

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

Feb 11, 2021 • 49min
Episode 47: Building Generational Wealth Through 1031 Exchanges with Lauren Speidel
The term "1031 Exchange" is ubiquitous, but do you really know what it is or how to even engage in one? Lauren Speidel of Exeter1031 is a subject matter expert and breaks it down for you today. She'll explain the different parties involved, what the criteria are and what you need to know before having the necessary conversations. Our hosts, Tom and Mark, have great FAQs for Lauren and she delves into a lot of content on one of our most informative episodes yet. If you like what you hear today, share us on Facebook and tag us with what you found most interesting. If you want to see how we can improve your properties performance, reach out to us at GCRealtyInc.com. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Lauren Speidel of Exeter 1031 | Connect with Lauren on LinkedIn Sponsor: John Warren of Second City Real Estate Sponsor: Appeal.tax Link: The Exeter Group Launches Go Ahead, ASK! Podcast Link: Mandy McAllister Link: Exeter 1031 on Facebook ----------------- Guest Questions Guest Intro 6:20 What is a 1031 exchange? 7:15 What is a "like property" and how do you define it? 9:25 What is an intermediary and what happens before and after a closing? 13:15 What are some questions you should ask an intermediary? 14:55 How does the purchase of a new property differ from a regular closing when in a 1031 exchange? 21:32 Can I wrap a whole portfolio into a single 1031? 22:45 How does househacking fit into a 1031 exchange? 24:20 What can you do with a vacation rental or second home when it comes to a 1031? 28:50 Do you have conversations with clients' CPAs? 30:20 Is there a minimum dollar threshold you recommend clients have before it makes sense? 33:15 Can 1031 Exchanges work when an entity wants to split after a closing and put the proceeds in a new entity? 34:00 What are the time limits on seasoning and intent to hold? 37:00 What are the estate planning benefits to 1031 exchanges? 38:00 What is a reverse 1031 exchange? 40:45 Wrap Up Questions What is your competitive advantage? 43:00 What advice would you give someone who is about to sell in Chicago? 44:00 What do you do for fun? 44:35 What is a good self development activity you'd recommend? 45:20 Is there any way we can provide value to you or learn more about you? 46:50 Thanks so much for listening. Please share this with a friend and leave us a 5 star review. Thank you so much for listening. As always, we're here to help YOU. If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Feb 4, 2021 • 40min
Episode 46: Why Invest in Smaller Multifamily Properties in the North and Northwest Suburbs of Cook County - Anthony Citriglia
Chicagoland is an enormous market with a ton of sub markets. Anthony Citriglia of Essex Realty's submarket covers many of the near north and near northwest suburbs and he breaks down exactly what those markets are like; how they differ from Chicago; and how they differ from each other. Following the post-war boom, cheaper access to cars, and the development of several Metra lines, the 50s-80s were filled with tons of development, mostly still currently owned by mom & pop landlords. Find out what it takes to succeed in these markets as Anthony drops street-level knowledge including typical price-per door, dividing lines where this pricing adjusts, tenant expectations, and the physical housing stock. If you want to improve your own tenant performance, give GC Realty a call and visit our website at https://www.gcrealtyinc.com/ Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Anthony Citriglia of Essex Realty Group Link: Brian Kochendorfer Link: Brian Karmowski Link: Kevin Cawley - Senior Account Executive - Cost Segregation Services, Inc. ----------------- Guest Questions Landlord tip of the week 3:00 What markets do you focus on? 6:30 What is the market environment in Niles? 7:25 Is there a difference whether you're on the East or West side of Milwaukee in Niles? 8:30 How do property taxes change when you jump over the city limits? 9:35 When someone says they want to invest, how do you answer that? 11:00 How are prices different between Niles and Skokie? 11:50 What is the opportunity like in Evanston compared to Skokie? 14:45 What is the housing stock in the north suburbs? 15:30 What is something people should be aware of when investing in the north suburbs? 16:10 How does the northwest market differ from the north suburbs? 17:45 What is the housing stock like of the near northwest suburbs? 21:35 How important is it to be close to the NW metra line? 21:55 Is there opportunity for deals in the NW suburbs? 23:20 What are some problems buyers are seeing when properties are under contract? 29:30 What is a california style building and how do those trade? 32:50 Wrap Up Questions What is your competitive advantage? 33:40 What is one piece of advice you'd give a new investor? 34:25 What do you do for fun? 35:00 Who would you recommend and a quality resource? 36:05 How can we learn more about you? 37:12 Thanks so much for listening. Please share this with a friend and leave us a 5 star review. Thank you so much for listening. As always, we're here to help YOU. If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Jan 28, 2021 • 45min
Episode 45: Community Investment Corporation (CIC) - Chicago's Non for Profit Lender, with Jack Crane
For over 35 years, Jack Crane has been providing expertise on financing the acquisition and rehabilitation of commercial real estate. The majority of those years have been spent as Sr. VP of lending at CIC where he is responsible for carrying out the mission to be a leading force in both neighborhood revitalization and affordable housing. From lending during tough times, to helping analyze risk, Jack explains how CIC has played a predominant role over multiple decades in transforming Chicagoland neighborhoods. Jack also describes how you as an inverter can benefit from CIC's lending programs and experience to better rehab and finance your next investments. If you like what you hear, please share us with a friend and leave us a 5 star rating. Lending Tip of the Month brought to you by Renovo Financial - https://www.renovofinancial.com/ Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jack Crane of Community Investment Corporation Monthly Tip: Renovo Financial Link: Troubled Building Initiative (TBI) Link: Elevate Energy Link: The Resurrection Project Link: Jack Crane - Senior Vice President - Director of Lending - Community Investment Corporation Link: Caste (Oprah's Book Club): The Origins of Our Discontents Link: AIA | Jack Cassin Link: Property Management Training – Community Investment Corporation ----------------- Guest Questions Lending Tip of the Month brought to you by Renovo Financial Landlord Tip of the Week 4:00 Renovo Value Add 5:45 How to get started as a new flipper? 5:50 What is CIC's mission? 10:15 In what way is CIC different from typical lenders? 13:30 Where do the CIC's funds come from? 16:35 What does the typical deal someone brings to CIC look like? 18:20 Are there lending requirements for deals CIC finances? 19:50 Once rehab is complete, do investors need to refinance out of the loan? 21:30 What's the minimum size of property the CIC will fund and what do you focus on? 22:00 What are some everyday type of activities that might qualify for energy grants? 27:00 What are some other reasons investors would work with CIC over other lending institutions? 28:50 Is there any comparison to the 80s uptown and rogers park in today's market? 32:00 What is the resurrection project? 35:13 Wrap Up Questions What is CIC's competitive advantage? 38:20 What is one piece of advice you'd give a new investor? 38:45 What do you do for fun? 39:10 What is a good self development activity you'd recommend to our listeners? 40:00 Who is one person in Chicago you'd recommend as a quality resource? 40:50 How can we learn more about you? 41:40 Chicago Fact 43:15 Thank you so much for listening. As always, we're here to help YOU. If you want to make the most of your investment, connect with us at https://www.gcrealtyinc.com/. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Jan 21, 2021 • 45min
Episode 44: Understanding The Intricacies of Various Mortgage Products With Chris Puleo
How many ways are there to finance buying a property? Way more than I'm aware of which is why our guest Chris Puleo is here. With his robust 20+ year career, Chris has seen it all and explains a plethora of different popular products. With so much interest in househacking, of course we talk about the FHA product and calculating the self sufficiency tests. Not to mention some of the things investors AND brokers need to be aware of when putting offers on properties with an FHA loan product. Chris also compares the differences between buying in your personal name and buying in an LLC. There's a lot to unpack so let's get to it and if you like what you hear, or you learned something, please subscribe to our channel and give us a 5 star review. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: GC Realty & Development Guest: Chris Puleo of The Puleo Group Link: GC Realty & Development, LLC.: Chicago Property Management, Chicago Homes for Rent Link: Chris Puleo - The Puleo Group, Powered By Preferred Rate. NMLS 204168 | Call Chris | Email Chris ----------------- Guest Questions Landlord tip of the week 2:46 What are some differences between owner occupied and investment loans? 6:10 How have reserves changed before COVID vs now? 7:45 Can you talk about some of the contingencies regarding FHA loan for owner occupied properties? 9:20 Why is a 3 flat more difficult to underwrite than a 2 and 4 flat? 15:50 What are some risks FHA users need to consider when buying a property? 20:25 When would it make sense to buy down points on an FHA loan? 21:50 What are some differences between buying a property in a personal name vs an LLC? 24:20 Can you explain paydowns on wrap around loans and why a sale of one property would go to the debt of many properties? 26:50 What are some things you'd want to see from a new investor you've never done business with before? 30:00 What are some things that someone looking to househack should know when going to speak with you? 32:15 How do you think the lack of inventory has played into our current financing environment? 36:10 Wrap Up Questions What's your competitive advantage? 37:52 What is one piece of advice you'd give to a new investor? 39:00 What do you do for fun? 39:25 What is one good self development activity you would recommend to our listeners? 40:22 Who is one person you'd recommend from your local network? 41:10 How can we learn more about you? 42:50 That's our show! Thanks for tuning in once again! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Jan 14, 2021 • 52min
Episode 43: Househacking, Scaling, and Large Multifamily Deals With one of Chicago's Best Power Couples
Have you ever looked at your significant other and wanted to build an empire with them? That's exactly what Nicky and RJ De Leon have been doing since the early days of their relationship. Today, they tell their story from start to current day, diving into how they had all those hard conversations about deciding on the first location, getting on the same page as your partner and so on. Since that initial househack, they moved on into bigger projects but not alone. Listen to how they went about networking and building those partnerships that helped propel them further. All that they have accomplished has also been with full time jobs. Listen to their journey and leave us some feedback. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: GC Realty & Development Guest: Nicky and RJ De Leon of NVR Properties LLC, EJC Partners Link: Operation Family Secrets: How a Mobster's Son and the FBI Brought Down Chicago's Murderous Crime Family Chicago Multifamily Club (Chicago, IL): MeetUp | Facebook Link: The Real Estate InvestHer Link: EJC Partners - Value-add Construction for Real Estate Investors Link: First State Bank | Personal & Business Banking Link: The Only Woman in the Room: A Novel Link: The Miracle Morning: The Not-So-Obvious Secret Guaranteed to Transform Your Life (Before 8AM) Link: Shoe Dog: Knight, Phil, Butz, Norbert Leo: 9781508211808 ----------------- Guest Questions Landlord Tip of the Week 2:45 How did your first house hack get started? 6:20 What happened after your first househack was a success, where did you go next? 11:40 What was different about the due diligence between the 3 unit and 6 unit buildings? 13:20 What were some things that surprised you about owning a 6 unit? 15:07 What were some improvements you've considered doing when you bought the 6 unit building? 19:40 What did you do with the equity you gained from the first 3 flat in bronzeville? 22:40 Can you dive into the 3 flat rehab project details? 24:30 How did you get into Avondale? 29:40 Do you take on projects outside of your own investments for EJC Partners? 31:40 Can you share some details about how you found and got involved in your current large multifamily? 34:50 Where are deals coming from? 38:00 Wrap Up Questions What has been your competitive advantage? 43:05 What is one piece of advice you'd give a new investor? 44:08 What do you do for fun? 45:40 Who would you recommend as a quality resource? 48:25 That's our show! Thanks for taking the time to listen and please leave us a 5 star review. Also consider joining our Facebook group at https://www.facebook.com/groups/3265227216848263 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Jan 7, 2021 • 53min
Episode 42: Understanding Both the Updated RTLO and ADU Ordinance with Bob Floss
In today's episode, attorney Bob Floss dives further into the current RLTO ordinances and how the proposed ordinance affects investors, landlords, and tenants alike. With so much changing day to day, it can be challenging to keep track of best practice. This is why it's necessary to have solid legal representation on your team when dealing with tenant issues. Bob also discusses the new ADU ordinance and how investors can benefit from the current pilot. Listen in and let us know what you think. If you need help managing your tenants, connect with us and make the most out of your investment at https://www.gcrealtyinc.com/. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: GC Realty & Development Guest: Bob Floss of Floss Law Link: City Council to review revised ADU ordinance to apply in pilot areas only Link: Accessory Dwelling Units (ADU) Supporters in Chicago Link: The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich Link: Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork Link: Brie Schmidt, Managing Broker/Owner Link: North Shore Real Producers - Real Estate Link: Floss Law, LLC ----------------- Guest Questions Landlord Tip of the Week 4:20 What does the RTLO look like and how does it impact landlords? 8:45 What are some of the big things that will impact investors in the ordinance? 20:20 What kind of unintended consequences are of risk to the tenant? 23:15 What is proposed regarding the ADU changes? 31:40 How is it different if I'm in an approved ADU zone compared to getting a regular zoning variance? 38:00 Wrap Up Questions What's your competitive advantage? 44:42 What is one piece of advice you'd give a new investor? 45:30 What do you do for fun? 47:23 What is a good self development activity you'd recommend? 48:10 Who would you recommend as a quality resource? 49:10 How can we learn more about you? 50:40 That's our show! Thanks for taking the time to listen and please leave us a 5 star review. Also consider joining our Facebook group at https://www.facebook.com/groups/3265227216848263 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

Dec 30, 2020 • 36min
Episode 41: What We Learned in 2020 and What's On the Docket for SUCI
As we wrap up 2020, a huge thank you to all our listeners and active participants that have helped transform this podcast from a simple idea of sharing localized knowledge into its current state (which we view as a success). In this episode, Mark and Tom give a quick state of the union of the podcast and also dive into what they learned over 40 episodes, including some of their favorite episodes and nuggets. We also lay out what to expect from SUCI as we continue to try and add valuable content, while also soliciting your feedback. Congrats on what you've accomplished this year and keep plowing ahead. If you found this episode helpful, please give us a 5 star rating and share us with a friend. And if you own properties and do not manage yourself, please reach out if you want to see how we can improve your property performance, check us out at GC Realty & Development, LLC.: Chicago Property Management, Chicago Homes for Rent. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com That's our show! Thanks for taking the time to listen and please leave us a 5 star review. Also consider joining our Facebook group at https://www.facebook.com/groups/3265227216848263 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2020.

Dec 24, 2020 • 43min
Episode 40: Navigating Chicago's Eviction Process with Tom Raleigh
Tom Raleigh, of Halsted Law Group, breaks down the current environment for landlords as it relates to the eviction process. COVID has shaken things up, and understanding what you can and can't do is more confusing than ever, so having an ally who understands the rules and will fight for you is paramount. Listen to our hosts ask Tom some FAQs about landlord process and protocol and learn about a new service coming out to help landlord's screen tenants way more effectively! Rent Butter is coming in 2021 and you'll want access to it. If you found this episode helpful, please give us a 5 star rating and share us with a friend. And if you own properties and do not manage yourself, please reach out if you want to see how we can improve your property performance, check us out at GC Realty & Development, LLC.: Chicago Property Management, Chicago Homes for Rent. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: GC Realty & Development Guest: Tom Raleigh of the Halsted Law Group Link: Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork Link: Know Your Rights: COVID 19 Eviction Protection Ordinance Link: Rent Butter Link: Sell More Faster: The Ultimate Sales Playbook for Startups (Techstars) Link: Das Law – Litigation Attorney in Chicago, IL ----------------- Guest Questions Landlord tip of the week. 3:15 Can you tell us about what laws and rules landlords have to follow right now? 6:30 What do you do if you have a non paying tenant in Chicago? 8:10 How do you get a hold of tenants who are unresponsive? 10:40 Is there a difference with non paying tenants if there is an active lease or an expired lease? 12:50 What does the solution look like when you have a tenant who is not paying? 16:00 What happens if a tenant goes silent after giving all the notices? 21:00 Know your rights form rundown. 23:25 What happens to landlords who were filing evictions prior to covid? 25:20 What is your two minute rundown on Rent Butter? 29:20 Wrap Up Questions What is your competitive advantage? 36:40 What is one piece of advice you'd give a new investor? 39:14 What do you do for fun? 39:45 What's a good self development activity you would recommend? 40:25 Who would you recommend as a quality resource here in chicago? 40:45 That's our show! Thanks for taking the time to listen and please leave us a 5 star review. Also consider joining our Facebook group at https://www.facebook.com/groups/3265227216848263 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2020.

Dec 17, 2020 • 49min
Episode 39: Scaling a Multi-Million Dollar Real Estate Business in Chicago
In today's episode, Sean Connolly talks about his not so usual journey of scaling to a multi- million dollar portfolio and the lessons and tools he's acquired over the past 8 years. Sean provides his advice on investing in certain southside markets as a new investor and if you're not doing volume, why it's so important to control your material cost. Sean also provides his thoughts on the imminent future of the Chicago real estate market. Lastly, he explains the role and significance of virtual assistants and how they can help you scale. Listen in to hear all that he has to say, and if you learn something, hit that 5 star button. If you want to see how we can improve your property performance, check us out at GC Realty & Development, LLC.: Chicago Property Management, Chicago Homes for Rent. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: GC Realty & Development Guest: Sean Connolly of the Scale Virtually: Home | Email Sean | Call Sean Link: Emerging Real Estate Markets: How to Find and Profit from Up-and-Coming Areas Link: Scale Virtually: Home Link: Virtual Freedom: How to Work with Virtual Staff to Buy More Time, Become More Productive, and Build Your Dream Business Link: Traction: Get a Grip on Your Business: Wickman, Gino: 0783324916904 Link: Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork Link: The Experience Transformer - Fillable PDF Link: Straight Up Chicago Investor Club | FB Group ----------------- Guest Questions Guest Introduction 6:25 Where have you been investing over the past 8 years? 7:50 Why move from Austin to the southside? 10:00 Are you mostly flipping or holding? 10:25 How did you do your first 50 units in Austin? 11:18 What is your outlook on the Chicago housing market?19:10 How did you start using virtual assistants to scale? 27:18 At what point can an early investor get involved with a virtual assistant? 33:30 Tell us about your bad cash for keys experience? 39:55 Wrap Up Questions What is your competitive advantage? 43:04 What is one piece of advice you would give a new investor? 44:00 What do you do for fun? 44:55 What is a good self development activity you would recommend? 45:25 Can you name someone who you'd recommend as a resource? 46:00 How can we learn more about you? 47:10 That's our show! Thanks for taking the time to listen and please leave us a 5 star review. Also consider joining our facebook group at https://www.facebook.com/groups/3265227216848263 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2020.

Dec 10, 2020 • 57min
Episode 38: Can't Find Deals on the MLS? The Cook County Land Bank has Hundreds of Distressed Properties Waiting for Investors
Are you looking for distressed deals? The Cook County Land Bank (CCLB) has plenty and they go right under most investor's noses! In today's episode, Rob Rose provides an overview of the CCLB, a socially responsible wholesaler working with investors to turn dilapidated properties into newly remodeled homes. Rob describes CCLB's acquisition process, their commitment to neighborhoods, CCLB's unique ability to wipe out liens, and how you can engage with CCLB to get in on the action. Listen in to hear all that he has to say, and if you learn something, hit that 5 star button. If you want to see how we can improve your property performance, check us out at GC Realty & Development, LLC.: Chicago Property Management, Chicago Homes for Rent. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: GC Realty & Development Guest: Rob Rose of the Cook County Land Bank Link: Family Properties: How the Struggle Over Race and Real Estate Transformed Chicago and Urban America Link: Thurman Tony Smith on LinkedIn Link: Calvin L. Holmes ----------------- Guest Questions Landlord tip 4:30 What is the Cook County land bank? 7:22 What is the land bank able to do faster than the county/city can? 9:10 Besides REO, what are some other ways the land bank acquires property.10:00 What is a tax sale, annual sale and scavenger sale? 13:00 How is your budget funded? 23:00 What kind of activity have you guys been doing? 25:10 What's the distribution of property types that you acquire? 30:10 As an investor, how can I engage in the land bank? 34:35 What are things the land bank wants to see on applications for new applicants? 39:20 How often are inventories on the website updated? 43:10 What are the restrictions on the sale? 44:20 Wrap Up Questions What has the land bank done to be successful? 48:15 What is one piece of advice you'd tell someone who has yet to buy their first property through the land bank? 49:40 What do you do for fun? 51:48 What is a good self development product you'd recommend? 52:01 Who would you recommend as a resource in Chicago? 53:45 How can we find out more about you? 54:50 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2020.


