[acallwood]

1) https is life.

2)We are NOT from Nebraska, but we found an awesome tech-forward bank in Lincoln Savings Bank who saw a pain point in the 1099 world and got really excited about helping us build out a tax solution.

3) We don't automatically send quarterlies (yet) but we do send reminders and make it really easy to remit that payment every quarter. Shortly, you'll see an automated solution built into the product.

4) In answer to your W-2 question, yes, employers automatically withhold taxes for their employees and remit that money to the IRS throughout the year. Essentially the government holds on to this cash all year and if you've overpaid, you'll get a refund. This is what happens in a fair amount of W-2 job situations, but when you're self-employed, you're on the hook for taxes and are expected to separate funds and pay estimated quarterlies throughout the year - a tough thing to manage on top of client work, life, and whatnot.