Keeper.app: Reinventing Taxes for Freelancers and Independent Workers

Tax season is challenging for most people. But for freelancers, it can feel like a trap. No one takes tax out of your pay. So you have to track every cost, guess what you owe, and pay it yourself. Miss a step, and you either overpay or face a penalty. That is the exact pain Keeper.app set out to fix.

Keeper began as a small Y Combinator startup with a simple idea. Instead of asking you to dig through old receipts, it reads your bank feed and spots your tax write-offs for you. Today, the company says it has uncovered $1.2 billion in tax savings for its users.

In this startup story, you will learn how Keeper began, how the app works, and what it costs in 2026. Plus, you will get simple steps to start saving on your taxes.

Note: Keeper’s official brand name is Keeper Tax, and its website lives at keepertax.com. In this article, “Keeper.app” refers to the same product.

The Freelance Tax Problem Behind Keeper.app

First, let’s look at the problem. The number of independent workers in the US keeps growing. In fact, an Upwork study found that 64 million Americans did freelance work in 2023. That was 38% of the whole US workforce. Together, they earned about $1.27 trillion.

Yet most of these workers receive no help with taxes. When you have a regular job, your boss holds back taxes from each paycheck. However, as an Uber driver, dog walker, or logo designer, you must handle this function yourself. As a result, the full tax bill lands on you at once.

Why Independent Workers Overpay

On top of income tax, freelancers pay a self-employment tax of 15.3%. This covers Social Security and Medicare. Normally, an employer pays half of it. However, when you work for yourself, you pay both halves. And if you expect to owe $1,000 or more, the IRS wants you to pay in four parts across the year. These are called quarterly estimated taxes.

Still, many people skip them. Keeper’s founder once said that about 85% of freelancers don’t pay quarterly. So they end up paying a penalty at the end of the year.

Then there is the bigger issue: missed deductions. Freelancers can often write off phone bills, work software, mileage, and even supplies. For example, a dog walker can deduct leashes, poop bags, and parking.

But most people don’t know these deductions. So they simply pay too much. Back in 2019, Keeper guessed that the average gig worker overpaid by more than 20%, or about $1,550 a year.

Here’s our take: the real problem is not math. Instead, it’s memory. Nobody remembers in April why they bought something in July. Because of that, Keeper’s best idea was to catch each expense while you still remember it. That small shift in timing changes everything.

The Founders’ Journey: How Keeper.app Was Born

Next, let’s meet the people behind the app. Keeper was started by Paul Koullick and David Kang. They were childhood friends. Later, they even became debate partners.

Their skills fit together well. Koullick studied computer science at Harvard. After that, he worked in product analytics at Square. Then he joined a startup called Stride. There, he led the team that built Stride Tax, a mileage and expense app for small business owners.

Meanwhile, Kang studied math at the University of Chicago. Then he worked as an options trader. At Stride, Koullick saw how badly gig workers struggled with taxes. So the two friends tried a few startup ideas. In the end, they kept coming back to taxes.

As Koullick told TechCrunch, “We wanted to build something that actually mattered to real people.”

From Y Combinator to Series A

In early 2019, the pair joined Y Combinator. At first, they had little product to show. But by Demo Day, they had 200 paying customers. Soon after, they raised $1.65 million at a $10 million valuation. Matrix Partners led the round. Their goal was bold: reach 10,000 customers in 18 months.

Growth came fast. By early 2020, Keeper was growing 30% to 40% each month, according to Brazilian outlet NeoFeed. By then, Keeper had helped 50,000 workers save around $40 million.

Then, in March 2021, Keeper raised a $13 million Series A. Investors included e.ventures, Matrix Partners, and Foundation Capital. In total, the company has raised about $15.8 million.

Here’s our take: Many startups try to serve freelancers with invoices, contracts, and banking all at once. The keeper did the opposite. Kang said they wanted to go deep on taxes instead of broad. And it worked.

After all, a designer and a delivery driver run very different businesses. Yet both must file taxes. So taxes became the one door every freelancer walks through.

How Keeper.app Works: AI Write-Offs Meet Human Tax Pros

Now, let’s see how the app actually works. At its core, Keeper does three jobs. It finds your deductions, prepares your return, and gets a real expert to check it.

Automatic Write-Off Detection

First, you link your bank accounts and cards. Keeper uses a secure link to read your transactions. It does not store your bank login. Then its AI scans each purchase and flags the ones that look like work costs.

In the early days, Keeper sent you a quick text a few times a week. Each text asked a simple yes or no question, like “Was this a work expense?” You just tapped a reply. As a result, tax prep turned into a few seconds of effort each week. Users still praise this feature in reviews today.

Furthermore, you can upload last year’s tax return. Then Keeper’s AI looks for missed tax savings opportunities, such as a home office deduction or a SEP IRA.

AI Plus a Real Tax Professional

Here is where Keeper stands out from typical DIY tax software. Every return is reviewed and signed by a tax pro. Its team includes CPAs and IRS Enrolled Agents. In addition, you get an AI tax assistant that answers questions any time of day.

Keeper also handles more than freelance income. For instance, it supports W-2 jobs, rental property, investments, K-1s, and S-Corps. So if you have a day job and a side hustle, one app can file it all. On top of that, the company offers a 100% accuracy guarantee and audit protection.

Here’s our take: pure AI isn’t enough for taxes. People need to trust the result, because a mistake can cost real money. So Keeper uses AI for speed and humans for trust. In our view, this “AI does the work, a human signs off” model will likely shape many fintech tools in the future.

Keeper Pricing in 2026: Which Plan Fits You?

Of course, price matters. So let’s break it down. Keeper has changed its pricing over the years. In 2019, it cost just $10 a month. By 2021, it was $16 a month, plus $89 to file. Now, in 2026, it uses one flat yearly fee.

The Three Main Plans

• Standard ($199/year): This plan suits W-2 workers, contractors, and sole owners. It includes federal and state e-filing, deduction tracking, receipt uploads, and audit protection.
• Premium ($399/year): This plan is for more complex cases. Think LLCs, rental homes, or foreign income. It adds a dedicated accountant, help with quarterly taxes, and one amendment.
• Business ($1,199/year): Finally, this tier covers S-Corp and partnership returns. It also adds a year-end review of your books.

Each plan comes with a 14-day free trial. So you can test it before you pay.

Is Keeper Worth the Cost?

To decide, compare the fee with what you might save. For example, say you earn $40,000 from freelance work. If Keeper finds $3,000 in new deductions, you could save around $1,000 or more in tax. In that scenario, the standard plan becomes self-sustaining.

However, if you have very few expenses, a free tool may be enough. So be honest about how complex your taxes are. Also, think about your time. Many freelancers spend a full weekend sorting receipts each spring.

If your time is worth $50 an hour, those hours add up fast. So the fee may save you both money and stress.

Here’s our take: The keeper is clearly moving upmarket. It now serves S-Corps, landlords, and investors, not just gig drivers. That is smart business. However, the change also means that the cheapest gig worker might find the $199 fee to be quite high.

So if you earn under $20,000 a year, first try Keeper’s free tax calculators before you sign up.

How to Use Keeper.app: A Simple Step-by-Step Guide

Ready to try it? Then follow these steps to get the most from Keeper.

• Step 1: Sign up for the free trial: Download the app on iPhone or Android, or start on the website. The app holds a 4.8-star rating on the App Store.
• Step 2: Tell Keeper what you do: Pick your line of work, such as rideshare driver, designer, or real estate agent. This way, Keeper knows which deductions to look for.
• Step 3: Link your bank and cards: Then Keeper scans past transactions. Within minutes, you will see a list of possible write-offs.
• Step 4: Review flagged expenses each week: Spend five minutes marking what is work and what is personal. Because you still remember each purchase, your records stay accurate.
• Step 5: Set money aside for quarterly taxes: Next, use Keeper’s quarterly tax calculator. Federal payments are usually due April 15, June 15, September 15, and January 15. A smart habit is to move a set share of each payment into a separate savings account.
• Step 6: Upload your tax forms and file: When tax season comes, upload your 1099s and W-2s. Then Keeper fills in your return.

Finally, a tax pro checks it before it goes to the IRS.

Tips to Save Even More

Keep receipts for cash purchases, since a bank feed can’t see them. Furthermore, track your work mileage. Many drivers lose hundreds of dollars by skipping it. And if your income grows fast, ask your tax pro if an S-Corp could cut your self-employment tax.

Finally, check your quarterly estimate again whenever your income jumps. For example, a big new client can raise your tax bill fast. So update the number early, and you will avoid a surprise in April.

Here’s our take: the app is only as effective as your habits. In other words, a five-minute weekly check beats a five-hour panic in April.

Conclusion: Why Keeper.app Matters for the Future of Work

To sum up, Keeper.app grew from a simple insight. Freelancers don’t overpay because they’re careless. Rather, they overpay because the tax system was built for people with bosses. Paul Koullick and David Kang saw that gap. Then, they developed a tool to address this issue.

The startup’s path is impressive. It went from 200 paying users at Y Combinator to more than one million Americans who have used the app. Along the way, it raised about $15.8 million and uncovered $1.2 billion in tax savings. Most of all, it proved that a narrow focus can beat a broad one.

For you as a freelancer, the lesson is just as clear. Track your expenses all year. Please ensure that you pay your quarterly taxes on time. And make sure you take advantage of all available deductions. Whether you use Keeper or another tool, these habits will save you money and stress.

Meanwhile, the freelance workforce keeps growing. So tools that blend AI with human tax experts will only become more important. Keeper is one of the best examples of that shift today.

Frequently Asked Questions

1. What is Keeper.app and how does it help freelancers with their taxes?

Keeper.app, officially called Keeper Tax, is an AI-powered tax filing app for freelancers. It scans your bank transactions to find tax write-offs. Then a tax professional reviews and signs your return before it is filed.

2. How much does Keeper tax software cost for US freelancers in 2026?

Keeper charges a flat yearly fee. The Standard plan costs $199, the Premium plan costs $399, and the Business plan costs $1,199 per year. Each plan includes a 14-day free trial, so freelancers can test the tax software first.

3. Who founded Keeper, and how did the tax startup get its early funding?

Paul Koullick and David Kang founded Keeper. They joined Y Combinator in 2019 and raised $1.65 million led by Matrix Partners. Later, they raised a $13 million Series A, bringing total funding to about $15.8 million.

4. Can Keeper help independent contractors pay quarterly taxes on time?

Yes. Keeper offers a free quarterly tax calculator. Furthermore, its premium and business plans include quarterly tax support from a dedicated accountant. This helps independent contractors pay estimated taxes on time and avoid costly IRS penalties.

5. Is Keeper safe to link with my bank account for expense tracking?

Keeper uses 256-bit SSL encryption, the same level banks use. It does not store your online banking login or sell your data. So linking your bank for automatic expense tracking is designed to be secure.