CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

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...

Real estate investing rarely follows a straight line.For many Chicago investors, the first step is not buying a perfectly stabilized multifamily building. Sometimes it starts with handwritten bandit signs, cold calls, awkward seller conversations, small wins, bad deals, hard lessons, and figuring things out one step at a time.In this episode, Tom Shallcross and Mark Ainley sit down with Mark Skowron to talk about his progression from wh...

Getting started in Chicago real estate investing can feel overwhelming.There are neighborhoods to learn, lenders to understand, meetups to attend, properties to walk, numbers to run, and plenty of mistakes to make along the way.In this episode, Tom Shallcross and Mark Ainley sit down with Hart Turner, a Chicago investor who went from zero units to a nine-unit portfolio in under two years. Hart’s story is not about finding one perf...

Insurance is one of those things investors often do not think about until something goes wrong.But when a property is under construction, vacant, being gutted, or even just partially remodeled, a normal insurance policy may not protect you the way you think it does.In this Straight Up Tuesday Tip, Tom Shallcross and Mark Ainley sit down with Josh Steigelmann to break down builder’s risk insurance, when it is needed, how it works, ...

Wholesaling looks simple from the outside.Find a motivated seller, put the property under contract, assign the deal, make a fee, and move on.But as Eric Field explains in this episode, the real business is much more complicated. There are marketing costs, seller conversations, attorney issues, licensing rules, investor relationships, construction estimates, dispositions, distressed property problems, and the need to build a real company...

In this episode, Mark Ainley shares a live presentation from the WSBOA meetup, now part of the Neighborhood Building Owners Alliance. Instead of talking about property management, screening, leasing, or new landlord laws, Mark breaks down the investing he has personally done over the last 30 months.He walks through 15 deals, including buy-and-hold ranch homes, quick flips, sale leasebacks, industrial real estate, cost segregation, priva...

Property taxes are one of the biggest frustrations for Chicago real estate investors, landlords, homeowners, and small business owners. Most people know their bill went up. Fewer people understand why it went up, how the assessment system works, what the Cook County Assessor actually controls, and what can be done to make the process more predictable.In this episode, Tom Shallcross and Mark Ainley sit down with Pat Hynes to talk about C...

In this special Straight Up Tuesday Tip, Tom Shallcross and Mark Ainley bring back Mike Glasser to break down a proposed ordinance coming from Mayor Brandon Johnson's administration and the Chicago Department of Housing.Mike joined the episode one day after attending a Chicago City Council Housing Committee hearing, giving landlords a direct look at what is being proposed, what happened inside the meeting, and why Chicago housing pr...

Back of the Yards has always been a neighborhood with grit, history, and working-class pride.But for Juan Ignacio Gonzalez, it is also home, a place worth investing in, rebuilding, and fighting for.In this episode, Juan Ignacio returns to the Straight Up Chicago Investor Podcast to talk about what has changed since episode 212. A lot has happened. He has continued investing in Back of the Yards, opened Dreamcatcher Cafe on 47th Street, ...