Podcast

By Mark Ainley

Episode 371: How To Break Into Chicago Real Estate Investing In Your 20s w/Michael Kaplan

Michael Kaplan is a real estate broker and investor who has grinded to become a top broker at 24 years of age!Michael starts by explaining how he realized that college was not for him and pivoted to an entrepreneurial route in real estate! He explains the mindset required to star...

By Mark Ainley

Episode 370: How The Current 2025 Lending Market Differs From Previous Year

What's Different in Today's Lending Environment and How do Chicago Investors Capitalize? =============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 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson

Erik Swanson, owner of Fernweh Property Group, explains how he’s developed a track record with investors that has allowed him to build a Tap Room business and an impressive real estate portfolio!Erik starts with very cool stories about his days in the music industry includi...

By Mark Ainley

Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Liv...

Episode Title: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event)Episode Subtitle: 2025 Apartment Sales & Leasing TrendsEpisode Category: Buy and Hold, Commercial Real Estate, Multifamily, Leasing, Evict...

By Mark Ainley

Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg

How to Get Out In Front of Renewals With Jeff Weinberg How do I incentivize and optimize renewals?=============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: StraightUpChi...

By Mark Ainley

Episode 366: Networking Leader from Creative Financing to Six-Figure Commission Checks with Jeffrey ...

Jeffrey Ma joins us to share his experience as a real investor, broker, and wholesaler including various creatively structured deals!Jeffrey starts by discussing his upbringing, start in real estate, and how he established a focus on wholesaling. He dives deep into “creativ...

By Mark Ainley

Episode 365: Building a $20 Million Portfolio Using BRRRR with Wyatt Simon

Wyatt Simon, owner of Full Circle Real Estate, discusses the successes and lessons learned in his journey to building a $20 million real estate portfolio!Wyatt starts by talking about how a successful BRRRR deal allowed him to gain momentum early on in his investing career. After...

By Mark Ainley

Episode 364: Small Credit Items That Lead to Large Financial Impacts with Eric Workman

How does credit effect DSCR loans?=============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: StraightUpChicagoInvestor@g...

By Mark Ainley

Episode 363: 168 Western Suburb units In Less Than 10 Years with John Warren

John discusses his start in real estate over a decade ago and reflects on missed opportunities, lessons learned, and success stories! He shares practical advice on simply structuring partnerships and talks about Forte Properties’ plan for growth in the western suburbs. John...

By Mark Ainley

Episode 361: What To Do Regarding the Northwest Side Preservation Ordinance

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: StraightUpChicagoInvestor@gmail.comGuest: Brie Schmidt, Second City Real Estate...