At Keeper Tax, we’re not just building a product. We’re constantly building and iterating on processes that are both rewarding and fun for the team, and critical to the success our business.

Below are some examples of the practices we’ve been incubating.

#1) We watch user recordings weekly

While building a lightweight user research practice is important, it’s not enough. Traditional user research calls are abstract, and time-inefficient. There’s often too much people-pleasing and ego involved to get to the truth. Between scheduling, no-shows, and prep, user research is also incredibly time-consuming. …

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It’s a rush!

If you’re like most people, you checked around to see if there’s an obvious owner, took it, and went on your way. If only this happened more often …

Here’s the thing: if you’re self employed, there are $10 bills are laying around everywhere.

Calling an Uber to rush to a gig, lunch with a coworker, parking at a garage downtown… if you’ve ever forgotten to claim one of these expenses as a tax write off, you have walked past free money.

All you had to do is know the rules, and write it down. It’s as easy as bending over and picking up that $10 bill.

That’s why we’re building Keeper Tax. Too many people are working too damn hard to be walking by free money.

Post originally appeared on the Keeper Tax blog:

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Quarterly tax payments, also called estimated taxes, are possibly the most dreaded part of 1099 contractor taxes. It seems unfair that just because you earn money as a 1099 contractor, you have to file your taxes every three months. But is it true?

The IRS says: yes, you must file quarterly taxes

“Individuals, including sole proprietors, partners, and S corporation shareholders, generally have to make estimated tax payments if they expect to owe tax of $1,000 or more when their return is filed.”

Guess what: if you earn more than about $3,000 per year from 1099 contracting work, you’re included! Part-time independent consultants, Uber drivers, business owners, Airbnb hosts, Etsy sellers, it’s all the same to the IRS. Want to read the whole post? …

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If you don’t know what a mileage log is, ask your grandpa.

If you drive a car for your 1099 contractor work, you can claim a big tax write off on associated expenses. There are two ways: keeping track of car expense, or tracking mileage. The mileage method was introduced by the IRS to simplify the process of trying to keep track of all of your gas / car maintenance / receipts year-round. But does claiming mileage actually save you more money on taxes?

Option 1: Car expense records

At the end of the year, sum up all of your car expenses such as gas, insurance, repairs,️ oil, registration etc, and write off the approximate proportion of the time you drove your car for work. …

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Please stop filling your pant pockets and wallet with crumpled pieces of paper.

It’s quite common to think that you need to have a receipt for every tax deduction claimed at the end of the year. Every year, millions of Americans nationwide hoard receipts in their glove compartments, wallets, and shoe boxes. Is it true?

The IRS says: keep records.

“You may choose any recordkeeping system suited to your business that clearly shows your income and expenses”

The IRS says nothing about paper receipts specifically. All it says is to keep records that clearly show your transactions. If you’re masochistic like us, feel free to read the whole post on

What else might we all have that records transactions?‍

It’s the 21st century, people! Any purchase you make with a credit card, bank account, payment platform, etc are automatically recorded for you in a bank statement. These statements contain all the critical information needed to constitute an expense record: merchant name, date, and amount. Oftentimes, there are additional details emailed to you that can be pulled up if necessary. …

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Umbrella? Check.

I’ve been a product manager for five years. In that time, I launched features, product lines, and even entire apps from inception to scale… and I totally drank the whole CEO of the product and wearer of many hats Kool-Aid. So much, that three months ago I quit to start a company and become an actual CEO (of nothing!).

Very quickly, I learned that being a PM prepares you to be a startup founder in much the same way that running track prepares you for surviving in the wilderness. Not really. Here’s a list of reasons why.

#1 user acquisition

Holy moley… this one’s first for a reason. …

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Every year, nearly 7 million Americans start 1099 contracting for the first time. It’s a great way to make money on your own schedule… but taxes will be more complicated than you may have realized.‍

No, taxes are not withheld from your paychecks.

If you’re used to W2, it may come as a shock that 1099 tax payments weren’t being set aside during the year. Hopefully you’ve been setting money aside!

The only exception is if you’ve been paying estimated taxes (also known as quarterly tax payments). Most 1099 contractors don’t bother with estimated taxes because it’s a lot of work and the IRS hasn’t historically punished people for it. …

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👋 Hi friends, we’re starting a new business. Wish us luck!

Today is officially the first day of the rest of our lives! Just kidding. We’ve been at it for a few months now, I just hadn’t gotten around to posting about it.

What’s Keeper Tax

Keeper is a service that automatically finds tax write offs for self employed people. We do this by monitoring your bank statements with computer algorithms. Check us out >

Why taxes‍? Sounds boring.

Nope, taxes are awesome. Taxes are like someone offering you $1,000 per year in exchange for doing some research and writing stuff down every week. …

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Nobody reading your docs? This post is for you.

“Documentation” is a dirty word — especially at tech startups, where it seems to go against every grain in our rebellious, “move fast and break things” brains. Documentation, we say to ourselves, is for historians. Everyone on my team is already aligned, we tell ourselves, so why waste time on writing it down.

Wrong. Docs can be sexy. I would go so far as to say that keen documentation is a core competency of effective product management. That’s right. …

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How we do it at Amplitude, and why you should start doing it too

One of my most favorite books related to product management is Lean Analytics. Most famously, it outlines the role of data in the build -> measure -> learn product development cycle, and what makes a good metric.

A less well known concept discussed in Lean Analytics is a process in product development that they call ‘drawing a line in the sand’. …


Paul Koullick

Founder & CEO at | Previously, a happy product manager, and before that a miserable long-distance runner.

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