CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

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...

Welcome back to the Straight Up Chicago Investor Podcast! Today, Tom and Mark sit down with Moises (Mo) Correa, founder of Proximal Equity Group. Mo went from a 2020 Avondale house hack to GP’ing large multifamily, raising $4.1M on a Louisville acquisition, stacking adjacent assets to operate 200 units as one, and contract-to-close on a 168-unit LIHTC conversion in Fort Wayne. We cover networking that actually converts, conservati...

There’s no shortcut to success in real estate, only discipline, consistency, and a belief in the market you serve. Chicago multifamily broker Joe Smazal has proven that formula works. Over 15 years, Joe has built a career that surpassed $1 billion in closed real estate sales, all while helping investors navigate one of the most dynamic urban markets in the country.In this episode of the Straight Up Chicago Investor Podcast, J...

Some people talk about investing “one day.” Lantz Kurzawinski just did it, four properties by age 21, by saving aggressively, showing up for unglamorous work, and partnering smart. In this Straight Up Chicago Investor episode, Lantz shares the scrappy path from Juul stock boy and podcast tech to house-hacker, BRRRR-er, and deal partner, plus the exact numbers, mistakes, and mindsets that got him there.In This Episode of the ...

You’ve house hacked, maybe even two or three times, and now you’re ready for the next step: buying a true investment property where you won’t live in one of the units.This week on the Straight Up Chicago Investor Podcast, Mark Ainley and Tom Shallcross sit down with Chris Puleo from Neighborhood Loans to break down exactly what changes when you go from owner-occupied financing to non-owner-occupied investing....

When the market feels tight and opportunities seem scarce, some investors freeze — but others get creative. Jason Wagner, founder of Greystone Realty and author of The Wagner Report, is one of those who sees things differently.Jason returns to the Underground to share how he’s helping Chicago investors find success by combining creativity, data, and execution. From assumable loans and innovative financing strategies to under...