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Straight Up Chicago Investor

Business & Economics Podcasts

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 and not worked in Chicago, you are in the right place.

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 and not worked in Chicago, you are in the right place.

Location:

United States

Description:

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 and not worked in Chicago, you are in the right place.

Language:

English


Episodes

Episode 50: Building a Chicago Empire with Andrew Holmes

3/4/2021
For our 50th episode we thought we’d give everyone a special treat... Andrew Holmes is one of the most well-known names in Chicago Real Estate Investing. Andrew explains his incredible journey, from his early days as a hustling agent, to how he structured his first few investment deals. Andrew dives into specifics on how he finds deals, what attributes he looks for in an investment property, how he underwrites properties, and how he teaches others to scale. There is so much to break down...

Duration:00:57:50

Episode 49: Moving Fast and Weathering Storms with Investor and ClickInvest Co-Founder Rosario Terracciano

2/25/2021
For the past 15+ years, Rosario Terracciano has been cutting his teeth with a lot of hard learned lessons. In today’s episode, he shares some early mistakes he made about buying, working with contractors, estimating ARVs and leasing. He shares how he weathered the sub-prime crisis and emerged stronger - co-founding Clickinvest and ultimately representing banks and buyers in more than $300 million of real estate transactions . Some of the big industry shifts that took place during the...

Duration:00:56:48

Episode 48: The Doctor of Motor Row - David Shifrin

2/18/2021
For everyone working a W2 job, our guest today, David Shifrin, is a great example of how to incorporate real estate into your long-term plan without having to give up your current career. David Shifrin wanted a way to marry his professional career as a plastic surgeon to his interests in becoming a real estate investor. This path led him to Motor Row and an acquisition of a historic Chicago building. Listen as he describes why he is bullish Motor Row and the lessons he learned as he...

Duration:00:41:29

Episode 47: Building Generational Wealth Through 1031 Exchanges with Lauren Speidel

2/11/2021
The term “1031 Exchange” is ubiquitous, but do you really know what it is or how to even engage in one? Lauren Speidel of Exeter1031 is a subject matter expert and breaks it down for you today. She’ll explain the different parties involved, what the criteria are and what you need to know before having the necessary conversations. Our hosts, Tom and Mark, have great FAQs for Lauren and she delves into a lot of content on one of our most informative episodes yet. If you like what you hear...

Duration:00:48:55

Episode 46: Why Invest in Smaller Multifamily Properties in the North and Northwest Suburbs of Cook County - Anthony Citriglia

2/4/2021
Chicagoland is an enormous market with a ton of sub markets. Anthony Citriglia of Essex Realty’s submarket covers many of the near north and near northwest suburbs and he breaks down exactly what those markets are like; how they differ from Chicago; and how they differ from each other. Following the post-war boom, cheaper access to cars, and the development of several Metra lines, the 50s-80s were filled with tons of development, mostly still currently owned by mom & pop landlords. Find out...

Duration:00:39:52

Episode 45: Community Investment Corporation (CIC) - Chicago’s Non for Profit Lender, with Jack Crane

1/28/2021
For over 35 years, Jack Crane has been providing expertise on financing the acquisition and rehabilitation of commercial real estate. The majority of those years have been spent as Sr. VP of lending at CIC where he is responsible for carrying out the mission to be a leading force in both neighborhood revitalization and affordable housing. From lending during tough times, to helping analyze risk, Jack explains how CIC has played a predominant role over multiple decades in transforming...

Duration:00:45:23

Episode 44: Understanding The Intricacies of Various Mortgage Products With Chris Puleo

1/21/2021
How many ways are there to finance buying a property? Way more than I’m aware of which is why our guest Chris Puleo is here. With his robust 20+ year career, Chris has seen it all and explains a plethora of different popular products. With so much interest in househacking, of course we talk about the FHA product and calculating the self sufficiency tests. Not to mention some of the things investors AND brokers need to be aware of when putting offers on properties with an FHA loan product....

Duration:00:44:36

Episode 43: Househacking, Scaling, and Large Multifamily Deals With one of Chicago’s Best Power Couples

1/14/2021
Have you ever looked at your significant other and wanted to build an empire with them? That’s exactly what Nicky and RJ De Leon have been doing since the early days of their relationship. Today, they tell their story from start to current day, diving into how they had all those hard conversations about deciding on the first location, getting on the same page as your partner and so on. Since that initial househack, they moved on into bigger projects but not alone. Listen to how they went...

Duration:00:51:34

Episode 42: Understanding Both the Updated RTLO and ADU Ordinance with Bob Floss

1/7/2021
In today’s episode, attorney Bob Floss dives further into the current RLTO ordinances and how the proposed ordinance affects investors, landlords, and tenants alike. With so much changing day to day, it can be challenging to keep track of best practice. This is why it’s necessary to have solid legal representation on your team when dealing with tenant issues. Bob also discusses the new ADU ordinance and how investors can benefit from the current pilot. Listen in and let us know what you...

Duration:00:53:23

Episode 41: What We Learned in 2020 and What’s On the Docket for SUCI

12/30/2020
As we wrap up 2020, a huge thank you to all our listeners and active participants that have helped transform this podcast from a simple idea of sharing localized knowledge into its current state (which we view as a success). In this episode, Mark and Tom give a quick state of the union of the podcast and also dive into what they learned over 40 episodes, including some of their favorite episodes and nuggets. We also lay out what to expect from SUCI as we continue to try and add valuable...

Duration:00:36:03

Episode 40: Navigating Chicago’s Eviction Process with Tom Raleigh

12/24/2020
Tom Raleigh, of Halsted Law Group, breaks down the current environment for landlords as it relates to the eviction process. COVID has shaken things up, and understanding what you can and can’t do is more confusing than ever, so having an ally who understands the rules and will fight for you is paramount. Listen to our hosts ask Tom some FAQs about landlord process and protocol and learn about a new service coming out to help landlord’s screen tenants way more effectively! Rent Butter is...

Duration:00:43:21

Episode 39: Scaling a Multi-Million Dollar Real Estate Business in Chicago

12/17/2020
In today’s episode, Sean Connolly talks about his not so usual journey of scaling to a multi- million dollar portfolio and the lessons and tools he’s acquired over the past 8 years. Sean provides his advice on investing in certain southside markets as a new investor and if you’re not doing volume, why it’s so important to control your material cost. Sean also provides his thoughts on the imminent future of the Chicago real estate market. Lastly, he explains the role and significance of...

Duration:00:48:57

Episode 38: Can’t Find Deals on the MLS? The Cook County Land Bank has Hundreds of Distressed Properties Waiting for Investors

12/10/2020
Are you looking for distressed deals? The Cook County Land Bank (CCLB) has plenty and they go right under most investor’s noses! In today’s episode, Rob Rose provides an overview of the CCLB, a socially responsible wholesaler working with investors to turn dilapidated properties into newly remodeled homes. Rob describes CCLB’s acquisition process, their commitment to neighborhoods, CCLB’s unique ability to wipe out liens, and how you can engage with CCLB to get in on the action. Listen in...

Duration:00:56:55

Episode 37: The NBOA - Your Ally and Voice as a Chicagoland Housing Provider

12/3/2020
In today’s episode, our guest Mike Glasser, President of the Neighborhood Builders Owner Alliance, explains how neighborhood housing provider advocacy groups are fighting for fair and lawful protection for investors in and around Chicago. Mike lays out the current advocacy campaign against the proposed CRTLO, the differences between the CRLTO and the RTLO, and the unintended consequences from previous legislation. Lastly, he gives advice on what you can do to help support the fight. Listen...

Duration:00:45:37

Episode 36: Inaugural SUCI Thanksgiving Episode - What to be Thanking for in Chicago

11/25/2020
First and foremost, a huge thank you to all our listeners! Please continue to be active members of our community and help spread the good word! This Thanksgiving, we want to take a quick moment to reflect on all the great things and opportunities we have in this great city of Chicago. A rich history, epic sports franchises, an extensive park network and some of the best food in the world are only the tip of the iceberg. With one of the largest metros in the country, we’ve been able to build...

Duration:00:42:13

Episode 35: Diving into Belmont Cragin, North Austin, and the Northwest Side Building Coalition with Jon Womack

11/19/2020
Jon Womack of Third City Properties has been investing in the Chicago market for four years focusing on the northwest neighborhoods of Belmont Cragin and North Austin. Jon dives into what the investment landscape looks like in these areas, including tenant expectations of finishes and his general investment strategies. One of the key differentiators for Jon is his involvement in local neighborhood coalitions. Jon heads up the Northwest Side Building Coalition and is also an active member of...

Duration:00:41:27

Episode 34: Hustling From a Househacker to over 40 Units in the Western Burbs in 2 Years!

11/12/2020
With the right mindset, anything can be achieved. Shantanu Kamra is living proof, having moved to the US 8 years ago and Chicagoland just about 2 years ago, he’s been able to scale his portfolio in the western suburbs to over 40 units. In today’s episode he talks about househacking, BRRRR strategy execution, and scaling into larger buildings. He also gives advice on why coaching has worked for him while so many others do nothing with the information from a mentor. Shantanu breaks down...

Duration:00:44:00

Episode 33: Block by Block in Bronzeville and Kenwood with Ted Stratman

11/5/2020
Are you interested in multifamily buildings in the southside of Chicago? Are you looking to know the ins and outs of Bronzeville along with some of its adjacent neighborhoods? Ted Stratman is one of the leading brokers in Chicago and in this episode he lays out invaluable block by block knowledge - including what rents have done over the last twelve months, how demand in Bronzeville and its surrounding area has fared through COVID, and what types of opportunities are available in specific...

Duration:00:52:47

Episode 32: The Streets and Boulevards of Logan Square and Its Surrounding Neighborhoods with Luke Blahnik

10/29/2020
Luke Blahnik of Flor Blahnik, is a true real estate entrepreneur (and owner of Avondale Bowl!). In this episode, Luke provides block by block insights investors need to know to successfully invest in Logan Square. He explains what attracted him to the area as well as the future prospects for growth despite the massive run up over the past 10 years. Luke dives into tenant expectations, rehab expectations, demand as it relates to Boulevard proximity, and the long-term value of brick buildings...

Duration:00:44:54

Episode 31: Understanding and Appealing Property Taxes in Cook County

10/22/2020
“You have to watch out for your property taxes,” has been said in numerous episodes. On today’s episode we bring a tax appeal expert to explain how to proactively protect your investment against increasing property taxes. Tim Jacobs of KSN Law dives deep into the complex world of Illinois property taxes and about the multiple ways you can appeal property taxes in Chicago, the tax assessment cycle and what data points you can leverage to strengthen your apparel cases. Tim also gives a tip on...

Duration:00:48:59