CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

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...

In today’s Chicago market, competition is fierce. Buyers are offering over asking, deals move in hours, and multiple bids have become the norm. So how can investors, rehabbers, or even first-time buyers stand out when price isn’t the only factor?In this episode of the Straight Up Chicago Investor Podcast, hosts Mark Ainley and Tom Shallcross break down actionable ways to make your offer more attractive, even when y...

Finding great real estate deals in Chicago has never been more competitive. MLS listings are crowded, buyers are aggressive, and off-market deals are often locked down before they’re even public. In this episode, Tom Shallcross and Mark Ainley sit down with Eli Goodman, founder of Illinois Real Estate Buyers and host of one of Chicago’s largest real estate meetups, to unpack exactly how he built a thriving wholesaling busine...

Land development in the Chicago suburbs isn’t something we talk about often, but it’s one of the most important (and misunderstood) parts of real estate investing. In this episode, Tom Shallcross and Mark Ainley sit down with veteran land developer Jim Paul, who shares how he started from scratch in 1995 and built award-winning communities across Will County.Jim’s story is one of discipline, vision, and risk, putting h...

There’s a lot of talk out there about zoning in Chicago, but not many investors truly understand how those letters,  R2, R3, R4, and R5,  can change the outcome of a deal. In this Straight-Up Tuesday Tip, Tom Shallcross and Mark Ainley break down how residential zoning actually works on a standard 25’×125’ Chicago lot, what FAR (floor area ratio) means for what you can build, and how setbacks and unit a...