CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

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...

For the past few years, conversations around interest rates have dominated real estate headlines. Investors have been waiting for clarity, and in this Straight Up Tuesday Tip, Chris Puleo of Neighborhood Loans joins Mark Ainley and Tom Shallcross to explain why we might finally be seeing a turn.According to Chris, the writing is on the wall: political pressure, an upcoming Fed leadership change, and improving inflation numbers are all a...

For our milestone 400th episode, we sat down with a Chicago heavy-hitter whose career spans lending, development, and commercial brokerage. Kevin Rocio doesn’t do small talk — he does numbers, systems, and results. From building union-focused mortgage programs in the ’90s to exiting lending before the 2008 crash, to training brokers on how to properly price two- to four-flats with GRM (not cap rate), Kevin lays out a b...

There’s no shortage of real estate hustle stories in Chicago, but few are as practical — and repeatable — as what Micah White is doing. He didn’t start with millions, institutional investors, or shiny new construction. He started like most Chicago landlords: with an old three-flat, below-market rents, and an inspection report thicker than a phone book.Through transparent conversations with residents, calculated ...

House hacking continues to be one of the most powerful ways for Chicago investors to build wealth and more importantly jump start their investment journey. Few strategies combine affordability, leverage, and cash flow potential like living in one unit while renting out the others. Paul De Luca, broker with the Axon Group, has personally house-hacked four different properties across Berwyn, Belmont Cragin, and Portage Park — and h...

Most landlords only think about insurance on renewal day—until a pipe bursts, a kitchen burns, or hail rips through a roof. That’s when the sequence of your next few moves can save you thousands or make a mess of your premiums and insurability.In this Straight Up Chicago Investor Tuesday Tip, State Farm agent Josh Steigelmann joins Tom and Mark to break down the claim decision tree, what to do before ...