For me, my money is mostly automated through taking payments via ACH and Credit Cards, that are deposited directly into my business checking... well, except one client that insists on sending me a check every time, but even this is roughly automated (a check scanner on my desk at home).

I've used Quick Books Online and Gusto for years, now, and I don't really have to think about it.

I am an S-Corp, so I have to pay myself a W2 with a reasonable salary. So I deposit all of the business income at once into my business checking account, and Gusto (for a pretty hefty fee) direct deposits my paycheck weekly into my personal accounts.

QBO only takes a few minutes each week (or month if I'm lazy) to go in an categorize expenses and income, then at the end of every "tax quarter", I look at my profit for previous period, and cut a check for 20%.

Then at the end of the year, my CPA goes over everything and does all of the year end stuff that I don't understand, and moves registers around and categorizes stuff that I did wrong throughout the year.

I've adopted profit-first accounting (https://profitfirstbook.com/), which basically boils down to: For any revenue you generate set aside a fixed percentage of that revenue for both taxes and profit.

It's a habit rather than an automated process, though. There's no banking software that I know of that allows you to automatically initiate a new bank transfer for any incoming funds.

There is a service call Track (https://www.track.tax/) that kind of does this specifically for self-employment taxes.

It wouldn't be TOO dificult to implement a similar service for yourself that did a bank transfer of X% using plaid+stripe. Problem is that it would cost 0.8% (max $5) per transfer.

Usually, if you are a contractor or small business with less than 5 people, an Excel spread sheet should be sufficient to get a rough idea of how much money you need to set aside for expenses & taxes. From that, I knew that I had to set aside roughly 50% of my revenue (in the beginning).

The details are best left to your accountant / tax advisor, who will book everything correctly once a month / quarter / year, depending on the details of what kind of business you run.

Now that my income is pretty stable, I just "pay" myself a monthly salary (since I am a "sole proprietor", there isn't really a legal difference between me and my company, so this just means moving money from my business account to my personal account).

At the end of the year, I see how much money is left over and I put it in a savings account.

I've tried all kids of automation, but I found that just creating a manual excel spreadsheet is the easiest, and the most flexible.

Similar to a few other comments, I use Intuit payroll (Gusto might be better in terms of UI and support) and pay myself as an employee through S-Corp. Every US freelance should structure things this way IMO, so that you can take advantage of 401k contribution and company match. You can match up to 50k roughly and that match is a business expense, so you get the money plus a deduction. As you said, this is reaping the benefits of regular employment, with the additional benefit of being able to crank up the company match in years where you make more (or can pay yourself less).

In terms of cash management, I do quarterly transfers to Vanguard which is the 401k admin. Then 1-2 times per year I pay myself a close approximation of my final S-Corp distribution (plus regular monthly payroll).

Why did you chose to go with a 401k instead of a SEP-IRA?

I could have done a SEP but AFAIK the only difference is supposed to be less expenses vs. a 401k, but my 401k plan admin has very low fees. Also not sure if the SEP allows for a pre-tax benefit for the employee.

Something I learned about on HN a while back was a Self-Employed 401k offered by most large providers (https://www.fidelity.com/retirement-ira/small-business/self-...)

It's great as I can contribute 18k of personal funds and a max of 36k of business profits (or max of 25% of profits, whichever is less). For the fidelity plan I have there are no annual or associated fees. I put all my money into index funds and those are the only fees I pay. It's really been excellent for me.

I do this 100% manually with the help of a CPA. It's far too important to trust some app to handle for me.

Agreed. A lot more time and money will be wasted trying to automate this. A CPA is not that expensive.

I pay for zenefits. I have my own company and I pay myself a salary and zenefits takes care of all taxes and government forms. It’s not that cheap (I think $400 for the year) but I never have to think or worry about forms or taxes until I file my full taxes at the end of the year with my accountant.

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