Straight Up Chicago Investor

Straight Up Chicago Investor

Business EN ↓ 468 episodes

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...

Author

Straight Up Chicago Investor

Category

Business

Latest episode

Jul 9, 2026

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Episodes

Episode 341: Cracking the Code to Large Scale Developments with Susan Tjarksen 12.12.2024

Susan Tjarksen is the Managing Director at Cushman & Wakefield and has led the development of residential and commercial across the country! Susan discusses her time in hotel management and shares some funny/horror stories! She explains how receiverships work and how investors can capitalize on this opportunity. She breaks down the nuances of large scale developments including insane time frames o...

Episode 340: You Might Be Exempt From Paying Sales Tax on Your Materials 10.12.2024

What is an enterprise zone and how can investors benefit from these areas? ============= If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Tom Shallcross, Straight Up Chicago Investor Podcast Link: Chicago Enterpri...

Episode 339: How to Get to 1,000 Units in 20 Years… The Blueprint With Jeff Weinberg 05.12.2024

Jeff Weinberg returns to the show after two years to share the impressive growth of Drexel Properties! Jeff explains how Drexel Properties has grown from 600 units to over 1000 units over the last 2 years. He discusses how his team leverages technology to streamline their property management business. Jeff dives deep on how to find deals in a competitive market and emphasizes the importance of tre...

Episode 338: Skills Earned On The Floor of Wall Street Become Secret Power In Moving Apartment Buildings with Andy Friedman 28.11.2024

Andy Friedman is a Senior Director at Kiser Group and has a proven track record of success in Chicago Multifamily Real Estate. Andy shares his experience as a stock trader and brewery owner, including how the skills he obtained in those endeavors translated to real estate! Andy explains the grit required to get off the ground in commercial real estate. He provides valuable tips for new commercial...

Episode 337: How to Establish Credibility and Raise Capital 26.11.2024

What are the appropriate steps to take to raise capital from investors? ============= If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Aram Ghazaryan, AMG Realty Link: Episode 335: The Growth Every Chicago Investo...

Episode 336: Can Both Sides Get What They Need Around Chicago Landlord-Tenant Laws with Michelle Gilbert 21.11.2024

Michelle starts by explaining both Chicago's RLTO and Cook County's RTLO, and the differences between the two ordinances. She gets granular on disclosures required from Housing Providers to remain in compliance with the ordinance(s) and breaks down security deposits and move-in fees. Michelle dives deep on the eviction process and shares resolution tips to aid with landlord-tenant issues. She clos...

Episode 335: The Growth Every Chicago Investor Wants - Listen To What Aram Ghazaryan Did in 24 Months 14.11.2024

Aram Ghazaryan returns to explain how he transitioned from a successful RE broker to a flipper executing over ten profitable flips per year. Aram starts by discussing his first multifamily investment which was a 7-unit building. He explains his decision to stop being an agent and jump into flipping properties full time. Aram shares tremendous lessons learned from flipping and has great insights on...

Episode 334: Canceling a Contract After All Contingencies Have Passed 12.11.2024

What can you cancel a contract for after all contingencies have passed? ============= If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chance Badertscher  of Lavelle Law Link: Build Your Team | Straight Up Chicago...

Episode 333: Chicago Building Code Violations and How to Work the System with Zack Limbaugh 07.11.2024

Zack Limbaugh of the Limbaugh Law Firm provides his clients with legal representation and strategy to remedy Building Code Violations and other matters associated with Chicago Buildings! Zack starts by explaining how he got his foot in the door with the City of Chicago before becoming an attorney and leveraged those relationships to build a niche in legally handling Building Code Violations! Zack...

Episode 332: From Slangin' Windows To Building Chicago 6 Flats in 10 Year with Joey Halperin 31.10.2024

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 discus...

Episode 331: These Neighborhoods Have the Most Potential for Chicago Investors 29.10.2024

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! C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Aaron Sklar , Kiser Group Link: Episode...

Episode 330: Condo Conversions, Building Violations, and How to Stay Compliant with the New CTA with James Erwin 24.10.2024

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 or...

Episode 329: From W2 To Investor Overnight… See How This Played Out For Sean Douglas 17.10.2024

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...

Episode 328: What to Focus on When Negotiating A Multifamily Transaction 15.10.2024

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! C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Noah Birk , Kiser Group Link: Kiser Group ----------------- Production House:  Flint...

Episode 327: Logan & Humboldt Property Owners' Rights Taken By The New NW Preservation Ordinance with Luke Blahnik 10.10.2024

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...

Episode 326: How This Chicago Investor Grew 10x in Just 3 Years with RJ de Leon 03.10.2024

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 plan...

Episode 325: How Much Does it Cost to Construct an ADU in Chicago? 01.10.2024

What are the construction costs associated with building out a new ADU unit? C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Jonathan Klemm , Quality Builders Link: SUCI Episode 264: Unlocking Zoning Secrets: Your Guide to Chicago Zoning, ADUs, and Other Essential Information ----------------- Production House:  Flint Stone Medi...

Episode 324: How to Combat Squatters and Title Deed Fraud with George McCleary 26.09.2024

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 s...

PW Cabinetry Grand Opening 23.09.2024

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: 630-487-5811 Visit:...

Episode 323: Leveraging a W2 to Grow a Chicago Portfolio and Brokerage with Horacio Tristan 19.09.2024

Horacio Tristan is a born and raised Chicagoan and full-time government employee who has built an impressive real estate portfolio and brokerage business! Horacio starts by discussing his upbringing and his first few real estate deals on Chicago's South Side. He explains how he built and maintained his real estate brokerage business during the housing crash. Horacio shares his geographic areas of...

Episode 322: FHA Financing vs 5% Down; Pros and Cons For Each Option With Perry Farella 17.09.2024

What type of financing are investors utilizing to get deals done and what are the pros and cons of each option? C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Perry Farella , First Community Mortgage Link: How 2 Fund Renovation Blog ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor...

Episode 321: Flipping, Short-Term Rentals, & Helping Veterans Secure Housing with Kirby Atwell 12.09.2024

Kirby Atwell is a former US Army Officer turned real estate investor and podcast host with a focus on short-term rentals! Kirby starts with his experience in the military and jumping into real estate shortly after reading "Rich Dad, Poor Dad"! With over 100 renovated properties under his belt, he shares great insights on small and large flips including pros and cons of both options. Kirby discusse...

Episode 320: The Godfather of Chicago Property Management, Taft West 05.09.2024

Taft West is the Vice President of Technical Assistance and Sustainability for the Chicago Community Loan Fund and is a renown property management instructor! Taft starts by sharing his background which includes some autopsy experience! He talks about starting in Chicago real estate, managing condominiums, and public housing in the late 1970s. Taft discusses the differences in leasing now compared...

Episode 319: Great Tips on How To Manage Your Contractors 03.09.2024

What Should Investors Do To Ensure a Successful Rehab? C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Jonathan Klemm, 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 2024.

Episode 318: How to 4X Your Real Estate Business with Michael Valente 29.08.2024

Michael Valente is the founder and CEO of Renovation Sells Franchising; general contracting experts that focus on cosmetic renovations of pre-market homes to maximize sales price! Michael shares how he left his corporate job and began working for his mentor to learn the ropes of general contracting and renovation! He talks about starting his own general contracting business and the biggest lessons...

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