Today, contractors make up a third of the workforce. We're talking about drivers, designers, even doctors. It’s a number that’s climbing steadily. So how do they get insurance? Sara Horowitz is working on just this. Having spent more than two decades cultivating the Freelancer’s Union, she's now the CEO of Trupo, a new benefits startup. Plus, a conversation between Jessi and her producer, Laura Sim, who is also a freelancer.