Skip to main content


Straight Up Chicago Investor Podcast Episode 275: Keys To Off-Market Real Estate Acquisitions At Scale With Chicago’s Mike Kehoe

Straight Up Chicago Investor Podcast Episode 275: Keys To Off-Market Real Estate Acquisitions At Scale With Chicago’s Mike Kehoe

In our latest episode of Straight Up Chicago Investor, we had the honor of hosting Mike Kehoe, a seasoned investor and serial entrepreneur with a penchant for creating and selling multiple technology companies. Mike shared invaluable insights into the world of off-market real estate acquisitions and dispositions, offering a glimpse into his journey, strategies, and the importance of cultivating a growth mindset.

Pioneering Off-Market Real Estate

Mike's journey into off-market real estate began with a vision to carve out a niche in a competitive market. He regaled us with tales of choosing a real estate market to focus on and the grind of driving for dollars to uncover hidden opportunities. His tenacity and determination underscored the importance of perseverance in the pursuit of off-market deals—a sentiment that resonated deeply with our audience of savvy investors.

Engaging Potential Sellers

As Mike delved into the intricacies of engaging potential sellers of off-market real estate, he shared invaluable tips and strategies that have yielded success for his team. From personalized outreach to leveraging technology, his insights illuminated the path to building meaningful connections and nurturing relationships with sellers—a cornerstone of off-market acquisitions.

Core Values and Building Quality Teams

One of the key takeaways from our conversation with Mike was the importance of core values in driving success. He emphasized the significance of building a quality team that aligns with these values, fostering a culture of excellence and integrity that underpins every aspect of the business. For Mike, success isn't just about numbers—it's about building relationships, fostering trust, and making a positive impact on the communities we serve.

Cultivating a Growth Mindset

To close the show, Mike left us with motivating words on cultivating a growth mindset to become the best version of ourselves. He underscored the importance of embracing challenges, seeking opportunities for learning and growth, and never settling for mediocrity. His message resonated deeply with our audience, inspiring us to push beyond our limits and unlock our full potential in the dynamic world of real estate investment.

Embracing the Journey

As the episode drew to a close, one thing became abundantly clear: Mike Kehoe's journey is a testament to the power of perseverance, integrity, and a relentless pursuit of excellence. Through his insights and experiences, he has illuminated the path to success in off-market real estate, offering invaluable guidance to investors seeking to carve out their own niche in the market.

Watch Straight Up Chicago Investor Podcast Episode 275 in Full Here

Questions We Answer In this Show:

Q. How Someone Stole $100,000 From This Investor

A. Video

Q. How a Strong Team Leads to Success...

A. Video

Q. How To Acquire Off-Market Chicago Properties

A. Video

Show Notes:

  • 02:51 Housing Provider Tip - Ensure you’re up to date on the new Security Deposit laws.

  • 04:00 Intro to our guest, Mike Kehoe!

  • 08:28 Picking a market to invest in.

  • 11:42 Driving for Dollars!

  • 13:23 Engaging Sellers!

  • 19:31 Growing a quality team.

  • 27:24 Common mistakes when scaling and establishing core values.

  • 32:20 Bottlenecks in Mike’s business.

  • 39:35 Mike’s focus on personal growth!

  • 43:25 What is Mike’s competitive advantage?

  • 43:44 One piece of advice for new investors.

  • 43:54 What do you do for fun?

  • 44:04 Good book, podcast, or self-development activity that you would recommend?

  • 44:37 Local Network Recommendation?

  • 45:04 How can the listeners learn more about you and provide value to you?

Connect with Mark and Tom:

Email the Show:

Guest Name: Mike Kehoe

Guest Company: VentureStack

Guest Link:

Other Links for show notes:

Mike’s Email:

Mike Kehoe's LinkedIn

Tenant Radon Protection Act 2024

SUCI Ep 253 - Jeff Nydegger

SUCI Ep 86 - Fernando Angelucci

Traction (Book Recommendation)

Show Sponsors:

Build Your Team
Looking for a property manager?

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