CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

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...

This is one of those episodes that matters if you care about where Chicago housing is actually headed, not just where people say it should go. Alderman Bennett Lawson gives a grounded look at what development, housing policy, neighborhood politics, and practical city decision-making really look like inside one of Chicago’s most active wards. That is what makes this conversation so useful. It is not theory. It is someone who has sp...

There are a lot of episodes in real estate where the lesson is to save more money, wait until you are ready, or keep analyzing until the perfect deal shows up. This is not one of those episodes. Mike Scanlon’s story is about getting in the game with almost no cash, figuring out how to make the numbers work anyway, and using creativity to build real momentum in Chicago real estate.What makes this one hit is how many different ways ...

If you buy or sell property in Chicago often enough, you know small contract changes can create big confusion fast. That is what this Tuesday Tip with Chance Badertscher gets into. The CAR 8.0 contract did not completely reinvent how deals get done, but it did clean up a few areas that had become messy, especially after the commission lawsuits and the awkward period where brokers, attorneys, and investors were all trying to patch things...

There are some episodes where the value comes from a new tactic or a very specific strategy. This one is different. Dan Nelson’s conversation is really about mindset, conviction, and understanding what makes Chicago such a unique place to build wealth through real estate. He is not coming at this as someone who just sells property. He is coming at it as an investor, a broker, and someone who has been living this over the long term...

A lot of people look at wholesalers and assume they started by blasting out marketing, locking up deals, and flipping contracts right away. That is not how Brendan Mlaney’s story started. His path began with house hacking, learning construction the hard way, screening tenants himself, and slowly building enough confidence to move from owning a couple of properties into creating off market opportunities for other investors across C...

A lot of investors think tax strategy starts in March and ends in April. This episode is a good reminder that it does not work that way. Ryan Bakke breaks down the difference between somebody who simply prepares a return and somebody who helps architect better outcomes before the year is over. That is the core of the conversation, but it also turns into something bigger than taxes.What makes this episode valuable is that Ryan does not j...