CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

Pilsen has always been one of Chicago’s most recognizable neighborhoods.It has history, architecture, culture, small businesses, long-time owners, new development pressure, and some of the biggest housing debates happening in the city right now. In this episode, Tom Shallcross and Mark Ainley sit down with Miguel Chacon to talk about Pilsen, Chicago’s 25th Ward, housing policy, zoning, ADUs, small property owners, developmen...

Getting started in real estate often comes down to one question.How do I finance the first deal?In this Straight Up Tuesday Tip, Tom Shallcross and Mark Ainley sit down with Chris Puleo to talk through financing options for newer investors, especially those looking at house hacking, small multifamily, FHA loans, conventional loans, DSCR loans, down payment strategies, seller credits, tax prorations, and long-term ownership.Chris explain...

Senior housing is not just another version of multifamily.It may look like real estate from the outside, but once you move past 55-plus active adult housing, the business becomes more operational, more regulated, more labor-intensive, and more complex than a typical apartment deal.In this episode, Tom Shallcross and Mark Ainley sit down with Mark Myers to break down the senior housing sector from the perspective of an experienced broker...

Cash flow in Chicago’s A-class neighborhoods is not impossible.It just requires a different mindset than chasing the cheapest two-flat on the market.In this episode, Tom Shallcross and Mark Ainley sit down with David Shifrin, a plastic surgeon and Chicago real estate investor, to talk about how he built a 40-unit portfolio across seven multifamily buildings in Bucktown, Wicker Park, Ukrainian Village, and the Logan Square/Avondale...

Sometimes it starts with one building, one partner, one refinance, one off-market call, and the willingness to move faster than most people are comfortable moving.In this episode, Tom Shallcross and Mark Ainley sit down with Arthur Barkan to talk about how he went from working as a chemist to building an 80-unit portfolio in roughly two years. Arthur shares how he bought his first building in Rogers Park with his brother, moved into Eva...

Financing can make or break a real estate deal.For Chicago investors, especially those moving from house hacking or small multifamily ownership into heavier rehabs, flips, or construction loans, the capital stack matters just as much as the purchase price. Too much leverage can create risk. Too little capital can slow growth. And bad underwriting can turn a good-looking deal into a painful lesson. In this episode, Tom Shallcross and Mar...

The problem is that the information is scattered across different city, county, and public record systems. If you want to understand 311 complaints, building violations, permits, ownership information, assessments, administrative hearings, or other property-related records, you usually have to know where to look and how to connect the dots.In this Straight Up Tuesday Tip, Tom Shallcross and Mark Ainley sit down with Jim McMahon to talk ...

It is also about knowing the right people, staying involved, understanding legislation, supporting housing provider advocacy, and learning from the investors, brokers, lenders, and organizations that are actively shaping the market.In this episode, Mark Ainley and Tom Shallcross take the Straight Up Chicago Investor Podcast on the road to the NBOA Summer Soiree. Instead of one long-form guest interview, this episode features short conve...

AI is no longer just a marketing topic or a future trend.For property managers, landlords, and real estate investors, AI is already starting to change how maintenance gets handled, how residents communicate, how companies scale, and how teams decide where human attention is most needed.In this episode, Tom Shallcross and Mark Ainley sit down with Pablo Gonzalez to talk about community, content, AI, and the future of property management....

Chicago porches are easy to overlook until they become a problem.For many small multifamily investors, especially anyone buying a two-flat, three-flat, or six-unit building in Chicago, the rear porch can become one of the biggest surprise expenses in the deal. It may look fine from the alley, but small warning signs like slanting, weak stair stringers, bad drainage, rusted connections, or old columns can point to a much larger repair or...