Midwest

When real estate investors first started discovering the internet, back in the late 90s, a lot of old-timers—think classic Chicagoans, thick accents, and thicker mustaches—dismissed it. Me, I was [...]

Not too long ago, I was sitting on a patio in Andersonville with another long-time Chicago real estate investor. We were talking leads and how hard it typically is to find quality ones. He [...]

Whenever I’m talking to people about investing in Chicago real estate, I get asked the same question: what’s the single-most-important source of information? And my answer is always the same: [...]

A friend of mine who rents in Ravenswood, just off Montrose, was telling me that the heat was off in her rental. This being a Chicago winter, I mentioned that the landlord should fix it quickly. [...]

Right before stay at home orders were issued in March, I was at Cork and Kerry in Bridgeport for my regular hangout with other real estate investors. A few of them were pretty new to the [...]

The other day, I was on an informal virtual happy hour with other Chicago real estate investors when one person brought up Englewood; a sort of nervous titter went through the group. “Who invests [...]

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 [...]