Straight Up Chicago Investor

Straight Up Chicago Investor

Business EN ↓ 468 episodes

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...

Author

Straight Up Chicago Investor

Category

Business

Latest episode

Jul 9, 2026

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Episodes

Episode 243: A New Chicago Lending Option to Assist With Rehab Funding 12.09.2023

What is this new lending option that could finance my rehab funds? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Perry Farella , First Community Mortgage ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Episode 242: From Rookie Status to Seasoned House Hacker, Flipper, and BRRRR Conductor on Chicago's Northwest Side with Manny Escarpita 07.09.2023

Manny Escarpita is a young Chicago Real Estate Investor and Licensed General Contractor who has built up an impressive real estate portfolio since starting in 2019!  Manny leads by explaining the hungry mindset he cultivated when starting in real estate and the lessons learned on his first deal. After discussing his first couple house hacks, he breaks down a successful BRRRR project that ultimatel...

Episode 241: Game-Changing Appraisal Insights with Steve Zidek 31.08.2023

Steve Zidek has nearly two decades of real estate experience as a broker and appraiser! Steve kicks off with how he got into the appraising business and breaks down the appraisal process! He gets granular on adjustments that may or may not be considered and speaks to the "art" components of an appraisal. Steve discusses how income factors into residential appraisals and even throws in a crazy appr...

Episode 240: What is Going On In the Chicago Multifamily Market? 29.08.2023

What is Going On In the Chicago Multifamily Market? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Jordan Gottlieb , Essex Realty Group ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Episode 239: Cook County's New Program To Reduce Your Assessed Value and Maximize Profitability with Cook County Assessor Fritz Kaegi and CIC's Stacie Young 24.08.2023

Assessor Kaegi and Stacie Young explain how the Assessor's Office and CIC created a program to incentivize affordable housing providers! To kick things off, Assessor Kaegi explains how properties are assessed in Illinois and Stacie shares the history of the Class 9 Program. They then break down the Affordable Housing Special Assessment Program including how it works, the increased profits for part...

Episode 238: Dissecting 20 Years of Real Estate and Lending Experience; Mike Facchini's Journey to a Thriving Portfolio in Chicago 17.08.2023

Mike Facchini of Fairway Mortgage is a Mortgage Lender and Investor with over 20 years of real estate experience! Mike starts with insights on the real estate environment leading up to the Housing Crash and compares it to today's market! He drops golden nuggets on indicators by the lending industry that precede and foreshadow what is to come in the economy. Mike shares his investment strategy and...

Episode 237: Mastering the Maze: 5 Savvy Tactics to Conquer the High-Interest rate, Low-Inventory Real Estate Market with Perry Farella 15.08.2023

How do you navigate a low inventory & higher interest rate environment? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Perry Farella , First Community Mortgage ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Episode 236: Grinding and Unlocking Success in Chicago's West Town Neighborhood with Alex Morsch 10.08.2023

Alex Morsch of Peak Realty is a Commercial Broker and Investor with vast experience in repositioning assets in West Town.  Alex starts by discussing the grind of being a leasing agent and transitioning to brokering real estate! He lays out his experience walking 100 buildings prior to making his first purchase and the valuable lessons gained through that process. Alex breaks down how his "nose to...

Episode 235: Exploring Portage Park; An Interview With Special Guest and Straight Up Chicago Investor Podcast Co-Host Tom Shallcross 03.08.2023

Mark is flying solo as co-host this week as he interviews a very special guest; flipper, investor, and fellow SUCI podcast co-host Tom Shallcross! Mark takes a different spin to start the show by asking Tom about his childhood and upbringing in Portage Park! Tom talks about the differences between Jefferson and Portage Park. Tom breaks down Portage Park at a street-level including the lesser and m...

Episode 234: How To Get Deals Done in Today's Environment 01.08.2023

What are successful investors doing to make deals happen in the current investor? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Eric Workman, Renovo Financial Link:

Episode 233: Navigating Chicago's North Side: Insights from Commercial Real Estate Expert Alan Goldberg 27.07.2023

Introduction: Meet Alan Goldberg, a titan in the Chicago real estate scene, with a career spanning decades. Alan's journey began in the late 70s when he made his very first deal in the world of real estate. Prospecting and Generating Business: Alan sheds light on his early days and discusses the importance of prospecting to drive business growth. Learn how Alan's proactive approach to seeking out...

Episode 232: Chicago Real Estate in the 1970s vs 2020s with Veteran Broker Jerry Ettinger 20.07.2023

Jerry Ettinger of Ettinger Realty joins us to share jewels of wisdom accumulated over roughly 50 years in the real estate industry! Jerry kicks off with how he transitioned from being a teacher to real estate agent back in the 70s! He talks about Rogers Park and other North Side Neighborhoods and how they have changed over the years. Jerry shifts south and talks about his investments in Hyde Park!...

Episode 231: Proactive Maintenance Techniques for Brick Buildings 18.07.2023

What proactive maintenance should I be doing to my building? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests:

Episode 230: How Interning for Brandon Turner Helped BrightInvestor's Co-Founder Drew McCluskey Revolutionize Market Research 12.07.2023

Drew McCluskey is an active real estate investor, previous intern of BiggerPockets' Brandon Turner, and Co-Founder of BrightInvestor; a data visualization software helping investors streamline market research! Drew leads off with a horror story on his first deal; a rehab on a 4-unit building! He jumps into how he leveraged the opportunity to meet and provide value to Brandon Turner which led to an...

Episode 229: From Roofing to Real Estate: Ivan and Jackie Hernandez's Journey to Success in Chicago's Southwest Side 06.07.2023

Ivan and Jackie Hernandez discuss their journey from a  thriving roofing business to a real estate portfolio on Chicago's Southwest side! Ivan and Jackie lead off with their start in the entrepreneurial realm and how they started their roofing business. They discuss starting their real estate investing in Englewood and expanding further west into Gage Park, Brighton Park, and Marquette Park. They...

Episode 228: The Chicago Guide to Evaluating Brick Buildings 04.07.2023

How do I know if my building is in need of masonry work? Connect   with Mark and Tom:   StraightUpChicagoInvestor.com Email the Show:   StraightUpChicagoInvestor@gmail.com Guest: Les O'Hara, North Shore Brickwork  Sponsors: North Shore Brickwork  ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Episode 227: Unlocking Success As a Top-Producing Realtor and Expert in Wheaton with Michael Thornton 29.06.2023

Michael Thorton of Compass leads a top producing real estate team serving Wheaton and surrounding Chicago suburbs!  Michael kicks things off with a topic many of us have likely considered; leaving a W2 job to become an entrepreneur and start a business! He explains the challenges of getting the ball rolling and identifies low-hanging fruit that new agents can target to jump start their business. M...

Episode 226: Unlocking Off-Market Deals Using Rescover's Analysis Platform for Maximum ROI with Ben Smith and Kristen Lopez 22.06.2023

Ben Smith and Kristen Lopez break down how Rescover's All-in-One Analysis Platform can be your competitive edge to find off-market deals and maximize your ROI! Ben and Kristen lead off with the basics and low-hanging fruit investors must be aware of when planning an off-market property campaign. They discuss the power of leveraging resources; from utilizing Rescover and skip tracing to implementin...

Episode 225: A Dive Into Current and Future Interest Rates with Chris Puleo 20.06.2023

What will interest rates do over the next 6-12 months? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chris Puleo , Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo Sponsors:  Puleo Group -----------------   Production House:  Flint Stone Media Copyright of Straight Up Chic...

Episode 224: Expert Insights On Chicago's Northwest Side with Jason Wagner 15.06.2023

Jason Wagner is the Managing Broker of Greystone Realty; a brokerage where every agent is also an investor. If you don't already know, Jason is a huge proponent of 75 Hard, and he explains the program and the amazing impact it's had on his life! He breaks down how he started and continues to invest in Portage Park and Jefferson Park. Jason dives deep into the housing supply shortage, recent trends...

Episode 223: From New York to the Windy City - Curtis Lefebvre's Real Estate Journey and Success in East Garfield Park 08.06.2023

Curtis Lefebvre shares why he left New York for the Windy City to start investing in Real Estate! Curtis jumps right in by getting granular on acquiring and stabilizing his first househack in East Garfield Park. He discusses everything from dealing with problem tenants to DYI'ing renovations. He dives into the numbers of his killer househack which allows him to not only live for free, but also cas...

Episode 222: Essential Insights - 5 Must-Address Items in Your Attorney Review Letter - Expert Advice with Chance Badertscher from Lavelle Law" 06.06.2023

What Are Five Items Every Investor Should Address in Their Attorney Review Letter? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest:   Chance Badertscher, Lavelle Law Sponsors: Lavelle Law ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Episode 221: Unveiling Real Estate Market Insights - The Mad Scientist of Multifamily, Neal Bawa, Shares Data Trends and Future Outlook! 01.06.2023

The Mad Scientist of Multifamily, Neal Bawa, returns to the show to share the latest data trends and his outlook on the Real Estate market! Neal jumps right in by summarizing changes in the real estate market over the last 18 months. He explains how his underwriting has changed as a result of market conditions. Neal gives a warning to those investing in office-space and talks about the challenges...

Episode 220: A Seasoned Investor's Journey in Chicago Real Estate - Insights, Strategies, and Neighborhood Outlook with Baris Yuksel 25.05.2023

Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Baris Yuksel, Supreme Capital Link: Multifamily Insights Podcast Link: Baris' LinkedIn Link: John Warren SUCI Ep 196 (Network Referral) Sponsors: Pentwater Cabinetry and  Essex Realty Group ----------------- Guest Questions 03:25 Housing Provider Tip: Understand Gross vs Net Income w...

Episode 219: The Focus of Chicago's NBOA in 2023 and Why Housing Providers Should Take Notice 23.05.2023

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