Podcast

By Mark Ainley

Episode 459: North Side Neighborhoods and Market Opportunities with John Preston

John Preston Shares Insights From The Front Lines Of Chicago Multifamily BrokerageJohn Preston of Horvath & Tremblay joins us to discuss opportunities in multifamily and mixed-use assets on Chicago’s North Side!John begins by discussing what it takes to build a successf...

By Mark Ainley

Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)

Insightful Real Estate Discussions with Renovo and Business Partners!Tom and Mark interview some of Chicago’s Brightest Real Estate Stars during a Renovo Networking Event featuring an interview of Thad Wong! Discussions range from areas investors are targeting in Chicago, ...

By Mark Ainley

Episode 457: Proactive Tax Planning Advice to Save on your 2026 Tax Returns

What steps should I take to best prepare for my 2026 tax returns?=============Connect with Mark and Tom: StraightUpChicagoInvestor.comGuest: Aaron Zimmerman, Brick House CPAs Link: SUCI Episode 52Email the Show: StraightUpChicagoInvestor@gmail.comLink: Build Your Team |...

By Mark Ainley

Episode 456: Inside Chicago’s Commercial Lending Landscape w/ Asher Motew and Quinn Keenan

Asher Motew and Quinn Keenan Explain the Value of Essex Capital MarketsAsher Motew and Quinn Keenan of Essex Capital Markets break down keys to their early career success in the Chicago Commercial Lending Market!Asher and Keenan start by explaining their background coming from re...

By Mark Ainley

Episode 455: The Facts Behind The Red Hot Chicago Market with Jason Wagner

Jason Wagner, Managing Broker of Greystone Realty, returns to discuss the state of the Chicago Real Estate market and the power of buy and hold investments.Jason starts by discussing buyer expectations and demand in today’s market. He dives into the data behind Chicago pro...

By Mark Ainley

Episode 454: How To Assign Contracts Like a Pro with Chance Badertscher

Chance The Lawyer is back to discuss assigning contracts between individuals or different LLCs What do I need to be aware of when assigning a contract? Guest Company: Chance The Lawyer Guest Name: Chance Badertscher Guest Link: https://www.chanceblaw.co...

By Mark Ainley

Episode 453: Breaking Down Chicagoland Syndications w/Duke Dennis & Bryan Sonn

Duke Dennis and Bryan Sonn of GC Realty & Development join us to explain the ins and outs of Chicagoland Industrial Investments!Duke and Bryan explain how they got their start in industrial real estate. They dive deep on the differences between residential and indus...

By Mark Ainley

Episode 452: Crazy Stories of Off-Market Real Estate Deals with Igor Mike Kajpust

Igor Mike Kajpust, president of Evolved Property Group, shares his REI journey which started at 17 years of age and spans across multiple states!Igor breaks down his first few deals which includes an $800 land deal in Colorado and a distressed single family home in Indi...

By Mark Ainley

Episode 451: Leveraging the Big Beautiful Bill to Minimize Tax Exposure

What do real estate investors need to know about the Big Beautiful Bill?=============Connect with Mark and Tom: StraightUpChicagoInvestor.comGuest: Aaron Zimmerman, Brick House CPAsEmail the Show: StraightUpChicagoInvestor@gmail.comLink: Build Your Team | Straight Up Ch...

By Mark Ainley

Episode 450: Alderman Bennett Lawson & The 44th Ward

Alderman Bennett Lawson discusses historical developments in his 44th Ward and how that success can be applied across the City of Chicago!Alderman Lawson jumps right in by explaining the successful development in Wrigleyville including partnering with the Ricketts family! He brea...

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