However, I think asking some people to change their bank accounts is going to be resisted. Also, waiting an additional 2-3 days to access your money when you're living paycheck to paycheck (as most independent contractors are) is not an option.
My cofounders and I are working on solving this same problem, however we took a different approach. (https://www.track.tax)
Track.tax creates a savings account in the user's name (same as Painless1099), but we also connect to the user's existing financial accounts to calculate taxes. Our chatbot (named Aida) communicates via SMS to ask simple questions to hash out the gory details. This means:
1. You can get paid via check, cash, or any other way you (or your clients) would like.
2. Money comes into your account first, then taxes are calculated and moved to your tax savings account.
3. Saving for taxes is as simple as responding "yes" to a text.
We'd love your feedback, and any comparison (strengths/weaknesses) you see between us an Painless1099.
Although we know solving this problem is really worth it, we'd greatly appreciate honest additional feedback from you guys, so feel free to text "HN" to TRACK (87225) and we'll give you a full year on the service!