I'd love to be in a position to work with/learn from someone that's been as succesful as you in building a more or less solo business.

You didn't share a whole lot regarding which area/niche you target in your eLearning business (I'm guessing that it doesn't cover a wide variety of topics, unless you're a superstar that has a whole bunch of knowledge across a wide variety of topics :-).

But if I were in your shoes and looking to expand it would probably make sense to want to try and recreate the same success as the existing eLearning products in a new niche/area so you might need to recruit someone with a different specialty that has the requisite knowledge.

Another strategy I've seen used (this was about 10 years ago when I was fresh out of college and looking into how I could make money online), mainly by folks that were selling products in the "how to make money online" category, was the cross-selling between different groups of these people. Essentially, if you had purchased from one of them, it wouldn't take too long until you started getting emails from the one you had purchased from that mentioned a product from "one of their good friends" that sounded very good too and it was difficult to pass up wanting to purchase the other products (I definitely spent way too much during this period on these sorts of things before I realized how much money I was spending and realized I really needed to tone it down). It was effective though, and was more of a collaboration between similar eLearning companies selling products in this cross-selling fashion.

From the pure employee side, it looks like ZenPayroll has changed their name to Gusto (https://gusto.com/), but I think they have a pretty good offering for a small business wanting to expand and hire employees by helping to simplify the tax parts of things for you.

You also didn't mention if you were operating as a sole proprietorship or already as some sort of safer Corporation/LLC organization, which you would want to consider doing as well to help protect yourself, particularly if you would be hiring employees.

I myself have wondered / thought about the same problem you yourself have asked here though...I've just never been successful enough to actually be able to act on it (my little software business only makes about $100/sales or so per month so not enough to hire anybody unfortunately :-). How do small companies deal with this stuff? I think in a lot of ways they deal with it by having someone that's experienced with all of the "paperwork" side of things. My uncle for example ran a small business with his son painting cars, and neither was particularly knowledgeable about any of the business side...they just knew how to paint cars. My aunt on the other hand had experience with that sort of paperwork and taking care of it so she "abstracted" that away from having to deal with it. You'd likely need someone similar to help with those sorts of things (though again, Gusto may help with quite a bit of it, at least with some of the regular stuff related to taxes if their product hasn't changed much from the ZenPayroll days).

I wish you the best of luck, and if you ever want an eager, young fellow to work with feel free to contact me (email's in my profile :-)!