Straight Up Chicago Investor

Mark Ainley

Booking Overview

A local real-estate interview show focused on Chicago-area investing, property management, and practical deal-making, typically featuring investors, property professionals, insurance specialists, and public officials. Agencies could credibly pitch Chicago-market investors, landlords, property managers, tax and assessment experts, insurance professionals, and other locally relevant real-estate authorities; booking difficulty is low because the show favors accessible practitioners with direct market expertise over nationally famous guests.

Metrics

Episodes: 473

Frequency: Multiple_weekly

Rating: 5.0/5.0

Estimated listeners: 1k-10k

Gender skew: Male

Location: USA

YouTube: 2.7k subscribers

Instagram: 1.7k followers

Contact Information

mark@gcrealtyinc.com

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Host

Mark Ainley - Chicago real estate investor associated with GC Realty & Development, with experience in acquisitions, flips, BRRRR projects, syndication, short-term rentals, and property management.

Booking Intelligence

Booking Requirements

low
Typical Credentials:  
Chicago-area real estate investors, property managers, insurance professionals, tax and assessment specialists, public officials, and other practitioners with direct local-market expertise.
Required Achievements:  
Operating or investing in Chicago-area properties, Managing rental portfolios or property-management operations, Professional expertise in insurance, taxation, assessment, or real-estate services, Holding relevant public-sector leadership or decision-making roles

Recent Guest Discussions

Josh Steigelmann - Insurance Claims And Government Intervention In The Claims Process

Pat Hynes - Property Assessments, Property-tax Appeals, Valuation Methodology, Affordable-housing Incentives, And Chicago-area Development Issues

Recent Topics

Chicago Real Estate, Real Estate Investing, Property Management, Landlording, Real Estate Finance

Episodes

Here's the recent few episodes on
Straight Up Chicago Investor
:

Episode 469: Different Scenarios That Require Builder's Risk Insurance With Josh Steigelmann

August 04, 2026

What is Builders risk insurance and as an investor when do I need this policy? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Josh Steigelmann, State Farm Insurance Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your ...

Episode 468: Scaling a Wholesale Business Quickly with Eric Field

July 30, 2026

Eric Field of Big Door Home Buyers joins us to share how he has successfully built his real estate wholesaling business! Eric jumps right in by explaining how he got into wholesaling and how he scaled his business! He provides tactical advice on marketing, wholesaling overhead expenses, and estimating rehab costs. Eric shares wholesaling horror stories and his biggest lessons learned from underwriting mistakes. He closes with an outlook on fine tuning his business to further propel growth! If...

Episode 467: Lessons from Mark Ainley's Real Estate Deals Over the Last 30 Months

July 23, 2026

SUCI Co-Host Mark Ainley gives a presentation on his deals over the last 30 months at the WSBOA meetup!  Mark shares details on various deals including flips, BRRRRs, and even short-term rentals. He  explains how he sourced, financed, and stabilized these deals. He discusses biggest wins and top lessons learned. Mark closes the presentation with the biggest REI takeaways and a Q&A session that you won't want to miss! If you enjoy today's episode, please leave us a review and share with someon...

mark@gcrealtyinc.com

For verified host and producer emails, sign up to view.

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