Straight Up Chicago Investor

Straight Up Chicago Investor

Business EN ↓ 468 episodes

Are you a real estate investor in Chicago or someone looking to invest in the Chicagoland Market? If so, this podcast is for you! We break down the neighborhoods, different sides of the city, and surrounding suburbs so you can understand the uniqueness of investing in Chicago real estate. The hosts and guests are Chicago investors and Property Managers who are making it happen in and around the Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked...

Author

Straight Up Chicago Investor

Category

Business

Latest episode

Jul 9, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

Episode 18: Top 10 Mistakes We See From Chicago Investors - with Brandon Moulton of Renovo Financial (Part 1) 23.07.2020

You've heard their name tossed around on earlier episodes, and now we have Renovo Financial here to address some of the biggest mistakes they see when dealing with Chicagoland investors. Brandon Moulton is the Senior VP of Lending at Renovo Financial and has been featured on Crain's Chicago People on the Move. Brandon takes on Part 1 of the top ten mistakes Renovo sees in their day to day interact...

Episode 17: Legal Pitfalls to Avoid As A Chicago Real Estate Investor - With Bibek Das 16.07.2020

Local real estate and commercial litigator, Bibek Das, has spent the last 20+ years educating and protecting Chicagoland investors and landlords. In this episode, Bibek drops a ton of knowledge (and NUGGETS!) to ensure you are running your real estate business appropriately. This includes an overview of Chicago's Residential and Landlord Tenant Ordinance (RLTO) (and what to know if you are a house...

Episode 16: Northside Property Manager/Investor Breaks Down Types of Investors and Receivership Opportunities 10.07.2020

After a successful career in corporate finance, Eric took his skillset (which he originally honed at THE University of Illinois) and transitioned full-time into real estate. Eric is a co-founder of 33 Realty, a vertically integrated company that has the ability to takes its clients through the entire lifecycle of a real estate investment. In this episode Eric discusses the Northside neighborhoods...

Episode 15: From Househacking in North Center to $90M in Real Estate Holdings with John Casmon 02.07.2020

John Casmon is a successful Chicago househacker turned syndicator and the founder of Casmon Capital Group. In addition, John hosts the Target Market Insights Podcast, heads up the Chicago Multifamily Club Meetup, and is the co-creator of the Midwest RE Networking Summit (coming up on 7/25-7/26). In this episode, John provides a wealth of knowledge, including his experience investing in Chicago, ta...

Episode 14: Multifamily Investing in the Southwest 'Burbs with Brian Kochendorfer 26.06.2020

One doesn't accomplish $600,000,000 in real estate transactions without thoroughly understanding the ins and outs of the business and which neighborhoods are primed for sound investments. Our guest today, Brian Kochendorfer, has a ton of nuggets to drop from his experience as a broker, passive investor, and managing member of Arc Equity Group, where he is a general and limited partner of $60M in r...

Episode 13: Consistent and Disciplined Action to Arrive at 70 Units in Dupage County with Ben Walhood 19.06.2020

There's a reason Ben Walhood has already been a featured guest on numerous high-profile podcasts, including Bigger Pockets, The Best Ever Real Estate Podcast with Joe Fairless, Target Market Insights with John Casmon, and has been interviewed by CNBC and The Chicago Tribune. Over the last decade, Ben has consistently grown his portfolio in Dupage County by expanding his network and buying the best...

Episode 12: Investment Opportunities in The Far Northwest Chicago Suburbs with Joe Mueller 12.06.2020

With 20 years in the business, Joe Mueller got his start buying REO (bank owned) properties at auctions. From there, Joe networked extensively to develop a robust acquisitions strategy and eventually implement multiple streams of income. Most recently, Joe started a title company suited for investors who wanted to transact in off market property without a broker.    Joe shares remarkably deep insi...

Episode 11: The Boss of the Southeast, Jared Kott 05.06.2020

Investor and property manager Jared Kott lives and breathes the Southeast neighborhoods of Chicago. After leaving corporate America in 2013, Jared enrolled in a property management class the following Monday to get his feet wet doing whatever takes. This experience was the springboard that lead to Jared owning over 100 properties, predominately in the Southeast. Jared gives detailed descriptions o...

Episode 10: 80 Off-Market Leads Calling YOU Each Month with Blake McCreight 29.05.2020

Chicagoland is an insanely competitive market, making constant deal flow one of the toughest challenges for investors across the city. As an investor, how successful would you be if you constantly had 80-100 off-market deals calling you each month asking you to make an offer? Through years of hard work, our guest, Blake McCreight, has created that exact infrastructure. Not only has Blake developed...

Episode 9: Dominating the Western Suburbs With John Warren 29.05.2020

Price points can be appealing in the Western Suburbs, especially compared to each areas of the city. However, it's not as simple as looking at rental rates and population statistics; our guest today is uniquely qualified to shed light on all the pros and cons that come along with investing in the numerous Western Suburbs East of 294.    John Warren is both an agent and investor and founder of the...

Episode 8: Working a 9-5 While Building a Robust Real Estate Operation with Ibn Abney 29.05.2020

So many people working day jobs want to build wealth through real estate but don't know how to get started. Ibn gives great advice on how to leverage the day job as a springboard to grow your real estate business. Ibn not only oversee his own rehabs and self-manage his tenants, but goes the extra mile to understand his community and create win-wins for everyone.   And where there wasn't a meet-up...

Episode 7: Over 500 Rehabs on the Southside of Chicago with Bryan Sonn 29.05.2020

Nothing kills a real estate investing career quicker than a horrendous rehab experience that spirals from the original budget and timeline. In this episode, Bryan Sonn gives golden advise on how to avoid this scenario and ultimately scale your construction process.  Bryan has a skill for people that has earned him a consistent network of quality workers. This network, combined with his proven appr...

Episode 6: 250+ Properties and 1% Vacancy in Lake County with Bill Powers 29.05.2020

Have you considered investing in Lake County? Or minimizing vacancies with a 3yr rent-to-own lease? Our guest today, Bill Powers, has successfully done both of these actions to scale his business to 250+ rent to own properties in the last ten years. Listen to Bill lay out his strategies on how to find the perfect asset, screen each tenant, and assist tenants with lending programs, thus enabling hi...

Episode 5: North Side House Hacking & How It Has Changed In Last 5 Years 22.05.2020

If you've gone on the Bigger Pockets forums, you've probably seen the wealth of knowledge she shares with everyone, but today Brie Schmidt of Second City Real Estate is getting down to the Chicago specific details for you. Ever wonder why north center has had such a strong population decline while prices have skyrocketed? Or how you can house hack a property yourself? Brie tells it all for you wit...

Episode 4: Building & Selling 600 Unit SFR Portfolio in South Suburbs 22.05.2020

How can you use your skills from your day job to scale an investment portfolio to 450 units? Listen to our guest, Ron Plonis, explain how he used his computer science background to help him build systems and scale his own portfolio, then sold it off completely. His career has spanned nearly 15 years, and his experiences give insight into how things have changed from pre '08 to now. Things from rai...

Episode 3: BRRRR Strategy to Scale With Andrew and Angie Taggart 22.05.2020

Andrew and Angie Taggart, an electrician and a teacher by trade, walk us through how their drive for learning and growth has pivoted their careers into scaling up a real estate portfolio. They give tons of great information on networking events that have been pivotal in getting momentum, the strategy they use and unique rules relating to BRRRR investing that young investors can easily overlook. --...

Episode 2: Chicago's Best Up & Coming Areas To Invest By Zip Code 22.05.2020

Originally from Philadelphia, Dan is a great case study of how an out of state investor can crush it in this market. Today he operates in three markets: Chicago, Philadelphia and Atlanta. Starting in '06 as a wholesaler with not much guidance, Dan gives tremendous insight into his journey from those early days wholesaling to today where in 2019 he closed on 223 deals with 5MM in profit for him and...

Episode 1: Meet the Hosts, Mark Ainley and Tom Shallcross 12.05.2020

Mark and Tom introduce the first podcast to deep dive into real estate investing in Chicago and its surrounding suburbs. We are going to take a look at specific neighborhoods and specific strategies, dissect obstacles that real investors have dealt and explore the solutions used to overcome them. Listen to Mark and Tom have a candid conversation about how the current environment has impacted their...

Listen to the Straight Up Chicago Investor podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.