Show overview
Straight Up Chicago Investor has been publishing since 2020, and across the 6 years since has built a catalogue of 465 episodes, alongside 3 trailers or bonus episodes. That works out to roughly 320 hours of audio in total. Releases follow a weekly cadence.
Episodes typically run thirty-five to sixty minutes — most land between 17 min and 56 min — with run-times ranging widely across the catalogue. None of the episodes are flagged explicit by the publisher. It is catalogued as a EN-language Business show.
The show is actively publishing — the most recent episode landed 5 days ago, with 41 episodes already out so far this year. Published by Mark Ainley and Tom Shallcross.
From the publisher
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 Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked and not worked in Chicago, you are in the right place.
Latest Episodes
View all 465 episodesEpisode 461: Chicago Ground-Up Developments with Matt Katsaros
Episode 460: Who Should (and Shouldn't) Buy in Chicago Right Now?
Episode 459: North Side Neighborhoods and Market Opportunities with John Preston
Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)
Episode 457: Proactive Tax Planning Advice to Save on your 2026 Tax Returns
Episode 456: Inside Chicago's Commercial Lending Landscape w/ Asher Motew and Quinn Keenan
Episode 455: The Facts Behind The Red Hot Chicago Market with Jason Wagner
Episode 454: How To Assign Contracts Like a Pro with Chance Badertscher
Episode 453: Breaking Down Chicagoland Syndications w/Duke Dennis & Bryan Sonn
Episode 452: Crazy Stories of Off-Market Real Estate Deals with Igor Mike Kajpust
Episode 451: Leveraging the Big Beautiful Bill to Minimize Tax Exposure
Episode 450: Alderman Bennett Lawson & The 44th Ward
Episode 449: Zero to Thirty Units Creatively with Mike Scanlon
Episode 448: Understanding the CAR 8.0 Real Estate Contract with Chance Badertscher
Episode 447: Dan Nelson Chicago Investment Minded Power Broker & Investor
Episode 446: Brendan McElhaney's Journey To Wholesaling Deal Flow
Episode 445: Understanding 2-4 Unit Appraisals
Ep 444Episode 444: Leveraging Tax Strategy to Boost ROI with Ryan Bakke
Ryan Bakke turns to discuss the power of smart business acquisitions and tax strategy to skyrocket returns and keep more money in your pocket! Ryan starts by reminding us the tax benefits of short-term rentals and real estate professional status. He explains the process of buying businesses including defining a buy box, identifying opportunities, and improving operations upon acquisition. He dives deep on lessons learned from operating businesses and tips on how to improve efficiencies through off-shore staffing. The show closes with great insights on assessing return on equity and investment to ensure your capital is working as hard as possible. If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guests: Ryan Bakke, Tax Strategy 365 Link: SUCI Ep 244 - Ryan Bakke Link: Ryan's Instagram Link: Influence (Book Recommendation) Link: SUCI Investor Meetups Page Guest Questions: 01:24 Housing Provider Tip - Understand the maintenance and life span of hot water heaters. 03:34 Intro to our guest, Ryan Bakke! 06:42 Leveraging short-term rentals for tax benefits. 11:26 Efficiently delegating to grow your business. 22:37 How to hire off-shore employees. 28:32 The process of buying a business. 32:03 Defining a "buy box" for a business. 39:07 Lessons learned from buying businesses. 46:08 Ryan's take on ROI and Chicago's future! 53:28 What is your competitive advantage? 53:37 One piece of advice for new investors. 53:46 What do you do for fun? 53:59 Good book, podcast, or self development activity that you would recommend? 54:17 Local Network Recommendation? 54:35 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.
Ep 443Episode 443: Adaptive Reuse & Ground Up Development with Adam Friedberg
Adam Friedberg, CEO of Mavrek Development, joins us to discuss the ins and outs of large-scale developments in Chicago. Adam starts by explaining how he started in real estate and hustled early on to learn development and value-add construction. He breaks down pitching development deals to investors and various methods for raising money. Adam talks about projects during COVID and how his team pivoted given the unforeseen circumstances. He gets granular on how to most efficiently cut construction costs without negatively impacting the quality of the final product. In typical SUCI fashion, Adam explains why he is doubling down on Chicago investments and why you should too! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guests: Adam Friedberg, Mavrek Development Link: Adam's LinkedIn Link: SUCI Ep 421 - Alec Greenberg Link: Abundance (Book Recommendation) Link: Crain's Chicago Guest Questions: 01:50 Housing Provider Tip - Simplify property management by setting expectations! 03:16 Intro to our guest, Adam Friedberg! 06:41 How to learn value-add construction in real estate. 10:35 Taking down commercial projects in Oak Park. 23:18 Pitching large development deals to investors! 27:10 Lessons learned from developments in 2020. 30:53 Acquiring The Saint Grand development. 37:20 Getting lean on construction costs. 44:14 Upcoming Mavrek developments! 55:31 Adam's bullish outlook on Chicago! 57:53 What is your competitive advantage? 58:00 One piece of advice for new investors. 58:15 What do you do for fun? 58:53 Good book, podcast, or self development activity that you would recommend? 59:34 Local Network Recommendation? 60:33 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.