Podcast

By Mark Ainley

Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez

Real Estate Nate shares how he has accumulated 26-units with healthy cash flow all while having a demanding W2 job!Nate shares lessons learned from his first few deals and compares small vs large multifamily buildings. He explains how he and his wife leverage their high-income W2...

By Mark Ainley

Episode 374: Taking On Opportunity In Chicago’s Toughest Neighborhoods with Corey Oliver

Corey Oliver, CEO of Strength in Management, is back three years later to share additional insights on managing in C/D neighborhoods. Corey starts by discussing recent compression of cap rates and investment financials in Chicago C/D class neighborhoods. He gets granular on ...

By Mark Ainley

Episode 373: A New Option to Fund Renovations For Chicago 2-4 Properties

A New Option to Fund Renovations For Chicago 2-4 PropertiesProperties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.comHave a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCReal...

By Mark Ainley

Episode 372: Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell

Kevin Schnell of Concord Capital has amassed a portfolio of over 400 rental units and has vast experience repositioning multi-family and mixed-use real estate investments!Kevin hits the ground running with how he grinded early in his real estate career to learn his markets and ef...

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...