"Sometimes the people who break the rules win and sometimes they push it too far,"
implying that Uber could be doing wrong things in some more correct way and continue to thrive, and that there isn't anything wrong with that. He doesn't say "broke rules," or "did bad things," he said "pushed the envelope."
Look at the implication there - you can and maybe should do unethical things, break some rules, "push the envelope" with questionable behaviors as long as you get away with it.