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...

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Autor

Straight Up Chicago Investor

Categorie

Business

Site-ul podcastului

www.straightupchicagoinvestor.com

Cel mai nou episod

1 oct. 2026

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Episoade

Episode 311: Managing and Operating 100+ Units at 25 Years Old with James Thompson 25.07.2024

James Thompson is broker and property manager with vast experience acquiring, renovating, and managing apartment buildings all at the young age of 25 years old! James shares the early grind required to get off the ground in the commercial real estate game! He discusses the biggest lessons learned from renovating and managing 100+ apartments. James gives the scoop on investing in student housing an...

Episode 310: Guidelines Investors Can Utilize To Estimate Rehab Costs 23.07.2024

What Are Some High-Level Guidelines Chicago Investors Can Leverage to Estimate Rehab Costs? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Jonathan Klemm, Quality Builders Link: Episode 76: Big Business Processes Make a Powerful Small Business with Jonathan Klemm   ----------------- Production House:  Flint Stone Media Copyright...

Episode 309: How To Build a Community of Experts and Influencers with Tony Arce 18.07.2024

Tony Arce and his Team at The Face of Community & Business provide a media platform for leaders in business to connect, teach, and grow together. Tony starts by sharing how he discovered his passion for media and creating human-to-human connections not only in his personal life but in business. He explains how this passion sparked the idea of creating The Face of Community & Business (TFOCB); a me...

Episode 308: D1 Athlete's Journey: From Immigrant to Finance Mentor with Alex Filin 11.07.2024

Alex Filin is a seasoned Loan Office, Coach, and Investor with over $385 Million in funded loans! Alex shares his upbringing as an immigrant in America, experiences that cultivated grit, and his journey to becoming a D1 football player! He discusses his successful career shift to mortgage lending where he closed $95 million in funded loans in the first 5 years. Alex emphasizes the importance of ha...

Episode 307: Steps For Investors To Take During the Tax Off-Season 09.07.2024

What Steps Should Investors Take During the Tax-Offseason to Minimize Tax Liability? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Michael Procaccio, Pro Financial Services Group Inc Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicag...

Episode 306: Drugs, Death, and Big Mistakes Never Spoken Of with Mark Ainley 04.07.2024

The tables turn this week as Mark Ainley gets interviewed by Tom Shallcross, returning the favor from Episode 235 (episode link in show notes)! Tom starts by asking Mark about his childhood and upbringing; spoiler alert - there is mention of Mark's frosted-tips phase while vacationing in Mexico!! Mark breaks down his start in real estate, the genesis of GC Realty & Development, and the early REI v...

Episode 305: Three Chicago Pockets No One is Talking About With Sarita Scherpereel and Megan Osberger 27.06.2024

Sarita Scherpereel and Megan Osberger join us to discuss three overlooked neighborhoods and why they anticipate tremendous growth in those areas! Sarita and Megan start by discussing how a new Metra stop in the Andersonville and Edgewater neighborhoods is going to take that area to the next level! They break down the new CTA green line stop at Damen/Lake and explain the growth that it could bring...

Episode 304: What Are the Different Items Holding Up Closings in 2024? 25.06.2024

How are local Chicago real estate transactions different than they were a year ago? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Bibek Das , Das Law ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Episode 303: How Two Teachers Found Financial Independence Through Real Estate with Blaine and Lily Kosek 20.06.2024

Want to hear an inspirational story about two teachers leaving their W2 and amassing over 20 rental units over a few short years? If so, then this show is for you! Blaine and Lily talk about their decision to leave their jobs as educators to become full-time real estate agents and investors! They discuss specific suburb markets that they target along with pros and cons of the BRRRR strategy. Lily...

Episode 302: Strategies for Acquiring Off Market Real Estate with Dain Laverty 13.06.2024

Dain Laverty is a Managing Partner of Property Pals; a company that specializes in acquiring off market real estate through a variety of methods! Dain shares his start in real estate including his first deal on Chicago's south side sourced from Craigslist! He discusses finding his business partner and how he identified their complementary skill sets. Dain discusses different strategies for acquiri...

Episode 301: How to Maximize Showing Value by Professionally Decluttering With Karen Welch 11.06.2024

What is the easiest way to declutter a home to maximize it's showing value? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Karen Welch, Moovers Chicago Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Episode 300: 300th Episode Celebration - Answers To Burning REI Questions Amongst Chicago Investors with Mark and Tom 06.06.2024

Straight Up Chicago Investor Podcast celebrates its 300th Episode! To celebrate the huge milestone, Mark and Tom answer questions from guests on all things Chicago REI! If you enjoy all the value the SUCI podcast brings, 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: StraightUpChicago...

Episode 299: The Top 25 Lists to Find Motivated Sellers with DealMachine's David Lecko 30.05.2024

David Lecko is an investor and CEO of DealMachine; a software that helps investors streamline the process of off-market property lead generation! David starts by discussing the genesis of DealMachine He does a deep dive on the 25 motivated seller lists that can be found on DealMachine or other applications. He emphasizes the importance of being persistent and putting in the reps as off-market lead...

Episode 298: How To Fund Renovations with Larry Baszynski and Scott Hodgden 23.05.2024

Larry Baszynski and Scott Hodgden of Finance of America Commercial are seasoned lenders who have helped their investor clients build tremendous real estate portfolios and wealth.  Larry and Scott discuss the products that their company offers including Fix and Flip loans, Construction Loans, and Long-Term loans for stabilized properties. They share common pitfalls and root causes of failed renovat...

Episode 297: How to Pay Less in Taxes Via Tangible Property Regulations with Brenten Blakeman 21.05.2024

What are tangible property regulations and how can investors leverage this IRS code to pay less in taxes? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Brenten Blakeman, Tangible Property Tax Methods Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House:  Flint Stone Media Copyright of S...

Episode 296: How to Crush RE Investments on Chicago's South Side with Moses Hall 16.05.2024

Moses Hall is a top producing commercial real estate broker and leads a brokerage that serves investors, landlords, and tenants. Moses discusses his start in real estate, taking the plunge to start his own business, and the challenges that came with that. He dives into his geographical areas of focus in Chicago and his investment strategy. Moses sheds light on the Chicago Association of Realtors (...

Episode 295: The Ultimate HACK to Long-Term Wealth with Brian Tibbs 09.05.2024

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...

Episode 294: Creating a Successful Operating Agreement with Chance Badertscher 07.05.2024

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.

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...

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