Meet the startup that wants to give you $1500 per year. Kind of.

Tax time can be very frustrating, knowing that you have to fork over a chunk of your hard-earned money to the ‘gubment’. Like that wasn’t bad enough already, the entire tax system is so frustrating that you could possibly pay more than your fair share in taxes — with no thanks from the IRS.

In fact, studies show that most businesses overpay as much as $1500 in federal taxes come tax season, with contractors being the most hard-bitten. All thanks to a tax system that was almost deliberately designed to squeeze as much money as possible out of you — by being as confusing as possible.

Now, paying taxes aren’t inherently bad or are they unnecessary, since they’re the price we pay for a civilized society.

Sure, you could hire a CPA to help work out how much you hand over but what if you could, sitting in the comfort of your home, calculate how much you owe in taxes, without giving as much as a free overdraft to the IRS? Almost seems too good to be true, given that tax help could end up costing more than the possible tax savings.

Well, meet Keeper Tax, the tax assistant that wants to save you $1500 per year.

In essence, Keeper is your intelligent, personal tax assistant that connects with your bank account or card statement, scans your expenses and automatically fetches you tax savings. Keeper classifies your expenses and helps you qualify tax-deductible expenses that keep more money in your purse. And it gets interesting. Did we mention that Keeper is basically a chatbot?

What Keeper does is to hook up with your account, review your day-to-day expenses and chat you up to classify which one of your expenses qualify as business-related. That info is then imported to your tax software (H&R Block, TurboTax) where your expense is safely marked as business-related, for when tax time comes knocking.

That way, you pay less — actually, you pay your fair share and get to keep more money in your purse.

When I spoke with Paul Koullick, Keeper’s CEO, he mentioned that Keeper was designed to bring the kind of tax smarts only the 1% exploit to the 99%. In his own words, “Keeper was designed to do just one thing: help you keep more money at tax time."

And it does that quite well. On the Keeper Tax website, there are a bunch of tax-deductible expenses you could still be making out of purse, such as:

1. Bought a new phone? Keeper knows it’s virtually impossible to run any business without jumping on the phone to either take a business-related call, doing a Google search, etc. With Keeper, you can easily deduct a good chunk of the cost of your smartphone from your tax bill. You keep more money at tax time. Yay!
2. Work Uber. To client meetings, out-of-town projects, you name it — it’s safe to say that Ubers probably already a habitual part of your work life — and what could be better than having the government pay for a good part of your Uber habit? Literally, of course! You guessed it: whether you’re riding to lunch with a client, or taking a ride out for onsite work, Keeper verifies with you and marks it down as tax-deductible.
3. Work lunches. There’s no need saying you need to eat to stay alive, keep working, and keep paying taxes. That said, a good amount of your work feeding qualifies as business expenses and therefore are quite deductible. Whether it’s lunch with the sushi-loving client, the potpourri of self-love you usually order for Friday all-nighters, or just the pizzas that quickly add up and get you thinking, ‘seriously, do I really eat that much pizza?’, (yes, you do!), Keeper helps to legally subtract a good part of these expenses from the money you hand over to the IRS.
4. Perhaps your card registers a charge for a SaaS subscription like say, Office 365, Dropbox, or MailChimp? Keeper analyses your software expenses and once you qualify them as business-related, you get that tax markdown recorded.

What’s crazy is that most small business owners, freelancers and contractors overlook these drop-in-the-bucket deductions and either wait to begin classifying them with their CPA, come tax season, but over time, these measure up to a few thousand dollars in tax overpayment per year.

And if you run a bigger business or work in a more complex scenario, the situation gets more twisted — you could be overpaying as much as two thousand dollars in federal taxes per year.

And that’s where Keeper beats your CPA hands down. Keeper analyses your expenses on the go, and keeps real-time tabs on tax-deductibles, ensuring that they’re easier to file, come tax season. And with time, machine learning gets Keeper smarter, automatically categorizing repeat work-related expenses as such, without you having to confirm over and again.

Loving it already? Get your check for $1,500 for the year here. Literally, 👍👍.