The baby boomers liked their suburban homes, with lots of room inside and out. The millennials, many of whom will be relied upon to buy them, not so much. Between now and 2037 it is projected that 21 million homes will hit the market as boomers downsize, move in with family and require assisted living situations. That will put a lot of downward pressure on the housing market as young people want to smaller, more urban-like and transit friendly environments. So, what happens to these homes? That’s a big part of the conversation we have with Tara Mastroeni who writes about real estate for Forbes, Realtor.com and others. We also discuss the new I Buying approach to making the real estate experience more seamless and less splintered. It rolls up buying and selling your home, as well as title and home insurance and the move, too, into one package. These algorithm-powered home flipping platforms suggest a huge change in the way we do real estate business going forward as giants like Zillow and Keller-Williams adjust their business models to accommodate.