

Straight Up Chicago Investor
Straight Up Chicago Investor
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.
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.
Episodes
Mentioned books

May 9, 2024 • 1h 5min
Episode 295: The Ultimate HACK to Long-Term Wealth with Brian Tibbs
Brian Tibbs is an investor and best-selling author who teaches others how to thrive financially! Brian starts by sharing how he hit the ground running by house hacking multiple properties and scaling up to 10-units before the age of 30! He explains how he saved money for down payments and the setbacks he experienced during his early REI days. Brian explains "The HACKER Method" - a wealth-building system to "hack" your lifestyle to grow great wealth. He breaks down each part of the system and reveals the practical steps to save more, invest more, and build wealth. Throughout the show, Brian emphasizes the importance of strategically budgeting and investing for anyone looking to thrive financially! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Brian Tibbs of The Unexpected Investor Link: The Unexpected Investor Calculators Link: All-In Podcast Link: The 21 Irrefutable Laws of Leadership Link: Brandon Turner Instagram ----------------- Guest Questions 03:11 Housing Provider Tip - Understand HOA rules if you're considering changing flooring! 05:15 Intro to our guest, Brian Tibbs! 11:24 Brian's RE acquisitions following his first duplex. 16:21 Early setbacks that Brian experienced! 19:07 Intro to The HACKER Method! 29:50 The power of compounding money. 41:00 How to scale responsibly. 43:55 Jumping into short-term rentals. 49:45 How anyone can apply the HACKER method! 54:16 Passing on good financial habits to your children. 57:33 What is your competitive advantage? 58:19 One piece of advice for new investors. 59:08 What do you do for fun? 59:37 Good book, podcast, or self development activity that you would recommend? 60:56 Local Network Recommendation? 61:56 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

May 7, 2024 • 12min
Episode 294: Creating a Successful Operating Agreement with Chance Badertscher
What items need to be covered in a successful operating agreement? 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.

May 2, 2024 • 54min
Episode 293: Help! Firefighters, City Inspectors, and Police Officers Are All at My Building With Anthony Rodriguez From Drexel Properties
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 City and other stakeholders, relocated tenants, coordinated the boiler repair and City Inspections, and finally returned tenants back to the building! This episode is full of great insights on how to correctly handle building emergencies and the importance of having a network to manage these unfortunate incidents! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Anthony Rodriguez, Drexel Properties Link: SUCI Ep 154 - Jeff Weinberg ----------------- Guest Questions 02:10 Housing Provider Tip - Ensure you have contacts for special equipment repairs! 03:54 Intro to our guest, Anthony Rodriguez! 05:57 Anthony's start with Drexel Properties! 10:08 The Boiler Blowup Story! 24:06 Relocating tenants during an emergency. 30:26 Other damages caused by the incident. 36:46 Tenants return to the building. 39:02 Could the incident have been prevented with additional due diligence? 48:12 What is your competitive advantage? 48:37 One piece of advice for new investors. 48:57 What do you do for fun? 49:19 Good book, podcast, or self development activity that you would recommend? 49:47 Local Network Recommendation? 50:14 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Apr 25, 2024 • 59min
Episode 292: Why Investors Need to Know a Good Public Adjuster with Dorian Bezanis
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 fires and other losses at investment properties. He closes with a five year outlook on Chicago including a bullish take on rent growth! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Dorian Bezanis, ALPHA Adjusting | Email Dorian (Dorian@AlphaAdjusting.com) Link: The Mysterious Case of Rudolf Diesel (Book Recommendation) Link: Andy Dolliff (Network Referral) ----------------- Guest Questions 01:16 Housing Provider Tip - Ensure you have a punch list for turnover to handle! 02:44 Intro to our guest, Dorian Bezanis! 06:57 Breaking down Dorian's portfolio! 17:28 Advice to new investors from 37 years of experience! 25:17 Understanding the value of Public Adjusters. 37:15 Handling fires and other claims! 48:48 Dorian's 5 year outlook on Chicago real estate. 54:02 What is your competitive advantage? 54:15 One piece of advice for new investors. 54:24 What do you do for fun? 54:41 Good book, podcast, or self development activity that you would recommend? 55:46 Local Network Recommendation? 57:14 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Apr 23, 2024 • 22min
Episode 291: What Every Investor Needs To Know About the Rehab Draw Process
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.

Apr 18, 2024 • 51min
Episode 290: Want To Make It 20+ years in Chicago REI? Learn How With Neena Vlamis
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 and talks about what makes A and N unique. Neena gives her take on adapting to a higher interest rate market and the recent NAR settlement. She closes with a bullish outlook on the Chicago Real Estate market! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Neena Vlamis, A and N Mortgage Link: SUCI Ep 250 - Jonathan Klemm ----------------- Guest Questions 01:10 Housing Provider Tip - Keep up with landscaping to avoid fines from the city! 03:01 Intro to our guest, Neena Vlamis! 07:01 Neena's early lending and investing days! 13:47 Scaling the mortgage lending business. 16:18 Maintaining culture in a business. 20:19 Behind the scenes lending challenges. 24:16 Neena's other investments! 32:24 Differences in lending across states. 35:08 What makes A and N Mortgage unique? 38:29 Adapting to higher interest rates. 41:44 Neena's outlook on Chicago and the Real Estate Industry! 45:50 What is your competitive advantage? 46:04 One piece of advice for new investors. 46:13 What do you do for fun? 46:36 Good book, podcast, or self development activity that you would recommend? 47:03 Local Network Recommendation? 48:13 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Apr 11, 2024 • 1h 2min
Episode 289: VA Loans, ADUs, and Turning a Funeral Home Into an Airbnb with Andrew Dorazio
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. He does a deep dive on the Zoning Change Process in Chicago! Throughout the show, Andrew emphasizes the importance of taking action to propel your growth in real estate and any other endeavor! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Andrew Dorazio, Dorazio Real Estate Link: BCG Real Estate Group Link: Andrew's ADU Blog Link: My First Million (Podcast Recommendation) Link: Buy Then Build (Book Recommendation) Link: SUCI Ep 245 - JD Modrak Link: SUCI Ep 224 - Jason Wagner ----------------- Guest Questions 02:00 Housing Provider Tip - Maintain AC units as the weather gets warmer! 03:15 Intro to our guest, Andrew Dorazio! 03:45 Andrew's "killer" deal! 07:28 Andrew's start in real estate. 12:11 How to find partners to scale faster? 17:00 Early mistakes on Short Term Rentals. 24:04 Ways to reposition an asset. 35:05 The Process of a Zoning Change! 44:56 Building Department for requirements for ADUs! 50:25 What's next for Andrew and his team? 53:14 What is your competitive advantage? 54:03 One piece of advice for new investors. 55:34 What do you do for fun? 56:17 Good book, podcast, or self development activity that you would recommend? 57:48 Local Network Recommendation? 58:38 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Apr 9, 2024 • 15min
Episode 288: This Is Where Interest Rates Are Going Next...
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.

Apr 4, 2024 • 1h 8min
Episode 287: Why Your Customer Experience is Falling Short with Joey Coleman
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 how the Eight Phases to "Never Lose a Customer Again" apply to prospective tenants. Joey closes with an amazing story of how a human-level connection and a small gift resulted in a tremendous business opportunity! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Joey Coleman, Design Symphony Link: Never Lose A Customer Again Link: Never Lose An Employee Again Link: Dan Gingiss (Network Referral) Link: Careers | GC Realty & Development, LLC ----------------- Guest Questions 03:23 Housing Provider Tip - Run your investment properties like a business and treat your residents like clients. 03:51 Intro to our guest, Joey Coleman! 07:04 Customer service vs customer experience! 14:00 To check in with the tenant or not? 16:29 Reassuring tenants after move-in. 23:47 Phases to Never Lose a Customer Again! 41:10 How to handle disagreements with tenants? 50:58 Gifts and the $35,000 golf ball! 56:56 Advice to 20 year old Joey Coleman. 59:16 What is your competitive advantage? 59:42 One piece of advice for new investors. 60:16 What do you do for fun? 60:57 Good book, podcast, or self development activity that you would recommend? 62:44 Local Network Recommendation? 64:00 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Mar 28, 2024 • 59min
Episode 286: The Chicago Investor's Guide to Public Relations with Sabrina Wottreng
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 estate investors and gives tips on building an online presence and reputation. Sabrina emphasizes the importance of LinkedIn, building your network, and even updated headshots if you're an investor looking to scale. This show is full of amazing tips you likely have not considered and can easily leverage to scale your real estate business. If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Sabrina Wottreng of Sabrina Wottreng Public Relations Link: Sabrina's LinkedIn Link: SUCI Ep 274 - Marc Rutzen Link: SUCI Ep 275 - Mike Kehoe Link: SUCI Ep 124 - Aaron Galvin Link: The Messy Middle (Book Recommendation) Link: Brian McConkey Photography ----------------- Guest Questions 03:23 Housing Provider Tip - Consult with your attorney before negotiating with problem tenants. 05:07 Intro to our guest, Sabrina Wottreng! 08:18 Sabrina's start in real estate! 11:48 Sabrina's PR services! 20:08 Importance of reviews and reputation. 24:58 When should investors start caring about their online presence? 29:12 Marketing for Investors 101! 36:17 Building your network as a new investor! 40:49 Importance of headshots! 45:36 Sabrina's value proposition to investors! 51:18 What's next for Sabrina? 52:30 What is your competitive advantage? 52:50 One piece of advice for new investors. 53:18 What do you do for fun? 53:40 Good book, podcast, or self development activity that you would recommend? 54:22 Local Network Recommendation? 55:04 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2024.


