Rephonic
Artwork for Straight Up Chicago Investor

Straight Up Chicago Investor

Straight Up Chicago Investor
Real Estate Investing
Chicago Real Estate
Chicago
Real Estate Investment
Property Management
Real Estate
Chicago Real Estate Market
House Hacking
Affordable Housing
Networking
Interest Rates
Illinois
Cost Segregation
NBOA
Operating Agreement
Wholesaling
Investment Strategies
Insurance Claims
Rental Market
Real Estate Investment Strategies

Are you a real estate investor in Chicago or someone looking to invest in the Chicagoland Market? If so, this podcast is for you! We break down the neighborhoods, different sides of the city, and surrounding suburbs so you can understand the uniqueness of investing in Chicago real estate. The hosts and guests are Chicago investors and Property Managers who are making it happen in and around the Wi... more

PublishesTwice weeklyEpisodes468Founded6 years ago
Number of ListenersCategories
BusinessCareersInvesting

Listen to this Podcast

Artwork for Straight Up Chicago Investor

Latest Episodes

SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down a fraud story on a West Town property that he purchased!

Tom dives deep into a recent purchase in West Town that involved ownership fraud when transferring title. He expla... more

YouTube

More Tenant Protections... Less Housing? Breaking Down Chicago's New RLTO

=============

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Mike Glasser, NBOA

Link: Amendment of Municipal Code Chapter 5-12 regarding Residential La... more

Ignacio Gonzalez returns to discuss his Back of the Yards Coffee Shop development and his campaign for Chicago School Board! Ignacio jumps right in by sharing rent growth and property appreciation trends in the Back of the Yards neighborhood. He expl... more

Matt Katsaros of Wildwood Investments returns to break down ground-up development projects that he's taking down in Chicago!

Matt jumps right in by explaining how his experience in commercial real estate brokerage and acquisitions led him to starti... more

YouTube

Key Facts

Accepts Guests
Accepts Sponsors
Contact Information
Podcast Host
Number of Listeners
Find out how many people listen to this podcast per episode and each month.

Similar Podcasts

People also subscribe to these shows.

Recent Guests

Matt Katsaros
Founder of Wildwood Investments; experienced developer and investor
Wildwood Investments LLC
Episode: Episode 461: Chicago Ground-Up Developments with Matt Katsaros
Gabby Gomez
Contestant featured in a sponsor-supported trivia segment
Episode: Episode 460: Who Should (and Shouldn't) Buy in Chicago Right Now?
John Preston
Real estate broker at Horvath & Tremblay
Horvath & Tremblay
Episode: Episode 459: North Side Neighborhoods and Market Opportunities with John Preston
Thad Wong
Founder of App Properties, guest speaker on real estate brokerage and market shifts
App Properties
Episode: Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)
Eric Workman
Lender, Renovo executive, broker/partner
Renovo
Episode: Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)
Daniela Rodriguez
Member of Workman Lending Team at Renovo
Renovo Workman Lending
Episode: Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)
Joe Smazal
Real estate broker with App Properties, Chicago market expert
App Properties
Episode: Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)
Anthony Flora
Broker with App Properties, Northwest Side specialist
App Properties
Episode: Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)
RJ de Leon
Renovo event host, broker network organizer
Renovo
Episode: Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)

Hosts

Tom Schellcross
Host of the show; leads conversations and anchors episodes.
Mark Ainley
Co-host; co-leads episodes and guest introductions.
Mark Ailey
Co-host; provides hosting duties and anchors discussions.

Reviews

5.0 out of 5 stars from 428 ratings
  • Learn Something with Every from Every Episode

    Tom & Mark are seasoned investors with a wealth of knowledge that they share with their listeners. Every episode I listen to, I learn things that I can apply to my portfolio. In addition, their guests share their experience which helps me avoid potential issues and motivates me to keep investing. This show is a must for new and seasoned income property professionals.

    Apple Podcasts
    5
    Imdb - find the movie
    United States2 months ago
  • Super informative podcast for Chicago real estate investors

    Mark and Tom put on a great podcast and do a really good job finding guests, spanning different asset types, and experience.

    Apple Podcasts
    5
    mputnick
    United States2 months ago
  • Investing in Chicago? Must listen

    Mark has so much information and experience in the Chicago market. This show is a must-follow!

    Apple Podcasts
    5
    stacey ss
    United States3 months ago
  • #1 Podcast about Chicago Real Estate

    Best podcast about insights on the Chicagoland real estate market and amazing hosts!

    Apple Podcasts
    5
    Hogggjbegf
    United States4 months ago
  • Great podcast

    Also full of good insights!

    Apple Podcasts
    5
    Butta s
    United States5 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners praise local focus, actionable advice, and useful guest perspectives.
The hosts share boots-on-the-ground Chicago knowledge with practical takeaways.
Guests bring diverse Chicago real estate expertise, from development to tax strategy.

Top Investing Podcasts

The Ramsey Show
The Ramsey ShowRamsey Network
Prof G Markets
Prof G MarketsVox Media Podcast Network
Financial Audit
Financial AuditCaleb Hammer
Wake Up to Wealth
Wake Up to WealthBrandon Brittingham
NerdWallet's Smart Money Podcast
NerdWallet's Smart Money PodcastNerdWallet Personal Finance
The MORE Show
The MORE ShowJustin Colby, Bleav, Justin Colby
Money Guy Show
Money Guy ShowBrian Preston and Bo Hanson

Talking Points

Recent interactions between the hosts and their guests.

Episode 457: Proactive Tax Planning Advice to Save on your 2026 Tax Returns
Q: What should investors be doing now to prepare for their 2026 returns?
Start by getting your March books in order, ensure the income statement and balance sheet are clean, document hours for real estate professional status, and schedule a planning call with a CPA to map out entity structure, deductions, and potential payments throughout the year to avoid December surprises.
Episode 459: North Side Neighborhoods and Market Opportunities with John Preston
Q: What one piece of advice would you give someone looking to buy their first property in Chicago?
Start talking to brokers, underwriting deals, and getting involved in local groups; identify what you like and don't like, and actively pursue deal underwriting and networking to build the necessary experience and connections.
Episode 459: North Side Neighborhoods and Market Opportunities with John Preston
Q: What's your competitive advantage and how have you built this in a tough market?
John attributes his competitive edge to relentless work ethic, willingness to fail and learn, consistent outreach, honing his market knowledge, and the ability to add value to owners by understanding each building's unique plan and factoring in neighborhood dynamics.
Episode 455: The Facts Behind The Red Hot Chicago Market with Jason Wagner
Q: What's your competitive advantage?
Jason Wagner explains that Greystone Realty's hands-on approach—owning and managing properties, investing personally, and having real-world experience—gives them a practical edge over purely traditional brokerages.
Episode 453: Breaking Down Chicagoland Syndications w/Duke Dennis & Bryan Sonn
Q: Why did you decide to move from residential to industrial, and what makes industrial attractive now?
Industrial offered higher long-term returns, lower perceived risk due to hedges like longer leases and tenant improvements, and Chicago's distribution footprint provides strong demand, giving a durable tailwind even as cap rates compress.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Straight Up Chicago Investor

What is Straight Up Chicago Investor about and what kind of topics does it cover?

This show delivers practical Chicago real estate insight through interviews with seasoned local investors, developers, and industry pros. Episodes center on navigating the Chicago market, off-market strategies, creative financing, policy and zoning developments, and hands-on lessons from hands-on practitioners. Listeners gain tactical takeaways on deal sourcing, due diligence, tax planning, renovation financing, and navigating regulatory hurdles, all rooted in Chicago neighborhoods and nearby suburbs. The format tends to feature deeply experienced guests sharing real-world journeys, win/loss stories, and scalable approaches, making it especially valuable for local operators, brokers, and property managers seeking actionable guidance. A nota... more

Where can I find podcast stats for Straight Up Chicago Investor?

Rephonic provides a wide range of podcast stats for Straight Up Chicago Investor. We scanned the web and collated all of the information that we could find in our comprehensive podcast database. See how many people listen to Straight Up Chicago Investor and access YouTube viewership numbers, download stats, audience demographics, chart rankings, ratings, reviews and more.

How many listeners does Straight Up Chicago Investor get?

Rephonic provides a full set of podcast information for three million podcasts, including the number of listeners. View further listenership figures for Straight Up Chicago Investor, including podcast download numbers and subscriber numbers, so you can make better decisions about which podcasts to sponsor or be a guest on. You will need to upgrade your account to access this premium data.

What are the audience demographics for Straight Up Chicago Investor?

Rephonic provides comprehensive predictive audience data for Straight Up Chicago Investor, including gender skew, age, country, political leaning, income, professions, education level, and interests. You can access these listener demographics by upgrading your account.

How many subscribers and views does Straight Up Chicago Investor have?

To see how many followers or subscribers Straight Up Chicago Investor has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

Which podcasts are similar to Straight Up Chicago Investor?

These podcasts share a similar audience with Straight Up Chicago Investor:

1. Real Estate Chicago Style Podcast
2. Lifetime Cash Flow Through Real Estate Investing
3. Real Estate Rookie
4. BiggerPockets Money Podcast
5. On The Market

How many episodes of Straight Up Chicago Investor are there?

Straight Up Chicago Investor launched 6 years ago and published 468 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Straight Up Chicago Investor?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

Where can I see ratings and reviews for Straight Up Chicago Investor?

Rephonic pulls ratings and reviews for Straight Up Chicago Investor from multiple sources, including Spotify, Apple Podcasts, Castbox, and Podcast Addict.

View all the reviews in one place instead of visiting each platform individually and use this information to decide if a show is worth pitching or not.

How do I access podcast episode transcripts for Straight Up Chicago Investor?

Rephonic provides full transcripts for episodes of Straight Up Chicago Investor. Search within each transcript for your keywords, whether they be topics, brands or people, and figure out if it's worth pitching as a guest or sponsor. You can even set-up alerts to get notified when your keywords are mentioned.

What guests have appeared on Straight Up Chicago Investor?

Recent guests on Straight Up Chicago Investor include:

1. Matt Katsaros
2. Gabby Gomez
3. John Preston
4. Thad Wong
5. Eric Workman
6. Daniela Rodriguez
7. Joe Smazal
8. Anthony Flora

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

Find and pitch the right podcasts

We help savvy brands, marketers and PR professionals to find the right podcasts for any topic or niche. Get the data and contacts you need to pitch podcasts at scale and turn listeners into customers.
Try it free for 7 days