Straight Up Chicago Investor

Are you looking to learn about acquiring and managing multifamily properties in Chicago's Northside? If so, you'll get great value out of this show! John starts by talking about his military background and how that has served him in his real estate career. He provides details on managing his first large scale, multifamily property and how that success propelled his growth. John gets granular on rehabbing occupied buildings, the emergence of some northside neighborhoods, and managing tenants. John closes by emphasizing the importance of quality relationships and properties - slow and steady wins the race! 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: John McGeown, High Fidelity Property Management Link: SUCI Ep 124 - Aaron Galvin (Network Recommendation) Link: Tools Of Titans (Book Recommendation) Sponsors: Essex Realty Group and Appeal.tax ----------------- Guest Questions 03:00 House Provider Tip: Make sure you are considering debt-to-income ratios when screening tenants! 05:20 Intro to our guest, John McGeown! 07:14 How has John's military background served him in real estate? 08:58 Why did John choose to go into real estate after the military? 11:10 How did John establish an area of focus for his property management business? 16:56 How did John leverage his success on the 45-unit project to propel his growth? 22:04 What are some tips for accurately underwriting rents? 25:51 Where did John start investing? 27:32 John describes the emergence of developed neighborhoods that he's invested in! 29:22 How do you prepare for a renovation of an occupied multi-unit building? 35:43 What are John's plans over the next few years? Wrap Up Questions 38:15 What is John's competitive advantage? 38:30 One piece of advice for new investors. 38:58 What do you do for fun? 39:50 Good book, podcast, or self development activity that you would recommend? 41:05 Local Network Recommendation? 42:00 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.

Looking for insight on the nuances of acquiring and managing properties on the south side of Chicago? If so, this episode is for you! Tim starts by talking about his start in real estate and how he identified a need for quality property management on the south side. He provides insight on tenant screening, underwriting expenses, and subsidized housing for the C/D class assets he operates. Tim gets granular on the housing stock, values, and neighborhood borders in the Chicago Lawn, West Elsdon, and West Englewood neighborhoods. Tim closes this knowledge packed show by sharing the pockets of these neighborhoods that he's bullish on and will continue to invest in for years to come! 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: Tim Harstead, Chicago Style Management Link: Never Split the Difference (Book Recommendation) Link: SUCI Ep 146 - RJ Deleon Sponsors: State Farm and Appeal.tax ----------------- Guest Questions 03:42 House Provider Tip: Be mindful of how the number of touchpoints required can vary for properties across different classes! 05:29 Intro to our guest, Tim Harstead! 06:33 How did Tim get started in real estate? 08:19 What sparked Tim's interest in property management? 09:57 What are some nuances about Chicago's south side that Tim has to communicate to out of state investors? 12:28 How does Tim forecast expense ratios in lower class neighborhoods? 16:05 What neighborhoods is Tim heavily involved in? 19:00 Tim's shares tips for screening tenants in lower class neighborhoods! 21:04 How does the typical term of lease vary between section 8 and market rate tenants? 26:06 Tim provides insight on the West Lawn and Chicago Lawn neighborhoods! 31:43 Tim shares the differences in the leasing process across the different south side neighborhoods he manages units in. 35:08 What is the housing inventory like in these south side neighborhoods like West Englewood and Chicago Lawn? 36:55 What is Tim's opinion on Gage Park and West Elsdon? 39:17 What areas is Tim planning to invest in over the next 5-10 years? Wrap Up Questions 41:55 What is Tim's competitive advantage? 42:18 One piece of advice for new investors. 42:38 What do you do for fun? 42:15 Good book, podcast, or self development activity that you would recommend? 43:23 Local Network Recommendation? 43:48 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.

What are the recent changes within Freddie Mac that now allows for financing the rehab of an ADU project? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending Link: https://perryfarella.com/blog/ ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Brian Kochendorfer returns to the show after 2 years! This time around Brian provides an objective analysis on how his investment properties in Indiana and Ohio compared to his Chicago portfolio. Brian kicks things off by sharing his investment parameters and how he ended up pursuing opportunities in Ohio and Indiana in addition to Chicago. He dives deep into the nuances of acquiring, repositioning, and managing assets in those other markets. Brian speaks to differences in tenant expectations, rent growth, taxes, and cap rates in NW Indiana, Indianapolis, and Cincinnati compared to Chicago! This show is filled with great insight on the current state of the market, identifying opportunities given buyer/seller sentiment, and why Chicago is a great place to invest in even with all the headwinds! 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: Brian Kochendorfer, Essex Realty Group Link: Arc Equity Group Link: SUCI Episode 14 - Brian Kochendorfer (1st Episode) Link: SUCI Episode 151 - Fritz Kaegi Link: Kevin Claffy (Network Recommendation) Sponsors: State Farm and Essex Realty Group ----------------- Guest Questions 03:15 House Provider Tip: Add lighting to your properties for added, cost-effective security! 04:55 Intro to our guest, Brian Kochendorfer! 06:41 How did Brian make the jump from being a broker to investing? 07:28 What were the parameters in Brian's investment property search when he started off? 10:11 Brian talks about key differences between Chicago and the other markets he's invested in (i.e. NW Indiana, Indianapolis, Cincinnati). 16:33 Are the higher returns worth it given the headwinds in Chicago? 18:07 How does the building stock differ between Chicago and the other markets Brian has invested in? 21:28 What would Brian have done differently on his Cincinnati project? 22:11 How do the landlord-tenant laws in those other markets compare to Chicago? 28:30 Brian compares expectations in Chicago vs NW Indiana and Cincinnati. 32:10 What is Brian's macro-level outlook on Chicago? 34:14 How is Brian approaching acquisitions given the market conditions? 37:15 Brian shares the sentiment he's seeing from buyers and sellers today and the opportunities that could bring. Wrap Up Questions 44:47 What is Brian's competitive advantage? 45:25 One piece of advice for new investors. 45:53 What do you do for fun? 46:43 Good book, podcast, or self-development activity that you would recommend? 47:08 Local Network Recommendation? 48:05 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.

From successful BRRRR to a delayed, over-budget project, Zach Gring shares lessons learned from his investing journey! Zack starts by explaining how he established an asset class to focus on and the reasons for his criteria. He talks through a successful BRRRR project in Batavia and speaks to managing the rehab of a tenant-occupied property. He also shares some lessons learned from his delayed project in Glen Ellyn. Throughout this episode, Zach shares the importance of establishing a network and a focus when getting into real estate to set yourself up for success! 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: Zach Gring, The Axon Group Link: Landlording on Autopilot (Book Recommendation) Link: Vince Incopero (Network Recommendation) Sponsors: The Axon Group (EXP Realty) and Appeal.tax ----------------- Guest Questions 03:21 House Provider Tip: Be sure to check alleys for excess garbage left behind by tenants during turnovers! 05:07 Intro to our guest, Zach Gring! 07:27 What sparked Zach's interest in real estate investing? 08:30 Where did Zach start investing and what are some of the nuances of small-town investing? 10:56 How did Zach get "scrappy" to increase his savings rate to invest in real estate? 12:30 Zach dives into his first deal in Batavia! 13:50 How did Zach manage rehab of a tenant-occupied unit? 19:50 How was the GC selected/managed and what were the unforeseen construction items? 24:15 Zack talks about his next deal in Glen Ellyn! 29:28 What is the exit strategy on the Glen Ellyn property? 31:48 Where is Zack focusing on geographically? 38:10 Zack shares his hindsight perspective on research that should be done when getting into real estate. Wrap Up Questions 40:30 What is Zachi's competitive advantage? 41:40 One piece of advice for new investors. 42:02 What do you do for fun? 42:15 Good book, podcast, or self-development activity that you would recommend? 43:04 Local Network Recommendation? 43:39 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.

What is builder's risk insurance and as an investor why do I need to be aware of builder's risk insurance? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Josh Steigelmann, State Farm Insurance ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

After staying in an Airbnb while on vacation, Rishi Bajaj realized how we can leverage this strategy and used midterm rentals to multiply his rental income! Rishi shares how he got the idea to venture out into the niche space of midterm rentals. He talks about furnishing, costs, and additional considerations when comparing midterm rentals to traditional long-term rentals. He dives into why he sees value and has been investing in some south side neighborhoods and also shares the characteristics he looks for in properties! Throughout the show, Rishi provides valuable tips on thinking outside the box to maximize profit and ROI! 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: Rishi Bajaj, West Loop Capital Partners Link: Multifamily Insights (Podcast Recommendation) Link: The Short Term Show (Podcast Recommendation) Link: Eric Hubbard (Network Recommendation) Sponsors: GC Reality and Appeal.tax ----------------- Guest Questions 04:45 House Provider Tip: Hire professional and reputable HVAC contractors to ensure systems function properly! 05:13 Intro to our guest, Rishi Bajaj! 08:15 What motivated Rishi to get into real estate? 12:07 How did Rishi live frugally when he first got started? 13:53 What are some considerations when furnishing a unit? 17:30 What are some additional costs to consider on midterm rentals that differ from long-term rentals? 24:18 How is Rishi marketing his midterm rentals? 28:16 Why did Rishi start purchasing property in Bridgeport and the Heart of Chicago neighborhood? 31:15 What property characteristics does Rishi look for? 34:28 How are these properties being financed? 39:19 How does Rishi underwrite for vacancy? 43:57 How has Rishi managed a growing Chicago portfolio from a remote location? Wrap Up Questions 49:34 What is Rishi's competitive advantage? 50:34 One piece of advice for new investors. 51:42 What do you do for fun? 52:19 Good book, podcast, or self-development activity that you would recommend? 53:32 Local Network Recommendation? 55:10 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.

It first took Joe Smazal of Interra Realty six years to sell $100M of multifamily real estate. Six months into 2022, Joe has already sold $100M of assets THIS YEAR ALONE! Joe explains how he left his stable day job to become a Chicago commercial broker, and the growing pains and hustle required to get started. He then speaks to the importance of developing relationships for increased deal flow and identifying areas of focus to become a trusted expert in your market. In classic SUCI fashion, Joe dives in at a street-level to define the boundaries of some north side neighborhoods! This episode is full of golden nuggets if you're interested in getting into Chicago Multifamily Real Estate! 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: Joe Smazal, Interra Realty Link: Podcast 1 Recommendation Link: Podcast 2 Recommendation Link: Sam Gutierrez (Network Recommendation) Link: Max Grossman (Network Recommendation) Sponsors: Prime Lending and Appeal.tax ----------------- Guest Questions 02:55 House Provider Tip: Be mindful of the leasing season and make your leases end during the peak leasing cycle! 05:13 Intro to our guest, Joe Smazal! 06:08 How did Joe get started in real estate? 15:05 How much time and effort did it take before Joe got his first big deal? 26:07 How did Joe identify his areas of focus? 30:52 How have things changed as Joe's business has grown? 33:00 How are investors analyzing properties and justifying investments in the Lakeview neighborhood? 37:17 What are the boundaries of Lakeview? 39:08 What are the boundaries of North Center? Wrap Up Questions 40:45 What is Joe's competitive advantage? 41:15 One piece of advice for new investors. 42:10 What do you do for fun? 43:40 Good book, podcast, or self development activity that you would recommend? 44:40 Local Network Recommendation? 45:32 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.

What are some of the useful technologies/apps that can help you scale your REI business? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Bolanle Ogunmakin, Quality Builders Link: Episode 76: Big Business Processes Make a Powerful Small Business with Jonathan Klemm ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Jeff Weinberg of Drexel Properties joins us to discuss the importance of systems and relationships when scaling a large Chicago Real Estate portfolio. Jeff kicks things off by talking about his start in real estate and leaving his W2 job to pursue his passion full time. He jumps into the mindset and strategies that will help in scaling a portfolio. Jeff drops street level knowledge on the North and Northwest side and explains why he is bullish on Chicago. Throughout the show, Jeff emphasizes the importance of cultivating long term relationships with brokers, contractors, and other vendors, and attributes much of his success to implementing this principle! 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: Jeff Weinberg from Drexel Properties Link: The Splendid and the Vile (Book Recommendation) Link: Jeff Weinberg's LinkedIn Sponsors: The Axon Group (EXP Realty) and Appeal.tax ----------------- Guest Questions 03:55 House Provider Tip: Remember to have a baseline for utilities to identify irregular bills! 06:04 Intro to our guest, Jeff Weinberg! 07:22 How did Jeff get started in real estate? 09:52 At what point did Jeff decide to leave his W2 job? 11:47 Jeff talks about how he scaled his portfolio. 15:32 In hindsight, what would Jeff change about his investing career? 17:46 What attracted Jeff to investing in the Northwest side of Chicago? 26:11 Why does Jeff choose to buy-and-hold and why is he continuing to scale an already large portfolio? 29:04 Why is Jeff still bullish on Chicago? 30:50 How is Jeff's portfolio setup? 38:12 How do you develop relationships with brokers and vendors? Wrap Up Questions 42:14 What is Jeff's competitive advantage? 42:42 One piece of advice for new investors. 44:37 What do you do for fun? 46:27 Good book, podcast, or self development activity that you would recommend? 49:05 Local Network Recommendation? 50:55 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.