How does a kid from Brooklyn became one of Boston's top startup CEOs? We invested on Hometap because it's a market opportunity on the scale of a whole new capital class, and because my friend Jeffrey Glass is one of the most backable CEO's in Boston.For this week's episode Jeff and I sat down to talk about why, and how he got to that place from the unlikely starting point of a humble household in pre-hipster, working class Brooklyn.

Jeff is a remarkable guy with a remarkable story, hear him tell it and you'll learn along the way how he thinks about hiring, scaling a business, the important difference between execution and strategy problems, and why Hometap may just end up being the single most important thing he's done so far. Enjoy.