Midwest

I love wholesaling. I’ve been buying from and selling to wholesalers in Chicago for decades. We can kind of represent the best of the city: moving fast, always looking for a deal, filled with [...]

Not too long ago, while walking with a friend down 37th street in Bridgeport, near Wallace, I saw a house that had clearly been abandoned and the back of my neck started to tingle. Partly it’s [...]

One of the key secrets of real estate investing in Chicago is that there is never a bad time to pick up an investment property. We’ve always been a city of renters-—51% of the population lives in [...]

Wholesaling real estate in Illinois—whether you’re in Chicago or Cairo, Galesburg or Galena, or anywhere in-between—has always been about hustle. Since I started my professional real estate [...]

As a longtime real estate investor here in Chicago, I get asked two questions more than any others. The first: What is the most challenging part of being in Chicago and flipping rehabs? The [...]

Recently, during a Zoom call with some real estate investors I mentor here in Chicago, one of the younger participants brought up Instagram and then coyly asked me if I had ever heard of it. It [...]

As any longtime Chicagoan could tell you, the year doesn’t really start until baseball starts. We get out of our long winter freeze, begin to thaw out a bit, and get back outside. This year, that [...]

I have a secret that, as a lifelong Chicagoan and a real estate investor, I shouldn’t admit: I’m not a Chicago snob. You want to put ketchup on your hot dog? Go ahead. You want to root for the [...]

One of my favorite books about my beloved home is by the great Nelson Algren. It’s called Chicago: City on the Make, and is a raucous, sharp, and oftentimes brilliantly funny book on this city. [...]