For one thing, much of the market sets the rate for top quality fonts at $0, just as it did with music before legal download sites killed off the $20+ CD album with three good tracks and a dozen fillers.
On a personal note, I do value good quality typography in various professional and occasionally even personal work, and I do spend my own hard-earned money to buy the fonts I use legally. However, I have certainly paid less than I would have, because even as a typophile willing to open his wallet, now that I've got a few really good choices available, any further purchases are luxuries.
One of my companies recently bought some fonts for branding purposes. Initially we bought three from a family that we were fairly sure we wanted. Happy with the results of our initial design work, we went back a few weeks later to find the foundry had hiked up prices to nearly double their previous rate. Instead of completing the set for future-proofing purposes, we just walked away and made do with what we already had. And we didn't hire the web fonts at all, we just created some PNGs in Photoshop for key branding graphics, and use good, free web fonts for the rest.
If we could pay $20 for a real web font licence (not some renewable/pay per view/pay per server/other junk) or $100 for a whole family, then I imagine we'd be buying new stuff every time we ran a themed campaign on our site. At closer to $100 for a single font and $1,000+ for a serious family without even getting a web licence thrown in, it's just not worth it. It's the 21st century, and we have the Internet now. Maybe foundries that want to make a good return on all their hard work need to think less like the movie/music dinosaurs and more like Apple and Valve.
As you know, the "thing you refer to as the market but isn't" also doesn't set the rate for top quality fonts at $0. By all means, pirate fonts for your meaningless project that nobody will ever see or give a shit about. But if that project ever goes anywhere, it's pretty hard to hide the fact that you stole FF Meta or H+FJ Vitesse or Chaparral. You'll just get sued, and you'll lose. Fonts are not like music. People steal music for private enjoyment and primarily get caught when they redistribute their stolen tracks. That's not what happens with fonts.
I think you are wildly overestimating the odds of being successfully sued for ripping off a font.
And black markets generally arise precisely when the official market isn't working effectively. You can deny reality or work with it, but for most of us changing it because we don't like it isn't an option.
Risks like these --- along with not incorporating, mishandling your capital structure, working without contracts, &c --- are the most pernicious startups have to reason about, because they only sting in the unlikely case that you actually succeed. As a result, they're easy to discount. Unfortunately, when you do that, you end up counterfeiting your success, because it's only when you actually get your break that you realize you've made the mistake.
If you're knowingly wasting your life on projects that you don't expect to come to fruition, by all means, steal the fonts you use to promote them with. You have bigger problems than the font police.
As someone who does pay for fonts legally, and who makes his own living creating knowledge works, I find this intensely annoying.
But I've still never heard of a single project being undermined or seen anyone suddenly change their branding as a result of a lawsuit about font usage rights. For a start, if the font is being used to generate graphics or for anything in print rather than embedded electronically, you'd have a tough time proving any kind of infringement in jurisdictions where the design of a font isn't subject to protection.
Frankly, I don't believe that most small type foundries have the will, the time or the money to go after anything but large-scale, flagrant infringement anyway, any more than my company would realistically go after a client who didn't pay a small invoice. Whatever protection the law theoretically affords, in practice the overhead of exercising your rights are greater than the benefit you stand to gain by doing so. Pragmatically, your best bet is not to work with people who are likely to rip you off, which you can do by working with nicer people or by reducing the incentive for less nice people to screw you over.
You claim that there is a bogeyman out there who will come and sue infringers, but it seems to me that this is the rare exception rather than the rule. Ironically, the last case I heard about was HADOPI, the French anti-piracy watchdog, which got caught with its pants down almost immediately over the font it was using for its logo.
You seem to be living in this HN dream world where all projects are high-value and all clients are high payers. If you want to argue that font licensing works effectively in that market, sure, maybe it does. But most of the design world isn't like that, and the current copyright/licensing regime for fonts is doing precious little to promote their use in the rest of the industry.
You don't seem to get it: it is a perfectly sane business decision to choose your client base. Most of the foundries haven't chosen "random web apps". They're probably smart to make that decision, given the fact that most of the people who make "random web apps" don't really value typography. How I know that is, they bitch loudly over pricing that is a tiny fraction of what the foundries real customers routinely pay.
Well, OK, I'm not disputing that. But this discussion isn't about those high-value projects, it's about using fonts in native apps.
And if you don't think what you're building has the potential to be high-value, why are you working on it?
Because not every project in the world has to be Google or Facebook. I think your definition of high-value is probably a lot higher than what many people would consider a successful project, assuming the project is even being done for profit in the first place.
You don't seem to get it: it is a perfectly sane business decision to choose your client base.
I get that just fine. It's just that you seem to be the only person in this entire discussion who is talking almost exclusively about high-end projects, while the rest of us seem to be generally agreeing that the current state of type licensing is not helpful for anywhere below high-end.
The rest of us are talking about what is holding back typography in apps and how the current licensing regime isn't promoting the use of better fonts in that context. It's right there in the title of the discussion.
That said, there are hundreds of thousands of apps out there right now. Unless you think someone from each major foundry is checking every one of them to make sure they're not infringing, it is self-evident that there are very many companies so small that nobody will notice if they infringe the copyright on a font or two.
It happens all the time, when creating apps, in professional design work at studios, when creating content in-house, etc. Pretending otherwise is like pretending software doesn't get pirated by small businesses all the time, completely unrealistic. You might not have to be Google's scale to get noticed, but I expect the vast majority of people working professionally with fonts could use any extra ones they downloaded illegally with complete impunity. But every time they do, that's probably a failure of the market to generate some revenue for whoever created that font.