Dodging the law is risky but can have upsides. Maybe you get Aereo'd or maybe you can pull an Uber. Both airbnb and Uber exploited holes in current regulation.
Just breaking the law is stupid.
Just breaking the law is stupid.
Airbnb and Uber are managing to fight the regulatory hurdles with ~5x is ~13x the valuation of Zenefits, respectively. While Zenefits is ~5x the valuation of Aereo, it seems they have some catching up (read: fundraising) to do.
Plus sometimes you know how bad the worst case legal scenario is and it's the best option. With stuff like taxi regulations the fines probably aren't too bad.