CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

Back of the Yards has always been a neighborhood with grit, history, and working-class pride.But for Juan Ignacio Gonzalez, it is also home, a place worth investing in, rebuilding, and fighting for.In this episode, Juan Ignacio returns to the Straight Up Chicago Investor Podcast to talk about what has changed since episode 212. A lot has happened. He has continued investing in Back of the Yards, opened Dreamcatcher Cafe on 47th Street, ...

Chicago investors keep asking the same question: should I buy right now, or should I wait?Tom and I broke this down because the market feels confusing. Prices are up, inventory is tight, rates are still not where buyers want them, and a lot of people are trying to figure out whether they should jump in or stay on the sidelines.The answer depends on who you are.If you are a house hacker with a long-term mindset, the opportunity is still ...

In this episode, we bring back Matt Katsaros from Wildwood Investments. Matt was previously on episode 109, and a lot has changed since then. At that point, Wildwood was still getting started. Today, Matt and his partners have developed around 400 apartments across Chicago and have worked through ground-up development, adaptive reuse, ARO requirements, capital raises, lease-ups, and the kind of project-level surprises that only show up ...

There are two things that show up over and over again in Chicago real estate: the people who keep showing up eventually win, and the neighborhoods that look “boring” today often become the ones everyone wishes they had bought in five years ago.https://youtu.be/c76qFdf02mIThat’s a big part of this episode with John Preston from Horvath & Tremblay.John has been grinding in Chicago apartment brokerage since 2019, most...

This episode is different.We recorded it live at a Renovo event, pulled a bunch of heavy hitters off to the side, and grabbed 10 minutes from each person while the room was packed with movers and shakers actually doing deals in Chicago. We talk brokerage changes, the Zillow fight, how real investors are thinking about Chicago right now, what Renovo looks like behind the curtain, and what it takes to scale whether you’re buyin...

Most investors have a “bank guy.” And if that bank guy has come through for you a couple times, it’s easy to assume you’ve solved financing.But commercial lending doesn’t work like residential, and it doesn’t even work like it did two years ago. And yes… Asher talks fast. Tom and Mark talk fast. Quinn tries to keep everyone on the road.In this episode, we sit down with Asher Motew and ...

If you’ve been waiting for Chicago to “cool off” so you can finally buy, I’ve got bad news. The market hasn’t cooled. It’s gotten weirder, tighter, and more competitive in the exact ways that frustrate buyers and reward owners who already have real estate.In this episode, we bring back Jason Wagner from Greystone Realty to break down what’s actually happening right now, not the hot takes, n...

A lot of investors talk about “wholesaling” like it’s just finding a deal and blasting it out to a buyer list. But the real skill, the part that keeps you from getting sued, from paying unnecessary taxes, or from looking shady in front of a seller and their attorney, is how you structure the contract from day one.That’s what this Tuesday Tip is about.Mark and Tom sit down with Chance Badertscher (Chance the Lawye...

Most Chicago landlords and property managers understand residential because they live it every day, leasing season, showings, renewals, maintenance calls, and the occasional headache that ruins your weekend.Industrial is different.In this episode, we brought in Bryan Sonn and John Duke Dennis to talk about the part of the Chicagoland real estate market that a lot of investors hear about, but don’t really understand, small and mid-...

Most real estate investors do not lose money on taxes because they are reckless. They lose money because the rules move, the details pile up, and they assume their CPA or their old strategy already has it covered. This Tuesday Tip gets right to that problem. Aaron Zimmerman breaks down what the Big Beautiful Bill actually changes for real estate investors, business owners, house hackers, parents, W2 earners, and people who are trying to...