

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 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.
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.
Episodes
Mentioned books

Oct 9, 2025 • 1h 6min
Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= Joe Smazal, Senior Managing Partner of Interra Realty, has over a decade of experience selling mid-market apartment buildings and recently surpassed $1 Billion in transaction volume! Joe kicks things off by sharing the genesis and overview of his “Real Estate Chicago Style Podcast”! He reflects on his career’s progression and highlights that have led him to crossing the $1 billion mark in total transaction volume. Joe dives deep on the market trends for Chicago’s North Side including prime neighborhoods like Lincoln Park and Lakeview. Joe closes with takeaways from some recent personal transactions and provides an optimistic outlook on the Chicago Real Estate market! 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: StraightUpChicagoInvestor@gmail.com Guest: Joe Smazal, Interra Realty Link: Joe Smazal - Interra Realty LLC | LinkedIn Link: Real Estate Chicago Style Podcast Link: SUCI Ep 156 - Joe Smazal Link: SUCI Ep 368 - Joe Smazal (NSBC Live Event) Link: Mark Wilczak (Inspector Referral) Link: Scott Weinstein (Field and Goldberg) Guest Questions 02:38 Housing Provider Tip - Understand rules and regulations around security deposits! 05:00 Intro to our guest, Joe Smazal! 07:10 Joe’s Real Estate Chicago Style Podcast! 15:25 Joe’s path to $1 Billion of Commercial RE sales. 23:11 Chicago market trends in 2025. 31:27 Navigating the Predominance of the Block (606) Ordinance. 49:50 Joe’s 5-year plan. 54:57 The outlook on Chicago! 58:29 What is your competitive advantage? 58:53 One piece of advice for new investors. 59:19 What do you do for fun? 59:51 Good book, podcast, or self development activity that you would recommend? 60:55 Local Network Recommendation? 62:09 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Oct 7, 2025 • 12min
Episode 404: Lending Options For Non-Owner Occupied Investors With Chris Puleo
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= What are my lending options for a non-owner occupied investor? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chris Puleo of Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Oct 2, 2025 • 50min
Episode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= Lantz Kurzawinski, Marketing Specialist for the Straight Up Chicago Investor Podcast, tells his story of grinding to succeed in real estate at an early age. Lantz explains how he recognized his entrepreneurial spirit at an early age and decided to dive into real estate. He shares his experience as a leasing agent and how that led him to discover his enjoyment for getting his hands dirty. Lantz gets granular on partnering on a few BRRRR deals and the value he brought to the partnership despite not having much liquidity! He shares insights on closing a house hack deal with a hilarious story about living in a “work in progress” basement apartment! Lantz demonstrates how hard work and bringing value to others is very much the key to succeeding in REI like other areas of life! 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: StraightUpChicagoInvestor@gmail.com Guest: Lantz Kurzawinksi, GC Realty & Development Link: SUCI Ep 253 - Jeff Nydegger Link: The Obstacle Is the Way (Book Recommendation) Link: Meditations (Book Recommendation) Link: Michael Procaccio (Network Referral) Guest Questions 02:49 Housing Provider Tip - Consider giving renters storage unit options to maximize your units’ appeal. 04:39 Intro to our guest, Lantz Kurzawinski! 12:56 Starting off as a leasing agent. 18:38 Lantz’s first deal! 23:06 Cranking through another BRRRR project and structuring partnerships. 28:00 House hacking in Jefferson Park! 40:30 Taking down deals in Itasca and Downers Grove. 46:51 What is your competitive advantage? 47:20 One piece of advice for new investors. 48:22 What do you do for fun? 48:28 Good book, podcast, or self development activity that you would recommend? 49:10 Local Network Recommendation? 49:41 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Sep 25, 2025 • 1h 1min
Episode 402: Looking At Chicago Investing Differently with Jason Wagner
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= Jason shares why he chose to invest in Chicago’s northwest side and how he’s achieved success in that area. He breaks down assumable loans and 2-1 buydowns including how these tools can be leveraged to improve an asset’s ROI! Jason discusses the power of the data he compiles in the Wagner Report and how investors can utilize it for a competitive edge. He closes with bullish remarks on Arlington Heights and powerful advice for new, aspiring investors! 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: StraightUpChicagoInvestor@gmail.com Guest: Jason Wagner, Greystone Realty Link: SUCI Ep 224 - Jason Wagner Link: Real Life Investing with Jason & Rachel Wagner (Podcast) Link: Wagner Report Link: The 5 Types of Wealth (Book Recommendation) Link: SUCI Ep 244 - Ryan Bakke Guest Questions 02:36 Housing Provider Tip - Ensure utilities are put back in your name in between tenant turnovers! 04:52 Intro to our guest, Jason Wagner! 10:53 Emerging neighborhoods and creative strategies for cash flow! 28:42 Ins and outs of assumable loans. 36:06 Insights on VA loan assumptions. 38:03 The background on Greystone Realty. 42:56 Housing market takeaways from the Wagner Report! 45:58 Opportunities in Arlington Heights. 50:26 Best of advice for aspiring real estate investors. 52:42 What is your competitive advantage? 53:07 One piece of advice for new investors. 53:20 What do you do for fun? 54:28 Good book, podcast, or self development activity that you would recommend? 56:19 Local Network Recommendation? 57:11 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Sep 23, 2025 • 13min
Episode 401: Interest Rates Are Coming Down According to Chris Puleo
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= Chris Puleo lays out tangible reasons why he feels interest rates will be coming down in the upcoming future. ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chris Puleo of Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Sep 18, 2025 • 1h 1min
Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= Kevin Rocio, founder of ROC Advisory Group, is an award winning commercial real estate broker, mentor, and investor. Kevin shares how he built a business and sphere of influence in the mortgage lending industry. He discusses his start in commercial real estate and gets granular on various valuation metrics. Kevin talks about the rapid growth of his business during and after the pandemic. He closes with explaining the importance of building a great reputation to set yourself up for success in this relationship-based business! 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: StraightUpChicagoInvestor@gmail.com Guest: Kevin Rocio, ROC Advisory Group Link: Kevin Rocio's Instagram Link: Crain's Chicago Business Link: SUCI Ep 296 - Moses Hall Link: Mike Levin (Network Referral) Guest Questions 04:09 Housing Provider Tip - Let insurance representatives know about property improvements to reduce your premium! 05:50 Intro to our guest, Kevin Rocio! 14:45 Transitioning out of mortgage lending after 17 years. 20:46 Starting in real estate brokerage in 2009. 33:16 Utilizing GRM for valuations. 34:51 Kevin’s business through and post COVID. 48:31 How to find a mentor! 52:32 Importance of marketing and building a reputation. 55:05 What is your competitive advantage? 55:32 One piece of advice for new investors. 56:08 What do you do for fun? 56:50 Good book, podcast, or self development activity that you would recommend? 58:18 Local Network Recommendation? 59:09 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Sep 11, 2025 • 1h 5min
Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= Micah White is a real estate coach with a proven track record of finding cash flowing real estate with great ROI! Micah starts by explaining the ins and outs of his first couple house hacks in Logan Square and North Lawndale. He provides great pointers on proper due diligence to mitigate risk on an investment. Micah shares a hilarious DIY story; moral of the story, hire a professional! He closes with valuable insights on structuring partnerships and building a track record to attract investors! 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: StraightUpChicagoInvestor@gmail.com Guest: Micah White, Brick by Brick Blueprint Link: Real Estate with Micah Link: Micah's Instagram Link: A Long Way Gone (Book Recommendation) Link: Shoe Dog (Book Recommendation) Link: Block Club Chicago Guest Questions 02:22 Housing Provider Tip - Remove window AC units to improve heat efficiency this winter! 03:45 Intro to our guest, Micah White! 14:31 Micah’s start in REI! 22:12 Due diligence on your first deal. 26:58 Bumping rents and stabilizing a building. 31:28 The DIY wax ring story! 37:27 Micah’s North Lawndale deal. 44:38 Structuring partnerships with investors. 53:20 Reputation building to attract investors. 57:22 What is your competitive advantage? 58:01 One piece of advice for new investors. 58:35 What do you do for fun? 59:45 Good book, podcast, or self development activity that you would recommend? 61:56 Local Network Recommendation? 62:17 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Sep 4, 2025 • 53min
Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= Paul de Luca of The Axon Group joins us to provide great insights on leveraging house hacking to grow a portfolio and how to succeed as an investor-friendly real estate agent! Paul jumps right into the nitty gritty of his first couple house hack deals! He gives tips on getting off the ground as a new real estate agent and the 101 on Chicago non-conforming units. Paul shares how he handled various troublesome tenants and provides his take on emerging neighborhoods where he’s investing! Throughout the episode, Paul demonstrates how focus and taking action have been keys to his investing success! 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: StraightUpChicagoInvestor@gmail.com Guest: Paul de Luca, eXp Realty - The Axon Group Link: Paul's Instagram Link: Paul's BiggerPockets Link: SUCI Ep 354 - Jake Fugman & Mike Scanlon Link: 5 Types of Wealth (Book Recommendation) Link: On The Market (Podcast Recommendation) Link: Adam Gurney (Attorney Referral) Guest Questions 03:25 Housing Provider Tip - Consider the ROI on central HVAC! 05:08 Intro to our guest, Paul de Luca! 10:52 Reflecting on Paul’s first house hack. 13:45 Getting into house hack #2! 21:20 Getting started as a new real estate agent. 25:32 Valuing non-conforming units. 31:33 Handling problem tenants. 36:18 Neighborhood guide for investors! 42:35 Paul’s 5 year outlook! 48:48 What is your competitive advantage? 49:23 One piece of advice for new investors. 49:50 What do you do for fun? 50:00 Good book, podcast, or self development activity that you would recommend? 50:31 Local Network Recommendation? 50:55 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Sep 2, 2025 • 21min
Episode 397: When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property?
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= What are the "do's" and "don'ts" when filing an insurance claim? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Josh Steigelmann, State Farm Insurance Link: Investor Stories Featuring Sean Morrissey ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Aug 28, 2025 • 1h 9min
Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com 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 ============= Fernando Angelucci returns to the podcast to explain how he has rapidly grown his self storage business and the drivers behind increasing self storage demand! Fernando explains his marketing strategy to optimize deal flow despite the low inventory environment. He delves deep into the underwriting and feasibility studies performed on self storage investments to maximize returns. Fernando provides the 101 on various financing options and repositioning strategies for self storage investments. He closes with a motivating 5-year outlook including a detailed plan to reach financial independence! 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: StraightUpChicagoInvestor@gmail.com Guest: Fernando Angelucci, Self Storage Syndicated Equities Link: Fernando's Instagram Link: SUCI Ep 86 - Fernando Angelucci Link: Vagabonding (Book Recommendation) Link: SUCI Ep 392 - Cost Seg Kev Guest Questions 01:49 Housing Provider Tip - Be sure to perform maintenance on AC units after a long summer! 03:25 Intro to our guest, Fernando Angelucci! 06:41 Growing a portfolio in a low inventory market! 12:10 Feasibility studies on self storage projects. 16:44 Building a self storage investment team! 21:56 Financing self storage deals. 37:33 Repositioning a self storage investment. 47:57 Obtaining special use permits. 52:01 Ideal self storage projects! 55:23 Fernando’s 5-year outlook. 60:26 What is your competitive advantage? 62:55 One piece of advice for new investors. 63:32 What do you do for fun? 64:14 Good book, podcast, or self development activity that you would recommend? 64:48 Local Network Recommendation? 65:53 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.