All it takes is one costly misstep or miscalculation to turn you into a cautious, research-driven real estate investor. And as an experienced investor myself, it’s something I’ve witnessed too many times. A novice proceeds with an overconfidence that ultimately translates into reckless abandon and they acquire a property that just doesn’t deliver a good
Like any big city, Chicago has its ups and downs: friendly people, Millennium Park, high taxes, and expensive parking lots. But as an investor, there's no place I would rather be. I moved to Chicago just after the real estate crash in 2008. As a former financial analyst, it seemed like everything around me was
The Chicago real estate market can be challenging for new investors due to the constantly changing landscape. Yesterday’s up-and-coming neighborhood is now the most expensive market in the city, whereas previously untouchable boroughs are quietly gentrifying. When I mentor new Chicago-area investors, I always stress the importance of doing neighborhood research before buying a property.
In my years as a real estate investor, Chicago has proven time and time again to be brimming with profitable opportunities and great people. Overall, the Chicago investment property market is on the competitive side, which means that you'll need all the help you can get when you're launching your business. Deals tend to be
My best friend’s son, Dave, recently started investing in real estate, and a few days ago he invited me to lunch at Mr. D’s so he could pick my brain. I love mentoring new investors (and steak sandwiches), so I was happy to meet with him and answer his questions about the Chicago real estate
When I first started investing in real estate, the hardest part was finding leads on good investment properties. The Chicago real estate market is highly competitive and full of ambitious young investors who will do anything they can to beat you to a good deal. Even the more established real estate investors are often too
One thing that real estate investors love to do is analyze the housing market in an area of interest, and I’m no exception. Every minute spent learning more about the environment you plan to do business in is a minute well spent, right? Not quite. In my experience as a real estate investor, it’s way
I’ve lived in Chicago my whole life, and over the course of my 20-year real estate investing career, I’ve bought and sold dozens of properties. I know the Chicago real estate market like the back of my hand, and through my skills, experience, and the use of cutting-edge software tools, I can easily tell when
In an effort to find the best real estate investments in Chicago, an old colleague of mine, Josh, came to me for some direction. He’d tried his hand at investing in the past, but quickly gave up after getting burned on a deal that was too good to be true. Not wanting to waste his
All cities change, but for those of us who have been in Chicago real estate for a long time, the changes have been dizzying. I got into it in the early ’90s—when the South Loop was still a no-go zone, and the West Loop was all warehouses and packing plants. The idea that those markets
