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 293: Help! Firefighters, City Inspectors, and Police Officers Are All at My Building With Anthony Rodriguez From Drexel Properties 02.05.2024

Anthony Rodriguez is an experienced Chicago Property Manager who manages over 300 units for Drexel Properties! Anthony starts by discussing his previous experience in other industries and how those skills have translated into his real estate career. Then, Tom and Anthony retell the story of how their team managed a boiler explosion in a multifamily building. They break down how they notified the C...

Episode 292: Why Investors Need to Know a Good Public Adjuster with Dorian Bezanis 25.04.2024

Chicago Native Dorian Bezanis is the president of ALPHA Adjusting and has nearly four decades of investing experience in Chicago's Northside! Dorian jumps right in by discussing the investing portfolio he's built in Edgewater and Rogers Park over the last 37 years. He explains the role of a public adjuster, the immense value they bring to investors. Dorian gets granular by sharing how to handle fi...

Episode 291: What Every Investor Needs To Know About the Rehab Draw Process 23.04.2024

How does the draw process work when taking on a construction loan? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial Link: Workman Lending Team - Renovo Financial - Real Estate Investment Loans ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Episode 290: Want To Make It 20+ years in Chicago REI? Learn How With Neena Vlamis 18.04.2024

Neena Vlamis is the President and Owner of A and N Mortgage. Born and raised in Chicago, she discusses building her mortgage company along with developing an impressive real estate investment portfolio in Chicago. Neena starts by explaining how she scaled her mortgage company, building a culture, and behind the scenes challenges. She provides insights on how lending regulations vary across states...

Episode 289: VA Loans, ADUs, and Turning a Funeral Home Into an Airbnb with Andrew Dorazio 11.04.2024

Andrew Dorazion is a former Army officer and accomplished real estate broker, investor, and property manager! Andrew jumps right in with a cool story involving a funeral home turned short term rental! He shares tips on finding partners and structuring partnerships to help scale more quickly. Andrew drops valuable nuggets on pumping a building's NOI through reconfigured floor plans and adding ADUs....

Episode 288: This Is Where Interest Rates Are Going Next... 09.04.2024

Where Are Interest Rates Heading and What's Happening in The Capital Markets? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Episode 287: Why Your Customer Experience is Falling Short with Joey Coleman 04.04.2024

Joey Coleman is a best selling author and founder of a branding firm that specializes in helping businesses retain customers and employees! Joey jumps right in by explaining the difference between customer service and customer experience. He explains the best ways to handle routine tenant check ins and disagreements with tenants all through the lens of optimizing customer experience. Joey shares h...

Episode 286: The Chicago Investor's Guide to Public Relations with Sabrina Wottreng 28.03.2024

Sabrina Wottreng is a Chicago-based Publicist and a "Friend of the Pod." Sabrina's company specializes in the real estate sector and has helped many Chicago-area real estate teams with their public relations (PR) and communications strategies. Sabrina explains how she got started in PR and her introduction into commercial real estate. She dives into the value-add that her company brings to real es...

Episode 285: Diving into DSCR with Eric Workman of Renovo Financial 26.03.2024
Episode 284: Triumphs and Troubles From a Decade of Experience on Chicago's Southeast Side with Jared Kott 21.03.2024

Jared Kott returns to share the ups and downs of his real estate journey that started just over 10 years ago when he left the corporate world! Jared gets right into it by talking about the challenges of operating in C/D class neighborhoods! He shares the cold hard truth of dealing with a slip-and-fall incident at one of his properties where he was found guilty in court. Jared provides insights on...

Episode 283: Container Homes: Innovative and Affordable Housing with Rory Rubin 14.03.2024

Rory Rubin, founder of S.I. Container Builds, joins us to explain how her company's Container Homes is a high-quality solution to current housing affordability and inventory issues! Rory starts by explaining her background in social work and the process of starting up S.I. Container Builds! She breaks down specs and pricing of container homes illustrating the quality and affordability when compare...

Episode 282: Decoding the Final Walkthrough: A Comprehensive Guide for Buyers and Sellers 12.03.2024

What should I expect on the final walk through from both the buyer and seller side? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chance Badertscher, Lavelle Law Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Episode 281: One of the First Investors to Leverage The New 5% Down Lending Product on a Successful Househack With Brendon Heneks and Sarita Scherpereel 07.03.2024

Brendon starts by sharing his buy box and how he was ready to pounce when he found the right property. Brendon and Sarita share great insights on how to jump at opportunities when the competition is fearful. Brendon explains worrisome moments and lessons learned during the purchase of his househack both before and after closing. Brendon breaks down the new 5% down lending product that everyone is...

Episode 280: Investing in Premier Chicago Neighborhoods as a Busy Professional with David Shifrin and Rob Sikkel 29.02.2024

David Shifrin, the doctor of Motor Row, returns with his real estate agent Rob Sikkel to discuss how he's grown his portfolio with quality multifamily properties over the last 2 years! David starts by explaining his investing strategy and how he's acquired 5 multifamily buildings since his last appearance on SUCI! David and Rob dive into the details of how they built their buyer-agent relationship...

Episode 279: Best Practices For Tenant Move-Outs 27.02.2024
Episode 278: BiggerPockets Host David Greene Gets Real On Overcoming Recent REI Adversity 22.02.2024

BiggerPockets Host, Author, and Real Estate Expert, David Greene returns to Straight Up Chicago Investor and holds nothing back as he explains how he dealt with fraud in his real estate portfolio. David explains why real estate is not an end-all solution to your financse and discusses the importances of reserves and playing defense, as outlined in his recent book Pillars of Wealth. He shares how h...

Episode 277: The Chicago Investor Playbook Against Pests with Janelle Iaccino 15.02.2024

Janelle Iaccinio is Rose Pest Solutions' Marketing Director and Chicago's "Bug Girl"! Janelle starts with the history of Rose Pest Solutions which dates back to the Abraham Lincoln era! She dives deep on rats, roaches, and bedbugs including common causes and practices to control them. Janelle mixes in a couple pest horror stories and debunks pest myths! Throughout the show, Janelle emphasizes the...

Episode 276: The Best Ways to Protect Your Largest Asset 13.02.2024
Episode 275: Keys to Off-Market Real Estate Acquisitions at Scale with Chicago's Mike Kehoe 08.02.2024

Mike Kehoe is an experienced investor and entrepreneur who has created and sold multiple technology companies! He joins us to explain how his latest company is thriving in off-market real estate acquisitions and dispositions. Mike explains how he chose a real estate market to focus on and the grind of driving for dollars to find opportunities! He shares great tips on how to engage potential seller...

Episode 274: Leveraging AI to Optimize Real Estate Underwriting with Chicago's Marc Rutzen 01.02.2024

Marc Rutzen is an experienced investor with over 12 years of real estate and technology experience. He joins the guys to explain the power of knowing your rental comps and how HelloData can help accelerate that knowledge.  Marc discusses his start in market analysis along with the creation of his analytics startup which he sold in 2019. He breaks down the creation and value proposition of HelloDat...

Episode 273: How To Leverage an Escalation Clause to Win Deals 30.01.2024

What is an escalation clause and how can investors utilize it? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Sarita Scherpereel, Sarita Sells ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Episode 272: Procuring Over 700 Off-Market Properties with Ben Allgeyer 25.01.2024

Ben Allgeyer has flipped over 200 properties and wholesaled over 500 properties! Ben talks about his brief stint in corporate America before leaving to pursue a career in Real Estate. He discusses the early days of making cold calls and door knocking for lead generation. Ben dives into building a team and vetting candidates for potential partnerships. He touches on his team's disposition strategy...

Episode 271: Exploring Some of Chicago's Premier Neighborhoods with Vik Wadhwa 18.01.2024

Vik Wadhwa is a top producing real estate broker with a focus on architecture and modern design in Chicago's Premier Neighborhoods! Vik shares his start in real estate back in 2006 and how he's been able to grow his business to become a top producing broker. Vik gets granular on Lincoln Park; defining the boundaries, desirable blocks, and investment opportunities in the neighborhood. He provides i...

Episode 270: It's 2024 And Your Chicago Property is Being Reassessed Again! 16.01.2024

What do investors need to be aware of with the 2024 property tax reassessments? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Andrea Raila, Raila & Associates Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Episode 269: Tax Auctions, Break-Ins, and More with Daniel Kaufman 11.01.2024

Daniel Kaufman is an attorney with over a decade of vast experience representing real estate developers with transactions, as well as litigation, with a lot of practice involving the foreclosure auction! Daniel is also an investor who purchases at the tax auction for himself, using the assistance of another attorney who specializes in that specific legal work. Daniel kicks things off by discussing...

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