

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 19, 2023 • 1h 5min
Episode 193: The 2023 Guide to The Chicago Eviction Process with Jessica Ryan
Jessica Ryan, Head of KSN's Landlord/Tenant Department, joins us to educate Chicago Landlords on the eviction process and best practices! Jessica begins by explaining the first step in the process; properly serving a 5-day notice. She talks about utilizing process servers for notices and summarizes the filing fees associated with an eviction. Jessica then gives a detailed breakdown of the phases of an eviction including time frames that can be expected. It's never fun to have to go through this, but in the event you have to evict a tenant in Chicago, this show will be a tremendous resource to help you minimize your headaches and costs! 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: Jessica Ryan, Head of KSN's Landlord/Tenant Department Link: SUCI Ep 143 - Jessica Ryan's First Episode Link: Chicago Real Estate Investor Meetups ----------------- Guest Questions 01:14 Housing Provider Tip: Safety precautions to take when encountering squatters in vacant properties! 07:10 Intro to our guest, Jessica Ryan! 09:03 What are the best practices for serving notices to non-paying tenants? 11:07 Jessica explains a 5-day notice! 21:59 What are Jessica's thoughts on utilizing process servers for notices? 24:38 What happens after the 5-day notice? 28:38 Jessica summarizes the filing fees for an eviction. 33:04 Jessica breaks down the phases of the eviction process! 48:29 What's the difference between possession and judgment? 52:00 What's the approximate time frame from placing an eviction order to when the sheriff shows up? 54:04 How should landlords handle tenants during the eviction process? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Jan 12, 2023 • 52min
Episode 192: Scaling Up In Albany Park, Lincoln Square, and Ravenswood with Nick Yassan
Nick Yassan, President of Rany Management, grew up in a family of real estate investors and has been instrumental to growing his company's real estate portfolio! Nick begins by explaining how he was involved in real estate from an early age and the competitive advantage that it has given him. He shares what the 2008 housing crash was like and how that impacted his real estate investing. Nick jumps into his investing philosophy, particularly the quality of the finished project he provides and the neighborhoods he focuses on which include Albany Park, Lincoln Square, and Ravenswood. Building a strong team and leveraging technology to improve business operations are also topics addressed on this show! Nick closes by sharing his outlook on the 2023 real estate market and his plan to double the size of his portfolio in the coming years! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Nick Yassan, Rany Management Link: Nick Yassan's LinkedIn Link: Chicago Real Estate Investor Meetups ----------------- Guest Questions 02:06 Housing Provider Tip: Take care of your brick buildings by tuckpointing and keeping up with maintenance! 04:05 Intro to our guest, Nick Yassan! 04:52 How did Nick get started in real estate? 08:09 Nick talks about the real estate market during the housing crash of 2008! 11:17 Nick provides insight on balancing paying down debt and cash flow! 14:25 What areas did Nick start investing in and how has he migrated? 16:49 Would Nick start investing in Albany Park in 2022/2023? 20:36 Nick discusses the process of acquiring and stabilizing a storefront! 27:52 How was Nick able to scale so quickly and what would he have done differently? 31:50 How has Nick incentivized his team to perform at a high level? 33:47 How has Nick leveraged technology and other resources to more efficiently run his business? 36:09 Nick talks about having opportunities in better neighborhoods after proving himself as a serious buyer. 42:58 Nick provides his outlook on the real estate market in 2023! 44:25 What does Nick see as his biggest challenge with growing his portfolio moving forward? Wrap Up Questions 46:14 What is Nick's competitive advantage? 46:31 One piece of advice for new investors. 46:49 What do you do for fun? 47:11 Good book, podcast, or self-development activity that you would recommend? 47:27 Local Network Recommendation? 49:33 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Jan 10, 2023 • 15min
Episode 191: Understanding Your Insurance Premium and Potential Money Saving Credits
What goes into an insurance premium and what are some items investors should look out for? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Josh Steigelmann, State Farm Insurance Link: Investor Stories Featuring Sean Morrisey ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jan 5, 2023 • 58min
Episode 190: Everything Chicago Investors Need to Know About Logan Square with Luke Blahnik
Real Estate Broker, Developer, and Entrepreneur Luke Blahnik joins us to discuss his neighborhood of expertise: Logan Square! Luke knows the neighborhood block by block and outlines some of the premier streets that feature phenomenal housing stock on oversized lots. Luke elaborates on the different pockets of the neighborhood including the higher priced areas around the Boulevards and other more affordable options near the edges of Logan. Redevelopment around the Bloomingdale / 606 Trail, the associated Anti-Deconversion Ordinance, and Zoning in Logan Square are hot topics discussed during the show. Luke closes by sharing some current and upcoming developments that will keep propelling Logan Square forward! 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: Luke Blahnik, Flora | Blahnik @properties Link: Flora Blahnik Instagram Link: SUCI Investor Story - Luke Blahnik Link: SUCI Ep 32 - Luke Blahnik's First Episode Link: SUCI Ep 21 - Prashanth Mahakali Link: Building Science Fight Club Instagram Link: Anthony Flora (Network Recommendation) Sponsors: State Farm and Appeal.Tax ----------------- Guest Questions 02:37 Housing Provider Tip: Utilize new delivery services to manage your properties more efficiently! 04:29 Intro to our guest, Luke Blahnik! 05:18 Luke gives an overview on different pockets of the Logan Square neighborhood! 09:15 Why does the width of a property's lot matter? 12:00 Luke talks about the growth within the different areas of Logan Square! 15:45 Where can investors get the best bang for their buck in Logan Square? 20:30 What is the history of the 606 Trail? 22:57 What is the Anti-Deconversion Ordinance around the 606 Trail? 27:30 Where did the push for Ordinance come from? 34:55 How does the extension of the 606 Trail to Lincoln Yards impact homes close to the trail in Logan Square? 36:16 Why did choose Logan Square as his real estate focus? 39:20 Why are values in prime Logan Square higher than other neighborhoods with superior schools? 43:48 Luke talks about new developments in Logan Square! Wrap Up Questions 48:50 What is Luke's competitive advantage? 49:55 One piece of advice for new investors. 50:47 What do you do for fun? 51:38 Good book, podcast, or self development activity that you would recommend? 52:35 Local Network Recommendation? 53:27 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Dec 29, 2022 • 59min
Episode 189: How To Underwrite Chicago Multifamily Buildings with Essex Director Rick Ofman
Rick Ofman has over six years of experience in commercial real estate and is a Director at Essex Realty Group. Rick kicks things off by defining underwriting and associated terminology. He provides a thorough breakdown of income, expenses, and necessary assumptions. Rick shares insight on forecasting variables such as rehab costs, rent increases, and tax increases to name a few. He explains some valuation terms such as gross rent multiplier (GRM) and cap rate and the impact that interest rates have on these metrics. Rick closes with a bullish outlook on projected rent growth in Chicago and emphasizes the importance of teaming up with a broker that is transparent and has your best interest in mind! 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: Rick Ofman, Essex Realty Group Link: And Then We Had Kids (Podcast Recommendation) Link: Matt Cohen (Network Recommendation) Sponsors: State Farm and Essex Realty Group ----------------- Guest Questions 04:40 Housing Provider Tip: Consider hiring a process server to best utilize your time! 07:34 Intro to our guest, Rick Ofman! 09:24 What is the definition of underwriting? 10:54 Rick discusses making assumptions and explains other variables during underwriting! 19:54 How are expenses underwritten? 23:18 What are some additional underwriting considerations when evaluating C/D class properties? 23:57 Rick explains "hard" and "soft" costs! 32:37 How can buyers accurately determine utility costs? 34:34 What is the next step in underwriting after determining income and expenses? 46:09 How have rental "seasons" varied over recent years in Chicago? 50:02 How is Rick forecasting expense increases for buyers/owners? Wrap Up Questions 52:42 What is Rick's competitive advantage? 54:02 One piece of advice for new investors. 54:26 What do you do for fun? 54:34 Good book, podcast, or self development activity that you would recommend? 55:30 Local Network Recommendation? 55:50 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Dec 27, 2022 • 13min
Episode 188: Forewarn - A Powerful Tool to Validate Personal Information and Criminal History (and it's free for most Chicago agents!)
What is Forewarn? How does it benefit agents and housing providers and how can I utilize the tool? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Megyn Christensen, Forewarn ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Dec 22, 2022 • 1h 4min
Episode 187: Department of Housing Commissioner Marisa Novara; Moving Chicago Forward
Marisa Novara was appointed as Commissioner of the Department of Housing (DOH) in 2019 and has since led the creation of policies to promote equitably distributed affordable housing across the City. Commissioner Novara starts by explaining the purpose of the DOH. She dives deep on a fascinating study on segregation across the City that her team conducted. She speaks to the results of the segregation study and how her team is utilizing the findings to create policies that promote affordable housing development. The Commissioner explains how the Affordable Requirements Ordinance (ARO) and Additional Dwelling Units (ADU) Ordinance are also tools that the DOH is utilizing to combat the affordable housing issues. Commissioner Novara closes with powerful words on the importance of making your voice heard to address these issues within your community! 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: Commissioner Marisa Novara of the City of Chicago Department of Housing Link: Affordable Requirements Ordinance (ARO) Link: Additional Dwelling Units (ADU) Ordinance Link: City-owned Vacant Land for Sale Link: SUCI Ep 38 - Cook County Land Bank Link: How to Meet Yourself (Book Recommendation) Sponsors: Pentwater Cabinetry and Appeal.Tax ----------------- Guest Questions 04:00 Housing Provider Tip: Understand how legal notices work! 05:54 Intro to our guest, Commissioner Marisa Novara of the Chicago Department of Housing (DOH)! 07:05 Commissioner Novara explains the origin and purpose of the Chicago Department of Housing! 10:30 Commissioner Novara talks about the segregation study her team conducted? 15:35 How was Commissioner Novara's team able to perform a study on such a complex topic? 19:47 How were the findings of the study quantified? 26:33 How were the findings of the study received? 27:40 Where does Commissioner Novara's passion for her work come from? 30:33 Commissioner Novara discusses the Affordable Requirements Ordinance (ARO) and its challenges! 39:04 Commissioner Novara explains the Additional Dwelling Units (ADU) Ordinance! 44:32 What are some things happening behind the scenes at the DOH? 49:00 Commissioner Novara talks about Tiny Homes and affordable housing communities in general! Wrap Up Questions 53:37 What is Commissioner Novara's competitive advantage? 55:13 One piece of advice for new investors. 56:22 What do you do for fun? 57:26 Good book, podcast, or self-development activity that you would recommend? 58:37 Local Network Recommendation? 59:30 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Dec 15, 2022 • 1h 9min
Episode 186: CEO Scott Trench Pulls Back The Curtain at BiggerPockets
At the age of 32 years old, Scott Trench has already become CEO of BiggerPockets, and his contributions have helped countless investors build wealth. Scott discusses meeting Josh Dorkin and the early start-up days at BiggerPockets (BP). He speaks to BP's rapid growth, challenges along the way, and of course, BP's loyal customer base. Scott fills us in on BP's current vision and some potential upcoming enhancements to the platform. Inflation, interest rates, the housing market, and goal-setting/tracking systems are also among the many valuable topics discussed in this episode 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 Guest: Scott Trench, BiggerPockets Link: Scott's Instagram Link: Set For Life (Scott's Book) Link: Huberman Lab Podcast Link: The Outsiders (Book Recommendation) Link: David Greene Episode Sponsors: Essex Realty Group and Cost Seg Kev ----------------- Guest Questions 01:50 Housing Provider Tip: Don't forget to cultivate perseverance! 03:12 Intro to our guest, Scott Trench! 03:46 Scott talks about meeting Josh Dorkin from BiggerPockets! 06:30 What were the early days like at BiggerPockets? 09:23 How has BiggerPockets created such a loyal customer base? 16:09 How has BiggerPockets managed their rapid growth? 23:46 What is the EOS system? 25:10 How many BP users go inactive after creating an account? 28:08 How has Scott grown so rapidly in his role within BP? 32:06 What motivates Scott at this stage of his career? 34:51 What can we expect from BP in the near future? 43:18 Why did Scott write Set For Life? 47:26 Scott gives his out on inflation and employment! 58:27 Scott predicts housing values in relation to interest rates! Wrap Up Questions 62:00 What is Scott's competitive advantage? 62:30 One piece of advice for new investors. 62:54 What do you do for fun? 63:22 Good book, podcast, or self development activity that you would recommend? 64:32 Local Network Recommendation? 65:12 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Dec 13, 2022 • 12min
Episode 185: What Chicago Investors Need to Know About the Updated FHA Limits
What are the new FHA limits and what do investors need to know when exploring these FHA options? 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Dec 8, 2022 • 56min
Episode 184: Overseeing $8 Billion in Real Estate Transactions with Chicago Local Collete English Dixon
Collete English Dixon has overseen over $8 Billion in real estate transactions and joins us to discuss how the industry has changed. Collete explains how large real estate transactions are different today compared to 25 years ago and discusses the impact that large institutional investors have had on the market. She breaks down the difference between large scale deals and smaller transactions. Collete talks about her transition into the education field and the value offered by her real estate programs at Roosevelt University's College of Business. She elaborates on the variety of academic real estate offerings by her team and closes by talking about her advisory work with our friends at CIC! 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: Collete English Dixon, Roosevelt University - Walter E. Heller College of Business Link: CIC Chicago Link: Fifth Dimensional Leadership (Podcast Recommendation) Link: The Color of Law (Book Recommendation) Link: Stacie Young CIC (SUCI Ep 94) Sponsors: Essex Realty Group and State Farm ----------------- Guest Questions 02:30 Housing Provider Tip: Consider items required to make your flip project rent ready if necessary! 05:13 Intro to our guest, Collete English Dixon! 06:49 What attracted Collete to real estate? 08:05 How are real estate transactions different now compared to 25 years ago? 12:53 How has capital from large institutional investors impacted small investors? 14:35 What's different about large commercial transactions when compared to smaller multifamily and/or residential transactions? 19:58 Collete shares some hiccups she's seen in dispositions of large commercial assets! 22:35 Collete talks about investment strategies! 25:42 How did Collete transition into education? 31:00 Who should be looking into the programs at the Marshall Bennett Institute of Real Estate? 39:17 Collete talks about her role within the CIC Board! 42:12 How would Collete tackle the affordable housing issue in Chicago? Wrap Up Questions 47:55 What is Collete's competitive advantage? 48:28 One piece of advice for new investors. 49:04 What do you do for fun? 49:45 Good book, podcast, or self-development activity that you would recommend? 51:18 Local Network Recommendation? 52:00 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.


