Evan Estola (https://twitter.com/estola) is a Director of Engineering at Flatiron Health where he's leading software engineering teams focused on building Machine Learning products. Throughout this episode, Evan shares various stories when recommendation systems didn’t work as expected, like this one time when members saw mathematically worst recommendations for meetups near them. He also shares why Schenectady, NY pops up on some lists of most popular cities and the story behind the Wall Street Journal article titled 'Orbitz steers Mac users to pricier hotels'. We also discuss skills Evan looks for when hiring ML engineers, how to give constructive feedback, filter bubbles and much more.