Shows / Straight Up Chicago Investor
Straight Up Chicago Investor
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…
Episodes
Straight Up Chicago InvestorEpisode 488: Chicago New Construction Creating Housing with Andy Ahitow
Andy Ahitow, Co-Founder of City Pads and 25-year real estate veteran, joins us to share his journey from building and selling a leasing business to becoming a…
Straight Up Chicago InvestorEpisode 487: The State of The Chicago Market and The Top 5 Neighborhoods with Jason Wagner
What do investors need to know about the current Chicago market? ============= Guest: Jason Wagner, Greystone Realty, Real Life Investing with Jason Rachel…
Straight Up Chicago InvestorEpisode 486: Chicago House Flipping Thru Wholesaling, Subject-To, and Creative Financing with Oscar Medina
Oscar Medina of AMG Realty joins us to discuss his journey from wholesaling to a thriving fix-and-flip business at only 23 years old! Oscar starts by…
- Straight Up Chicago Investor
Episode 485: Investing & Managing In Lake County With Bill and Shannon Powers
Bill Powers, who first joined us back in Episode 6, returns with his daughter Shannon Powers to share how their real estate business has evolved since 2021!…
Straight Up Chicago InvestorEpisode 484: 3 Simple Steps To Find Deals in Today's Market with Mark Ainley
What simple steps I can take to find more deals in this market? ============= Guest: Mark Ainley of GC Realty and Co-host of Straight Up Chicago Investor…
Straight Up Chicago InvestorEpisode 483: Screening Pets in Rentals with John Bradford of Petscreening.com
John Bradford, founder of PetScreening.com, joins us to discuss pros, cons, and mitigating risks associated with having pets in rental properties! John jumps…
Straight Up Chicago InvestorEpisode 482: The Future of Pilsen and Chicago's 25th Ward with Miguel Chacon
Miguel Chacon, 25th Ward Aldermanic candidate and seasoned investor, joins us to discuss the past, present, and future of Pilsen and Chicago Housing Policy as…
Straight Up Chicago InvestorEpisode 481: Multiple Financing Options For Your Next Investment With Chris Puleo
What are the different financing products I can leverage as a Chicago investor? ============= Guest: Chris Puleo, Puleo Group Link: SUCI Build Your Team Link…
Straight Up Chicago InvestorEpisode 480: Senior Housing Sector: Underwriting, Markets, and Opportunities with Mark Myers
Mark Myers of Kiser Group joins us to share insights from over three decades of experience in senior housing investments and brokerage! Mark starts with how he…
Straight Up Chicago InvestorEpisode 479: Finding Cash Flow in Chicago's A Class Neighborhoods with David Shifrin
David Shifrin of Elite Properties Chicago returns to share how he has scaled his portfolio since his last SUCI podcast appearance in 2024! David opens up by…
Straight Up Chicago InvestorEpisode 478: The Proposed Move Act: Where Owners Can Transfer Their Existing Mortgage
What do investors need to know regarding the proposed legislation for both the Road To Housing and Move Act? ============= Connect with Mark and Tom…
Straight Up Chicago InvestorEpisode 477: Building an 80-Unit Portfolio in 2 Years with Arthur Barkan
Arthur Barkan of Barkan Realty joins us to share how he rapidly scaled his multifamily portfolio to 80 units! Arthur breaks down the ins and outs of investing…
Straight Up Chicago InvestorEpisode 476: Jake Rome on Leverage, Underwriting, and the Future of Real Estate Financing: How Backflip Is Revolutionizing Fix & Flip Lending
Jake Rome, co-founder of Backflip, joins us to share the wild journey from institutional real estate private equity to building a vertically integrated lending…
Straight Up Chicago InvestorEpisode 475: Leveraging 311 and Scattered Public Data Sources For Chicago Buildings with Jim McMahon
How can Property Sentinel help me as a Chicago building owner? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Jim McMahon…
Straight Up Chicago InvestorEpisode 474: Inside the NBOA Summer Soiree: Chicago Real Estate Advocacy, Networking, and Investor Lessons
We're taking Straight Up Chicago Investor on the road for a special live episode from the NBOA Summer Soiree! We catch up with some of Chicago's most active…
Straight Up Chicago InvestorEpisode 473: How AI is Changing Property Management with Pablo Gonzalez
Pablo Gonzalez of Vendoroo joins us to discuss how AI is changing the way real estate investors and property managers operate and scale their businesses!…
Straight Up Chicago InvestorEpisode 472: The 101 on Porch Issues and Repairs with Mr. Porch Frank Knight
How do I evaluate and fix a Chicago porch? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Frank Knight, Mr. Porch Link…
Straight Up Chicago InvestorEpisode 471: Progression Of Wholesaling to Investor with Mark Skowron
Mark Skowron of Festival Properties joins us to share top insights from his real estate journey which began back in 2010! Mark explains how he got started in…
Straight Up Chicago InvestorEpisode 470: 0-9 Unit Portfolio in Under Two Years with Hart Turner
Hart Turner joins us to share how he went from a career in Los Angeles to building a Chicago multifamily portfolio through house hacking and partnerships! Hart…
Straight Up Chicago InvestorEpisode 469: Different Scenarios That Require Builder's Risk Insurance With Josh Steigelmann
What is Builders risk insurance and as an investor when do I need this policy? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest…
Straight Up Chicago InvestorEpisode 468: Scaling a Wholesale Business Quickly with Eric Field
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…
Straight Up Chicago InvestorEpisode 467: Lessons from Mark Ainley's Real Estate Deals Over the Last 30 Months
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…
Straight Up Chicago InvestorEpisode 466: How the Government Can Stop Your Insurance Claim with Josh Steigelmann
Can the government stop my insurance claim? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Josh Steigelmann, State Farm…
Straight Up Chicago InvestorEpisode 465: Pat Hynes Is Bringing Transparency to the Cook County Assessor's Office
Newly elected Cook County Assessor Pat Hynes joins us to share his plan for bringing fair, accurate, and predictable property assessments! Pat starts by…
Straight Up Chicago InvestorEpisode 464: Ownership Fraud in West Town: Tom Shallcross and the $1.6 Million Fight to Unwind
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…
Straight Up Chicago InvestorEpisode 463: Inside Chicago's Proposed Rental Overhaul
More Tenant Protections... Less Housing? Breaking Down Chicago's New RLTO ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike…
Straight Up Chicago InvestorEpisode 462: Back Of The Yards Community with Ignacio Gonzalez
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…
Straight Up Chicago InvestorEpisode 461: Chicago Ground-Up Developments with Matt Katsaros
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…
Straight Up Chicago InvestorEpisode 460: Who Should (and Shouldn't) Buy in Chicago Right Now?
Mark and Tom discuss the current fundamentals of the Chicago market with statistics provided by Jason Wagner. ============= Connect with Mark and Tom…
Straight Up Chicago InvestorEpisode 459: North Side Neighborhoods and Market Opportunities with John Preston
John Preston of Horvath & Tremblay joins us to discuss opportunities in multifamily and mixed-use assets on Chicago's North Side! John begins by discussing…
Straight Up Chicago InvestorEpisode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)
Tom and Mark interview some of Chicago's Brightest Real Estate Stars during a Renovo Networking Event featuring an interview of Thad Wong! Discussions range…
Straight Up Chicago InvestorEpisode 457: Proactive Tax Planning Advice to Save on your 2026 Tax Returns
What steps should I take to best prepare for my 2026 tax returns? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Aaron…
Straight Up Chicago InvestorEpisode 456: Inside Chicago's Commercial Lending Landscape w/ Asher Motew and Quinn Keenan
Asher Motew and Quinn Keenan of Essex Capital Markets break down keys to their early career success in the Chicago Commercial Lending Market! Asher and Keenan…
Straight Up Chicago InvestorEpisode 455: The Facts Behind The Red Hot Chicago Market with Jason Wagner
Jason Wagner, Managing Broker of Greystone Realty, returns to discuss the state of the Chicago Real Estate market and the power of buy and hold investments…
Straight Up Chicago InvestorEpisode 454: How To Assign Contracts Like a Pro with Chance Badertscher
What do I need to be aware of when assigning a contract? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Chance Badertscher…
Straight Up Chicago InvestorEpisode 453: Breaking Down Chicagoland Syndications w/Duke Dennis & Bryan Sonn
Duke Dennis and Bryan Sonn of GC Realty & Development join us to explain the ins and outs of Chicagoland Industrial Investments! Duke and Bryan explain how…
Straight Up Chicago InvestorEpisode 452: Crazy Stories of Off-Market Real Estate Deals with Igor Mike Kajpust
Igor Mike Kajpust, president of Evolved Property Group, shares his REI journey which started at 17 years of age and spans across multiple states! Igor breaks…
Straight Up Chicago InvestorEpisode 451: Leveraging the Big Beautiful Bill to Minimize Tax Exposure
What do real estate investors need to know about the Big Beautiful Bill? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Aaron…
Straight Up Chicago InvestorEpisode 450: Alderman Bennett Lawson & The 44th Ward
Alderman Bennett Lawson discusses historical developments in his 44th Ward and how that success can be applied across the City of Chicago! Alderman Lawson…
Straight Up Chicago InvestorEpisode 449: Zero to Thirty Units Creatively with Mike Scanlon
Mike Scanlon of the Axon Group returns to share his personal real estate journey with several insights on how he has reached his success! Mike starts by…
Straight Up Chicago InvestorEpisode 448: Understanding the CAR 8.0 Real Estate Contract with Chance Badertscher
What are the main differences in the 8.0 CAR contract vs the previous 7.0? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Chance…
Straight Up Chicago InvestorEpisode 447: Dan Nelson Chicago Investment Minded Power Broker & Investor
Dan Nelson is a real estate agent and investor with over 2 decades of experience flipping properties and buying rentals! Dan jumps right in by explaining his…
Straight Up Chicago InvestorEpisode 446: Brendan McElhaney's Journey To Wholesaling Deal Flow
Brendan McElhaney, founder of Cash for Chicago Houses, is a real estate wholesaler and investor who specializes in sourcing off-market deals through…
Straight Up Chicago InvestorEpisode 445: Understanding 2-4 Unit Appraisals
How do I best prepare for an upcoming appraisal? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Tom & Mark, Straight Up Chicago…
Straight Up Chicago InvestorEpisode 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…
Straight Up Chicago InvestorEpisode 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…
Straight Up Chicago InvestorEpisode 443: Adaptive Reuse & Ground Up Development with Adam Friedberg (VIDEO)
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…
Straight Up Chicago InvestorEpisode 442: How To Identify and Execute on Assumable Loans with Michael Scanlon
What is the process for assuming a VA or FHA loan? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Scanlon, The Axon Group…
Straight Up Chicago InvestorEpisode 441: Chicago's Josh Bandoch Using Neuroscience to Win Negotiations
Josh Bandoch is the Head of Policy at the Illinois Policy Institute, TED Talk Speaker, and Author who joins to discuss his new book, How to Get What You Want!…
Straight Up Chicago InvestorEpisode 441: Chicago's Josh Bandoch Using Neuroscience to Win Negotiations (VIDEO)
Josh Bandoch is the Head of Policy at the Illinois Policy Institute, TED Talk Speaker, and Author who joins to discuss his new book, How to Get What You Want!…
Straight Up Chicago InvestorEpisode 440: Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati
Jay Patel and Tedi Nati of JP Acquisitions join us to explain how they've leveraged mentors and discipline to build a sizable multifamily portfolio on…
Straight Up Chicago InvestorEpisode 439: The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm
What do investors need to be aware of when taking on a 203k or Homestyle Renovation loan? ============= Connect with Mark and Tom…
Straight Up Chicago InvestorEpisode 438: Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik
Samuel Pavlovcik of the Pavlovcik Architecture returns to explain opportunities brought by the expanded city-wide Additional Dwelling Unit (ADU) Ordinance!…
Straight Up Chicago InvestorEpisode 437: Energy Efficiency in Chicago Real Estate with Joe Konopacki
Joe Konopacki, Founder and CEO of Insight Property Services, is a seasoned home inspector with various professional certifications on Building Performance and…
Straight Up Chicago InvestorEpisode 436: Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel
What are the upcoming elections that every investor should be aware of, and what's this dinner with Rahm Emanuel I heard about? ============= Connect with Mark…
Straight Up Chicago InvestorEpisode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas
Gil Villegas is the alderperson of Chicago's 36th ward and has focused on generating opportunities for economic and business development to best serve the…
Straight Up Chicago InvestorEpisode 434: Interesting Lease Renewal Statistics and Strategies with Mark Ainley
What are the common mistakes made when handling lease renewals? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley…
Straight Up Chicago InvestorEpisode 433: Chicago Building Code Violations with Zack Limbaugh
Zack Limbaugh of the Limbaugh Law Firm returns to dive deep on code violations including top pitfalls to avoid! Zack starts by explaining the 101 on buying…
Straight Up Chicago InvestorEpisode 432: Strategic Chicago House Hacking with Zach Posey
Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career! Zach starts off…
Straight Up Chicago InvestorEpisode 431: What You Need To Know About Real Estate Professional Status with Mike Procaccio
What is real estate professional status and why is it important for investors? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest…