Podcast

By Mark Ainley

Episode 359: 2025 Cook County Evictions with Tom Raleigh

Tom Raleigh, Founding Attorney of Halsted Law Group, returns after being on Episode 40 to talk evictions!Tom jumps right in by breaking down the eviction process and the timelines in 2025. He gives great tips on getting ahead of the process and emphasizes the importance of stayin...

By Mark Ainley

Episode 358: Prepping for Tax Season and Commonly Missed Deductions with Mike Procaccio

What can I do to maximize my tax returns?=============If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!Connect with Mark and Tom: StraightUpChicagoInvestor.comEmail the Show: StraightUpChicagoInv...

By Mark Ainley

Episode 357: Celebrating 20 Years of Kiser Group: Great Chicago insights From Their Network

Tom and Mark interview some of Chicago’s Real Estate Heavy Hitters during Kiser Group’s 20 Year Anniversary Celebration! Conversations range from condo deconversions, the attorney review side of a commercial deal, and the origins and evolution of Kiser Group. This sho...

By Mark Ainley

Episode 356: The No BS Guide to Thriving in Chicago Real Estate, Even in Tough Markets… with Frank...

Frank Montro, the King of Chicagoland, returns to share how he and his real estate team have remained top producers during recent years of high interest rates and prices.Frank explains how he coaches buyers to understand monthly payments as opposed to being scared off by rates an...

By Mark Ainley

Episode 355: How To Optimize Tax Deductions as a Househacker

What Can I Write Off as a Chicago Househacker?=============If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!Connect with Mark and Tom: StraightUpChicagoInvestor.comEmail the Show: StraightUpChica...

By Mark Ainley

Episode 354: 2025 Chicago Market Predictions with Jake Fugman and Mike Scanlon

Jake Fugman and Mike Scanlon of The Axon Group return to discuss Chicago’s REI market performance, predictions, and exciting developments!Jake and Mike kick things off by assessing their 2024 predictions regarding mortgage rates, appreciation, and cap rates! They then break...

By Mark Ainley

Episode 353: From Near Death Experience, to Disciplined Financial Freedom with Mike Bednarz

Mike Bednarz, an accomplished real estate investor and HVAC business owner, joins us to share his inspiring trajectory of growing a real estate portfolio and overcoming a scary accident!Mike explains how he lived frugally to save a down payment and buy his first multifamily inves...

By Mark Ainley

Episode 352: Current Issues The NBOA is Fighting with Mike Glasser

What are the current political issues Chicago investors need to be aware of and how can the NBOA help?=============If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!Connect with Mark and Tom: StraightU...

By Mark Ainley

Episode 351: Obstacles Affordable Housing Developers Face in Illinois with Richard Koenig

Richard Koenig is HODC’s Executive Director and has led the development of over 600 units of affordable housing!Richard starts with how he found his “Why” and discovering that he wanted to dedicate his career to helping solve the lack of affordable housing. He g...

By Mark Ainley

Episode 350: Reality TV to Realty… Everything Chicago Investor Mike Tenerelli Has Accomplished

Mike Tenerelli not only has a background in Reality TV, but also in construction, management, and sales which have propelled his explosive growth in real estate!Mike discusses his journey from flipping homes to helping others find the right property. He breaks down analyzing remo...