Hi HN, We are Keeper Tax (https://keepertax.com). We help US contract workers automatically find tax write offs in bank statements. We do this by monitoring their purchases for tax deductible expenses -- like phone expenses, insurance payments, and home office expenses -- using a team of accountants aided by fancy computer stuff. The company is born out of frustration with how many people doing 1099 gig work -- rideshare, taskrabbit, online tutoring, and so on -- are overpaying on taxes. By our estimates, the average gig worker overpays on taxes by 21% (for context, that’s around $2,000 if you earn 40k) [1]. A fancy accountant could prevent, but fancy accounts are expensive. That’s why we’re building Keeper. But it’s more than just a low price. We want to make something accessible to people who don’t actually know much about taxes, or care to (i.e. most of us). That’s why we think the solution is to tell, not ask, when it comes to tax deductions. Your monthly phone bill is a great example. Many gig workers wouldn’t think their phone bill is a tax deductible expense. However, it’s partially deductible since you undoubtedly use your phone for work. But that sword cuts both ways -- many people will eagerly try to deduct haircuts, clothes, and other personal effects. The IRS is very strict that these are not tax write offs, so these folks risk getting themselves in trouble for an understandable mistake. The user experience is: we text you yes / no questions a few times a week. Examples include “Hey, was today’s lunch at McDonald’s shared with clients / coworkers?”, or “Do you use your Spotify account to play music for your rideshare passengers?”. The text messages are partially automated, but we hire an accountant to monitor things and jump in when needed. At the end of the year, you can export your write offs seamlessly into TurboTax, H&R Block, etc to file. We’re currently piloting the service with +100 paying users. We charge $10 per month because it’s simple, but eventually want to move to a model where we charge a small percent of the tax write offs we find for you. Aligned incentives :) Thank you HN! Looking forward to hearing your ideas and feedback! [1] 21% stat is based on comparing a sample of eleven 1099 contractor’s 2017 tax returns against what we found when digging through their bank statements. Biggest sources of this discrepancy is missing the home office deduction, forgetting to claim car insurance payments and other non-obvious transportation expenses, and forgetting to track business meals.