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Episode 311: Managing and Operating 100+ Units at 25 Years Old with James Thompson

Straight Up Chicago Investor

Release Date: 07/25/2024

Episode 332: From Slangin’ Windows To Building Chicago 6 Flats in 10 Year with Joey Halperin show art Episode 332: From Slangin’ Windows To Building Chicago 6 Flats in 10 Year with Joey Halperin

Straight Up Chicago Investor

Joey Halperin is a real estate broker and developer with vast experience in ground up development and renovation projects across Chicago! Joey starts by explaining how he left the corporate world to jump into general contracting and real estate brokerage! He gets granular on difficult renovation projects and the importance of having skilled contractors to help assess and mitigate risk. Joey discusses how he's finding deal flow in this tough market and explains how understanding Zoning can be a cheat code. He closes with a bullish outlook on Lincoln Square and other “path of progress”...

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Episode 331: These Neighborhoods Have the Most Potential for Chicago Investors show art Episode 331: These Neighborhoods Have the Most Potential for Chicago Investors

Straight Up Chicago Investor

Which South Side neighborhoods have been the biggest surprise and which neighborhoods have the most potential? ============= 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: Email the Show: Guest: , Link: ----------------- Production House:  Copyright of Straight Up Chicago Investor 2024.

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Episode 330: Condo Conversions, Building Violations, and How to Stay Compliant with the New CTA with James Erwin show art Episode 330: Condo Conversions, Building Violations, and How to Stay Compliant with the New CTA with James Erwin

Straight Up Chicago Investor

James Erwin has decades of experience practicing Real Estate Law and is a board member of the NSBC! James starts by breaking down the legal ins and outs for condo deconversions. He dives deep on the process for clearing building violations on properties including tips to keep the City and lenders happy. James explains the Corporate Transparency Act (CTA) and everything that must be disclosed in order to stay compliant. Throughout the show, James displays his deep knowledge of real estate law and how his firm is providing top notch service to their clients! If you enjoy today’s episode,...

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Episode 329: From W2 To Investor Overnight… See How This Played Out For Sean Douglas show art Episode 329: From W2 To Investor Overnight… See How This Played Out For Sean Douglas

Straight Up Chicago Investor

Sean Douglas of the Axon Group discusses his adventurous start to his real estate journey! Sean began his investment career when he inherited his grandparent’s home, which after numerous setbacks, he eventually flipped! He breaks down how he jumped into the deep end by doing construction himself. After having a contractor steal $7000 from him, Sean recaps the long days of work that it took to get his flip project to the finish line. Sean also shares details on his 4-unit house hack and considerations when investing in “picky” towns and villages. Throughout the show, Sean demonstrates how...

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Episode 328: What to Focus on When Negotiating A Multifamily Transaction show art Episode 328: What to Focus on When Negotiating A Multifamily Transaction

Straight Up Chicago Investor

What should I focus on in negotiating a multifamily transaction? ============= 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: Email the Show: Guest: , Kiser Group Link: ----------------- Production House:  Copyright of Straight Up Chicago Investor 2024.

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Episode 327: Logan & Humboldt Property Owners’ Rights Taken By The New NW Preservation Ordinance with Luke Blahnik show art Episode 327: Logan & Humboldt Property Owners’ Rights Taken By The New NW Preservation Ordinance with Luke Blahnik

Straight Up Chicago Investor

Luke Blahnik returns to educate us on the new Northwest Side Preservation Ordinance. Luke jumps right in by explaining the ins and outs of the expansion of the Predominance of the Block (606) District under this new ordinance. He breaks down the increased fees to demolish a multi-unit building, limitations on building single family homes, and requirements for selling a tenant-occupied building in the area. Luke, Mark, and Tom discuss how the Ordinance will not be able to accomplish the goal of preserving affordable housing and instead could have negative impacts to landlords and tenants. A...

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Episode 326: How This Chicago Investor Grew 10x in Just 3 Years with RJ de Leon show art Episode 326: How This Chicago Investor Grew 10x in Just 3 Years with RJ de Leon

Straight Up Chicago Investor

RJ de Leon returns to the show to tell us about his most recent investments and how he’s managing his portfolio remotely as he and his family spend most of the year traveling! RJ starts by discussing how he and his wife Nicky set up their investments and businesses to be able to manage them remotely and travel the country for months at a time! He gives tips for aspiring entrepreneurs that are planning to embark on a new journey. RJ explains all the benefits and considerations of passive investments and gets granular on analyzing investments. He also provides insights on capital raising and...

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Episode 325: How Much Does it Cost to Construct an ADU in Chicago? show art Episode 325: How Much Does it Cost to Construct an ADU in Chicago?

Straight Up Chicago Investor

What are the construction costs associated with building out a new ADU unit? Connect with Mark and Tom: Email the Show: Guests: Jonathan Klemm, Link: ----------------- Production House:  Copyright of Straight Up Chicago Investor 2024.

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Episode 324: How to Combat Squatters and Title Deed Fraud with George McCleary show art Episode 324: How to Combat Squatters and Title Deed Fraud with George McCleary

Straight Up Chicago Investor

George McCleary is a real estate investor and developer with two decades of experience. He is also the creator of courses that teach investors to protect themselves from Squatters and Deed Fraud! George starts by discussing his viral “I Stole a House” video which explains how sophisticated squatters are able to steal a property owner's equity. He dives into the top precautionary measures against squatters and shines light on some wild “unconventional methods” to remove squatters. George explains the value that his Squatter Defender and Title Fraud Defender courses bring to investors....

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PW Cabinetry Grand Opening show art PW Cabinetry Grand Opening

Straight Up Chicago Investor

Join us for the grand opening and ribbon-cutting clebration of Pentwater Cabinetry's newly renovated showroom! On September 25th at 4pm, we cut the ribbon on the future for Pentwater Cabinetry and their ability to fill your cabinet needs. Enjoy complimentary snacks and beverages throughout the event! When: September 25th at 4pm Where: 920 N Lombard Road, Lombard, IL 60148 Call: Visit: ----------------- Production House:  Copyright of Straight Up Chicago Investor 2024.

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More Episodes

James Thompson is broker and property manager with vast experience acquiring, renovating, and managing apartment buildings all at the young age of 25 years old!

James shares the early grind required to get off the ground in the commercial real estate game! He discusses the biggest lessons learned from renovating and managing 100+ apartments. James gives the scoop on investing in student housing and also provides some good REI horror stories. James closes with great advice for newer investors and a positive outlook on Chicago!

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: [email protected]

Guest: James Thompson, Triton Realty Group

Link: SUCI Ep 22 - Matt Fritzshall (Network Referral)

Link: Morning Brew Daily (Podcast Recommendation)

Link: Jay Parsons (Rental Housing Economist)

Link: Jay Martin - Article on Rent Control Drawbacks

Guest Questions

03:30 Housing Provider Tip - Be aware of required inspections when replacing hot water heaters!

05:36 Intro to our guest, James Thompson!

09:37 The grind of starting in commercial real estate.

17:22 Biggest lessons learned from construction and management of buildings!

22:50 The 101 on student housing.

26:32 Growing the management company and horror stories!

35:15 Advice for new and aspiring investors.

37:07 James’ outlook on Chicago.

43:55 What is your competitive advantage?

44:27 One piece of advice for new investors.

44:57 What do you do for fun?

45:08 Good book, podcast, or self development activity that you would recommend? 

45:37 Local Network Recommendation? 

46:16 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2024.