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    Business

    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.

    Advertise

    Copyright: © Copyright of Straight Up Chicago Investor 2020.

    • Apple Podcasts
    • Google Play
    • Spotify

    Latest Episodes:
    Episode 64: King of Chicagoland; Easy Makes You Soft May 20, 2021
    Show notes

    With nearly 30 years of experience as a broker, Frank Montro, the King of Chicagoland, shares his reflections on how the industry has changed from the early '80s to today. While touching on strategies his team uses to generate business, and cementing what it takes to succeed, Frank gives a compelling presentation that is certain to teach you something about winning in Chicago. Do NOT play with your money, work with an expert and learn to avoid the pitfalls of most new investors. It's what we're all about here at the Straight Up Chicago Investor.

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Frank Montro of Frank Montro Homes | Call Frank: (708) 307-0777 | Email Frank: montrof@aol.com

    Sponsors: Puleo Group and Appeal.tax Link: Chicago Deal Vault | Never miss an MLS property deal again and increase your productivity y 10,000% Link: Tony Robbins Podcast, Catch the Latest Podcast Here Link: Podcast Cardone Zone Link: Motiversity YouTube Channel Link: Barnett Capital Link: The Devil in the White City: Murder, Magic, and Madness at the Fair That Changed America Link: Straight Up Chicago Investor Podcast: Expert Perspectives on Investing in Chicago Real Estate -----------------

    Guest Questions

    Overview of real estate industry 5:00

    Tax certificate sales. 18:50

    Do you factor commercial financing into deal analysis? 21:15

    Where do you see rates going? 23:30

    Do you think about the pre 2008 high's as a benchmark? 31:00

    What's the impact of people leaving Chicago? 33:30

    Appraisal insights? 35:30

    Steps to find off market deals? 39:45

    What's your competitive advantage? 48:00

    What is one piece of advice you'd give a new investor? 49:45

    Wrap Up Questions

    What do you do for fun? 52:55

    Self development activity? 53:30

    Local Network Recommendation? 57:00

    How can we learn more about you? 58:00

    That's our show! Thank you so much for listening and tune in next week!

    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.


    Episode 63: Straight-Up Tuesday Tip 3 - Chance Badertscher Answers "What are some items I should look out for during Attorney Review?" May 18, 2021
    Show notes

    What are some items I should look out for during Attorney Review?

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Chance Badertscher of Lavelle Law

    -----------------

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2021.


    Episode 62: How a Single Mom Created A Real Estate Empire Across Chicagoland May 13, 2021
    Show notes

    Be honest with yourself...how many excuses do you tell yourself? Farrah Ali was a single mom in debt, working full time, but did not let that deter her from financial freedom. Listen to her incredible story and how it has impacted all areas of her life. She details even more of this in her book, "Diaries of A Female Real Estate Investor." If you liked what you heard, please share it with a friend and let us know what you think! Enjoy the show!

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Farrah Ali

    Link: Diaries of a Female Real Estate Investor: Learn How A Single Mom Went From 80k in Debt To a Multi Million Dollar Portfolio

    Link: We Win Chicago: Home Link: Rich Dad Poor Dad: What the Rich Teach Their Kids About Money That the Poor and Middle Class Do Not! Link: Andrew Holmes | HOME Sponsor: ChicagoREIA Sponsor: Appeal.tax

    -----------------

    Guest Questions

    How did you get into real estate investing? 6:15

    How did you decide on specific areas? 10:30

    Investing in the suburbs vs the city. 14:15

    Are you planning on going into bigger properties soon? 20:00

    Tell us about the book? 22:30

    What is "We Win"? 26:45

    What are your near term plans? 28:45

    What is your competitive advantage? 32:00

    What is one piece of advice you'd give a new investor? 32:15

    Wrap Up Questions

    What do you do for fun? 32:45

    What is a good self development activity? 34:45

    Network Recommendation? 35:15

    How can we learn more about you? 35:45

    That's our show! Thank you so much for listening!

    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.


    Episode 61: Understanding the Economics and Risks of Chicago's Pension Crisis May 06, 2021
    Show notes

    What does Chicago look like from an economist' perspective and why should investors care? Today, Dr. Joseph Pagliari explains some of his economic thesis related to Illinois' long term fiscal issues that are top of mind for so many investors. He provides options Illinois might have to address these issues, but are they specific to only Chicago or are the issues more widespread? Listen in today to a fascinating conversation. If you learned something, please share it with a friend!

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Dr. Joseph Pagliari of The University of Chicago Booth School of Business

    Sponsor: ChicagoREIA Sponsor: Appeal.tax

    -----------------

    Guest Questions

    Overview of state of Illinois fiscal conditions. 6:00

    What options does Illinois have to improve their financial outlook? 13:15

    What are some negative things we need to consider with tax issues?19:00

    Will the tax classification system between commercial and residential properties ever go away? 22:30

    What will post Covid downtown look like? 24:45

    How will different markets react to tax issues? 29:30

    How would foreclosures affect pricing today vs the financial crisis? 33:20

    What are your thoughts on rent control? 41:30

    What has been your competitive advantage? 46:15

    What is one piece of advice you'd give a new investor? 47:43

    Wrap Up Questions

    What do you do for fun? 49:30

    Self development activity 50:00

    Network Recommendations 51:15

    How can we learn more about you? 52:15

    That's our show! Thank you so much for tuning in.

    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.


    Episode 60: Straight-Up Tuesday Tip 2 - Rosario Terracciano Answers "What are some common mistakes that cause investors to overpay for an investment property?" May 04, 2021
    Show notes

    What are some common mistakes that cause investors to overpay for an investment property?

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Rosario Terracciano | ClickInvest

    -----------------

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2021.


    Episode 59: Chicago's Very Own Cost Segregation Expert - Kevin Cawley Apr 29, 2021
    Show notes

    The word "taxes" inspires fear from all types of investors, but especially in Chicago. From income tax, to property tax, we're paying a lot. Depreciation is one of Real Estate's greatest benefits, and there is a way to maximize that benefit immediately. Cost Seg Kev is here today to explain what cost segregation is and how it can be used to offset your tax liability. If you're not trying to save hundreds of thousands of dollars from here on out, well, this isn't the episode for you. Listen in and if you learned something, please share us with someone who can also benefit.

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Kevin Cawley of Cost Segregation Services

    Sponsor: Puleo Group Sponsor: Appeal.tax Link: The Miracle Morning: The Not-So-Obvious Secret Guaranteed to Transform Your Life Link: Think and Grow Rich: The Landmark Bestseller Now Revised and Updated for the 21st Century (Think and Grow Rich Series) Link: David Pezzola of the Icarus Investment Group | Call David: 773-931-6498

    -----------------

    Guest Questions

    How did you get started? 6:00

    What is depreciation? 10:00

    What asset classes depreciate at 39% vs 27.5%?

    What is the benefit of cost segregation to an investor? 15:15

    What kinds of things are broken out for smaller multifamily? 16:30

    Is this right for everyone? 19:45

    Is there a minimum threshold for when this makes sense? 23:45

    How does the pricing structure for cost segregation studies work? 27:00

    What are questions someone should ask when getting a cost seg offering? 33:00

    What has been your competitive advantage? 35:25

    What is one piece of advice you'd give? 36:40

    Wrap Up Questions

    What do you do for fun? 37:30

    Self development recommendation? 38:00

    Network Recommendation? 38:45

    How can we learn more about you? 40:00

    That's our show, thanks so much for listening! Tune in next week!

    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.


    Episode 58: Multi Family Investing in Chicago's Northwest Side with Gloria Weikert Apr 22, 2021
    Show notes

    One of the most important allies to an investor is the broker they work with. Gloria Weikert runs the X-Plus team and has a specialty in helping clients buy investment properties. In today's episode, Gloria gives some insight on what it takes to win deals in a competitive market that go past just offering more money; breakdowns of different neighborhoods; tenant and rental profiles in varying neighborhoods as well as plenty more. Listen in and if you liked what you heard, or learned something today, give us a 5-star review and share us with a friend.

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Gloria Wiekert of X-Plus Realty

    Sponsor: Chicago REIA Sponsor: Appeal.tax Link: Sam Sharp Link: Tannehill Law LLC

    -----------------

    Guest Questions

    Strategies to win deals in a competitive market.

    What does the market look like in the north Chicago neighborhoods? 5:45

    Who are going to be the sellers in this market? 8:25

    Are you able to find two units on the northside that make sense? 9:40

    How do you handle clients who come and want to see a two flat with a non conforming unit? 11:20

    Overview of the Avondale area? 13:30

    Rental Expectations in Avondale? 16:15

    Tenant profile on the west end of Avondale? 17:15

    Escalation Rider explanation. 22:20

    How do the rents change as you move south from Avondale? 27:45

    Where are some people looking that are up and coming? 32:30

    How do you see the future of the Loop? 35:50

    What expectations do you give new buyers? 37:30

    What is your competitive advantage? 39:30

    Advice for new investors? 40:10

    Wrap Up Questions

    What do you do for fun? 40:30

    Self Development recommendation? 41:30

    Local network recommendation? 42:10

    How can we learn more about you? 42:55

    That's our show! Thanks so much for listening. Tune in next week.

    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.


    Episode 57: Straight-Up Tuesday Tip 1 - Eric Workman Answers "How does an acquisition lender structure my financing when I'm looking to flip a property?" Apr 20, 2021
    Show notes

    How does an acquisition lender structure my financing when I'm looking to flip a property?

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Eric Workman of Renovo 1

    -----------------

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2021.


    Episode 56: Fighting for Good Chicago Housing Policy with Kris Anderson Apr 15, 2021
    Show notes

    Chicago is known for complex and restrictive landlord and tenant policies, but there are dozens of people fighting for change and protection. Kris Anderson of the Chicago Association of Realtors is one of those people on the front lines. Not everyone knows the role of CAR, so Kris explains what they do and his role in the machine as well as other groups and associations who are allies. Some hot button topics covered in today's episode include RLTO reforms and rent control; some of the biggest issues for individual landlords as well as some great reasons to be optimistic about Chicago's future. Listen in and if you like what you hear, give us a like, subscribe and leave a review.

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Kris Anderson of Chicago Association of Realtors | E-mail Kris | Call Kris

    Sponsor: Appeal.tax and Showdigs Link: Additional Dwelling Units (ADU) Ordinance Link: The Color of Law: A Forgotten History of How Our Government Segregated America Link: Sarah Ware Link: Tammy Hajjar Miller

    -----------------

    Guest Questions

    What do you do at the Realtor Association? 6:30

    What other groups does CAR associate with? 9:00

    What do you think is one of the biggest issues for mom and pop investors? 14:00

    What are some of the main reforms pushed for in RLTO reform? 16:30

    What can a Realtor do to push for this reform? 18:50

    What's going on with Rent Control? 25:00

    Why are you still bullish on Chicago? 31:00

    Wrap Up Questions

    What is your competitive advantage? 37:30

    What is one piece of advice for a new investor? 38:20

    What do you do for fun? 39:20

    Self development tool? 39:55

    Local network recommendation? 41:15

    How can we learn more about you? 42:25

    That's our show! Thanks so much for listening. Tune in next week.

    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.


    Episode 55: Understanding The Diverse Opportunities and Multiple Pockets of Elgin Apr 08, 2021
    Show notes

    Elgin has a long history of being one of the most significant cities located just outside of Chicago. Spanning two counties and one of the largest populations in Illinois, it offers a wide variety of housing options and investment strategies. Broker and investor, Mike Zwemke, takes us through his experiences of getting started and scaling in the area; his strategy and why he's interested in HOAs. We cover the economy of Elgin and the workforce, the different pockets and their associated housing stock and so much more. If you like what you hear, please leave us a 5 star review. Enjoy the show!

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Mike Zwemke of Property Partners FV | Find Mike Zwemke on LinkedIn

    Sponsor: Chicago REIA Sponsor: Appeal.tax Link: Rich Dad Poor Dad: What the Rich Teach Their Kids About Money That the Poor and Middle Class Do Not! Link: Chris Davis - Full Service Real Estate Brokerage - Inspire Realty Group Link: Ottawa Savings Bank Link: Resource Bank - A National Bank Link: The First National Bank of Ottawa Link: Property Partners Of Fox Valley - Home

    -----------------

    Guest Questions

    What excites you about Elgin? 7:15

    What are some different pockets of Elgin that investors should be looking for? 8:20

    Do you have a specific housing type that you look for? 10:10

    What is the rehab process like when working in an HOA? 12:45

    How did you buy your first rental? 14:00

    How did you eventually decide on your areas of Elgin? 15:40

    Where are the Elgin tenants working/commuting to? 16:50

    What is the tax levy like in Elgin? 18:15

    Elgin has multiple counties, do you focus on which county you're in? 20:25

    What is the process of the Elgin sheriff sale? 20:55

    What are some mistakes you've made with a sheriff sale? 22:15

    How do you account for the township rental license programs? 25:00

    What do you like about the fox valley economy that makes it independent from Chicago? 27:40

    Is there anything you wish Elgin had more or less of? 32:30

    Are you seeing a migration from Chicago to Elgin? 33:00

    What is important to starting a relationship with community banks? 33:50

    Wrap Up Questions

    What is your competitive advantage? 38:10

    Advice for new investors? 39:00

    What do you do for fun? 39:50

    Self development activity? 40:10

    Network recommendation? 41:30

    Local Banker recommendations? 42:00

    How can we learn more about you? 42:45

    That's our show! Thank you so much for listening!

    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.


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