

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 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.

Dec 3, 2020 • 46min
Episode 37: The NBOA - Your Ally and Voice as a Chicagoland Housing Provider
In today's episode, our guest Mike Glasser, President of the Neighborhood Builders Owner Alliance, explains how neighborhood housing provider advocacy groups are fighting for fair and lawful protection for investors in and around Chicago. Mike lays out the current advocacy campaign against the proposed CRTLO, the differences between the CRLTO and the RTLO, and the unintended consequences from previous legislation. Lastly, he gives advice on what you can do to help support the fight. Listen in and if you find value in today's episode, please leave us a 5 star review and recommend us with a friend. 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. Also, check out our Straight Up Chicago Investor Club at https://www.facebook.com/groups/3265227216848263 Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: John Warren Guest: Mike Glasser of Magellen Properties Link: Neighborhood Building Owners Alliance (NBOA) Link: Chicago Tribune Link: Chicago Sun-Times ----------------- Guest Questions Landlord Tip 6:15 What is the NBOA and the current coalitions in it? 9:10 If I'm a landlord, why should I care about these groups? 11:50 Who are the advocacy groups advocating to? 14:25 What were some of the unintended consequences of the CRLTO? 18:45 If the RTLO passes, what does this mean for property owners? 23:10 Has there been any pushback from individual cook county cities? 28:20 What can investors do to help with the advocacy campaign? 33:15 Do you think rent control will come up again? 34:50 Wrap Up Questions What is your competitive advantage? 39:15 What is one piece of advice you'd give a new investor? 40:05 What do you do for fun? 40:40 What is a good self development activity you'd recommend? 42:00 Who would you recommend as a quality resource? 43:00 How can we learn more about you? 43:30 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2020.

Nov 25, 2020 • 42min
Episode 36: Inaugural SUCI Thanksgiving Episode - What to be Thanking for in Chicago
First and foremost, a huge thank you to all our listeners! Please continue to be active members of our community and help spread the good word! This Thanksgiving, we want to take a quick moment to reflect on all the great things and opportunities we have in this great city of Chicago. A rich history, epic sports franchises, an extensive park network and some of the best food in the world are only the tip of the iceberg. With one of the largest metros in the country, we've been able to build this podcast and develop this network of investors and entrepreneurs. Listen in as we talk about some of the city's highlights and teach each other a bunch of things about our home. Listen in and if you like what you hear, leave us a 5 star review and share us with a friend. 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. Also, check out our Straight Up Chicago Investor Club at https://www.facebook.com/groups/3265227216848263 Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: John Warren Guest: Tony Angelos of IRPINO Real Estate Link: Geoffrey Baer Tours Link: Unusual Attractions in Chicago Book: Am I Being Too Subtle?: The Adventures of a Business Maverick by Sam Zell Book: South Side by Natalie Y Moore Link: The City Podcast Episode 1 - Six Stories Book: The Jungle by Upton Sinclair Link: Papa Joe's Pizza ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2020.

Nov 19, 2020 • 41min
Episode 35: Diving into Belmont Cragin, North Austin, and the Northwest Side Building Coalition with Jon Womack
Jon Womack of Third City Properties has been investing in the Chicago market for four years focusing on the northwest neighborhoods of Belmont Cragin and North Austin. Jon dives into what the investment landscape looks like in these areas, including tenant expectations of finishes and his general investment strategies. One of the key differentiators for Jon is his involvement in local neighborhood coalitions. Jon heads up the Northwest Side Building Coalition and is also an active member of the NBOA. Jon lays out several Chicago neighborhood coalitions that you can participate in to help move your neighborhood forward. Listen in and if you like what you hear, leave us a 5 star review and share us with a friend. 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. Also, check out our Straight Up Chicago Investor Club at https://www.facebook.com/groups/3265227216848263 Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: John Warren Guest: Jon Womack of Third City Properties Link: Northwest Side Housing Center Link: AAABNA | The Austin African American Business Networking Association Inc. | Chicago IL Link: HOME | Nonviolence Chicago Link: Uptown United: Home Link: Rogers Park Builders Group Link: Northwest Side Building Coalition Link: Know Your Rights: Fair Notice Ordinance Link: Home - Drexel Properties LLC Link: Jeff Weinberg on LinkedIn Link: The Wilcox Company Link: Joseph J. Wilcox - Chicago, IL Real Estate Agent | realtor.com® Link: Neighborhood Building Owner's Alliance – A Voice for Chicago's Building Owners ----------------- Guest Questions Landlord tip of the week 2:25 Guest Intro 6:00 What neighborhoods are you focused on in Chicago? 7:50 Why Belmont Cragin 8:50 What's different in Belmont Cragin since when you started in 2016? 10:45 What's the housing stock like in Belmont Cragin? 12:45 What are tenant expectations on finishes in this area? 14:25 What's your strategy in the Belmont Cragin area and what should a prospective investor be looking out for? 16:00 How do you do the financing on a place that is gradually renovated? 17:30 How do rental rates change as you move across the Belmont area? 19:15 What opportunities do you see in North Austin? 21:00 Can you walk us through the community groups you're involved with? 28:40 What drove you to be so involved in the community? 33:20 Wrap Up Questions What's your competitive advantage? 36:30 What is one piece of advice you'd give a new investor in Chicago? 37:08 What do you do for fun? 38:00 What's a good self development activity you'd recommend? 38:15 Who would you recommend as a quality resource? 38:35 How can we learn more about you? 39:20 That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2020.

Nov 12, 2020 • 44min
Episode 34: Hustling From a Househacker to over 40 Units in the Western Burbs in 2 Years!
With the right mindset, anything can be achieved. Shantanu Kamra is living proof, having moved to the US 8 years ago and Chicagoland just about 2 years ago, he's been able to scale his portfolio in the western suburbs to over 40 units. In today's episode he talks about househacking, BRRRR strategy execution, and scaling into larger buildings. He also gives advice on why coaching has worked for him while so many others do nothing with the information from a mentor. Shantanu breaks down certain suburbs like Bellwood, Franklin Park and Maywood and dives into the concept of pocket investing. Also, to get a free white paper on "Advantages of Private Lending for Multi-family Deals", email Shan at chicagoapartmentinvestor@gmail.com. His cellphone is: (847) 644-0262. Like what you hear? Please take the 5 second to leave us a review. Listen in and share with a friend! Also, check out our Straight Up Chicago Investor Club at https://www.facebook.com/groups/3265227216848263 Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Sponsor: John Warren Guest: Shantanu Kamra of Homesmart Link: Chicago REIA Link: Lawyer Georgina Diaz - Berwyn, IL Attorney Link: Drew Stiegemeier | Loan Specialist ----------------- Guest Questions Landlord Tip of the Day 3:18 Guest Intro 5:30 When did you decide to get into real estate? 7:05 What was the backstory behind the first house hack? 8:00 How did you decide on Elmwood park for your househack? 9:15 What was the next step after the first house hack? 10:30 How did you allocate time to identify properties that had signs of distress? 14:50 How much time would you spend nurturing prospects after you've had your first conversation? 16:00 How did you finance your deals? 19:07 When did you get involved in the MFH that are larger than 4 units? 22:50 What are some experiences you learned from your first 6 unit building? 24:10 What are some of the things you like about Bellwood and Northlake? 26:30 How do you maintain discipline when looking at investments? 32:20 How do you run your numbers and get to your cashflow number? 35:00 Why did you get involved in coaching programs and why did you succeed when so many failed? 36:25 Wrap Up Questions What is your competitive advantage? 38:00 What is one piece of advice you'd give a new investor? 38:50 What do you do for fun? 40:45 What's a good self development activity you'd recommend? 41:10 Who is one person in your local network you'd recommend as a resource? 41:46 How can we learn more about you? 42:20 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2020.


