The Housing Provider Show

Most real estate investors don't fail because of bad deals—they fail because they underestimate risk. In this episode of The Housing Provider Show with guest Ed Thelen from 79th Ave Lending , we uncover the truth behind the popular "no money down" real estate strategy and discuss why cash reserves, risk management, and proper planning are critical for long-term success. Our conversat...

Most people think bad tenants = unpaid rent. That’s not the real problem. In this episode, we break down a real situation where a tenant was paying rent… while destroying an entire building, breaking into units, renting them out illegally, and creating a dangerous environment for everyone. And here’s the worst part… 👉 It was harder to evict them than a tenant who doesn’t pay. We also answer the b...

If you’re a Chicago landlord or real estate investor, this episode could save you thousands, or even millions, in insurance mistakes. In Episode 6 of The Housing Providers Show, host Tim Harstead sits down with public adjuster Dorian Bezanis from Alpha Adjusting to break down how insurance claims REALLY work for rental property owners. Most landlords misunderstand their policy, from 3% deductibles...

Most real estate investors chase cash flow, and that’s why many give up too early. In this episode of The Housing Provider Show , we explain the five real ways real estate makes you money , why cash flow is often the smallest return early on, and how Chicago investors build long-term wealth through appreciation, leverage, mortgage paydown, and tax strategies. We also break down Chicago landlord la...

Learn how to protect your rental property, prevent costly repairs, and navigate Chicago’s changing real estate market. In this episode of The Housing Provider Show, Tim Harstead and Dave Bovyn break down 2025 landlord strategies, winterizing your property, market trends, evictions, tenant disputes, ICE-related leasing delays, and how to avoid losing money this season. What you’ll learn:Chicago hou...

Ever wonder how some Chicago landlords go from one rental property to an entire portfolio of doors? In this episode of The Housing Provider Show , Tim and Dave break down The Monopoly Strategy, a real-world approach to scaling your real estate investments without waiting for the “perfect deal.” You’ll learn how to: - - - Start small and build equity fast in the Chicago real estate market - - - Use...

This episode of The Housing Provider Show is packed with strategies you can use right now. Host Tim Harstead (CEO, Chicago Style Management) sits down with Jackie Jablonski and Ivan Hernandez (Southwest Housing Provider Group, Chicago Friendly Landlord Group, Roofing by Hernandez) to break down: - Why landlord communities in Chicago matter more than “how many doors you own” - Real estate investing...

Welcome to the first episode of The Housing Provider Show, the rebranded podcast for Chicago landlords, property managers, and real estate investors. We’re diving into the challenges housing providers face in 2025: - Why Chicago tenant laws are becoming tougher - New regulations like the Fair Notice Act & 606 Pilot Program - How tenant unions and political pressure are changing the rental land...

In this episode, Tim Harstead from Chicago Style Management breaks down the key legal changes every Illinois landlord must understand for 2025. From mandatory flood disclosures to updated late fee limits and a streamlined eviction process, Tim explains what’s new, what’s risky, and how to stay compliant. He also dives into the new retaliation law and offers tips on how to legally justify non-renew...

Want to save thousands on your rental property taxes? In this episode of The Landlording Show, Tim Harstead reveals the #1 strategy smart real estate investors use to reduce taxes and grow their profits. Learn about depreciation, cost segregation, and the powerful short-term rental tax loophole that could save you big—even if you're not a full-time investor.

In this episode, Tim Harstead reveals how an abundance mindset can transform your real estate journey. Learn how viewing money as a tool, embracing opportunities, and breaking free from scarcity thinking can help you achieve financial freedom and amplify your impact.

The Landlording Show - Episode 18 - From House Hacking to Private Lending: With Bryce Matheson In this episode, host Tim Harstead sits down with Bryce Matheson from Holbrook Capital to discuss Bryce’s journey from house hacking to managing millions in real estate investments. They dive into essential strategies for new and experienced investors, highlighting the value of long-term planning, creati...

The Cash Flow Myth: What Real Estate Gurus Don’t Tell You! In this eye-opening episode host Tim Harstead from Chicago Style Management, challenges one of the biggest myths in real estate investing — the promise of instant cash flow. While many gurus sell the dream of rental properties generating passive income from day one, Tim reveals the hidden truth about the real cost of property management. H...

In this must-listen episode, host Tim Harstead sits down with Attorney and Realtor Tosh Chandy to break down the latest legal changes shaking up the real estate market. With new regulations set to take effect on August 17th, Tosh brings a unique perspective as both a legal expert and a practicing realtor.

Things that you should be doing to save yourself some money and things like that after you close in Chicago.

On this episode of the Landlording, we interview Laura Dantuma, a mortgage broker from Femme Capital, and discuss. How to use an FHA loan to buy investment propertiesCan you use FHA loans to buy more than one investment property? What are the different types of loans you can use to buy real estate investments? Why you should use a mortgage broker vs going through a bank? What do you need for a dow...

Episode 13 - Optimize Your Lease From smoking policies to pet regulations, and missed appointments to unauthorized occupants, we delve into crucial lease clauses that can protect your property and streamline your management process. Don't miss out, ensure smooth tenancies and maximize your rental income.

Strategic Estate Planning Guest: Security Benefits Center Dive deep into the world of estate planning with our latest podcast episode! Join Tim Fordham & Ben Smith from the Security Benefits Center as they explain the intricate details of trusts, tax implications, and the probate process. Gain practical tips on protecting your assets and ensuring your family's financial security. ** If you...

In this episode, host Tim Harstead explores how to expand your portfolio using the Monopoly strategy.

Today, we have a special episode featuring our host's $100 challenge. If you've ever thought about getting into real estate but felt held back by financial constraints, this episode is for you! Join us as we break down the barriers to entry in real estate investing and show you how to overcome the hurdle of a down payment. Our host shares valuable insights and strategies that prove anyone...

On today's episode, I'm going to do a Q&A. We're going to go and take some questions that we got off of Facebook groups and answer them. Always check with your attorney before doing anything. ENJOY!

We're going to give you some good tips today on how to best save money and things that you should be doing to make sure that you're going to be in a spot where your profits stay high.

Explore the strategies for building your portfolio, whether aiming for retirement tranquility or an empire of income. Join us on this insightful adventure! #RealEstateInvesting #InvestmentGoals #SuccessInRealEstate #chicago

Join Tim Harstead & attorney Tosh Chandy in this podcast dedicated to unraveling the legal intricacies of the Chicago real estate scene. Discover essential strategies for success, whether you're dealing with building violations, LLC representation, or other legal challenges. Get the inside scoop on how to thrive in Chicago's dynamic real estate market.

In this episode, Tim from Chicago Style Mgmt delves into the critical mindset needed for successful property management, emphasizing the importance of planning for capex projects, building reserves, managing taxes, and understanding the real estate cycle. Subscribe now to gain valuable insights and secure your financial future through real estate investing.