Keeper

Keeper envisions a future where freelancers, contractors, and gig workers reclaim the wealth they lose each year to inefficient tax filing. By harnessing the precision of patented AI technology, we transform the complicated landscape of taxation into a personalized, intuitive experience tailored to the unique needs of the self-employed.

Our mission is to eliminate the barriers that cause millions to overpay taxes, empowering independent workers with smart automation that identifies every eligible deduction while integrating human expertise to ensure maximum refund accuracy. Through continuous innovation in AI-assisted financial insights and easy-to-use platforms, we are building a new standard of tax justice and confidence in the digital economy.

We've been tracking Keeper since their Y Combinator days, and honestly, they've built something pretty clever here. While most tax software treats everyone the same, Keeper zeroed in on the 40 million Americans juggling freelance work — and the fact that they're collectively losing over a billion dollars annually by missing deductions.

The "Freelance Tax Tragedy" isn't just marketing speak. It's a real problem, and Keeper's approach feels refreshingly targeted.

The AI Actually Works

Here's where Keeper surprised us: their patented AI doesn't just categorize expenses randomly. It learns your profession and builds custom rules around what you can actually deduct. Connect your bank accounts, and it starts flagging potential write-offs automatically.

We've seen plenty of "AI-powered" tax tools that are basically glorified spreadsheets. Keeper's system feels different — it's genuinely hunting for money you might've missed.

Beyond Basic Filing

What caught our attention is how Keeper handles complexity without overwhelming users. K-1s, rental properties, AMT calculations — stuff that usually sends people running to expensive CPAs. They've managed to automate the heavy lifting while keeping human tax professionals in the loop for review.

The fact that they can handle S Corp and partnership filings with professional oversight is impressive for a platform that started focused on freelancers.

Who This Really Serves

Keeper isn't trying to be everything to everyone, which we respect. If you're a W-2 employee with straightforward taxes, you're probably overcomplicating things here. But if you're drowning in 1099s, tracking business expenses on napkins, or constantly wondering what you can write off, this clicks.

The 14-day trial gives you enough time to connect accounts and see if their AI finds deductions you missed. For most freelancers, that first discovery session probably pays for the subscription.