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Straight Up Chicago Investor Podcast Episode Episode 224: Expert Insights On Chicago’s Northwest Side With Jason Wagner

Straight Up Chicago Investor Podcast Episode Episode 224: Expert Insights On Chicago’s Northwest Side With Jason Wagner

In this exciting episode, we sit down with Jason Wagner, the Managing Broker of Greystone Realty, a unique brokerage where every agent is also an investor. Jason shares his journey and the transformative impact of the 75 Hard program on his life. Additionally, he delves into his investment strategies in Portage Park and Jefferson Park, shedding light on the housing supply shortage, recent inventory trends, and what lies ahead. Join us as we explore how Greystone Realty and The Wagner Report are revolutionizing the Chicago real estate market.

  1. The Power of 75 Hard: Jason Wagner is not only a successful real estate professional but also a passionate advocate of the 75 Hard program. He explains how this intense mental and physical challenge has had a profound impact on his personal and professional life. Through discipline, perseverance, and self-improvement, Jason has experienced remarkable growth and success.

  2. Investing in Portage Park and Jefferson Park: Jason takes us on a deep dive into his investment strategies in two thriving Chicago neighborhoods: Portage Park and Jefferson Park. He shares his insights on why these areas present lucrative opportunities for real estate investors. From analyzing market trends to identifying potential growth areas, Jason provides valuable advice for those looking to invest in these neighborhoods.

  3. Navigating the Housing Supply Shortage: The housing supply shortage has been a pressing issue in many real estate markets, and Chicago is no exception. Jason sheds light on the challenges posed by this shortage and offers his perspective on how investors can adapt and thrive in this environment. He discusses creative solutions, such as exploring off-market deals and leveraging technology to uncover hidden opportunities.

  4. Recent Inventory Trends and Future Projections: Drawing from his extensive experience, Jason analyzes recent inventory trends in the Chicago real estate market. He discusses the impact of changing buyer preferences, construction costs, and zoning regulations on the availability of housing. Furthermore, he projects what the future might hold for the market, providing valuable insights for investors and industry professionals alike.

  5. Greystone Realty and The Wagner Report: Jason concludes the episode by highlighting the unique value that Greystone Realty and The Wagner Report bring to Chicago real estate investors. He explains how their innovative approach, combining brokerage services with investment expertise, sets them apart in the industry. Jason also discusses the resources and insights provided by The Wagner Report, empowering investors to make informed decisions and stay ahead of the curve.


In this captivating episode, Jason Wagner shares his personal journey, investment strategies, and expert insights into the Chicago real estate market. From the transformative power of the 75 Hard program to navigating the housing supply shortage, Jason's wealth of knowledge and experience provide listeners with valuable takeaways. Greystone Realty and The Wagner Report continue to add immense value to Chicago real estate investors, making them a force to be reckoned with in the industry. Tune in to this episode and unlock the secrets to success in the ever-evolving world of real estate investing.

Watch Straight Up Chicago Investor Podcast Episode 224 in Full Here


Questions We Answer In this Show:

Q. Successfully House hacking in the Windy City

  1. Video

Q. The Battle of Chicago Real Estate: Low Inventory vs Neutral Market for Home Sales 

  1. Video

Q. Chicago's Rent Growth is Skyrocketing - Here's the Shocking Reason Why!

  1. Video


Show Notes:

  • 03:52 Housing Provider Tip: End leases at noon, instead of midnight, to allow time for turnover! 

  • 05:11 Intro to our guest, Jason Wagner!

  • 06:33 Jason explains 75 Hard!

  • 11:05 Jason breaks down investing in Portage and Jefferson Park!

  • 20:00 Discussing months of supply and the supply shortage over the last few years.

  • 31:12 What drew Jason to Belmont Cragin?

  • 36:18 Valuation of 2-4 units vs 5+ units.

  • 40:24 Concept of an investment-minded brokerage!

  • 45:14 How did Jason develop the Wagner Report?

  • 47:00 What is Jason’s competitive advantage? 

  • 47:22 One piece of advice for new investors. 

  • 48:34 What do you do for fun? 

  • 49:49 Good book, podcast, or self development activity that you would recommend?

  • 50:46 Local Network Recommendation? 

  • 52:25 How can the listeners learn more about you and provide value to you?


Guest Name: Jason Wagner

Guest Company: Greystone Realty

Guest Link: https://greystonerealtychicago.com/

Other Links for show notes:

Jason's Instagram

Traction (Book Recommendation)

SUCI Ep 43 - RJ and Nicky De Leon

SUCI Ep 82 - Property People


Chicago Investor Resources Shared


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