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 143: Ins and Outs to Navigating Chicago Short-Term Rentals with Jessica Ryan 26.05.2022

Have you also been considering short-term rentals to increase your NOI?! Jessica Ryan joins us to share valuable knowledge on considerations when planning your short-term rental! Jessica starts off by explaining the main points of the Chicago Shared-Housing Ordinance and how to get a license for a short-term rental. She touches on notice requirements to other tenants, percentage of short-term rent...

Episode 142: Generating Infinite ROI From Chicagoland Senior Living Investing with Brandon Schwab 19.05.2022

Wondering how you can invest in a niche asset class to reduce your competition? Brandon Schwab talks about how he is revolutionizing the Chicagoland Senior Living space and making it a very profitable investment. Brandon starts off by talking about his motivation to improve the Senior Living experience and the pitfalls he faced when starting out. He dives deep into the acquisition, rehab, and mana...

Episode 141: Straight Up Tues Tip 29 - Noah Birk and Aaron Sklar Sit Down to Explain How Investors New To The Multifamily Space Can Catch A Broker's Eye 17.05.2022

As an investor, how do I get the attention of the most successful brokers in the Chicagoland area? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Noah Birk & Aaron Sklar of Kiser Group Link: Episode 23 of Straight Up Chicago Investor ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2...

Episode 140: Providing Necessary Education for Chicago Investors with CIC's Jessica Sivels 12.05.2022

Interested in sharpening your education to propel your Chicago Real Estate Investments? Jessica Sivels explains the variety of resources that Community Investment Corporation (CIC) is providing.      Jessica provides a brief summary of CIC's extensive experience and explains how CIC can be a value add to investors given their knowledge of Chicago. She dives deep into CIC's vast educational resourc...

Episode 139: Leveraging Technology to Efficiently Manage your Chicago Property Portfolio with Kerri Davis 05.05.2022

Looking for a user-friendly, innovative property management software? Today's guest Kerri Davis dives deep into how her software Fortress can help you take your investment management to the next level. Kerri jumps right in by explaining the shortcomings of other management softwares and how Fortress addresses those concerns. She talks about when it makes sense for an investor to transition to mana...

Episode 138: Straight Up Tues Tip 28 - Mike Scanlon Talks Through How He Sourced An Off Market Househack Deal 03.05.2022

Mike Scanlon walks us through the numbers, rationale, and challenges of a recent househack in Elgin. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Mike Scanlon from The Axon Group (EXP Realty) ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Episode 137: Revitalizing Chicago's Bronzeville Neighborhood via a $4 Billion Dollar Development with Morgan Malone 28.04.2022

Ever wonder what goes into planning a multi-billion dollar equitable development and how those principles can be applied to your investing? Morgan Malone joins us to break down how this can be accomplished while maintaining the character of a neighborhood. Morgan provides a history of the Bronzeville Lakefront Planned Development and a behind-the-scenes look into overcoming challenges associated w...

Episode 136: From Failed Chicago Flip to a $90M in Multifamily Portfolio with John Casmon 21.04.2022

Return guest (Episode 15) John Casmon drops in to share golden nuggets on how he separates himself from the competition in this tight market! John starts off by reminding us of his humble real estate beginnings which came via a house hack in the North Center neighborhood of Chicago. He explains how his flipping experience helped propel his growth despite facing adversity. John provides tips on how...

Episode 135: Straight Up Tuesday Tip 27 - Jake Parker and Andy Friedman Answer "What is a Condo Deconversion and How Can Investors Benefit From Purchasing a Deconversion Opportunity?" 19.04.2022

What is a condo deconversion and how can investors benefit from purchasing a deconversion opportunity? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jake Parker & Andy Friedman from Kiser Group ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Episode 134: Building Affordable Housing Through Modular Construction in Chicago with Josh Braun 14.04.2022

Interested in Modular Housing? Josh Braun explains modular housing and how he's been able to be a pioneer in Chicago Modular Housing Construction.      Josh starts off by talking about his start in real estate and his early interactions with the City's Building Department. He discusses the specs of his different finished products and lessons learned that have helped him evolve his business. Josh s...

Episode 133: Leveraging Your IRA to Fund Your Chicago Real Estate Investments with Adam Sypniewski 07.04.2022

Did you know that you can raise or deploy funds found in IRAs to invest in Real Estate? Adam Sypniewski joins us to break down how this can be accomplished. Adam kicks things off by defining an IRA and explaining the limitations when withdrawing IRA funds. He dives into the different ways investors can leverage their IRA funds or someone else's funds to invest in real estate. Adam talks about rule...

Episode 132: Straight Up Tuesday Tip 26 - Jake Fugman Answers How to Break Down a 3-Unit Househack in Hermosa 05.04.2022

Jake Fugman walks us through the numbers, rationale, and challenges of a recent househack in Hermosa that our listeners can learn from. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jake Fugman, The Axon Group (EXP Realty) ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Episode 131: From Immigrant to Thriving Chicago Real Estate Broker Via the Power of Marketing with Aram Ghazaryan 31.03.2022

Want to know how to take your real estate marketing to the next level to grow your business? Our guest Aram Ghazaryan provides insight on how to differentiate yourself from your competition! Aram explains his tremendous story of how he got into real estate at the young age of 21 and methods used to achieve great success after 5 years in the business ! He shares how to consistently put out engaging...

Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo 24.03.2022

Return guest Chris Puleo drops in to share a lending market update! Chris starts off by commenting on the volatility in the market and looks back on how the pandemic shaped what is happening today . He explains "bait and switch" and the questions you should be asking your mortgage lender. Chris dives deep into the different loan programs available in today's market. Chris also delivers Chicago-spe...

Episode 129: Straight Up Tuesday Tip 25 - Ron Plonis and Jeff Leibovich Answer "What are the Many Factors Investors Must Consider if they are Looking to Sell in This Hot Market? 22.03.2022

What are the many factors investors must consider if they are looking to sell in this hot market? (And buyers need to know this info as well!) Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Ron Plonis & Jeff Leibovich from Kiser Group ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor...

Episode 128: How to Successfully Deconvert Chicago Condos, With Sean Connelly 17.03.2022

Ever wonder what it takes to convert a condo building into rental apartments? Sean Connelly of 33 Realty explains the ins and outs of deconverting condos as an investment strategy. Sean starts by defining basic terms and the strategy associated with deconverting condos. He then dives into the more technical aspects of underwriting and handling negotiations with owners and associations. Sean closes...

Episode 127: Scaling From W2 Employee to over 1,400 Units in Chicago's South Side with David Pezzola 10.03.2022

Think it's possible to scale to 80 rental units while working a W2 job? We know it sounds tough, but our guest David Pezzola explains how he did that and then continued on to build a massive portfolio! David shares insights on how was able to grow and manage his large portfolio while having his W2 job . He then talks about his post W2 investment journey including his acquisition strategy and lesso...

Episode 126: Straight Up Tuesday Tip 24 - Danny Mantis and Matt Halper Answer "How is inflation effecting the Chicagoland market?" 08.03.2022

How is inflation affecting the Chicagoland market? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Danny Mantis & Matt Halper from Kiser Group ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Episode 125: How Aldermen Effect Zoning and Development in Chicago with Nicholas Katsafados 03.03.2022

Thought about taking down a mixed-use building to improve your neighborhood's streetscape? Not sure where to start? Our guest Nicholas Katsafados explains how he found a niche in mixed-use buildings and what other things he is doing to contribute to redevelopment in his neighborhood! Nicholas provides insight on how investing in mixed-use buildings differs from other types of buildings . He talks...

Episode 124: Scaling Your Real Estate Business in Chicago with Aaron Galvin 24.02.2022

Wondering who is partnering with big developers to sell and lease their finished product? Our guest Aaron Galvin explains how his company is capturing a large market share in this space! Aaron provides insight on how his company's focus on people and relationships has led to tremendous growth . He talks about the mistakes he made while growing his business and how he had to learn to "elevate and d...

Episode 123: Straight Up Tuesday Tip 23 - Rosario Terracciano Answers "What should buyers expect in 2022?" 22.02.2022

What should buyers expect in 2022? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano from Clickinvest Link: AttomData.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Episode 122: A Case Study on Three Chicagoland Deals in a Low-Inventory Environment with John Warren 17.02.2022

Can't find a deal in this Chicago Real Estate Market? You are not alone! John Warren of Presto Properties joins us to discuss how he acquired his 3 most recent properties. John discusses properties he purchased in Bellwood, Albany Park, and Cicero. He shares how he acquired each deal, the strategy implemented, the nuances, and lessons learned. While breaking down the deals, John elaborates on part...

Episode 121: Breaking Down Why Chicago Public Housing Failed with Professor Brad Hunt 10.02.2022

Dr. Brad Hunt of Loyola University's Department of History joins the show to educate us on the complicated history of Chicago's Public Housing developments and why real estate investors should care.  Brad is the author of Blueprint for Disaster , in which he traces Chicago's Public Housing history and transformation under various government administrations. Leveraging this knowledge of poorly oper...

Episode 120: Straight Up Tuesday Tip 22 - Perry Farella Answers "What are the new 2022 conventional and FHA loan limits?" 08.02.2022

What are the new 2022 conventional and FHA loan limits? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Episode 119: How Blockchain is Impacting Chicago Real Estate with Simon Enwia 03.02.2022

Thinking about buying Real Estate or a Yacht in the Metaverse? Want to learn more about the Metaverse, Blockchain, and other innovations that will impact your real estate strategy? This episode will scratch that itch! Simon Enwia of Flawless Homes shares mind-blowing insight on developing technologies in real estate! Before jumping in, Simon lays out his background as a Chicago investor and breaks...

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