Shows
The Housing Provider ShowThe 5 Ways Real Estate Makes Money (For Chicago Investors & Landlords)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 laws, including rent increase notice requirements, late fee rules, legal entry notices, and when tenants can (and cannot) withhold rent.This episode is a must-listen for:...
2026-01-1039 min
The Housing Provider ShowChicago Landlord Winter Guide: Avoid Costly DamagesLearn 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 housing market update & interest rate changesWhy 2025 is a “weird” buyer’s marketHow landlords should winterize rentals to prevent frozen pipesWhy preventative furnace maintenance saves thousandsTenant communication rules for freezing tempsHow ICE activity is affecting leasing, employment & rent paymentsHow to handle evictions...
2025-12-0543 min
The Housing Provider ShowThe Monopoly Strategy: How Landlords Grow from 1 Door to 50Ever 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 the 1031 exchange to grow your portfolio and avoid capital gains tax- - - Understand what real cash flow looks like (and wh...
2025-10-3044 min
The Housing Provider ShowReal Estate Investing Tips, Tenant Management & Roofing Advice with jackie Jablonski & Ivan HernandezThis 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 tips for buying 2–4 flats & multifamily properties- Smart ways to raise rent, charge for extras, and boost cash flow- Avoiding costly rehab mistakes + must-know landlord metrics- Ro...
2025-09-031h 10
The Housing Provider ShowFrom Landlord to Housing Provider: Navigating Chicago’s Tougher Rental LawsWelcome 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 landscape- What small landlords and investors can do to protect their business and grow their portfolioWhether you own one rental or manage multiple properties, this episode gives you in...
2025-07-2328 min
The Housing Provider Show2025 Illinois Landlord Law Changes You Need to KnowIn 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-renewals and rent increases.Whether you self-manage or work with a property manager, this episode is packed with must-know updates that could save you time, money, and legal trouble.
2025-05-2711 minThe Housing Provider ShowTax Loopholes For Real Estate Investors (save money legally)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.
2025-03-1515 min
Evolve LeadershipBuild Wealth Without Entrepreneur Burn Out with Tim HarsteadWelcome:Welcome to the Evolve Leadership Show, where we provide powerhouse success strategies to high-performers who want to create and sustain generational wealth.🔍 In this Episode:In this episode, Angus Nelson is joined by Tim Harstead, founder of Chicago Style Management, to explore how delegation, planning, and scaling are key to entrepreneurial success. Tim discusses real estate strategies, building effective teams, and the mindset shifts needed to create a sustainable business while maintaining work-life balance. His insights on navigating the real estate market and building a thriving business are practical and inspiring.
2024-12-3115 minThe Housing Provider ShowAbundance Mindset for Real Estate SuccessIn 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.
2024-12-2410 min
The Housing Provider ShowFrom House Hacking to Private Lending: With Bryce MathesonThe 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, creative financing, and transitioning to lending for passive income.
Key Takeaways:
The Evolution from House Hacking to High-Capital Lending: Bryce shares his journey, starting with his first rental property and eventually scaling to a multi-million-dollar portfolio.
Building a Sustainable Po...
2024-11-0534 min
The Housing Provider ShowThe Cashflow MythThe 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. He dives deep into the importance of planning for maintenance, unexpected vacancies, and capital expenditures, all while highlighting the long-term value of real estate investment.
Key Takeaways:
The Myth of Cash Flow: Why it’s...
2024-09-2813 minThe Housing Provider ShowNavigating New Real Estate Regulations: Insights from Attorney & Realtor Tosh ChandyIn 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.
2024-09-0258 min
The Housing Provider ShowLegal Insights for Landlords with Guest: Anthony V. PanzicaThings that you should be doing to save yourself some money and things like that after you close in Chicago.
2024-08-1436 min
The Housing Provider ShowFinance For Your Investment PropertyOn 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 down payment when buying an investment propertyas well as answering many more questions about lending on your investment propertiesIf your looking a loan on your next property...
2024-06-1739 minThe Housing Provider ShowOptimize Your LeaseEpisode 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.
2024-05-1015 min
The Housing Provider ShowStrategic Estate PlanningStrategic 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 are looking to set up an estate plan or a trust please give Tim Fordham a call and mention you heard about him through Tim at Chicago Style Management, and receive $200 off of your fees! You can call Tim at 616...
2024-04-0829 min
The Housing Provider ShowThe Monopoly StrategyIn this episode, host Tim Harstead explores how to expand your portfolio using the Monopoly strategy.
2024-03-1114 minThe Housing Provider ShowInvesting / $100 ChallengeToday, 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 can enter the world of real estate with determination and the right mindset.
2024-02-2310 minThe Housing Provider ShowQ & AOn 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!
2024-01-2017 minThe Housing Provider ShowCost-Cutting to Increase Your ProfitWe'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.
2023-11-2415 minThe Housing Provider ShowReal Estate Goals for a Successful Investment JourneyExplore 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
2023-11-1012 minThe Housing Provider ShowLegal insights & expert advice with attorney Tosh ChandyJoin 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.
2023-10-2039 minThe Housing Provider ShowMindset and CashflowIn 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.
2023-09-2218 minThe Housing Provider ShowThe Art of Property Enhancement with Guest Robin NicoleToday's Guest: Robin Nicole Interiors
Dive into the world of property transformation as we chat with Robin Nicole, a seasoned interior designer. Explore her tips on making your investment properties stand out and attract top-tier tenants.
2023-09-0143 minThe Housing Provider ShowThe different classes of properties and how they vary for youIn this episode, host Tim Harstead, from Chicago Style Management, breaks down the differences between managing A-Class, B-Class, C-Class, and D-Class properties.
From newer, more affluent neighborhoods to well-worn gems in less desirable areas, we explore what each property class entails and how to navigate their unique management challenges.
Looking to invest wisely and gain passive income? Tune in and discover the strategies to maximize returns and mitigate risks. Whether you're a seasoned investor or just starting, this episode is packed with insights to elevate your property management game.
2023-08-1821 min
The Housing Provider ShowEpisode 02 - 5 Ways to Make Money with Investment PropertiesJoin host Tim Harstead from Chicago Style Management, as he shares 5 great ways to make money with investment properties in the Chicago area. Don't miss this valuable insight into real estate wealth-building! 🏠
The Landlording Show - Episode 02 - 5 Ways to Make Money with Investment Properties
2023-07-2815 min2023-07-0304 min
The Housing Provider ShowRent Price Increase in ChicagoTim from Chicago Style Mngmnt dives into the fascinating topic of rent price increases in the dynamic city of Chicago. Discover the factors contributing to rising rental costs, explore the impact on tenants and landlords, and gain valuable insights into navigating this evolving rental market.
In this episode, we'll discuss the economic drivers, market trends, and local influences that shape rent prices in Chicago. Whether you're a tenant concerned about affordability or a landlord seeking to understand the dynamics behind rent adjustments, this episode provides essential information to help you make informed decisions.
2023-06-1513 min
Straight Up Chicago InvestorProperty Management in Chicago's Southside with Tim HarsteadLooking for insight on the nuances of acquiring and managing properties on the south side of Chicago? If so, this episode is for you! Tim starts by talking about his start in real estate and how he identified a need for quality property management on the south side. He provides insight on tenant screening, underwriting expenses, and subsidized housing for the C/D class assets he operates. Tim gets granular on the housing stock, values, and neighborhood borders in the Chicago Lawn, West Elsdon, and West Englewood neighborhoods. Tim closes this knowledge packed show by sharing the...
2022-08-2546 min