Are you currently an investor in Chicago or have a desire to start investing in the Chicagoland real estate market? If so, then this podcast is for you!
We'll help you fully understand our city and its neighborhoods, and we'll discuss various investor opportunities in the suburban real estate market as well. Listen in as we talk with other investors in Chicago and Property Managers throughout the area who are successfully working in and around this great city. Join us as we share our winning strategies, success stories, obstacles we've encountered, and most importantly, the lessons we have learned along the way.
If you are ready to learn the ins and outs of the investor market here in Chicago, you are in the right place.
JD shares his real estate beginnings, including his purchase of a multi-family building with a VA loan. He dives into Short-Term Rentals (STRs) including income, expenses, and how those compare to traditional rentals. JD gets granular on STR pricing, occupancy, turn-over costs, and optimizing profitability. He drops golden nugge...
Let us guide you through Investment purchase journey
State Farm - Josh Steigelmann
Renovo Financial - Workman Lending Team
Essex Realty Group
North Shore Brickwork and Windows
Mark Ainley is an investor, Real Estate Managing Broker, and local Property Manager with nearly two decades of experience
in all facets of real estate. Mark is the co-founder of GC Realty & Development, LLC, a full-service real estate brokerage,
property management, and real estate investment firm in the Chicago real estate market. Through his brokerage, he consults with
both local and out-of-state investors on the acquisition, stabilization, and management of their rental property portfolios.
GCR&D recently made the “INC 5000 List” of the fastest growing companies in the United States.
He was featured on CNBC’s TV show The Deed, featuring one of his rehab projects. He has also been featured on podcasts
like Bigger Pockets(episode 72), The Real Estate Mogul Podcast , Joe Fairless, REI Diamonds, and Real Estate Money School.
In 2017 he was featured on the cover of Top Agent-Property Management Edition.
He has spoken at numerous events throughout the United States including investing summits in Dallas, Atlanta, San Francisco,
and Chicago. Mark takes pride in sharing his personal experiences, both good and bad, with new investors, out-of-state
investors, or even less experienced entrepreneurs on what steps to avoid when growing a business.
Through his years of experience, and having completed over 480 successful rehabilitation projects, Mark is able to share
his breadth of knowledge on such topics as Property Management, business scaling, the rehabilitation and flipping of
properties, asset management and stabilization, market analysis, and investing.
Tom Shallcross is a born and raised Chicagoan who specializes on the North and Northwest sides of Chicago. Tom is the co-host of the Straight Up Chicago Investor Podcast and owner of Now Serving Properties; an investment business that has completed over $40M of real estate transactions. Recently Tom joined Drexel Properties to help expand upon Drexel's current 600 unit portfolio.
Tom has scaled a successful Chicago rental portfolio while maintaining a full-time flipping business and helping other investors find their next investment as an agent at Second City Real Estate. Tom is an active father of four children.
Alejandro Martinez - Production Specialist
Born and raised in Chicago, Alex Martinez is a Pipeline Engineer, licensed real estate broker, and investor. He currently owns and manages 6-units in the East Humboldt Park and United Center neighborhoods. He has vast experience underwriting, acquiring, and renovating small multi-family buildings. In his free time, Alex likes to stay active and enjoys exploring Chicago's Historic Architecture/Neighborhoods!
Real estate investing offers numerous benefits, including potential long-term appreciation, passive income, and portfolio diversification. However, it's essential for investors to understand the tax implications associated wit...