Straight Up Chicago Investor

Latest Episodes:

Episode 264: Unlocking Zoning Secrets: Your Guide to Chicago Zoning, ADUs, and Other Essential Information Dec 19, 2023

Show notes

Where can I go to find all information around zoning, ADU, lot sizes and lot lines, and other essential information?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Samuel Pavlovcik, Pavlovcik Architecture Inc

Link: Zoning Cheat Sheet

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Production House: Flint Stone Media

Episode 263: Buying Chicago Lots For $1 and Other Successful Strategies with Tanisha Blakemore Dec 14, 2023

Show notes

Tanisha kicks things off by discussing her first deal back in 2005; a 2-unit in Auburn Gresham that she purchased with 0% down! She talks about learning to be a housing provider during a time when resources were much more scarce than today. Tanisha has a couple real estate horror stories including another fire story and the US Marshals arriving at her property. She closes with an outlook on Auburn Gresham and empowering words on getting into the real estate game!

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: Tanisha Blakemore, Dreamtown Realty

Link: The Richest Man in Babylon (Book Recommendation)

Link: Tanisha's Instagram

Link: ChiBlockBuilder

Link: SUCI Ep 250 - Jonathan Klemm

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Guest Questions

03:05 Housing Provider Tip: Routinely check smoke detectors to mitigate risk.

04:09 Intro to our guest, Tanisha Blakemore!

07:47 Tanisha's first deal at 25 years of age!

12:25 Tanisha's next steps following her first deal.

15:45 US Marshals at Tanisha's property!

18:14 Another property fire story!

26:14 Acquiring a Dollar lot!

30:44 Tanisha's decision to get licensed.

33:15 Outlook on Auburn Gresham.

35:27 What is Tanisha's competitive advantage?

36:05 One piece of advice for new investors.

36:42 What do you do for fun?

36:55 Good book, podcast, or self development activity that you would recommend?

37:55 Local Network Recommendation?

38:28 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 262: From FBI Agent to Hundreds of Doors In Chicago with James Williams Dec 07, 2023

Show notes

James Williams is a real estate investor, attorney, and former FBI agent who embarked on his real estate journey in the early 90s!

James starts by discussing how he chose a career path which includes a period of working in the FBI, all while having real estate investing on the back of his mind. He discusses his first real estate purchase, a graystone on Chicago's Northside purchased in the 90s! James shares insights raising capital, acquiring hundreds of units, and extremely rough times in his investing career that resulted in him selling off most of his portfolio. He shares the impact of losing a valued business partner and friend. The silver lining of the rough times is that James still holds a nice portfolio and has the team in place to continue scaling! Throughout the show, James emphasizes the importance of patience, due diligence, and building a great team. Most importantly, after 262 episodes, we finally get to drop a Point Break reference.

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: James Williams, Mainstreet Real Estate Services

Link: Boss (Book Recommendation)

Link: American Pharaoh (Book Recommendation)

Link: Henry Cardenas (Network Referral)

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Guest Questions

02:31 Clean leaves to prevent clogging of gutters and drains!

03:39 Intro to our guest, James Williams!

09:30 James' quest to buy his first piece of real estate!

18:53 Working in the FBI!

25:33 Raising capital for RE Investing.

37:32 Lessons learned from 4 years in a tough market.

47:55 Selling off most of the portfolio.

53:36 Costs of Selling.

56:35 What's next for James?

59:43 What is James' competitive advantage?

61:13 One piece of advice for new investors.

62:50 What do you do for fun?

63:45 Good book, podcast, or self development activity that you would recommend?

64:28 Local Network Recommendation?

65:04 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 261: Accelerate Your Expenses and Other Accounting Tips To Leverage Before 12/31 Dec 05, 2023

Show notes

What questions should I ask my tax professional before the end of the year?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Aaron Zimmerman, Lipschultz Levin & Gray

Link: Episode 52: Saving Thousands of Dollars With the Appropriate Tax Strategy and Deductions

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Production House: Flint Stone Media

Episode 260: Chicago Investors Cannot Have a Worse Day Than This, With Roman Viere Nov 30, 2023

Show notes

Roman Viere owns and operates over 1000 rentals in Chicago with the bulk of those in the Austin neighborhood. In this episode, he gives a detailed breakdown on a terrifying explosion that occurred at his 35-unit apartment building in Austin. He discusses all things from the day of the incident including arriving at the scene, speaking with the authorities, and handling the press. Roman discusses insurance implications resulting from the explosion, insurance claims, and a 1033 exchange. If things weren't bad enough, he talks about his million dollar water bill and how he got around that! Despite never planning for explosions and other catastrophic events at your rental properties, these are events that all housing providers should be prepared to handle for the safety and protection of all parties.

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: Roman Viere, Urban Alternatives

Link: SUCI Ep 77 - Roman Viere

Link: The Bomber Mafia (Book Recommendation)

Link: Greg Yearwood (Precision Consulting / 773-852-8246 / gyearwood1@gmail.com / pcllcclaims.com)

Link: Myk Snider (Sphere Public Relations / 312.816-5401 / myk@spherePR.com / SpherePR.com)

Link: Jeff Riechenbach (State Farm / (773) 685-3600 / jeff.reichenbach.vafdml@statefarm.com)

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Guest Questions

02:18 Housing Provider Tip: Be prepared to deal with emergencies at your rental properties!

03:16 Intro to our guest, Roman Viere!

03:55 The morning of a tragic event.

10:39 Arriving at the scene.

17:04 Being prepared for emergency events at rental properties.

27:55 Reflecting on the day of the incident.

35:57 Tactical items for dealing with an explosion.

43:01 Insurance implications.

60:13 Insurance Coverage and 1033 Exchange.

65:02 Lessons learned from this tragic event.

67:38 What is Roman's competitive advantage?

68:25 One piece of advice for new investors.

69:10 What do you do for fun?

69:44 Good book, podcast, or self development activity that you would recommend?

70:41 Local Network Recommendation?

71:36 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 259: Time For Serious Chicago Investors with Sal Becovic Nov 23, 2023

Show notes

Sal Becovic returns to the show to discuss how he has continued to grow his portfolio despite the challenging market!

Sal jumps right in by sharing his philosophy on acquisitions and being "rate agnostic". He gives an extremely bullish outlook on Chicago leaving us feeling great about this special city. Sal discusses the ins and outs of his latest and largest acquisition; a 28-story condo building with value-add potential. Throughout the show, Sal emphasizes the importance of establishing solid fundamentals, surrounding yourself with great people, and being a good person; rules of life not just RE investing.

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: Sal Becovic, Becovic Realty

Link: NBOA Chicago

Link: Bloomberg.com

Link: The Economist

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Guest Questions

02:35 Housing Provider Tip: Ideas to make unit turnovers more efficient!

04:10 Intro to our guest, Sal Becovic!

07:31 Being in acquisition mode!

13:57 Being "rate agnostic" in today's market.

18:52 Sal's perspective on the Chicago RE market.

23:32 Sal's latest and largest deal!

37:21 What's next for Sal?

41:55 Operations and building a team.

47:30 Sal's closing tips on optimizing your RE portfolio!

51:03 What is Sal's competitive advantage?

52:35 One piece of advice for new investors.

53:49 What do you do for fun?

54:38 Good book, podcast, or self development activity that you would recommend?

56:23 Local Network Recommendation?

57:34 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 258: Maximize Your Savings: Unveiling the Tax Advantages of Solar Panels and Electric Vehicles Nov 21, 2023

Show notes

What are the tax benefits of solar panels and electric vehicles?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Michael Procaccio, Pro Financial Services Group Inc

Link: Build Your Team | Straight Up Chicago Investor Podcast

Link: Episode 198: 2023 Tax Strategies for Chicagoland Real Estate Investors with Michael Procaccio

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Production House: Flint Stone Media

Episode 257: The Playbook For Short-Term Rentals in Chicago with Ditron Corker Nov 16, 2023

Show notes

Ditron is a seasoned Short-Term Rental (STR) Investor who is teaching others how to get started and maximize profitability with STRs.

Ditron shares how he got started in real estate and utilized the house hacking and rent-by-the-room strategy. He shares tremendous nuggets on finding good STR markets and typical expenses associated with setting up and running a short-term rental. Ditron gives tips on working with AirBNB, STR expectations, amenities, and FAQs to consider to set yourself up for success. Mid-Term Rentals, STR underwriting, and automation are also discussed on the episode. This show is full of STR jewels of wisdom that you won't want to miss!

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: Ditron Corker, Roam to Rome Spaces & STR Innovate

Link: Ditron's Meetup

Link: SUCI Ep 143 - Jessica Ryan

Link: Who Not How (Book Recommendation)

Link: Jeff Ma and Eli Goodman Meetup

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Guest Questions

03:10 Housing Provider Tip: Deliver a nicely landscaped property to encourage upkeep!

05:37 Intro to our guest, Ditron Corker!

08:00 Ditron's first deal!

09:20 Getting into short-term rentals (STRs)!

13:46 Expenses on STRs.

20:07 STR-Specific Features and FAQs!

24:27 Entertainment amenities in STRs.

25:56 Where are STRs allowed?

31:08 Underwriting STRs!

35:34 STRs vs MTRs.

38:55 Automation Systems.

40:50 Lessons Learned!

46:06 Tax Advantages to STRs.

49:22 Ditron's upcoming conference!

51:49 What is Ditron's competitive advantage?

52:25 One piece of advice for new STR investors.

53:02 What do you do for fun?

53:24 Good book, podcast, or self development activity that you would recommend?

54:05 Local Network Recommendation?

55:14 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 256: Home Inspection Insights For Chicago Investors With Andrew Fox Nov 09, 2023

Show notes

Andrew kicks things off by discussing necessary skills to succeed as an entrepreneur in Real Estate. He talks about the value of a building inspection even if the property will be rehabbed. Andrew clears the air on the need for auxiliary inspections such as radon, asbestos, and sewer scopes. Andrew drops golden nuggets on questions that investors should be asking inspectors to mitigate their risk. The show is closed out with technological advances in the inspection industry that investors should be aware of!

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: Andrew Fox, BrickKicker Inspection Services

Link: BrickKickerCommercial.com

Link: The Game with Alex Hormozi

Link: Good to Great (Book Recommendation)

Link: Mathew Tarailo (Network Referral)

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Guest Questions

02:58 Housing Provider Tip: Set up lock boxes for access during emergencies!

04:54 Intro to our guest, Andrew Fox!