Zen99 (YC S14) Makes Life Easier for Freelancers with Finance, Insurance Tools (opens in new tab)

What is with the Zen prefix? Zenefits, ZenPayroll, and now Zen99 - all went through YC and all do benefits/payroll/legal administrivia.

Just signed up. I am probably your ideal user. I work 100% on 1099, I buy my own health insurance, and I wouldn't mind paying you if the service was a net gain for me.

My thoughts:

1) The sign up form has a First________Last name field. I thought I would tab from First and land on a hidden Last field because of the gap between the two. Tabbing just moved me down to the next set of fields. If the words First and Last had been closer, I would not have been confused.

2) I cannot type in the date in the New Earning report. It sucks to click 5 times to get to Jan 31, Feb 28 etc.

3) I expected some Q&A about my consulting/tax profile. I file jointly with my wife who is on W2. I expense out things like home-office, cellphone bills etc. I would love to specify these in advance/batch so the tax estimate is more accurate. I don't want to put in every identical phone bill manually.

4) You don't cover Florida for health insurance yet. Understandable for a beta but please don't make this service just for CA/NY.

I can honestly say this was the biggest pain for me as a contractor. I decided to go without health insurance and paid the fine for not paying quarterly taxes just because I didn't want to deal with the hassle.

Even though this is a free tool, I would have gladly paid for it to help alleviate those issues.

Yan here, Zen99 CTO. Just wanted to thank everyone for their support over the past few months! I hope this can really help all of my fellow 1099er's out there(Not doing 1099 work anymore, but I did freelance development for a long time).

Tristan (CEO) here. Article went out right before we had a few hours of meetings, but I'll be around for the afternoon replying to any feedback!