Skip to main content

Podcasts


Straight Up Chicago Investor Podcast Episode 223: From New York To The Windy City - Curtis Lefebvre's Real Estate Journey And Success In East Garfield Park

Straight Up Chicago Investor Podcast Episode 223: From New York To The Windy City - Curtis Lefebvre's Real Estate Journey And Success In East Garfield Park

In this exciting podcast episode, Curtis Lefebvre takes us on a captivating journey of why he left the bustling streets of New York City for the Windy City, Chicago, to pursue real estate investing. Curtis shares his experiences, challenges, and successes in acquiring and stabilizing his first househack in the vibrant neighborhood of East Garfield Park. Join us as we delve into the details of Curtis' real estate adventure and discover why he believes in the potential of this up-and-coming neighborhood.

  1. A Granular Approach to House Hacking: Curtis wastes no time in sharing the nitty-gritty details of his first househack in East Garfield Park. He discusses the challenges he faced, from dealing with problem tenants to taking on do-it-yourself renovations. By getting into the specifics, Curtis provides valuable insights into the realities of real estate investing and the determination required to overcome obstacles.

  2. Living for Free and Cash Flowing: One of the most intriguing aspects of Curtis' househack is how he managed to not only live for free but also generate cash flow while residing there. By carefully analyzing the numbers and making strategic decisions, Curtis achieved a remarkable financial outcome. He breaks down the calculations and reveals the secrets behind his successful househack, inspiring listeners to explore similar opportunities.

  3. Exploring East Garfield Park: Curtis defines the borders of East Garfield Park and, with the input of his podcast host, Mark, discusses the differences between East and West Garfield Park. Curtis justifies his decision to bet big on East Garfield Park by sharing his bullish outlook on the neighborhood. Through his insights, listeners gain a deeper understanding of the area's potential for growth and investment opportunities.

  4. Embracing Challenges and Building Confidence: Throughout the episode, Curtis emphasizes the importance of embracing challenges and learning from them. He shares his experiences of dealing with problem tenants and tackling renovations, highlighting the personal growth and confidence that come with overcoming obstacles. Curtis' story serves as a reminder that perseverance and a positive mindset are key ingredients for success in real estate investing.


Curtis Lefebvre's decision to leave New York City and venture into real estate investing in Chicago's East Garfield Park is a testament to the opportunities that lie beyond one's comfort zone. By sharing his journey, Curtis inspires listeners to take calculated risks, get hands-on with their investments, and believe in the potential of emerging neighborhoods. His story serves as a reminder that with determination, strategic thinking, and a bullish outlook, real estate investors can achieve remarkable results. So, join us on this podcast episode as we explore Curtis' captivating adventure and gain valuable insights into the world of real estate investing.

Watch Straight Up Chicago Investor Podcast Episode 223 in Full Here

Questions We Answer In this Show:

Q. Mastering the Art of Landlord Diplomacy: Negotiating with a Problem Tenant

  1. Video

Q. Unlocking Your Home Equity: Why Premium on Cash-Out Refinancing is Worth the Investment

  1. Video

Q. House Hacking in Chicago's Small Multifamily Properties!

  1. Video

Show Notes:

  • 03:02 Housing Provider Tip: Processes to prevent loss of lock keys and codes!

  • 04:21 Intro to our guest, Curtis Lefebvre!

  • 07:03 How did Curtis decide on which Chicago neighborhoods to invest in?

  • 11:48 Curtis’ experience acquiring his first rental property in Chicago!

  • 21:39 Dealing with problem tenants.

  • 25:30 DYI’ing renovations on the first property!

  • 32:39 Curtis’ bullish outlook on East Garfield Park!

  • 36:04 Borders of East Garfield Park and Going West of the Park! 

  • 39:03 What is Curtis’ competitive advantage? 

  • 39:28 One piece of advice for new investors.

  • 39:40 What do you do for fun?

  • 40:13 Good book, podcast, or self-development activity that you would recommend?

  • 40:36 Local Network Recommendation?

  • 41:17 How can the listeners learn more about you and provide value to you?


Guest Name: Curtis Lefebvre

Other Links for show notes:

Brian Lindstrom (Lender Referral)

SUCI Ep 195 - Victoria Barkate

chi.multifamily@gmail.com (Curtis’ Email)


Chicago Investor Resources Shared


Want extra Hacks & Tricks? Follow us on Facebook & Youtube!

Looking for a breakthrough in your career? Join Our Team!

SUBSCRIBE on to our podcast on iTunes | Spotify | Stitcher | TuneIn Radio 

Need More Info?


Should I Rent or Sell

ROI Calculator

Rental Analysis

Speak To A GCR&D Team Member

back