Engaging in litigation claiming you don't have to follow the ADA simply because you don't want to deal with the tax implications of doing so is unbelievably low.
> if they start telling them what the can and cannot do during their time then they start to look more and more like employees (something they absolutely do not want)
Uber may not want it, but their drivers are undeniably employees, not contractors.
Whenever I see this discussed, people bring up that Uber satisfies some of the criteria for being employees but not others. However, that's not the way the IRS works. To the IRS, those criteria are all sufficient, not necessary - Uber doesn't need to satisfy all of them in order for the IRS to consider them to be employees.
> It's low in the same way that if a non-profit starts to use your IP or trademarks you must go after them for doing so.
Incidentally, this is common legal advice on Internet forums, but is not really true, as lawyers like DannyBee have explained more than once in other threads. It's a misconception that litigating companies tacitly condone, because it paints them in a more sympathetic light, but it's not actually "required" by any stretch of imagination.
If your mark is actually at risk of losing secondary meaning, then there is a risk to not doing so, but it takes a long time to get to that point. It's like saying that every time you have a beer, you're slowly developing cirrhosis - unless you're already drinking heavily and have been for a while, a single drink has literally no impact[0].
Also, since you say "IP or trademarks", not just trademarks, you're applying this principle to copyright and patents, which is also not true at all. Failure to enforce copyright rights is not tantamount to a free, irrevocable license.
> View this from the position of a business with investors they're beholden to, not from an emotional standpoint.
I'm viewing it with the exactly the same line of thinking that got us these antidiscrimination and labor protection laws in the first place.
[0] The liver is capable of regeneration, and cirrhosis only happens if you repeatedly subject it to levels of alcohol that it can't regenerate from faster than your intake. Likewise, losing secondary meaning isn't going to happen because you failed to go after a small non-profit that was using your mark in a way that wasn't really intended to confuse customers with your mark in the first place.
If you have IP that you know a non profit is using without an explicit licence, you do not have to "go after them" - you own the IP and if you feel they're a worthy cause worth supporting, offer them "support" in the form of a no cost licence for your IP.
> View this from the position of a business with investors they're beholden to
I'm pretty sure even the most vindictive of VC investors can't compel a startup to break the law "because profits".
> if they start telling them what the can and cannot do during their time then they start to look more and more like employees (something they absolutely do not want)
Uber may not want it, but their drivers are undeniably employees, not contractors.
Whenever I see this discussed, people bring up that Uber satisfies some of the criteria for being employees but not others. However, that's not the way the IRS works. To the IRS, those criteria are all sufficient, not necessary - Uber doesn't need to satisfy all of them in order for the IRS to consider them to be employees.