Straight Up Chicago Investor Podcast
Two active Chicago real estate investors and property managers break down the local market for fellow investors.
A hyper-local podcast for real estate investors focused exclusively on the Chicago market. Hosts Mark Ainley and Tom Shallcross mix interviews with local professionals (developers, brokers) with their own analysis of market trends. Episodes provide a granular look at specific neighborhoods, investment strategies like BRRRR and value-add, and the practical challenges of being a landlord in the city.
“Its singular focus on Chicago real estate sets it apart. Unlike national podcasts, every piece of advice, market data, and guest story is directly applicable to the local ecosystem, from navigating aldermanic requests to dealing with city-specific maintenance issues like catch basins.”
Who hosts this show
Hosted by Mark Ainley and Tom Shallcross, this is a podcast focused entirely on real estate investing in the Chicago area. Mark is the co-founder of GC Realty & Development, a property management and investment firm, with decades of experience in acquisitions and portfolio management. Tom is the owner of Now Serving Properties, a flipping and investment business, and an active investor with his own rental portfolio. Together, they share their street-level experiences and interview local experts to provide actionable advice for navigating the Windy City's market.
Credentials & credits
- Mark Ainley: Co-Founder, GC Realty & Development, LLC
- Mark Ainley: Illinois Licensed Real Estate Managing Broker
- Mark Ainley: Co-host, AM560 Real Estate Revealed Radio Show
- Tom Shallcross: Owner, Now Serving Properties
- Tom Shallcross: Real Estate Investor
Other ventures
- GC Realty & Development, LLC (Mark Ainley)
- Now Serving Properties (Tom Shallcross)
- AM560 Real Estate Revealed Radio Show (Mark Ainley)
What kind of podcast
- Country
- United States
- Region
- usa
When new episodes drop
- 01Neighbor Lying About Property Damage!!Jun 27, 2026 · 32s
- 02Chicago Real Estate Is Super Competitive Right NowJun 27, 2026 · 48s
- 03Ground Up Development - Avoid This HUGE GC Mistake!Jun 26, 2026 · 1 min
- 04Chicago Ground-Up Developments with Matt KatsarosJun 25, 2026 · 1h 07m
- 05Who Should (and Shouldn't) Buy in Chicago Right Now?Jun 23, 2026 · 15 min
- 06North Side Neighborhoods and Market Opportunities with John PrestonJun 18, 2026 · 59 min
- 07The State of the Chicago Real Estate Market and Brokerage (Renovo Live Event)Jun 11, 2026 · 1h 22m
- 08Proactive Tax Planning Advice to Save on your 2026 Tax ReturnsJun 9, 2026 · 13 min
Notable episodes
- 01Chicago Ground-Up Developments with Matt Katsaros
A deep dive into the realities of ground-up and adaptive reuse development in Chicago, including the process of getting zoning changes and raising capital.
- 02North Side Neighborhoods and Market Opportunities with John Preston
Provides a realistic look at the daily grind of a Chicago real estate broker, including the metrics of cold calling and the challenges of a commission-based career.
- 03Who Should (and Shouldn't) Buy in Chicago Right Now?
A good example of the hosts' non-interview format, where they analyze current market stats and offer direct advice to different types of buyers.
What you'll be asked on this show
Mark and Tom conduct interviews with a casual, back-and-forth rapport, often building on each other's questions. They use their own experiences as brokers and investors to establish common ground and ask highly specific, process-oriented questions. The goal is less about a guest's life story and more about extracting actionable, realistic advice for their audience. They frequently ask guests to walk them through a specific deal or process, from the initial phone call to the finish line, and to reflect on what they'd do differently now.
The show is a two-host conversational format, with Mark and Tom bringing their own experiences as active investors to the table. Episodes alternate between interviews and shorter "Tuesday Tip" segments. A recurring feature is the "Housing Provider Tip of the Week," offering practical advice for landlords.
Questions the host keeps coming back to
10 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when the host reaches for it.
origin
1- Q.01
“How did you get into the real estate game here in Chicago?”
This is a standard opening question to establish the guest's background and connection to the local market.
process
4- Q.01
“Walk us through the process of [getting a listing, a zoning change, etc.] from start to finish.”
A signature question used to break down a complex process into a step-by-step guide for listeners.
- Q.02
“How do you put together your numbers for what a project will cost?”
Aimed at developers and flippers, this question digs into the practicalities of underwriting and budgeting.
- Q.03
“What does that first six months look like for someone starting out as a [broker, etc.]?”
This question aims to set realistic expectations for listeners considering a career in the guest's field.
- Q.04
“Did you get any crazy requests from the neighborhood or the alderman on that project?”
This question seeks out anecdotes about navigating Chicago's unique local politics in development.
backstory
1- Q.01
“Can you share a story about an early deal that took years off your life?”
This question is used to elicit memorable stories about the struggles and learning experiences of a guest's early career.
advice
2- Q.01
“Looking back, what would you have done differently on that first deal or in your first year?”
This question prompts guests to reflect on their growth and offer hard-won advice.
- Q.02
“What advice would you give someone who's just starting to raise money?”
This is asked to provide direct, actionable tips for listeners looking for capital.
industry
1- Q.01
“How were conversations with [landlords, sellers, etc.] then versus now?”
This question is used to gauge how market shifts have impacted sentiment and negotiations over time.
mindset
1- Q.01
“Did you really understand what you were getting into when you first started?”
A mindset question that explores the gap between a new investor's expectations and the reality of the business.
Signature segments
- · Housing Provider Tip of the Week
- · Straight Up Tuesday Tip
- · Closing trivia question
Topics covered repeatedly
Who gets booked here
Guests are exclusively professionals active in the Chicago real estate scene. This includes developers, multi-family brokers, lenders, and data analysts who can provide on-the-ground insights into the local market.
- Matt Katsaroson Chicago Ground-Up Developments with Matt Katsaros
- John Prestonon North Side Neighborhoods and Market Opportunities with John Preston
- Jason Wagneron Who Should (and Shouldn't) Buy in Chicago Right Now?
- Aaron Zimmermanon Proactive Tax Planning Advice to Save on your 2026 Tax Returns
Where to find this show
Audience & reach
The podcast features sponsors that are relevant to its real estate investor audience, such as Greystone Realty. The show's website also has a "Build Your Team" page with a directory of paid vendor listings, from lawyers to lenders.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
Pitch this show
s•••@•••.comFree: limited reveals · Pro: unlimited reveals + CSV export
You’re only charged when we return a verified hit.
People also ask
- Who are the hosts of the Straight Up Chicago Investor Podcast?
- The podcast is hosted by Mark Ainley, co-founder of GC Realty & Development, and Tom Shallcross, owner of Now Serving Properties. Both are active real estate investors and property managers in Chicago.
- What is the format of the show?
- The show alternates between long-form interviews with Chicago real estate professionals and shorter "Tuesday Tip" episodes where the hosts discuss a specific market topic.
- Is this podcast still active?
- Yes, the podcast releases multiple episodes per week.
- Where can I listen to the podcast?
- The podcast is available on YouTube, Apple Podcasts, and other major streaming platforms.
- Is this podcast only for experienced investors?
- No, while it offers deep insights for seasoned professionals, the hosts make an effort to explain concepts and processes in a way that is accessible to new investors as well.
- How can I pitch a guest for the show?
- The show's website and episode descriptions provide an email address for show ideas: [email — gated].
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
Podcasts like Straight Up Chicago Investor Podcast
Silicon Valley Girl
Silicon Valley Girl
An entrepreneur interviews the founders and scientists building the next wave of AI to uncover practical strategies for career and business growth.
The Wolf Of All Streets
Scott Melker
A daily show from trader Scott Melker breaking down crypto, macro, and trading news with market experts and industry builders.
Donovan Sharpe
Donovan Sharpe
A confrontational live-stream show focused on dating, masculinity, and current events from a "Red Pill" perspective.
Simple Hai!
Vivek Law
A veteran Indian financial journalist demystifies money and markets by interviewing the C-suite executives running India's top financial institutions.
Neha Nagar
Neha Nagar
India's practical finance podcast where a financial educator interviews top experts on the stock market, economy, and geopolitics for retail investors.
Neeraj Bajpai
Neeraj Bajpai
A veteran Indian business journalist decodes stock markets, geopolitics, and economic shifts for active investors.
The Educated Homebuyer Podcast
A weekly podcast demystifying the US housing market and mortgage rates for aspiring homeowners, hosted by a realtor and a mortgage expert.
THE Bitcoin Podcast with Walker
A podcast exploring Bitcoin's role as a tool for separating money and state through interviews with leading developers and policy experts.