confirmed that she did, and showed her how.

What changed?

For the first time in years, they're expecting a refund instead of a bill. A Keeper tax expert reviews the whole return before anything is filed, which is the part that lets them exhale.

And Rebecca picked up something that reframes every return they've filed: you can claim business deductions on top of the standard deduction. So they're going back to amend past years and recover what they overpaid.

Now we can go back, amend past years, and get back the money we overpaid.