The Best App for Tracking Tax Deductions

How does the Keeper app work?

Keeper was designed to help freelancers, side hustlers, and small business owners track their write-offs. It uses AI to help you track and categorize expenses, helping you save money at tax time. 

To put it into perspective for you, I started using Keeper around May of 2022, and I still ended up saving around $1,000 on my taxes when I filed that year.

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How I use the Keeper app

While I’ve gone through periods of being self-employed in addition to working full-time, I’ve recently gone full-on freelance. The first year was daunting. But having the Keeper app to guide me on potential write-offs gave me more headspace to find clients, deal with invoices, and actually create the products I get paid for.

Even when I was taking on occasional side gigs while working full-time, I found that small, unexpected expenses quickly piled up. For example, I built a garden shed for a client and made a few unplanned trips to the hardware store — one because I got the wrong screws and two because the client asked to change the paint color halfway through. 

I was happy to change things up — it’s part of the freelance game. However, the new paint color was more expensive than the original, and it threw off my estimated budget for the project. 

Because I used Keeper as a receipt organizer, I could go back and categorize my purchases for the job and calculate how much I spent so I could adjust my invoice. The app helped me organize my those purchases to show my client, which gave them confidence in how much I charged.

What I write off with Keeper

As self-employed workers, we don’t get benefits, and we’re also denied certain protections given to employees. I knew this going in, which made me that much more invested in understanding the tax breaks I was entitled to. The resources provided by Keeper — both within the app and through their website — helped me learn about these.

In the time that I’ve been using Keeper, I’ve been able to identify common (and not-so-common) expenses in both fields I freelance in.

For example, the app helps me track these carpentry expenses:

• 🚗 Gas and car maintenance: It’s not uncommon at all to get a nail in your tire on a job site!
• 📱Phone bill: Primarily for calling clients and maintaining communication while actively on the job 
• 🥽 Personal protective equipment: Safety glasses, gloves, and ear muffs
• ⚡ Utilities: Running machines all day can spike your electricity bill!

It also helps me keep up with these writing-related expenses:

• ☕ Coffee and meals: When going out with clients for a pre-project meeting
• 💻 Grammarly: A client offered me the tool at a discount. It automatically renewed last year, which was unexpected, but luckily I got to write it off!
• 🏠 Rent: For my home office, alongside other expenses like Wi-Fi

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With Keeper, I can easily keep track of less regular expenses too. While most of my work comes from long-term anchor clients, I also still pick up side gigs here and there — like building a coffee table or editing a resume. (I typically get paid through Venmo for these gigs.)

If it’s a long-term project, I pay upfront for materials or space — for example, deciding to rent a coworking space for a few weeks. In the summer of 2023, for example, I picked up a lot of carpentry jobs that require me to do some light business travel, so gas was one of my primary expenses. I also got a flat while on the job, so I was able to mark my trip to the mechanic as a partial write-off. 

What features does Keeper offer?

This tax deduction tracker app lets you customize your profile by adding jobs, expected income, and the percentage of time you use your cell phone for freelance work. This allows the app to estimate your tax savings from each write-off — and surface write-offs you might have missed.

Once your tax profile is set up, you get access to a host of other features.

#1. Link your bank accounts

Linking your preferred bank accounts is what allows you to mark transactions as write-offs within the app.  

How many you link is, of course, up to you. For example, I started off by linking only a specific credit and debit card associated with my business account because I wanted to get a clear sense of how the app tracked purchases and bill payments. I got Keeper to mark every transaction on that card as a write-off.

You can add as many accounts as your heart desires, just by clicking on the “Link another account” button.

What if you use a card for business only some of the time?

If you use some cards for both business and personal purchases, the app makes it easy to mark what is and isn’t a write-off.

For example, I’ve been using a certain flight miles card when I have to travel for work. I can use the app to separate business from personal trips and make sure I can rack up miles without losing out on tax savings.

What happens if you pay with cash?

If you ever pay for a business expense with cash, you can manually add it to your list of write-offs. You’ll just have to enter:

• What you bought
• How much you paid
• The category of your purchase
• When you bought it

#2. Track receipts

Here’s one thing I’ve learned: When it comes to tax deductions, a streamlined recordkeeping system is better than an overly comprehensive recordkeeping system. 

When I started freelancing about ten years ago, I had a folder where I kept paper receipts and copies of checks and made notes on what I’d spent. Yet, I still missed out on a lot of tax deductions because I wasn’t sure what I was supposed to do with the growing pile of papers. 

When I decided to take the leap to full-time freelancing, I leaned on Keeper’s receipt tracking feature to stay organized, so now I can actually claim my write-offs.

Keeper sends regular emails and check-in notifications letting you know what the previous week looked like. This gives you a sense of what you’re spending as you go, not to mention how much you’re set to save on taxes.

These check-ins can be a real money-saver. Sometimes, I forget that a purchase I made was actually for work until I get an email. I’ve found them especially helpful for transactions on a card that I only sometimes use for work.

To separate out business expenses from personal purchases, I check the transactions from that card every week. I just spend about five to 10 minutes going over the most recent ones and making sure they are marked correctly.  

#3. Create rules

This is one of my favorite features of the Keeper app! The app recognizes when you write off the same thing multiple times, and it’ll prompt you to create a rule. 

These rules let you flag that transaction as a recurring business expense. Now, each time you make it appears, the app will categorize it as a write-off automatically. 

How do you update a rule?

If you say “no” when the app prompts you to create a rule, but find that your circumstances have changed and you want that rule after all, you can do that from the “Tax Help” tab. Your tax assistant will take care of it for you.

It’s best to create a rule when you know a recurring expense won’t change — although that doesn’t always happen when freelancing, especially if you work in multiple fields. 

For example, my carpentry and copywriting jobs couldn’t be more different when it comes to expenses. That’s why I find the rule feature most handy for recurring expenses that apply to both, like:

• 💵 Rent
• ⛽ Gas 
• ☂️ Car insurance
• 🛡️Liability insurance 

And don’t worry, the app also makes it easy to handle exceptions to your rules. For example, if I go to dinner with friends and end up using my business card because I lost my other one (it happens to the best of us!), I can mark this expense as “personal.” This works even if I’ve set the app off to write off everything I buy with that card. 

#4. Categorize expenses

Because my professional profile is pretty varied, I like Keeper’s “categories” feature. It lets me  mark expenses based on what I need for each project I take on.

For example, unlike my carpentry work, as a writer, I often use restaurants or cafes to host meetings or go over project details with clients. So I end up using the “Business meal” category a lot for my copywriting work. Additionally, I can use other categories to deal with writing-related expenses such as my website (“Advertising”), software I use (“Software”), and continuing, and online classes or workshops to enhance my skills (“Education”).

#5. Get tax help

Even if you’re an experienced freelancer, it can be overwhelming when tax laws change. The tax assistant Keeper assigns you can help you stay up to speed — or let you know when you don’t need to worry about it.

For example, there was the IRS decision to lower the 1099-K reporting threshold. Originally, freelancers only got a 1099-K tax form if we get paid $20,000 through credit cards or third-party payment processors, like Square, Venmo, and Cash App, and have at least 200 business transactions. But the change would bring that threshold down to $600 (and eliminate the “number of business transactions” requirement). 

It’s safe to say that most contractors use one or more of these platforms. With the massive decrease to $600, that meant a lot more 1099-Ks going out.

Luckily, this change was put on hold in December of 2022, giving us freelancers more time to wrap our heads around it. But when I became aware of it, I messaged my assigned tax assistant through Keeper’s Tax Help tab to better understand the rules meant for my taxes. She got back to me within the hour. 

While I could have done a simple Google search to learn what was going on, it was helpful to speak with a professional tax assistant, and it put my mind at ease. She even capped off the conversation by asking if I needed help with anything about my write-offs for the week. 

Additionally, Keeper’s “Tax University,” found at the bottom of the app, has a ton of short articles to help answer your questions about anything and everything tax-related. That includes my favorite, “Your 1099 tax bill (and why it’s so darn high)," because, yes, my thoughts exactly!

#6 Export expenses

The app lets you download an Excel sheet of your write-offs for the year, broken down by category. You can print this out and give it to an accountant, or refer to it if you’re doing your taxes by hand. My accountant was impressed with the format and said it saved her a lot of time on my tax return.

#7 File taxes

In addition to a business expense tracker, Keeper also doubles as a tax software. You can also file taxes directly through the app, using either your phone or your computer.

Now that I’m in a groove and have been using Keeper for over a year, I’ll file my 2023 taxes with the app. After using both the automated features and the Tax Help center, I’m confident that they’ll point me in the right direction if I have any questions.

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How much does Keeper cost?

Keeper comes with a one-week free trial. After that, there are two pricing options:

• A monthly subscription for $20
• An annual subscription for $192

The annual plan saves you $50 a year.

Of course, make sure your subscription fee is written off, since Keeper is considered a business tool!

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Why should freelancers use Keeper to track receipts for taxes?

If you’re wondering if I would recommend Keeper as an expense tracker app, the answer is a resounding yes. It’s helped me stay on top of my spending for each job, which could have easily gone overboard with multiple trips to the hardware store. And, of course, it’s helped me write off all of those expenses, something I rarely managed with my old folder of receipts.

Using Keeper has also helped to remind me when I can write something off, like a dinner or a trip to the coffee shop. Thanks to its helpful reminders, I realized that I was talking about work a lot more than I thought. (Guess I’m still finding that work-life balance.) As a result, I was able to write off a ton of meals that ultimately turned into business meetings. 

There are plenty of digital bookkeeping and tax tools out there. Still, Keeper is explicitly designed for self-employed professionals, so if anything changes on the legal end — or even in your day-to-day — it will adjust accordingly so you don’t miss out on tax benefits.

Now that I know what I typically spend per job and what I can and can’t write off, I’ve become much more confident in creating budgets and invoicing clients. Even beyond the $1,000 or so I saved in year one, the improvement to my financial health has been the biggest benefit of using Keeper.