

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

Jun 3, 2021 • 52min
Episode 67: Chicagoland Rehab Financing Without Using Hard Money or 203k Loans
Possibly the biggest consideration when taking on a rehab project is how to finance the deal. We've all considered hard money, FHA has their 203K loan program, and we've probably seen a late night commercial or two. Perry Farella of Prime Lending talks us through a loan program which is a cross between a conventional loan and hard money, something that you don't even need to refinance out of once the property is stabilized. Listen in as Perry tells us more about this product and how it can be best used to fund your next Chicago rehab. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending Sponsor: ChicagoREIA Sponsor: Appeal.tax Link: How 2 Fund Renovation Blog Link: Be Your Own House Contractor: Save 25% without Lifting a Hammer ----------------- Guest Questions Background 5:00 How do you qualify for rehab loans? 9:45 How do you determine and support the ARV? 11:30 What is the closing timeline for these loans? 13:45 How does the draw process work for construction? 17:45 Do you need to refi out of this loan product? 21:00 Are there price thresholds these loans work best for? 22:00 What goes wrong? 27:00 Hot investment neighborhoods? 31:00 What would need to happen for credit to tighten? 38:45 Competitive advantage? 42:45 What is one piece of advice you'd give a new investor? 43:50 Wrap Up Questions What do you do for fun? 44:20 Self development recommendations? 45:20 Quality resources? 47:20 How can we learn more about you? 48:00 That's our show! Thanks 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.

Jun 1, 2021 • 8min
Episode 66: Straight-Up Tuesday Tip 4 - Eric Workman Answers "Besides rate and term, what other items I should ask about when talking to different lenders?"
Besides rate and term, what other items I should ask about when talking to different lenders? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman of Renovo Financial ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.

May 27, 2021 • 45min
Episode 65: Figuring Out the Short Sale Process and Other Non-Traditional Closes with Gina Diaz
One of the most important team members that real estate investors rely on is their attorney. Not all closings are created equal and Gina Diaz explains some of the closing nuances both through the eyes of an attorney and as an investor. Gina provides great insights into how to successfully close on a short sale, what to be aware of in a double close, and how to work with a title company and attorney to successfully wholesale a deal. Tune in as you are sure to learn something in today's episode. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Gina Diaz of Diaz Case Law Sponsor: ChicagoREIA Sponsor: Appeal.tax Link: We Win Chicago Link: Diaries of a Female Real Estate Investor: Learn How A Single Mom Went From 80k in Debt To a Multi Million Dollar Portfolio by Farrah Ali Link: Andrew Holmes ----------------- Guest Questions What drew you to investing in real estate? 7:00 What is a short sale? 9:30 How is the final price determined in a short sale? 10:15 Is the closing process different for short sales versus traditional closings? 12:00 Are short sales expected to increase in frequency? 15:00 What are the nuances with buying short sales? 16:45 What are some ways for an investor to evaluate a wholesale property? 21:30 Challenges you've seen during closings? 31:00 What is We Win? 35:30 What is your competitive advantage? 39:15 Advice for new investors? 40:00 Wrap Up Questions What do you do for fun? 40:50 Self development activity? 41:15 Network recommendation? 42:20 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.

May 20, 2021 • 1h 1min
Episode 64: King of Chicagoland; Easy Makes You Soft
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.

May 18, 2021 • 8min
Episode 63: Straight-Up Tuesday Tip 3 - Chance Badertscher Answers "What are some items I should look out for during Attorney Review?"
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.

May 13, 2021 • 37min
Episode 62: How a Single Mom Created A Real Estate Empire Across Chicagoland
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.

May 6, 2021 • 56min
Episode 61: Understanding the Economics and Risks of Chicago's Pension Crisis
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.

May 4, 2021 • 13min
Episode 60: Straight-Up Tuesday Tip 2 - Rosario Terracciano Answers "What are some common mistakes that cause investors to overpay for an investment property?"
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.

Apr 29, 2021 • 43min
Episode 59: Chicago's Very Own Cost Segregation Expert - Kevin Cawley
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.

Apr 22, 2021 • 46min
Episode 58: Multi Family Investing in Chicago's Northwest Side with Gloria Weikert
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.


