CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

Kevin Werner, co-founder and CEO of Renovo Financial, shares the inside story of building one of Chicago’s leading private lending firms for real estate investors. From starting out as a residential loan officer to raising hundreds of millions for value-add residential projects, Kevin walks us through the mindset, relationships, and work ethic that built Renovo into a real estate lending powerhouse. Whether you're a Chicago la...

Rory Rubin, founder of S.I. Container Builds, joins the Straight Up Chicago Investor Podcast to share her inspiring journey into modular construction using recycled shipping containers. From her background in social work to becoming a pioneer in sustainable housing, Rory’s story is a masterclass in innovation, grit, and delivering scalable housing solutions for modern challenges in Chicago and beyond.From partnering with local non...

Wonderful Togbey overcame tragedy, numerous immigration hurdles, and limited finances to build a 20-unit real estate portfolio in the Chicagoland area. In this inspiring episode, he breaks down the practical mindset shifts that took him from a W-2 job and paycheck-to-paycheck, to living financial freedom and multi-family ownership. Whether you're a new Chicago property manager or a seasoned landlord looking to grow, this is a maste...

I love Daniel Baker and what he has done.  This episode was a lot of fun and it is all thanks to his positive viewpoint of his experiences. From starting with a single house hack to building a multi-property portfolio, Daniel Baker’s story is a blueprint for persistence in Chicago real estate. In this episode, Daniel shares how grit, hustle, and leveraging the right partnerships helped him succeed in one of the most comp...

Today we’re joined by Nate Fernandez, also known as "Real Estate Nate"—a full-time W2 employee, father of three, CRM consultant, and Chicago landlord with over 20 units. If you think you’re too busy to build a real estate portfolio in Chicago, this episode will absolutely change your mindset.From balancing family life to building systems that scale, Nate walks us through how he created a cash-flowing Chicago ...

Today, we’re bringing back Mike Procaccio for his third appearance on the show. Mike’s our trusted accountant and one of the most valued members on our Build Your Team page. If you’re a Chicago landlord or house hacker—especially one managing your own multi-unit—you’ll want to take notes on this episode.We dig into one of the most overlooked areas of owning a multi-unit property: how house hacking aff...

Michael Kaplan joins us to share his inspiring journey from a young broker struggling to make ends meet to scaling his real estate business and building a rental portfolio in the Chicago area. His story reflects grit, persistence, and strategic decision-making that any aspiring investor or broker can learn from.Michael opens up about his decision to leave college during the pandemic and dive into real estate full-time. He breaks down th...

What does it really mean to build a lifestyle around real estate investing in Chicago? In this episode of the Straight Up Chicago Investor Podcast, Erik Swanson walks us through his unique journey from audio engineer, touring with world-famous bands like Aerosmith and Green Day, to full-time real estate investor and bar owner. If you’ve ever asked, "Can I escape my 9-to-5 and live life on my terms through real estate?" t...

This episode was different!  In this live recording from the NSBC (Northwest Side Building Coalition) event, real estate powerhouses Joe Smazal and Ann Reilly join the Straight Up Chicago Investor Podcast to break down the latest leasing and sales trends in Chicago's apartment market. Whether you're a landlord, investor, broker, or property manager, this candid conversation sheds light on how properties are trading, what re...

Jeffrey Ma may have started out in his family’s restaurant business, but his mindset, discipline, and grit have transformed him into a rising force in Chicago real estate. In this episode, Jeffrey shares how the lessons learned in his family’s restaurant helped shape his real estate investing career, from building systems and automating processes to managing guilt, culture, and family obligations along the way.This one&rsquo...