

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

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.

Jun 22, 2023 • 55min
Episode 226: Unlocking Off-Market Deals Using Rescover's Analysis Platform for Maximum ROI with Ben Smith and Kristen Lopez
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 implementing "Who, Not How". They dive deep into cold calling and tracking off-market leads to increase your success rate. Throughout the show, Ben and Kristen share valuable insight on the mindset and approach required to get you your next Off-Market Deal! 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: Ben Smith and Kristen Lopez of Rescover Link: Buy Your Time Back (Book Recommendation) Link: SUCI Ep 195 - Victoria Barkate Link: Ryan Holiday Books Link: zInspector Sponsors: Pentwater Cabinetry and Essex Realty Group ----------------- Guest Questions 02:39 Housing Provider Tip: Ensure you have a registered agent as a point of contact in your LLC! 03:35 Intro to our guests, Ben Smith and Kristen Lopez! 13:20 Low Hanging Fruit to start prospecting! 17:13 Implementing "Who, Not How"! 22:35 What is skip tracing? 30:12 Approaches to cold calling. 39:11 Tracking off-market leads. 41:50 What is Rescover? 47:34 What is Ben's and Kristen's competitive advantage? 48:37 One piece of advice for new investors. 49:18 What do you do for fun? 49:48 Good book, podcast, or self-development activity that you would recommend? 50:40 Local Network Recommendation? 51:02 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.

Jun 20, 2023 • 15min
Episode 225: A Dive Into Current and Future Interest Rates with Chris Puleo
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 Chicago Investor 2023.

Jun 15, 2023 • 56min
Episode 224: Expert Insights On Chicago's Northwest Side with Jason Wagner
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 in inventory, and projects what could be on the horizon. Jason closes by discussing Greystone Realty and the Wagner Report and how they are adding huge value to Chicago Real Estate 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: Jason's Instagram Link: Traction (Book Recommendation) Link: SUCI Ep 43 - RJ and Nicky De Leon Link: SUCI Ep 82 - Property People Sponsors: Pentwater Cabinetry and Essex Realty Group ----------------- Guest Questions 03:52 Housing Provider Tip: End leases at noon, instead of midnight, to allow time for turnover! 05:11 Intro to our guest, Jason Wagner! 06:33 Jason explains 75 Hard! 11:05 Jason breaks down investing in Portage and Jefferson Park! 20:00 Discussing months of supply and the supply shortage over the last few years. 31:12 What drew Jason to Belmont Cragin? 36:18 Valuation of 2-4 units vs 5+ units. 40:24 Concept of an investment-minded brokerage! 45:14 How did Jason develop the Wagner Report? 47:00 What is Jason's competitive advantage? 47:22 One piece of advice for new investors. 48:34 What do you do for fun? 49:49 Good book, podcast, or self-development activity that you would recommend? 50:46 Local Network Recommendation? 52:25 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.


