Straight Up Chicago Investor

Entrepreneur, investor, and best-selling author J Scott of BiggerPockets and Bar Down Investments joins SUCI and drops tremendous wisdom! J shares the mindset and adaptability required to become a successful real estate investor. He draws on his past experience to break down the economic climate by speaking to various topics including inflation, stagflation, the debt crisis, consumer behavior, and the job market. J closes with insight on properly underwriting deals and emphasizes the power of buy-and-hold rental properties as a wealth building tool! If you enjoy today's episode and like what you hear, please leave us a review and share us with a friend! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: J Scott from BiggerPockets and Bar Down Investments Link: The Goal (Book Recommendation) Link: Ashley Wilson (Network Recommendation) Link: Real Estate by the Numbers (Pre-Order J Scott's New Book) Link: Connect with J Scott Sponsors: Essex Realty Group and Appeal.tax ----------------- Guest Questions 03:21 House Provider Tip: Understand that bull markets may cover up mistakes that wouldn't be covered in bear markets! 04:39 Intro to our guest, J Scott! 05:31 J talks about the mindset required to be successful in real estate! 12:41 J defines stagflation and talks about its relation to the debt crisis? 21:02 How does J predict lending will change in the near future? 27:19 Does J think that the expected recession can be a self-fulfilling prophecy as consumers get fearful and change their behavior? 30:52 What is J's outlook on the job market? 36:32 Is J still looking for real estate deals and how has his underwriting changed? 40:41 How can passive investors effectively vet an operator? 44:50 J shares mistakes he's made in his investing career! 49:01 J talks about accounting for expense increases when underwriting deals Wrap Up Questions 50:33 What is J's competitive advantage? 50:59 One piece of advice for new investors. 51:51 What do you do for fun? 52:33 Good book, podcast, or self development activity that you would recommend? 53:34 Local Network Recommendation? 54:29 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.

Kory Dieter is a Chicago-based is a house hacker and professional out of state investor with a portfolio mix that includes SFRs and small multi-families across 5 markets. In today's episode Kory shares with us how she started her real estate journey with a house hack in Andersonville to how she was able to leave behind her W2 job. Along the way she's dabbled in a variety of investing strategies, including house hacking, medium term rentals, BRRRR, and 1031 exchanges, with no signs of stopping now! This episode is full of nuggets on deal acquisition and things to keep in mind when looking for your next investment, whether it's in Chicago or a different market! 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: Kory Dieter Link: http://www.naiopchicago.org/ Link: https://www.gcrealtyinc.com/brrrr-investment-strategy-must-knows Link: https://www.gcrealtyinc.com/blog/house-hacking-101-in-chicago Link: https://www.straightupchicagoinvestor.com/house-hacking-calculator Link: https://www.straightupchicagoinvestor.com/podcast/episode-43-househacking-scaling-and-large-multifamily-deals-with-one-of-chicagos-best-power-couples Sponsors: State Farm and Appeal.tax ----------------- Guest Questions 03:30 House Provider Tip: Be Ready To Address Issues When Tenants First Move In 05:40 Intro to our guest, Kory Dieter! 06:45 Starting with a househack in Andersonville 12:15 The importance of knowing the neighborhood 21:15 Out of State Real Estate Investors Must Have Mindset 25:50 Pro Forma Vs Actual Is Usually Different in Real Estate Investing 27:57 Scaling As A House Hacker 30:58 How To Prepare Your Portfolio For the Future 34:01 Challenges Faced Transitioning From a W2 To Self Employed Real Estate Investor Wrap Up Questions 42:39 What is Kory's competitive advantage? 43:15 One piece of advice for new investors. 53:25 What do you do for fun? 43:42 Good book, podcast, or self development activity that you would recommend? 45:02 Local Network Recommendation? 45:53 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 the difference between actual cash value and replacement cost? 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.

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.