CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

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...

Determining rental pricing is already challenging in the Chicago market, but it becomes even more confusing when Section 8 inquiries start coming in, especially during slower leasing months. Many housing providers ask the same question, will a Section 8 tenant actually be approved at my asking rent, or am I wasting time going through the process? In this Straight Up Chicago Investor Tuesday Tip episode, Mark Ainley breaks down how Sect...

Evictions are one of those parts of Chicago real estate that no one plans for, but almost everyone eventually faces. You can screen well, communicate clearly, and still find yourself dealing with a resident who stops paying and stops responding. When that happens, the Cook County eviction process becomes less about fairness and more about understanding timelines, procedures, and how to minimize losses. In this episode of the Straight U...

If you’ve ever looked at Chicago real estate and thought, “Man… I just want to buy one small building and not screw it up,” this episode is for you. Because Niko Apostal isn’t out here selling a fantasy. He’s telling the real story, the one most people skip over. The long version. The messy version. The version where you start in residential, ride a hot market, get punched in the face by the crash, ...

Tenant screening in Chicago is getting harder, not easier. As the 2025 winter eviction moratorium approaches and rental scams evolve faster than ever, landlords are being hit with a wave of fake documents, unverifiable stories, and applicants who know exactly how to manipulate weaknesses in the system. In this episode, Mark Ainley breaks down the three biggest red flags he’s seeing right now, and what Chicago housing providers mu...

If you spend any time working in Chicago real estate, you eventually realize you’re playing a long game built around timing, neighborhoods, and understanding how the city evolves block by block. That’s why conversations like this one with Lawrence Dunning are so valuable. He’s an investor, developer-focused broker, and someone who has watched entire pockets of the city transform because of strategic new construction p...

Rental licensing in the Chicago suburbs is one of those topics that sounds simple, until you buy your first building in a village you’ve never dealt with and suddenly find yourself navigating inspections, point-of-sale requirements, annual renewals, surprise fees, and rules that vary wildly from suburb to suburb. For many landlords, this becomes a painful (and expensive) first lesson. In this episode, Mark Ainley breaks down the ...

If you own rental property in Chicago (or anywhere else) and you’ve heard the term cost segregation, there’s a good chance you’ve also felt that little panic around the end of the year:On this Straight Up Tuesday Tip, we brought back Cost Seg Kev from CSSI to clear that up once and for all, and then go deeper into how to time your study, how phased cost segs work when you’re doing big rehabs, and when it actually...

If you invest in Chicago long enough, there’s one truth you learn early: every building teaches you something. And in this episode, we got to hear from someone who has lived that lesson twice over. Luke Helliker joined us to break down the real-world experience behind buying his first Chicago multifamily, navigating the ADU conversion process, surviving a $300,000 basement rebuild, learning how to work with contractors, fighting ...

Some people wait for opportunity. Others create it. In this episode of the Straight Up Chicago Investor Podcast, hosts Mark Ainley and Tom Shallcross talk with Shawn Good, attorney, investor, and founder of the Palatine Real Estate Meetup, about how he turned a single bad condo purchase into a thriving portfolio of off-market deals across Chicagoland.From flipping hoarder houses and partnering with family to scaling direct mail campaign...