Straight Up Chicago Investor-logo

Straight Up Chicago Investor

Business & Economics Podcasts

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.

Location:

United States

Description:

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.

Language:

English


Episodes
Ask host to enable sharing for playback control

Episode 402: Looking At Chicago Investing Differently with Jason Wagner

9/25/2025
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.

Duration:01:01:02

Ask host to enable sharing for playback control

Episode 401: Interest Rates Are Coming Down According to Chris Puelo

9/23/2025
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.

Duration:00:13:21

Ask host to enable sharing for playback control

Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio

9/18/2025
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.

Duration:01:01:24

Ask host to enable sharing for playback control

Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White

9/11/2025
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.

Duration:01:05:07

Ask host to enable sharing for playback control

Episode 396: House Hacking Your Way to Lasting Wealth with Paul de Luca

9/4/2025
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.

Duration:00:53:20

Ask host to enable sharing for playback control

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?

9/2/2025
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.

Duration:00:21:14

Ask host to enable sharing for playback control

Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci

8/28/2025
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 Guests: 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.

Duration:01:08:56

Ask host to enable sharing for playback control

Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew

8/21/2025
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 ============= Max Motew, Director of Leasing at Mo2 Properties, joins us to share great insights on acquiring, renovating, and stabilizing small multifamily properties in Chicago’s north side! Max jumps right in by sharing top considerations when renovating Chicago landmarked properties! He talks about the importance of knowing your market to accurately project rents and pro-formas. Max gets granular on leasing including tips for screening out fraudulent applicants and best marketing practices. Throughout the episode, Max emphasizes the importance of having great relationships with tenants and being an expert in your geographical area of focus as keys to 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 Guests: Max Motew, Mo2 Properties Link: Max's LinkedIn Link: SUCI Ep 372 - Kevin Schnell Link: Neighborhood Building Owner's Alliance - Chicago Guest Questions 02:05 Housing Provider Tip - Take action and jump into real estate! 03:23 Intro to our guest, Max Motew! 07:10 Considerations on landmarked buildings. 14:04 Making deals “pencil” in today’s market. 23:36 Projecting rents and pro-formas! 32:55 Optimizing lease renewals. 43:15 Common leasing mistakes to avoid! 50:08 Screening best practices. 55:57 Up and coming Chicago neighborhoods! 61:18 What is your competitive advantage? 62:25 One piece of advice for new investors. 62:48 What do you do for fun? 63:30 Good book, podcast, or self development activity that you would recommend? 64:09 Local Network Recommendation? 64:37 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.

Duration:01:07:14

Ask host to enable sharing for playback control

Episode 394: The Legal Nuances of Different Real Estate Partnership Structures

8/19/2025
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 do investors need to consider from a legal perspective when setting up new partnerships? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Bibek Das, Das Law ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:13:19

Ask host to enable sharing for playback control

Episode 393: Chicago Veterans’ Guide to Real Estate Success with DuBois Toy

8/14/2025
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 ============= DuBois Toy is a seasoned real estate investor, veteran, and cybersecurity analyst who has a passion for helping veterans maximize their real estate benefits! DuBois kicks things off by discussing his start in real estate which involved a house hack and dealing with an eviction! He breaks down the rent-by-the-room strategy as a tool to maximize ROI. DuBois dives deep on VA loans, tax exemptions, and various other powerful real estate tools available to veterans! From leveraging AI for deal searching to veteran resources, this show is full of invaluable insights that you won’t want to miss! 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 Guests: DuBois Toy, Trading Technologies Link: DuBois' Facebook Link: Cook County Veterans with Disabilities Exemption Link: Cook County Returning Veterans Exemption Link: Andrew Dorazio's Veterans Real Estate Meetup Link: Academy of Ideas (YouTube Channel) Link: Meditations (Book Recommendation) Guest Questions 02:17 Housing Provider Tip - Understand rental license and inspection requirements in the suburbs! 04:00 Intro to our guest, DuBois Toy! 08:31 The future of tech in real estate! 15:49 DuBois’ background and start in real estate. 24:27 House hacking and dealing with an eviction in Oak Park! 29:27 Leveraging rent by the room strategy. 35:58 Educating veterans on VA loan benefits! 41:26 Revealing DuBois’ growth strategy! 49:09 DuBois’ bullish outlook on Chicago! 54:23 What is your competitive advantage? 55:03 One piece of advice for new investors. 55:41 What do you do for fun? 56:14 Good book, podcast, or self development activity that you would recommend? 57:20 Local Network Recommendation? 58:38 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.

Duration:01:01:28

Ask host to enable sharing for playback control

Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars

8/7/2025
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 Cawley, aka Cost Seg Kev, is a Senior Account Executive at CSSI Services - a firm with over 55,000 cost segregation studies completed since 2003. Cost Seg Kev starts by reviewing the 101 on cost segregation and how it can be used to offset your tax liability. He dives into the benefits of real estate professional status and recent tax code changes by the presidential administration. He also touches on frequently asked questions on cost segregation studies and closes with how he built his business and reputation! 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 Guests: Kevin Cawley, CSSI Services Link: CSSI Cost Segregation Calculator Link: SUCI Ep 59 - Cost Seg Kev Link: James Mahon (CPA Referral) Link: At Your Command (Book Recommendation) Guest Questions 02:46 Housing Provider Tip - Go above and beyond to acknowledge tenants after management mistakes. 05:00 Intro to our guest, Cost Seg Kev! 05:43 The 101 on Cost Segregation. 11:37 The benefits of real estate professional status! 25:42 Recent changes to depreciation rules. 32:15 Technical side of cost segregation! 34:23 Cost Seg on smaller properties. 43:43 What is your competitive advantage? 44:42 One piece of advice for new investors. 46:00 What do you do for fun? 46:37 Good book, podcast, or self development activity that you would recommend? 47:52 Local Network Recommendation? 48:55 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.

Duration:00:51:16

Ask host to enable sharing for playback control

Episode 391: Do You Have a Business Continuation Plan?

8/5/2025
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 ============= Josh Steigelmann explains the importance of a business continuation plan and provides step-by-step guidance on how investors can set-up a business continuation plan ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Josh Steigelmann, State Farm Insurance Link: Straight Up Chicago Investor Investor Stories Featuring Sean Morrissey ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:09:08

Ask host to enable sharing for playback control

Episode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims

7/31/2025
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 ============= Mitch Schoeneman is a Managing Partner at A. Schoeneman & Co. - a top rated Chicago public insurance adjusting firm that has been serving customers for over 55 years! Mitch starts by explaining the services rendered by insurance adjusters. He breaks down how investors can set themselves up for success with insurance claims and provides tactical steps for handling disastrous situations at properties. Mitch dives deep on insurance coverages, how investors can best protect themselves, and shares some wild insurance stories! This show is full of valuable insurance insights that you will want to put into practice! 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 Guests: Mitch Schoeneman, A. Schoeneman & Co | Email Mitch Link: Jimmy Sarnoff (Tax Appeal Attorney Referral) Guest Questions 03:14 Housing Provider Tip - Home insurance considerations to improve coverage and pricing! 04:56 Intro to our guest, Mitch Schoeonemen! 08:33 The value of insurance adjusters. 15:57 How investors can prepare for successful insurance claims. 21:17 Properly handling emergency situations at properties! 37:15 General timelines for insurance payouts. 45:00 Wild insurance stories! 53:39 What is your competitive advantage? 54:01 One piece of advice for new investors. 54:08 What do you do for fun? 54:59 Good book, podcast, or self development activity that you would recommend? 55:32 Local Network Recommendation? 55:53 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.

Duration:00:58:58

Ask host to enable sharing for playback control

Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec

7/24/2025
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 ============= Sebastian Mysliwiec, founder of The Dream Rentals, explains how he’s built a short-term and mid-term rental management company that delivers top guest experiences and maximizes profits! Sebastian talks about cutting his teeth and eventually thriving at a marketing company that helped build his real estate skill set. He provides tactical advice on underwriting, marketing, and managing short-term rentals (STRs). Sebastian explains how his team manages seasonality, shares a STR horror story, and top amenities for guests. He closes with remarks on refinancing considerations for STR properties and his team’s growth strategy. 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 Guests: Sebastian Mysliwiec, The Dream Rentals Link: The Dream Rentals Instagram Link: Skyscraper Tom's Instagram Link: The 12 Week Year (Book Recommendation) Guest Questions 01:58 Housing Provider Tip - Leverage Freedom of Information Act (FOIA) to request property info during due diligence! 04:25 Intro to our guest, Sebastian Mysliwiec! 08:31 Defining AirBnB arbitrage. 13:28 Underwriting basics of short-term rentals (STRs)! 20:10 Listing platforms for STRs. 26:09 Managing STR seasonality in Chicago to optimize profit. 35:36 STR Marketing Tips! 45:45 AirBnB Horror Story! 47:46 Top STR amenities. 49:23 Mid-Term Rental analysis and expanding to other markets! 55:13 Refinancing STR properties. 56:47 What is your competitive advantage? 57:15 One piece of advice for new investors. 57:42 What do you do for fun? 58:25. Good book, podcast, or self development activity that you would recommend? 58:54 Local Network Recommendation? 59:29 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.

Duration:01:02:15

Ask host to enable sharing for playback control

Episode 388: NBOA 2025 Summer Soiree Update

7/22/2025
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 is the NBOA Summer Soiree and how can investors benefit from this event? 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: Mike Glasser & Real Estate Nate, NBOA Link: Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:14:38

Ask host to enable sharing for playback control

Episode 387: This Is How You Make Money In Chicago In Your Early 20s with Alex Diaz

7/17/2025
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 ============= Alex Diaz explains how he left his day job as a barber to successfully flip and wholesale real estate for a living at 24 years of age! Alex starts by sharing how he made the jump from being a barber to wholesaling real estate. He explains how he acquired his first property; a househack sourced off-market! Alex provides tactical advice on marketing directly to sellers to create deal flow. He talks about lessons learned from flipping and gets granular on the real estate market in Aurora and the surrounding suburbs. This is another motivating show with an investor thriving at a young age! 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 Guests: Alex Diaz, Bluestone Property Solutions Link: Alex Diaz's Instagram Link: SUCI Ep 335 - Aram Ghazaryan Link: The Art of the Deal (Book Recommendation) Guest Questions 03:16 Housing Provider Tip - Maintain and understand misusage of water hose spigots! 05:09 Intro to our guest, Alex Diaz! 10:38 Alex’s first house hack sourced off-market! 14:24 Jumping into wholesaling and direct-to-seller marketing. 26:20 Marketing strategy and the 101 on Montgomery, IL. 29:11 Benefits of being around like-minded investors. 35:10 Lessons learned from flipping! 39:24 Alex’s geographic areas of focus. 44:06 What is your competitive advantage? 44:31 One piece of advice for new investors. 45:14 What do you do for fun? 45:31 Good book, podcast, or self development activity that you would recommend? 46:04 Local Network Recommendation? 46:23 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.

Duration:00:48:43

Ask host to enable sharing for playback control

Episode 386: How to Invest in DuPage County with Katie and Rob Hayes

7/10/2025
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 ============= Katie and Rob Hayes are investors and realtors with nearly 2 decades of experience acquiring and managing investment properties! The duo starts by sharing their background including investing in Florida before transitioning to the Chicago Western Suburbs. They share lessons learned from investing in lower cost areas and why they pivoted to higher class assets. Rob and Katie share golden nuggets on marketing to owners for deal flow and on operating short-term rentals. They close out with a positive outlet on Downer’s Grove and why investors should be considering it! 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 Guests: Katie and Rob Hayes, Platinum Partners Realtors Link: Team Hayes Realtors Facebook Link: Rob's LinkedIn Link: CAREIA Investor's Group Guest Questions 03:03 Housing Provider Tip - Utilize Starbucks gift cards to easily express gratitude towards tenants and vendors! 04:33 Intro to our guests, Katie and Rob Hayes! 09:54 Jumping from Florida to local investments! 14:30 Considerations when investing in lower price point areas. 17:45 Investments leading up to the housing crash. 23:47 Getting a real estate license during the housing crash. 29:05 Creating deal flow in a low inventory market. 34:40 Representing and adding value to buyers in this market. 39:17 Dialing back acquisitions and strategizing for retirement! 44:35 Short-term rentals in Chicago suburbs. 54:40 Advice for couples who invest together! 57:15 What is your competitive advantage? 58:31 One piece of advice for new investors. 59:45 What do you do for fun? 60:34 Good book, podcast, or self development activity that you would recommend? 61:42 Local Network Recommendation? 63:05 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.

Duration:01:06:44

Ask host to enable sharing for playback control

Episode 385: What is a Demand Letter and How to Handle Receipt of a Demand Letter

7/8/2025
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 ============= As an investor, how do I handle receipt of a demand letter? 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: Bibek Das, Das Law ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:16:24

Ask host to enable sharing for playback control

Episode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton

7/3/2025
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 ============= Jake Clopton, President of Clopton Capital, has successfully been running his commercial lending business for over 17 years. Jake shares how he grinded early in his career to get off the ground, and emphasizes the value of cold calling. He explains the different types of interest rates and provides the current state of rates. Jake speaks about macro-level economics including the stagflationary environment in today’s market. In typical SUCI fashion, he closes out with a bullish outlook on Chicago! 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: Jake Clopton, Clopton Capital Link: Jake Clopton's LinkedIn Link: Jake Clopton's Instagram Link: Never Split the Difference (Book Recommendation) Link: Elevate Energy (Network Referral) Guest Questions 02:07 Housing Provider Tip - Understand how to prioritize emergency work orders. 04:10 Intro to our guest, Jake Clopton! 12:20 Surviving as a lender during the real estate crash. 19:20 Jake’s “tipping point” deal! 20:21 The state of interest rates. 28:56 Rates on residential real estate. 34:04 Jake’s predictions on rates and the RE market! 41:53 The 101 on Stagflation. 43:50 Jake’s bullish remarks on Chicago! 48:05 What is your competitive advantage? 48:32 One piece of advice for new investors. 49:06 What do you do for fun? 49:17 Good book, podcast, or self development activity that you would recommend? 50:06 Local Network Recommendation? 51:40 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.

Duration:00:54:10

Ask host to enable sharing for playback control

Episode 383: From Chemist to Chicago’s “Bow Tie” Attorney w/Mahmoud Faisal Elkhatib

6/26/2025
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 ============= Mahmoud Faisal Elkhatib is an attorney with vast experience in real estate transactions, development, and litigation allowing him to bring huge value to his clients. Mahmoud gives his back story including time in the laboratory as a chemist and starting various businesses prior to landing into his current career as an attorney! He breaks down foreclosure defense and how he is going to bat for his clients. Mahmoud explains the roles of attorneys and Title Company personnel in a real estate transaction and how his unique fee structure allows his clients to save on fees. Throughout the show, Mahmoud conveys the importance of having a knowledgeable attorney in your corner in any real estate transaction! 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: Mahmoud Faisal Elkhatib, EV Has Link: Mahmoud's Instagram Link: No More Mr. Nice Guy (Book Recommendation) Link: The Subtle Art of Not Giving a F*ck (Book Recommendation) Link: Tammie Lester (Loan Officer Referral) Guest Questions 01:54 Housing Provider Tip - Understand new rules around HVAC to strategically maintain and repair systems! 03:18 Intro to our guest, Mahmoud Faisal Elkhatib! 06:40 How do foreclosure defense firms work? 10:33 Jumping to a new career despite being established in another career! 24:00 Breaking down the roles of Attorneys and Title Companies. 32:27 Mahmoud’s unique attorney fee structure. 38:58 Wild attorney stories! 49:05 Mahmoud’s next 5 years! 56:05 What is your competitive advantage? 56:23 One piece of advice for new investors. 57:00 What do you do for fun? 57:32 Good book, podcast, or self development activity that you would recommend? 58:17 Local Network Recommendation? 58:58 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.

Duration:01:01:32