show 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 importa ...
 
There are a lot of real estate podcasts out there, most of which focusing on the residential fix and flips or wholesaling, but Kevin Bupp believes there's a smarter way to build long term cash flow and generational wealth. On the Real Estate Investing For Cash Flow podcast, you'll learn firsthand how the most successful commercial real estate investors in the world have learned to leverage their multifamily and commercial properties to create a steady stream of passive income. We'll spend ti ...
 
The Mobile Home Park Investors Podcast is the world’s first podcast dedicated to mobile home park investing. This weekly podcast explains the intricacies of this unique real estate niche and details why an investor would want to own a mobile home park, either directly or through a real estate fund. Current manufactured housing community owners will find this podcast helpful in improving their mobile home park’s operations and profitability. The Podcast is hosted by Jefferson Lilly and Brad J ...
 
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show series
 
Ryan Smith is not an optimist, but a realist. With a stark numbers-based opinion, Ryan provides his thoughts on Chicago’s housing market, the strength and the validity of the recent appreciation, and how long it may take to get through upcoming foreclosure inventory. We’ve had Ryan on here before (Episode 28), but last time it was too good of a con…
 
Sterling Anderson is a real estate investor. Sterling is the President & CEO of Red Oak Development (Formerly Sterling Capital Investments), a Real Estate Development/Investment company based in Omaha, NE. The company invests in and develops single-family, Multifamily, and Hotel properties  Quotes: “It starts with the parent company. It starts with…
 
Lee Kiser is the co-founder of Kiser Group, a member of the Forbes Real Estate Council, and a wealth of knowledge in the Chicago market (and a local musician!). In today’s episode, Lee provides his thoughts on how today’s hot market differs from 2005, how institutional and private money has altered apartment investing in Chicago, and what neighborh…
 
Jill DeWit & Steven Butala are real estate and raw land experts. Since 1999, Jill and Steve have completed the acquisition and sale of more than 16,000 properties without incurring leverage or debt and continue to purchase property daily for immediate resale. Quotes: “The seller just doesn’t want it anymore. They are tired of getting the tax bills.…
 
Possibly the biggest consideration when taking on a rehab project is how to finance the deal. We’ve all considered hard money, FHA has their 203K loan program, and we’ve probably seen a late night commercial or two. Perry Farella of Prime Lending talks us through a loan program which is a cross between a conventional loan and hard money, something …
 
Besides rate and term, what other items I should ask about when talking to different lenders? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman of Renovo Financial ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.…
 
Vince Guzzo is a businessman, entrepreneur, and philanthropist, Vince is a Canadian entrepreneur who currently serves as CEO of Guzzo Cinemas, Guzzo Construction inc., Guzzo Medical, and Guzzo Hospitality. Vince received national attention in 2018 when he joined the cast of the CBC Television business reality shows Dragons' Den as one of the invest…
 
One of the most important team members that real estate investors rely on is their attorney. Not all closings are created equal and Gina Diaz explains some of the closing nuances both through the eyes of an attorney and as an investor. Gina provides great insights into how to successfully close on a short sale, what to be aware of in a double close…
 
Gene Guarino is a real estate and senior living expert. Gene is a certified financial planner in the US and Australia as well as a full-time real estate investor with over 30 years of experience in just about every area of real estate including both residential and commercial, with his primary focus today being in the senior living space, or more s…
 
With nearly 30 years of experience as a broker, Frank Montro, the King of Chicagoland, shares his reflections on how the industry has changed from the early ‘80s to today. While touching on strategies his team uses to generate business, and cementing what it takes to succeed, Frank gives a compelling presentation that is certain to teach you someth…
 
Steven Waldman is a real estate and ground lease expert. Steven is the founder and president of Ground Lease Capital Partners, LLC; a national leader in Acquiring, Originating, and Investing in Ground Lease transactions as well as an Advisor to Institutional Investors who are seeking exposure to this asset class. Prior to founding Ground Lease Capi…
 
Be honest with yourself...how many excuses do you tell yourself? Farrah Ali was a single mom in debt, working full time, but did not let that deter her from financial freedom. Listen to her incredible story and how it has impacted all areas of her life. She details even more of this in her book, “Diaries of A Female Real Estate Investor.” If you li…
 
Ray Alcorn is a real estate expert and president of Park Commercial Real Estate. Ray has extensive experience in business and real estate development, including hotels, restaurants, single- and multi-family housing, shopping centers, and office buildings. He is responsible for the overall direction of the Company, and the development and implementa…
 
What does Chicago look like from an economist’ perspective and why should investors care? Today, Dr. Joseph Pagliari explains some of his economic thesis related to Illinois’ long term fiscal issues that are top of mind for so many investors. He provides options Illinois might have to address these issues, but are they specific to only Chicago or a…
 
What are some common mistakes that cause investors to overpay for an investment property? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano | ClickInvest ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.…
 
Brent Sprenkle is a real estate expert and senior managing director at Berkadia. Berkadia is a leader in the commercial real estate industry, offering a robust suite of services to the multifamily and commercial property industry. Berkadia was formed in 2009 as a joint venture of Berkshire Hathaway and Leucadia National Corporation (now Jefferies F…
 
The word "taxes" inspires fear from all types of investors, but especially in Chicago. From income tax, to property tax, we’re paying a lot. Depreciation is one of Real Estate’s greatest benefits, and there is a way to maximize that benefit immediately. Cost Seg Kev is here today to explain what cost segregation is and how it can be used to offset …
 
Gene Trowbridge is a nationally recognized securities attorney. Gene has been in the commercial and investment real estate business continuously since 1972 and in the legal profession since 1996.  He is a member of the California Bar. And as the founding partner of Trowbridge Law Group LLP, Gene’s law practice concentrates on the syndication of com…
 
One of the most important allies to an investor is the broker they work with. Gloria Weikert runs the X-Plus team and has a specialty in helping clients buy investment properties. In today’s episode, Gloria gives some insight on what it takes to win deals in a competitive market that go past just offering more money; breakdowns of different neighbo…
 
Mike Conlon is CEO and majority owner of Affordable Communities Group (ACG), LLC based in Cary, NC. ACG currently owns 22 manufactured home communities totaling 4,000+ spaces in Alabama, Georgia, Florida, Maryland, North Carolina, Ohio, and West Virginia with a market value exceeding $110 million. Mike has also bought, rehabbed, and sold 20 mobile …
 
Chicago is known for complex and restrictive landlord and tenant policies, but there are dozens of people fighting for change and protection. Kris Anderson of the Chicago Association of Realtors is one of those people on the front lines. Not everyone knows the role of CAR, so Kris explains what they do and his role in the machine as well as other g…
 
Tom Burns is a surgeon and Real Estate Investment Expert. Tom is an orthopedic surgeon in Austin, Texas. He is a graduate of the University of Texas at Austin and Southwestern Medical School in Dallas. He received sports medicine training at the prestigious Steadman Hawkins Fellowship in Vail, Colorado and he is a physician for the United States Sk…
 
Elgin has a long history of being one of the most significant cities located just outside of Chicago. Spanning two counties and one of the largest populations in Illinois, it offers a wide variety of housing options and investment strategies. Broker and investor, Mike Zwemke, takes us through his experiences of getting started and scaling in the ar…
 
Donna Serdula is the creator of LinkedIn-Makeover.com and one of the most sought out LinkedIn experts. Donna pioneered the concept of LinkedIn profile optimization and is the author of LinkedIn Profile Optimization for Dummies. Through her Website, LinkedIn-Makeover.com, Donna and her team of over 20 writers, help thousands of LinkedIn users strate…
 
Lumi Ispas has been a determined and successful investor, broker, and coach in Chicago for two decades. She’s lost it all and gained it all back. In today’s episode she shares her journey of emigrating from communist Romania to truly experiencing the American Dream through real estate. She addresses several hot topic items including early mistakes,…
 
Darin Garman is the president of Heartland Investment Group. Darin is a published author, former bank owner, and currently owns and manages a $50+ million-dollar portfolio. He is widely recognized as one of America’s top “Go to Guys” for all things multi-family investing. His experience spans more than 30 years and is hyper-focused on investments i…
 
Many fear what they don’t understand. That’s exactly why we put together this round table discussion with two other great CHA section 8 property managers. Listen in as we address the entire workflow from screening the applicants, to the move in, and everything that happens in between. Section 8 can be a great investment strategy, but it’s imperativ…
 
Dick Anagnost is the president and CEO of Anagnost Investment Group. Dick has been recognized as a transformational leader and a dynamic force in the ongoing renaissance of Manchester, New Hampshire as he continues on his mission to revitalize the state’s largest city and change its skyline. Dick has over 40 years of demonstrated achievements in in…
 
It’s March and taxes are top of mind! However, by only reactively focusing on taxes during this one part of the year, you are potentially leaving money on the table. Aaron Zimmerman, a Chicago investor and CPA, provides great insights into how to best work with a CPA, the importance of maintaining good records, overlooked deductions, and proactive …
 
Thomas Jorglewich is the president and CEO of Toben Partners. Toben partners is a Christian centered real estate investment and management company guided by Biblical principles and a servant’s heart. They specialize in strip and neighborhood shopping centers ranging from 10,000 to 50,000 square feet in size. Quotes: “I’m in the mode now where I’m t…
 
Would you trade salary for knowledge? John Westbrook spent time straight out of college working for one of Chicago’s largest property managers to build-up his foundational knowledge of the industry. John has since transformed this knowledge into a substantial portfolio of multifamily buildings on the Northside. John explains how he plans for the lo…
 
Philip Morgan is the CEO of the Morgan Group. As Chief Executive Officer, Philip is responsible for leading MORGAN's strategic planning and growth across all business activities, including development, acquisitions, construction, and property management. Since joining MORGAN, Philip has been involved in the development and acquisitions of over 7,00…
 
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 attrib…
 
Spencer Cullor is a multifamily investor and syndicator. Spencer holds expertise in commercial, multifamily, and residential real estate.  He also spent several years as a homebuilder before moving over to the investment side.  Using his skills in project management, capital raising, financial analysis, construction, and contract management, he has…
 
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