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I received this in the Product Hunt newsletter today:

Little known fact: your favorite fonts aren't free.

The owners of your favorite fonts – Garamond, Times New Roman, Georgia – charge businesses who use their font on their website, app, and advertisements.

Instead of paying millions of dollars for licenses, tech companies are starting to design their own fonts.

I knew that they have proprietary licenses—but does that imply that they are not freebies for businesses?

How does the owner of Times New Roman, charge a business for using the font for commercial use?

Also, does it mean that if a company uses Times New Roman for commercial use, it is something illegal? If not, why would a business pay for such a font?

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    "How does Microsoft, let's say, charge a business for using Times New Roman for commercial use?" I would assume the license fee is included in the price of any copies of Office, etc. you buy. Have you ever noticed that student editions of Office products usually say "not for commercial use" or something similar in the title bar?
    – JAB
    May 25, 2018 at 15:19
  • @JAB Good point, but... currently, I'm using a Mac and it seems I do have the Times New Roman font installed, even I didn't install any apps from Microsoft.
    – Ionică Bizău
    May 25, 2018 at 15:20
  • Then Apple probably (reluctantly) licensed it from Microsoft in order to properly display all the many documents and websites that specify Times New Roman as their display font. Also note that for websites/apps/e-books/etc. there's a difference between specifying a font to use (no license needed by the website/app/e-book creators) and embedding the font directly (license needed for distribution). It's a pretty complicated topic, though, and my knowledge is still fairly limited, unfortunately, so I can't provide much more information.
    – JAB
    May 25, 2018 at 15:23
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    Just for future reference. Apple did not license it from Microsoft. They licensed from Linotype.
    – Oddthinking ♦
    May 26, 2018 at 1:40
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    Why would you assume that Microsoft owns Times New Roman?
    – phoog
    May 29, 2018 at 23:16

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I selected Times New Roman as an example for this answer.

The Wikipedia page on Times New Roman does a better job than I could of explaining the history of the typeface, including that, yes, its owner, Monotype has a proprietary licence available for it.

Licenses can be purchased from Monotype. [I hope you will appreciate this is a reference to show that licenses are for sale, and not an advert or endorsement.]

Microsoft directs people to license the font directly from Monotype.

Don't confuse Monotype's Times New Roman with the visually very similar Linotype's Times Roman.

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    As part of the question, there assumes some enforcement against businesses who've not purchased licenses. You haven't answered this. Does monotype et al follow up and actually collect on these?
    – user11643
    May 25, 2018 at 20:22
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    @fredsbend: I found cases where Monotype went to court with big players like Microsoft and ITC. I found a case where Monotype sued someone for copying their trademarked font name. I found cases where other font owners sued Hasbro and other end users of their fonts. I found the law to be complex. I haven't found a specific case of Monotype ending up in court with someone who used their font without permission (and didn't respond to demands).
    – Oddthinking ♦
    May 26, 2018 at 1:39

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