Gimlet Media: Alex Blumberg and Matt Lieber
Alex Blumberg made his early career by helping build two of the most successful shows in radio and podcasting: Planet Money and This American Life.
In 2014, convinced that podcasts could make money, he walked away from the safe umbrella of public media to start a new media company with co-founder Matt Lieber.
Every doubt, triumph and humiliation of building the business was documented on the podcast Startup, which included the back-and-forth over how the company got its name: Gimlet.
Many more successful podcasts followed, and five years after launch, Gimlet sold to Spotify for roughly $200 million.
How You Built That: Oesh Shoes
After years of researching how women's shoes wreak havoc on the joints, Casey Kerrigan quit her job in medicine to start 3D printing more comfortable designs: Oesh Shoes.