CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

In this episode of the Straight Up Chicago Investor Podcast, we get into how Sebastian scaled from Cutco sales to Airbnb arbitrage to property ownership. You’ll hear the no-BS version of what it takes to convince landlords, navigate Chicago's short-term rental laws, and balance profitability with hospitality. It’s a must-listen for any property manager or landlord curious about what’s really possible with short-ter...

There’s a lot of noise out there about what it takes to become a real estate investor. People talk big—“I’m going to own a hundred doors,” “I’m going to be financially free in two years,”—and then get stuck before they even make that first move. This episode is for those who are stuck, stalling, or simply need to see that it’s possible.Because Alex Diaz? He’s doing the da...

Let me just say this up front—if you're one of those investors thinking you need a hundred units and a fancy syndication to "make it," you’re missing the point. And in this episode, Katie and Rob Hayes make that crystal clear. They’ve built a portfolio that works for their lifestyle—not the other way around—and they’ve done it by staying local, staying focused, and staying in control. N...

A demand letter or legal notice from an attorney might be the first sign of legal trouble, or it could be just a bluff designed to scare you into overreacting. In this episode, attorney Bibek Das joins Mark Ainley and Tom Shallcross to demystify what a demand letter really is, what landlords should (and shouldn’t) do when receiving one, and why staying calm is your most powerful first move. If you own rental property in Chicago or...

Jake Clopton isn’t just another lender. He’s a Chicago-based real estate financing expert who built a commercial loan empire starting with cold calls during the 2008 financial crisis. In this episode, Jake breaks down how he scaled his business, the outlook on interest rates, and why property management thrives during downturns. From Fed policy to commercial lending networks, he offers real-world insights that every Chicago ...

Mahmoud Faisal Elkhatib’s journey from chemistry lab to real estate law firm founder is anything but conventional. In this episode of the Straight Up Chicago Investor Podcast, Faisal reveals how his immigrant background, early work ethic, and legal hustle helped him become one of the most trusted names for real estate legal services in Chicago. Whether you're a landlord, investor, or property manager, this episode offers inva...

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...