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 317: Kevin Dugan Does It From 2,000 Miles Away… What Excuse Do You Have? 22.08.2024

Kevin Dugan is the Managing Principal of Altus Investment Group. He runs multiple businesses that successfully operate in Chicago while managing them remotely from Los Angeles! Kevin starts by talking about the skills he gained working on oil rigs and as a sales engineer and how that translated to real estate! He breaks down his first flip in South Shore and the process of managing that project fr...

Episode 316: 3 Features That Increase Your Insurance Premium and 3 Features That May Decrease Your Insurance Premium 20.08.2024

What Are 3 Features That Increase Your Insurance Premium and 3 Features That May Decrease Your Insurance Premium? C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Josh Steigelmann , State Farm Insurance Link: Investor Stories Featuring Sean Morrissey ----------------- Production House:  Flint Stone Media Copyright of Straight Up...

Episode 315: Streeterville High-Rise Developments and Top Tier Leasing Tips with Domu Founder Noah Schatz 15.08.2024

Noah Schatz is the founder of Domu and CEO of Schatz Development. He has vast experience in design-driven developments in downtown Chicago and leasing apartments for operators through his apartment searching platform Domu. Noah kicks things off by talking about his first development and land banking! He provides insights on the 600 N Fairbanks development; a luxury high-rise condominium tower in S...

Episode 314: Due Diligence for Off-Market Properties Like You've Never Seen with Morgan Basham 08.08.2024

Morgan Basham is a real estate broker and investor with vast experience in off-market prospecting, acquisitions, and stabilization of investment properties! Morgan shares her start in real estate and the ins and outs of investing in Braidwood, IL! She breaks down her first deal in Chicago; an impressive story of tremendous due diligence as part of the acquisition of an auction property! Morgan, Ma...

Episode 313: Why Are Insurance Rates So High Right Now and What Can Investors Do to Minimize Premiums? 06.08.2024

Why are insurance rates so high right now? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Josh Steigelmann , State Farm Insurance Link: Investor Stories Featuring Sean Morrissey ----------------- Production House:  Flint Stone Media Copyright of Straight Up Chicago Investor 2024.

Episode 312: Redeveloping Over 2100 Units in Underserved Communities with Bernel Hall 01.08.2024

Bernel Hall is the president and CEO of New Jersey Community Capital and has executed over $5 billion in real estate investments and lending. Bernel starts off by explaining how playing Monopoly sparked his interest in real estate as a kid! He discusses how he got involved with public housing developments and gives his take on ways housing authorities can improve efficiencies. Bernel shares his pr...

Special NBOA Soiree Announcement 30.07.2024

Tom welcomes President of the Neighborhood Building Owner's Alliance, Mike Glasser, for a special announcement about their upcoming 12th Annual NBOA Summer Soiree. You don't want to miss it! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: NBOA ( Neighborhood Building Owner's Alliance ) President, Mike Glasser Link: 12th Annual NBO...

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.

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