CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

Breaking into Chicago real estate isn’t about flashy deals or perfect timing — it’s about learning the market from the ground up, understanding buildings, and taking action before you feel “ready.” On this episode of the Straight Up Chicago Investor Podcast, Reed Meyer joins Mark Ainley and Tom Shallcross to walk through his rapid growth from a first Logan Square three-flat to flipping small neighborhood wa...

If you’ve ever looked at a development project in Chicago and thought, “How did this even get financed?” — this episode answers that question. Real estate investing is already tax-advantaged, but once you understand Opportunity Zones, New Markets Tax Credits, and how capital gains can be redeployed, the game changes entirely.In this episode of the Straight Up Chicago Investor Podcast, we sit down with Darryl...

Every year, there’s no shortage of bold predictions about what’s coming next in real estate. Most of them are noise. But when experienced brokers and investors who are actively operating in Chicago take the time to review what actually happened,  and what’s realistically ahead,  that’s when the conversation becomes valuable. In this episode of the Straight Up Chicago Investor Podcast, Mark and Tom are ...

If you spend enough time in Chicago real estate circles, you’ll hear the same conversations over and over again. Housing affordability. High barriers to entry. Zoning headaches. Neighborhood resistance. The assumption is that meaningful development only happens inside the city, and that everything outside the city limits is either sleepy, restrictive, or already built out.This episode flips that assumption on its head.In this conv...

If you bought or refinanced investment property between 2020 and 2022, there’s a good chance you’re sitting on something incredibly valuable — not just equity, but cheap debt. And most investors don’t want to touch it. They locked in rates in the 2–3% range and now refuse to refinance, even when they want to buy again.That’s the exact problem we dig into on this Straight Up Chicago Investor Tuesday Ti...

Not sure if your rent is right? 👉 Get a free analysisIf you’re a Chicago landlord, investor, or Chicago property manager, you’ve probably heard the same recycled takes a thousand times, rates are going to do this, the market is going to do that, wait for “blood in the streets,” then buy. In this Tuesday Tip, Mark Ainley cuts through the noise with a street by street, suburb by suburb view of what actually mat...

If you’ve ever thought, “What’s the worst that could happen with a rental property?”, this episode answers that question in painful detail. Fires, squatters, drug activity, city violations, and an investor watching nearly $100,000 evaporate. This isn’t a horror story for clicks. It’s a real Chicago investment that went sideways fast, and a reminder of how quickly things can unravel when risk isn&rsquo...

Every time the word “foreclosure” starts trending, Chicago investors get the same question in their inbox, is this the wave? Are banks about to dump inventory? Is there a secret pipeline of discounted deals that only insiders know about? In this episode, top REO agent Ryan Smith brings some reality to the conversation. The Chicago foreclosure market is active, but it’s nothing like 2008, and understanding how it actua...

Some people “start in real estate” by buying a condo, reading BiggerPockets for three years, and telling everyone they’re “waiting for the market to shift.”He came out of the University of Wisconsin–Madison real estate program, took the traditional institutional route, quickly realized corporate real estate wasn’t the dream, and then jumped straight into owning Chicago multifamily… starti...

Permits are one of the most avoided topics in Chicago real estate investing. Many investors spend their entire careers trying to work around the system instead of through it. In this episode, Tom Shallcross breaks down why embracing the permitting process, rather than avoiding it, actually makes you a better investor and protects your downside long term.This conversation walks through the permitting process from start to finish, from de...