Less Accounting

There is a Stanford-based start up called Indinero.

https://indinero.com/

It does cash flow planning, integration with major banking ala Mint, and maybe some sort of accountant integration as well.

My wife is a tax guru and we've discussed this possibility you speak of many, many times. We even are poised for a product launch ourselves:

http://www.theseedsafe.com

With her heavy-technical multi-entity tax knowledge, and my web development experience, we could MVP something similar in a couple of months. Integrating with the banks and categorizing expenses is something I've been waiting for as a gem though. :)

Think of it, automatic bank reconciliation, budgeting, payroll, invoicing, AND TAX PLANNING. Aka - run your business, here are all of your W2s, 1099's (employee forms), and pre-filled forms for any and all entities you have set up.

Now, the biggest thing here - and I think this is where indinero is getting caught up - is liability. People outsource their tax preparation to Big-4 type businesses like PWC for liability reasons. Unless either the software, or the accountant is CPA certified you are walking on a thin line as a business (but I could be corrected here).

Budgeting, invoicing, cash flow, all the immediate stuff - is taken care of by a slew of web applications. Consider also Less Accounting - http://lessaccounting.com/, which puts a lot of this stuff together.

Really the cash-cow and home-run would be integrating the tax planning into the business. If…

Disclaimer: I doubt I'm a good role model to be answering this question. The majority of my experience has been spent working for someone. Granted most of the projects I've been able to choose, I am not yet a self-made man. I work with many consultancies and can only relate what I've observed.

The biggest problem is the overhead of managing your finances and business. It's a distraction that you'll have to learn to deal with one way or the other. In my opinion, find someone that will help you navigate these decisions early and often. (Look to your local Chamber of Commerce or entrepreneurial meetups for qualified mentors.)

Do NOT underestimate how important it is to track your time and money. My approach was to take things in small bites. I setup a DBA and opened a business account and tried my best to keep my finances separate. When I paid for stuff out of my personal account, I made sure I put together an expense form to track reimbursements. Even though there aren't much tax benefits running as a sole proprietorship, the taxes are much easier and you do get to write off a few things. Once you start making 4 figures a month, seek out assistance again and see if it makes sense to formalize your business into a corporation.

There are services which help manage your books (such as Florida startup, http://lessaccounting.com). If it makes sense, use them! They are awesome people and will be a net positive gain for your business. There are also lawyer services which will…

I would strongly advise against Quickbooks because of how terrible Intuit is to work with... I can't support that company at all - they have evil business practices. In our business, Intuit locks Quickbooks customers in to their extremely expensive processing solution, with no API to get transactions in or out.

A few great startups to try - I've heard good things about all of them.

http://Outright.com - $10/mo

http://waveaccounting.com - Free (double entry accounting).

http://lessaccounting.com/ seems to have a good interface - $30/mo

Intuit has put a good deal of lobbying money towards blocking proposals to have the federal government send you pre-filled out tax forms that would make everything much easier.
http://www.npr.org/templates/story/story.php?storyId=9112083 http://www.techdirt.com/articles/20100723/09055310339.shtml
They put a million dollars to Republican Tony Stricklands campaign for California Comptroller because the other guy wanted free e-filing http://www.consumercal.org/article.php?id=127

As a basic income / expenses tracker, I've used both Less Accounting (http://lessaccounting.com) and Outright (http://outright.com). Outright flowed better for me, but YMMV. This was for a single-founder startup, with very modest requirements.

I'm about to start managing the finances on a startup I'm founding with a partner, and in order to keep the books in order, we'll be using QuickBooks. It's possible that Outright or Less could handle our needs, but I want to make sure that everything is recorded properly, including paychecks and whatnot. This is important when running a solo operation, of course, but since the income is all pass-through, it's not as big a deal. When there are multiple founders, I'd recommend something more substantial.

Lovd is made by Less Everything (http://lesseverything.com/), which runs a thriving contract development firm and makes a beautifully elegant accounting application (http://lessaccounting.com/). We think Lovd is great---in fact, you'll find some Lovd code inside the current Insoshi code base, with more to come---but it's a side project for them. In contrast, Insoshi is our sole focus, which means we have more resources for community-building, documentation (http://docs.insoshi.com/), and future development.

This topic comes up here every now and again. Here's the most recent instance: http://news.ycombinator.com/item?id=317131

The quick and dirty list via ryanfelton:

http://liteaccounting.com/

http://gobootstrap.com/

http://www.netbooks.com/

http://www.freeagentcentral.com/

http://www.clarityaccounting.com/

Also, you might look into http://www.lessaccounting.com.