

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

Jan 6, 2022 • 38min
Episode 113: Refugee Tenant Placement in Chicago With World Relief Organization (WRO)
World Relief Organization (WRO) Chicagoland is a humanitarian organization whose focus is to aid refugees and immigrant families in finding housing and rebuilding their lives in Chicago. As a Chicagoland housing provider, there is not only good that you can do by partnering with WRO, but you can also benefit from a stream of applicants with specified subsidies. Today WRO's own Susan Sperry and Nathan White talk about the organization's mission, services, challenges with resettling families, and how others can provide value to WRO. It's easy to focus on goals that serve our own needs, but our guests share great ways that investors and landlords can help a bigger cause while sustaining a profitable business. Listen in to learn how WRO is providing tremendous value to refugees and how it may tie into your business goals. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Susan Sperry and Nathan White of World Relief Organization Chicagoland Link: The Neighbor Project Link: The Lead Stories Podcast Link: Questions on Specific Housing or Opportunities with WRO Link: Questions for Nathan Sponsors: Kiser Group and Pavlovcik Architecture. ----------------- Guest Questions 01:51 House Provider Tip: Submit an FOIA request as part of your due diligence during the buying process. 03:50 Quick background on Susan and Nathan and how they ended up on the podcast. 06:20 Who is the World Relief Organization (WRO) and what is their mission? 08:28 What are the services that WRO provides? 10:21 What large refugee surges have there been in Chicagoland recently and historically? 12:55 How are refugees chosen to resettle in Chicago? 14:48 How can investors and housing providers be of assistance to WRO? 16:15 Why aren't more landlords contacting WRO to fill vacancies and what are the challenges when trying to find housing for refugees? 21:58 Is there any specific type of housing or location that WRO is searching for? 25:10 How is WRO helping refugees with education? 29:12 What are other ways that listeners can provide value to WRO? 31:26 What is the typical housing size that WRO is searching for and how is WRO funded? Wrap Up Questions 32:18 What is the competitive advantage of WRO? 33:07 One piece of advice for anyone looking to work with WRO. 33:40 What do you do for fun? 34:13 Good book, podcast, or self development activity that you would recommend? 34:51 Local Network Recommendation? 35:25 How can we learn more about you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Dec 30, 2021 • 45min
Episode 112: Spotting Chicago Development Trends and Opportunities with Chicago Cityscape's Casey Smagala and Steven Vance
So what happened in the Chicago real estate market in 2021 and where are we headed in 2022? Our guests today, Casey Smagala and Steven Vance both of Chicago Cityscape, are here to share data you won't want to miss. Casey and Steven explain how their data aggregation software allows them to efficiently analyze neighborhoods and identify paths of progress. They present which areas in Chicago with planned developments that they are bullish on, and also provide insight on Additional-Dwelling Units (ADUs) and how the Pilot Program has unfolded since its inception. Casey and Steven close by providing their outlook on Chicago Real Estate and explain how the fundamentals to continuing growing are in place! Tune in to learn how Chicago Cityscape can help you save time and give you a competitive advantage when researching your next project! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Casey Smagala and Steven Vance of Chicago Cityscape Link: Chicago Cityscape Link: Chicago for Chicagoans Link: INVEST South/West Link: City of Chicago :: Additional Dwelling Units (ADU) Ordinance Sponsors: Pentwater Cabinetry and Pavelchak Architecture ----------------- Guest Questions 02:20 House Provider Tip: Ensure that tenants' holiday decorations are being taken down and cleaned up in a timely manner! 05:20 What is Chicago Cityscape and who uses the software? 06:20 What is the advantage of using Cityscape? 08:15 What areas in Chicago saw the highest increases in sales and development in 2021? 11:15 Were Casey and Steven able to foresee any trends given available data? 12:30 What were the biggest surprises in 2021 after reviewing the data and what are the implications of converting a non-conforming unit into an Additional-Dwelling Unit (ADU)? 18:22 What areas in Chicago still have room to grow? 22:15 What are overlooked data points when trying to find hidden value in properties? 25:18 How did the 5 ADU pilot areas get selected? 28:55 Is Cityscape beneficial to smaller investors or who can benefit from Cityscape? 30:52 Overall, do you see Chicago continuing to trend positively given development data? Wrap Up Questions 36:45 What competitive advantage does Cityscape provide? 37:10 One piece of advice for new investors. 37:36 What do you do for fun? 39:10 Good book, podcast, or self development activity that you would recommend? 40:55 Local Network Recommendation? 42:25 How can we learn more about you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Dec 28, 2021 • 10min
Episode 111: Straight Up Tuesday Tip 19 - Blake McCreight Answers "What is a wholesaler and as an investor why should I care?"
What is a wholesaler and as an investor why should I care? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Blake McCreight of Express Property Solutions ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Dec 23, 2021 • 1h 1min
Episode 110: The Future of Real Estate with Neal Bawa
Regardless of which real estate assets you fancy, you are about to experience massive disruption in the upcoming years. That's according to the mad scientist of multifamily and returning guest Neal Bawa (previously on episode 26). Neal drops a fascinating outlook on the retail sector, particularly shopping malls and their post-COVID recovery. He also shares why he believes cap rates will continue to compress, and the drastic effects of tokenization and 3D printing will have on REI. Listen in to get your mind blown and then leave us a review! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Neal Bawa of Grocapitus Link: Grocapitus Website Link: Multifamily University | Free eBook: Location Magic | Join Our Investor Club Link: The World's Largest 3D-Printed Community Is Coming to Texas | Architectural Digest Link: Disruptive Trends with Neal Bawa - Multifamily University Link: Episode 26: Neal Bawa's Thoughts on Chicago, Opportunity Zones, and Current Economic Conditions Link: Lofty AI Sponsors: Appeal.tax and Essex ----------------- Guest Questions 02:38 Use technology and other resources to improve efficiencies and recapture time in your business! 06:35 What are Neal's top disruptive trends in multi-family and his take on retail? 16:03 What is the final reason why most retail malls are not going out of business? 17:22 What is the future for small mixed-use buildings in typical neighborhoods? 20:32 Which sector is Neal focusing on? 22:55 How is the industrial/e-commerce sector projected to grow compared to multi-family? 24:30 How does Neal incorporate interest rate increases when underwriting? Neal debunks the myth of the relationship between cap rates and interest rates. 29:51 What does the future hold as cap rates continue to compress and how do cap rates in the United States compare to other developed economies in the world? 32:49 Will wages keep up with inflation and how this impacts rent increases? 37:20 Will the amount of people renting increase and how home affordability has changed? 38:42 What is tokenization in real estate and which players are leading the charge of tokenization? 49:35 How will 3D printing change real estate investing? Wrap Up Questions 54:18 What is Neal's competitive advantage? 55:09 One piece of advice for new investors. 56:10 What do you do for fun? 57:17 Good book, podcast, or self development activity that you would recommend? 57:47 Local Network Recommendation? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Dec 16, 2021 • 52min
Episode 109: How to Tackle Large Scale Developments in Chicago with Matt Katsaros
You know how you see larger developments on major intersections and wonder "who's doing that?" Well the answer is people like today's guest Matt Katsaros. Matt started his real estate career as a top-performing commercial broker at Kise before transitioning to a director of acquisitions at Pangea. Those extraordinary experiences primed him for investing in Chicago and he has found his best returns to be in the development space. Matt provides tremendous insights into the unique due diligence process, and zoning process required for development. In addition he covers how to successfully raise money, structure deals, and handle the current supply chain mayhem. Matt finishes the episode with his thoughts on Chicago's cap rates and why he's anchoring down here. Tune in to learn about extreme scaling that will certainly get you out of your comfort zone. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Matt Katsaros of Wildwood Investments LLC Link: SUCI's Facebook video showing a post-demo, but before the open web trusses are installed. Link: Real Estate for Breakfast Sponsors: Appeal.tax and Pavlovcik Architecture ----------------- Guest Questions Housing Provide Tip Of The Week 08:15 Transitioning from brokerage to development in Chicago 14:56 Takeaways for your career from working w/Pangea 19:43 How to exponentially grow your real estate portfolio? 24:39 How are you finding deals and raising money? 27:51 What does it take to get a zoning approval in Chicago? 30:58 How have you adjusted your rehab budget with the Covid price increases? 34:37 How do you structure your investors' payouts? 36:47 Real estate partnerships 41:44 Where do you see Chicago cap rates going in the next 12 months, 24 months? 44:46 Wrap Up Questions What is your competitive advantage? 51:48 Advice for a new investor? 52:56 What do you do for fun? 53:46 Self development activity? 54:22 Network recommendation? 55:13 How can we learn more about you? 55:57 That's our show! Thanks for tuning in! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Dec 14, 2021 • 17min
Episode 108: Straight Up Tuesday Tip 18 - Perry Farella Answers "What closing costs and credits can I expect on my HUD statement?"
What closing costs and credits can I expect on my HUD statement? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending | Perry's Blog ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Dec 9, 2021 • 54min
Episode 107: Lessons From a 300k Rehab on My Near West Side Househack with Alex Martinez
You may have already listened to our househacking from hell episode (Episode 89). Today, we don't have tenants stealing cars or anyone overdosing, but we do have typical obstacles faced with a first-time househack; all compounded with the fact that this project included a gut rehab. Our guest today, Alex Martinez, dove in head first, encountered numerous challenges, and has not only lived to tell about it, but he now owns a wonderful 3-unit building and accumulated more experience than most early investors. Whether you are experienced or just starting out, tune in as Alex candidly talks through his experience from start to finish to learn something new. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Alejandro Martinez of Century 21 SGR Link: Episode 89: My Tenants Stole My Car; The Chicago House Hack from Hell with Joey Pochinskas Link: Building Permit and Inspection Records: Agreement Sponsors: Appeal.tax and Pavlovcik Architecture ----------------- Guest Questions Housing Provide Tip Of The Week 02:14 Why did I buy my first investment property near the United Center? 05:06 What to look for when buying in a new Chicago neighborhood? 09:00 Understanding the negotiation & due diligence in a Chicago real estate transaction. 10:25 How do you look up City of Chicago building violations for a specific property? 16:49 Best advice when having to get plans and permits in Chicago! 18:40 Breaking down the emotional roller coaster of buying an investment property in Chicago. 22:32 Red flags looking back on my first Chicago rehab. 32:40 Wrap Up Questions Competitive advantage? 40:20 Advice for new investors? 51:10 What do you do for fun? 53:00 Self development recommendations? 53:50 That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Dec 2, 2021 • 47min
Episode 106: Restoring Pilsen's Old World Architecture Since 1998 with Gordy Payne
From toilets falling through ceilings, to gentrification, Gordy Payne has seen it all as a hands-on owner in Pilsen. Gordy took a chance on Pilsen due to its proximity to downtown and made a name for himself for his ability to restore beautiful vintage buildings. He fully committed to the community, and for this, the community has treated him well. Gordy provides a summarized oral history of Pilsen over the last two decades while pointing out rehab gotchas, investor nuggets, and local street-level nuances that all investors new or experienced can learn from. Tune in, get inspired, and learn something new.....and then leave us that review :) Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Gordy Payne from Pilsen Apts LLC | Email Gordy (pilsenapts@gmail.com) Link: Two New Affordable Developments Planned for Pilsen Sponsors: Appeal.tax and Pentwater Cabinetry ----------------- Guest Questions 04:30 City Of Chicago will fine you if you don't shovel your sidewalks! 07:18 What was the Neighborhood of Pilsen like in the 1990s? 10:59 What makes Pilsen residents so protective over their neighborhood? 13:28 Why was Pilsen attractive to investors in the early 2000s? 17:51 What is unique about the construction in Pilsen that Chicago investors need to plan for? 23:08 -What makes Pilsen floor plans unique? 24:22 What are potential tenant expectations in Pilsen, Chicago? 26:23 What year did Pilsen really start to turn into a neighborhood? 28:16 What does new construction look like in Pilsen? 33:54 What is the difference between the neighborhood Heart Of Chicago and Pilsen? 36:35 How has the City Of Chicago supported change in Pilsen? 38:33 Secret to success for Landlords in Pilsen. Wrap Up Questions 44:44 What is your competitive advantage? 45:50 You must fall in love with your property! 46:47 What do you do for fun? 47:11 Self Development activity? 48:09 Local Network Recommendation? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Nov 30, 2021 • 14min
Episode 105: Straight Up Tuesday Tip 17 - Sharad Mehta Answers "What are tactical steps to follow when sending, responding, and tracking mailers?"
What are tactical steps to follow when sending, responding, and tracking mailers? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Sharad Mehta of REsimpli ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Nov 24, 2021 • 52min
Episode 104: From Unpaid Intern to Running the City of Chicago's Building Department
Today, Tom and Mark have an excellent conversation with Judy Frydland, who served as the commissioner of buildings for the City of Chicago from 2015-2020. A lot happened under her leadership including the streamlining of the permit process to make it simpler and more efficient than ever to get work done. Listen in on her story for some excellent advice on life and business and where Chicago is going from here. If you like today's episode, be sure to leave us a review and share it with a friend. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Judy Frydland Link: Alternative Code Approval Request (ACAR) Process Link: Michael Glasser. - President - Magellen Properties Sponsors: Appeal.tax and Cost Seg Kev ----------------- Guest Questions Career progression and permit process changing 7:30 What was the hardest obstacle when transforming the department? 26:00 Nuances regarding Chicago building code? 28:15 What are you spending time on now? 32:30 What would you like to see more of? 34:30 Thoughts on ADU ordinance? 37:00 Wrap Up Questions What was your competitive advantage? 42:30 Advice for new investors? 45:00 What do you do for fun? 46:20 Self development activity? 47:40 Network recommendation? 48:15 How can we learn more about you? 49:15 That's our show! See you next week! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.


