Few operators become VCs, and even fewer go back to leading companies... so how does these perspectives change how one leads? Obviously, it's a lot easier to think of a solution than execute on one... but then how does a leader empower one's team to do the right thing without micromanaging or without being frustrated when they're not getting what they wanted? (Hint: it has to do with providing context). In this episode of the a16z Podcast, Andy Rachleff (president and CEO of Wealthfront and alum of Benchmark) shares his thoughts on leadership, as well as his own journey as an entrepreneur in a particular vertical, in conversation with Bethany Coates, founder and CEO of BreakLine, which helps vets transition into tech. (The discussion took place during one of BreakLine's programs, co-designed and hosted at a16z). And since both are/were also teachers at Stanford's Graduate School of Business (where Rachleff still lectures, and where Coates served as Assistant Dean for their Global Innovation Programs) -- how does teaching make one a more authentic leader, given all the styles of leadership out there? All this and more in this episode.

Focusing only on the technical, "crunchy, wonky stuff" behind policies or products sometimes misses the humanity at the center of why we're doing the thing in the first place. Because systems -- whether algorithms and artificial intelligence, or capitalism and other such "operating systems" -- need to work for people, not the other way around. Or so observes economist and author Arthur Brooks, president of the American Enterprise Institute (AEI) -- a public policy think tank focused on free enterprise (and where he recently announced he will be passing on the baton after a decade of leadership). So how does this philosophy of human dignity and human potential apply to automation and jobs, to education, to entrepreneurship? And not just in the "conventional" entrepreneurial sense of building companies and products -- but in changing one's life? The answer, argues Brooks in this quick, hallway-style episode of the a16z Podcast with Sonal Chokshi (recorded in one of our earlier Washington, D.C. roadshows) -- has to be rooted in the philosophy of human meaning. And that involves truly needing each other... so no one is left behind given technological progress and innovation. image credit: Maria Eklind/ Flickr