

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

Aug 10, 2023 • 1h 1min
Episode 236: Grinding and Unlocking Success in Chicago's West Town Neighborhood with Alex Morsch
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 the ground" approach to investment property acquisition has allowed him to add immense value to his clients and succeed as a broker. He also drops wisdom on house hacking, the West Town neighborhood, and creating opportunities in a tight inventory market. Alex closes with a bullish 5 year outlook on Chicago Real Estate! 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 Morsch, Peak Realty Link: Alex's Instagram Link: Rich Anselmo (Network Referral) ----------------- Guest Questions 02:24 Housing Provider Tip: Check the faucet aerator when troubleshooting low water pressure! 03:56 Intro to our guest, Alex Morsch! 07:33 The grind of being a leasing agent. 12:52 Transitioning from leasing to a commercial broker! 16:30 Walking properties to gain experience. 26:38 Alex's first investment! 37:57 The reality of House Hacking. 42:25 Breaking down the West Town neighborhood! 49:10 Finding deals and creating opportunities. 54:27 Alex's 5 year outlook on Chicago Real Estate! 55:18 What is Alex's competitive advantage? 55:35 One piece of advice for new investors. 55:53 What do you do for fun? 56:12 Good book, podcast, or self development activity that you would recommend? 57:05 Local Network Recommendation? 57:35 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Aug 3, 2023 • 57min
Episode 235: Exploring Portage Park; An Interview With Special Guest and Straight Up Chicago Investor Podcast Co-Host Tom Shallcross
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 more desirable pockets, rents and property values, and schools in the neighborhood! To close the show, Tom shares powerful words on committing to succeeding in real estate and encourages listeners to leverage all the SUCI resources that he and Mark have put out! 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: Tom Shallcross, Straight Up Chicago Investor Link: The Road Less Stupid (Book Recommendation) Link: The Ruthless Elimination of Hurry (Book Recommendation) Link: Chicago's ADU Ordinance - What Investors Need to Know ----------------- Guest Questions 01:00 Housing Provider Tip: Ensure you're adding sewer backup to your insurance policy. 02:51 Intro to our guest, Tom Shallcross! 04:02 What was young Tom like? 10:58 Portage Park vs Jefferson Park. 12:01 Breaking down Portage Park! 21:04 The original Six Corners! 28:14 Schools in Portage Park. 29:40 Tom's investment strategy. 35:32 Price points in Portage Park. 37:42 Opportunities for Additional Dwelling Units (ADUs)! 41:53 Rent Values in Portage Park. 49:29 What is Tom's competitive advantage? 50:07 One piece of advice for new investors. 50:16 What do you do for fun? 51:40 Good book, podcast, or self development activity that you would recommend? 53:01 Local Network Recommendation? 53:51 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Aug 1, 2023 • 19min
Episode 234: How To Get Deals Done in Today's Environment
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 Sponsors: Renovo Financial Link: SUCI Episode #19 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jul 27, 2023 • 1h
Episode 233: Navigating Chicago's North Side: Insights from Commercial Real Estate Expert Alan Goldberg
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 potential clients and opportunities helped him build a successful real estate career. Tackling Tough Real Estate Market Cycles: Over the years, Alan has weathered through various market cycles and shares his insights on the toughest ones in the last 50 years. Discover how he navigated through challenging times and the lessons learned from overcoming difficult markets. Transformations in Rogers Park, Uptown, and Surrounding Neighborhoods: Alan takes a deep dive into the history of neighborhoods like Rogers Park, Uptown, and more, shedding light on their significant transformations over the years. Gain valuable insights into the potential for investment in these evolving areas. A Bullish Outlook on the Future: Looking ahead, Alan shares his optimistic outlook for the commercial real estate market in Chicago's North Side. Learn about the factors driving this bullish sentiment and the opportunities that lie ahead. The Power of Real Estate as an Investment Vehicle: Throughout the episode, Alan emphasizes the potency of real estate as an investment vehicle. Gain valuable knowledge on how real estate can build wealth over time and why it remains a compelling option for investors. Time Is Your Biggest Asset: Alan hammers home the importance of patience and strategic decision-making in real estate investing. Explore why "time is your biggest asset" and how to harness it to maximize your real estate investments. Conclusion: We'd like to extend our heartfelt thanks to Alan Goldberg for sharing his invaluable experiences and insights with us today. Don't forget to subscribe to Real Estate Uncovered for more episodes featuring experts and thought leaders in the real estate industry. 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: Alan Goldberg, Alan Goldberg Real Estate LLC Link: NBOA / Mike Glasser (Network Referral) Link: Glenwood Ave Arts Fest Link: Rogers Park Builders Group ----------------- Guest Questions 02:30 Housing Provider Tip: Ensure you're getting warranty and all issues fixed when buying new construction. 04:33 Intro to our guest, Alan Goldberg! 06:26 Alan's start in real estate! 10:09 Alan talks about his first deal! 21:03 How did Alan establish his area of focus? 25:01 Areas that have drastically improved since the 70s. 27:12 What were rehabs like in the 70s? 33:30 Toughest stretch in real estate since the 70s! 36:37 Adjusting in a tough market. 48:27 Did Alan ever question being a real estate agent? 50:55 Outlook on Rogers Park, Uptown, and surrounding Neighborhoods. 52:56 What is Alan's competitive advantage? 54:02 One piece of advice for new investors. 54:20 What do you do for fun? 56:25 Good book, podcast, or self development activity that you would recommend? 57:24 Local Network Recommendation? 57:47 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jul 20, 2023 • 44min
Episode 232: Chicago Real Estate in the 1970s vs 2020s with Veteran Broker Jerry Ettinger
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! Jerry closes with neighborhoods he believes are primed for growth and emphasizes the power of buy and hold real estate; particularly impactful coming from a true real estate veteran! 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: Jerry Ettinger, Ettinger Realty Link: Build (Book Recommendation) Link: Powerhouse Principles (Book Recommendation) Link: NBOA / Mike Glasser (Network Referral) Link: Albany Bank (Network Referral) ----------------- Guest Questions 02:28 Housing Provider Tip: Ensure common area windows have screens to protect all parties! 04:15 Intro to our guest, Jerry Ettinger! 05:00 Jerry's start in real estate! 10:51 Commercial real estate in the 70s! 15:04 Rogers Park back in the 70s and 80s! 19:31 Looking back at other north side neighborhoods. 27:14 Being a Housing Provider: Then vs Now! 28:42 Jerry's advice to young investors! 31:06 How did Jerry end up investing in Hyde Park! 35:33 Chicago Neighborhoods that Jerry is bullish on! 37:00 What is Jerry's competitive advantage? 37:20 One piece of advice for new investors. 37:44 What do you do for fun? 39:01 Good book, podcast, or self development activity that you would recommend? 40:09 Local Network Recommendation? 40:56 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jul 18, 2023 • 13min
Episode 231: Proactive Maintenance Techniques for Brick Buildings
What proactive maintenance should I be doing to my building? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Les O'Hara, North Shore Brickwork Sponsors: North Shore Brickwork ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jul 12, 2023 • 55min
Episode 230: How Interning for Brandon Turner Helped BrightInvestor's Co-Founder Drew McCluskey Revolutionize Market Research
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 internship under the BiggerPockets legend. Drew discusses the creation and power of BrightInvestor; a data software that allows real estate investors to pull building permit info, crime stats, and other data to identify emerging markets! This episode is proof that taking action and providing value to others opens tremendous opportunities that can be life changing! 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: Drew McCluskey, BrightInvestor Link: Drew's Instagram Link: Tyler Madden Instagram (Network Referral) Link: Zosia Madden Instagram (Network Referral) Link: Rejection Proof (Book Recommendation) ----------------- Guest Questions 03:53 Housing Provider Tip: Understand risks with accepting credit cards for rent payments! 06:41 Intro to our guest, Drew McCluskey! 07:22 Drew's start in real estate! 15:02 Bouncing back from a rough start in real estate. 19:27 Exchanging value with BiggerPockets' Brandon Turner! 26:08 Drew's internship under Brandon Turner! 34:44 The development of BrightInvestor! 43:46 Value that BrightInvestor brings to local investors. 48:30 What is Drew's competitive advantage? 49:03 One piece of advice for new investors. 49:51 What do you do for fun? 50:20 Good book, podcast, or self development activity that you would recommend? 51:10 Local Network Recommendation? 51:55 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jul 6, 2023 • 57min
Episode 229: From Roofing to Real Estate: Ivan and Jackie Hernandez's Journey to Success in Chicago's Southwest Side
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 dive deep into screening tenants, scaling, and lessons learned during their investing journey. Ivan and Jackie with powerful words on the Southwest Housing Provider's Group and their mission to be a resource to investors in the area! 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: Ivan and Jackie Hernandez of Roofing by Hernandez & Southwest Housing Provider's Group Link: SUCI Ep 171 - Sonia Del Real Link: Everything Is Figureoutable (Book Recommendation) Link: Crushing It in Apartments and Commercial Real Estate (Book Recommendation) Link: Joe Kroc with FNBC Bank (Network Referral) Link: Roofing By Hernandez (Facebook Page) ----------------- Guest Questions 03:30 Housing Provider Tip: Ensure sewer lines and drains are clear! 04:34 Intro to our guests, Ivan and Jackie! 09:21 Starting a roofing business and other entrepreneurial ideas! 13:30 Early struggles in the roofing business. 17:09 Discussing the first rehab in Englewood! 23:12 Choosing the neighborhood(s) to invest in. 27:47 Lessons learned the hard way in C/D class neighborhoods! 31:02 Automating and creating systems. 32:54 Tenant screening in C/D class neighborhoods! 37:37 Discussing the Southwest Housing Provider's Group. 49:54 What is Ivan's and Jackie's competitive advantage? 50:09 One piece of advice for new investors. 51:16 What do you do for fun? 51:48 Good book, podcast, or self development activity that you would recommend? 52:36 Local Network Recommendation? 53:33 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jul 4, 2023 • 16min
Episode 228: The Chicago Guide to Evaluating Brick Buildings
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.

Jun 29, 2023 • 48min
Episode 227: Unlocking Success As a Top-Producing Realtor and Expert in Wheaton with Michael Thornton
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. Michael explains how new investors can bring value to seasoned investors for potential partnership opportunities. As a Wheaton real estate expert, he speaks to the financial returns and offerings Wheaton can provide to investors! Throughout the show, Michael emphasizes the importance of truely having clients' and other people's best interest to build lasting relationships that will explode your 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: Michael Thornton, Compass - The Michael Thornton Team Link: Michael's Instagram Link: Codie Sanchez (Self-Development Recommendation) Link: James Clear Newsletter ----------------- Guest Questions 04:08 Housing Provider Tip: Non-paying tenants will come back to units if they have valuables there; facilitate access to prevent break ins! 05:27 Intro to our guest, Michael Thornton! 10:22 Getting bit by the entrepreneurial bug. 13:24 How to start building a real estate business? 24:52 How to partner on a deal? 32:11 The future of real estate brokers. 35:16 Investing in Wheaton! 40:17 Michael's real estate team! 42:08 What is Michael's competitive advantage? 42:52 One piece of advice for new investors. 43:06 What do you do for fun? 43:30 Good book, podcast, or self-development activity that you would recommend? 44:20 Local Network Recommendation? 44:56 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.


