Hello Monday

Today, a third of the workforce are contractors: 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.

For the season finale, Jessi talks to former NFL talent scout Michael Lombardi about how to assemble teams, why you can’t teach someone to be more competitive, and how to weigh talent versus character. Featuring reporting from LinkedIn’s managing editor, Caroline Fairchild.

Facebook's Carolyn Everson helped launch one of the most iconic startups of the Web 1.0 era: Pets.com. But before it really even took off, and long before its catastrophic failure, she was fired. It was a shameful secret she kept for years....and then, finally, shared.  This episode, hear Carolyn's lessons on why leading with vulnerability takes courage. Featuring reporting from Caroline Fairchild.

How did we get from the large private offices seen in Mad Men, to the open desk plans we have today? This episode, WeWork’s VP of workplace strategy Liz Burow gives us a look at the office of the future. Featuring reporting from LinkedIn’s news editor, Andrew Murfett.

How do you balance calculated decision-making with trusting your gut? This episode, hear Angela Ahrendts talk with host Jessi Hempel about how following her intuition has shaped her career, from Burberry to Apple. Featuring reporting from LinkedIn's senior news editor Maya Pope-Chappell.