

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

Jun 22, 2023 • 55min
Episode 226: Unlocking Off-Market Deals Using Rescover's Analysis Platform for Maximum ROI with Ben Smith and Kristen Lopez
Ben Smith and Kristen Lopez break down how Rescover's All-in-One Analysis Platform can be your competitive edge to find off-market deals and maximize your ROI! Ben and Kristen lead off with the basics and low-hanging fruit investors must be aware of when planning an off-market property campaign. They discuss the power of leveraging resources; from utilizing Rescover and skip tracing to implementing "Who, Not How". They dive deep into cold calling and tracking off-market leads to increase your success rate. Throughout the show, Ben and Kristen share valuable insight on the mindset and approach required to get you your next Off-Market Deal! 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: Ben Smith and Kristen Lopez of Rescover Link: Buy Your Time Back (Book Recommendation) Link: SUCI Ep 195 - Victoria Barkate Link: Ryan Holiday Books Link: zInspector Sponsors: Pentwater Cabinetry and Essex Realty Group ----------------- Guest Questions 02:39 Housing Provider Tip: Ensure you have a registered agent as a point of contact in your LLC! 03:35 Intro to our guests, Ben Smith and Kristen Lopez! 13:20 Low Hanging Fruit to start prospecting! 17:13 Implementing "Who, Not How"! 22:35 What is skip tracing? 30:12 Approaches to cold calling. 39:11 Tracking off-market leads. 41:50 What is Rescover? 47:34 What is Ben's and Kristen's competitive advantage? 48:37 One piece of advice for new investors. 49:18 What do you do for fun? 49:48 Good book, podcast, or self-development activity that you would recommend? 50:40 Local Network Recommendation? 51:02 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jun 20, 2023 • 15min
Episode 225: A Dive Into Current and Future Interest Rates with Chris Puleo
What will interest rates do over the next 6-12 months? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chris Puleo, Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo Sponsors: Puleo Group ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jun 15, 2023 • 56min
Episode 224: Expert Insights On Chicago's Northwest Side with Jason Wagner
Jason Wagner is the Managing Broker of Greystone Realty; a brokerage where every agent is also an investor. If you don't already know, Jason is a huge proponent of 75 Hard, and he explains the program and the amazing impact it's had on his life! He breaks down how he started and continues to invest in Portage Park and Jefferson Park. Jason dives deep into the housing supply shortage, recent trends in inventory, and projects what could be on the horizon. Jason closes by discussing Greystone Realty and the Wagner Report and how they are adding huge value to Chicago Real Estate Investors! 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: Jason Wagner, Greystone Realty Link: Jason's Instagram Link: Traction (Book Recommendation) Link: SUCI Ep 43 - RJ and Nicky De Leon Link: SUCI Ep 82 - Property People Sponsors: Pentwater Cabinetry and Essex Realty Group ----------------- Guest Questions 03:52 Housing Provider Tip: End leases at noon, instead of midnight, to allow time for turnover! 05:11 Intro to our guest, Jason Wagner! 06:33 Jason explains 75 Hard! 11:05 Jason breaks down investing in Portage and Jefferson Park! 20:00 Discussing months of supply and the supply shortage over the last few years. 31:12 What drew Jason to Belmont Cragin? 36:18 Valuation of 2-4 units vs 5+ units. 40:24 Concept of an investment-minded brokerage! 45:14 How did Jason develop the Wagner Report? 47:00 What is Jason's competitive advantage? 47:22 One piece of advice for new investors. 48:34 What do you do for fun? 49:49 Good book, podcast, or self-development activity that you would recommend? 50:46 Local Network Recommendation? 52:25 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jun 8, 2023 • 45min
Episode 223: From New York to the Windy City - Curtis Lefebvre's Real Estate Journey and Success in East Garfield Park
Curtis Lefebvre shares why he left New York for the Windy City to start investing in Real Estate! Curtis jumps right in by getting granular on acquiring and stabilizing his first househack in East Garfield Park. He discusses everything from dealing with problem tenants to DYI'ing renovations. He dives into the numbers of his killer househack which allows him to not only live for free, but also cash flow while living there! Curtis defines the borders of the neighborhood, and with Mark's input, talks about the differences between East and West Garfield Park. Curtis justifies betting big on East Garfield Park by sharing his bullish outlook on the neighborhood! 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: Curtis Lefebvre | E-mail Link: Brian Lindstrom (Lender Referral) Link: SUCI Ep 195 - Victoria Barkate Sponsors: Build Your Team and NEGC Remodeling ----------------- Guest Questions 03:02 Housing Provider Tip: Processes to prevent loss of lock keys and codes! 04:21 Intro to our guest, Curtis Lefebvre! 07:03 How did Curtis decide on which Chicago neighborhoods to invest in? 11:48 Curtis' experience acquiring his first rental property in Chicago! 21:39 Dealing with problem tenants. 25:30 DYI'ing renovations on the first property! 32:39 Curtis' bullish outlook on East Garfield Park! 36:04 Borders of East Garfield Park and Going West of the Park! 39:03 What is Curtis' competitive advantage? 39:28 One piece of advice for new investors. 39:40 What do you do for fun? 40:13 Good book, podcast, or self-development activity that you would recommend? 40:36 Local Network Recommendation? 41:17 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jun 6, 2023 • 9min
Episode 222: Essential Insights - 5 Must-Address Items in Your Attorney Review Letter - Expert Advice with Chance Badertscher from Lavelle Law"
What Are Five Items Every Investor Should Address in Their Attorney Review Letter? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chance Badertscher, Lavelle Law Sponsors: Lavelle Law ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Jun 1, 2023 • 1h 2min
Episode 221: Unveiling Real Estate Market Insights - The Mad Scientist of Multifamily, Neal Bawa, Shares Data Trends and Future Outlook!
The Mad Scientist of Multifamily, Neal Bawa, returns to the show to share the latest data trends and his outlook on the Real Estate market! Neal jumps right in by summarizing changes in the real estate market over the last 18 months. He explains how his underwriting has changed as a result of market conditions. Neal gives a warning to those investing in office-space and talks about the challenges of converting office-space to residential. Neal concludes by telling us why he's putting his money into Build-to-Rent townhomes, the "next evolution of the Single Family Home!" 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: Neal Bawa, Grocapitus Link: SUCI Ep 26 - Neal's 1st Episode Link: SUCI Ep 110 - Neal's 2nd Episode Link: Grocapitus Website Link: Multifamily University Webinars | Free eBook: Location Magic | Join Our Investor Club Sponsors: North Shore Brickwork and Essex Realty Group ----------------- Guest Questions 02:32 Housing Provider Tip: Don't forget to set time aside daily for personal growth! 04:04 Intro to our guest, Neal Bawa! 04:52 What has happened in the real estate market over the last 18 months? 14:32 Discussing previous high-inflation periods! 23:45 How has Neal's underwriting changed given the market conditions? 29:28 Is it worth putting more money down to increase cash flow? 34:48 The future of office space! 43:18 Why Neal is bullish on Build-to-Rent! 52:22 Neal's revised outlook on tokenization. 54:24 What is Neal's competitive advantage? 54:56 One piece of advice for new investors. 55:54 What do you do for fun? 56:15 Good book, podcast, or self-development activity that you would recommend? 57:24 Local Network Recommendation? 57:49 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

May 25, 2023 • 47min
Episode 220: A Seasoned Investor's Journey in Chicago Real Estate - Insights, Strategies, and Neighborhood Outlook with Baris Yuksel
Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Baris Yuksel, Supreme Capital Link: Multifamily Insights Podcast Link: Baris' LinkedIn Link: John Warren SUCI Ep 196 (Network Referral) Sponsors: Pentwater Cabinetry and Essex Realty Group ----------------- Guest Questions 03:25 Housing Provider Tip: Understand Gross vs Net Income when screening tenants! 05:16 Intro to our guest, Baris 10:20 Why did Boris start with a mixed-use building? 19:31 Establishing a Geographical Focus and Finding Capital to Scale! 22:11 Self-Managing a Growing Portfolio. 31:39 Discussion on different Chicago neighborhoods! 37:15 Baris' outlook on Chicago Real Estate! 40:22 What is Baris' competitive advantage? 40:45 One piece of advice for new investors. 41:19 What do you do for fun? 41:37 Good book, podcast, or self-development activity that you would recommend? 42:08 Local Network Recommendation? 42:52 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

May 23, 2023 • 17min
Episode 219: The Focus of Chicago's NBOA in 2023 and Why Housing Providers Should Take Notice
What's new with the NBOA and how can the NBOA assist small-mid size housing providers? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Michael Glasser, NBOA Link: EUBA Chicago Facebook Link: South Side Community Investors Association Facebook Link: https://lreic.org/ Link: https://lincolnparkbuilders.com/ Link: https://www.rpbg.org/ Link: https://www.chicagonsbc.com/ Link: https://www.southsidebuilderschicago.com/ Sponsors: Pentwater Cabinetry and Essex Realty Group ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

May 18, 2023 • 48min
Episode 218: Sharing a Decade of Experience in Chicago Real Estate - Insights on Architecture, Renovation, and Investment Potential with Michaela Gordon
Michaela Gordon is a seasoned Realtor and Designer with over 10 years of experience acquiring and renovating properties in Chicago! Michaela kicks things off by talking about her background in architecture and design. She explains the significance of the different Chicago lot sizes and their impact on a building's footprints and redevelopment potential. Michaela also compares Chicago architecture to Los Angeles' architecture. She drops golden insight on modernizing units on a budget and also lays out improvements that are NOT worth the ROI. Michaela closes with powerful words on the value that investment-minded realtors offer and gives her outlook on the 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: Michaela Gordon, MG Home Chicago Link: MG Homes Instagram Link: Brandon Hood Instagram (Network Referral) Link: Per My Last Email (Michaela's Podcast) Sponsors: Cost Seg Kev and Essex Realty Group ----------------- Guest Questions 02:49 Housing Provider Tip: Understand Source of Income and other protected classes when screening tenants! 04:54 Intro to our guest, Michaela Gordon! 07:38 Michaela's real estate origin story! 11:32 Chicago Lot Sizes and their importance. 17:52 Modernizing units on a budget. 28:06 Property Improvements that are NOT worth it! 30:29 How can real estate brokers be more investment-minded? 35:32 Michaela's outlook on the real estate market! 40:20 What is Michaela's competitive advantage? 41:08 One piece of advice for new investors. 41:17 What do you do for fun? 41:57 Good book, podcast, or self-development activity that you would recommend? 43:20 Local Network Recommendation? 44:04 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

May 11, 2023 • 53min
Episode 217: Building Relationships with Community Banks - Insights from Chicagoan Kevin Greer on the Lending Market and Investor Strategies
Kevin Greer joins us to break down Community Banks, Commercial Lending, and the State of the Lending Market! Kevin explains the differences between Regional Banks and Community Banks. You'll learn how you can build and leverage a relationship with your local Community Bank. He also shares how his investor mindset and strategy have changed throughout his years of investing. Then, Kevin tells us his outlook on the lending market and how investors should prepare! 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: Kevin Greer, Bank Financial Link: Mark@securechoice.biz (Mark Wilczak - Secure Choice Property Inspector) Link: BISNOW Article Sponsors: NEGC Remodeling and Essex Realty Group ----------------- Guest Questions 03:02 Housing Provider Tip: Monitor the temperature on boiler buildings as the weather warms up! 05:32 Intro to our guest, Kevin Greer! 08:15 Kevin discusses the state of the lending market! 10:04 Ins and outs of a Community Bank. 14:15 How to build a relationship with a Community Bank? 21:32 How do banks stay afloat when business slows? 22:43 How has Kevin's investing mindset changed over the years? 26:32 Where in Chicago is Kevin seeing the most real estate activity? 32:18 DSCR and commercial loan underwriting! 41:32 Kevin's outlook on the lending market. 45:45 What is Kevin's competitive advantage? 46:08 One piece of advice for new investors. 46:35 What do you do for fun? 47:01 Good book, podcast, or self-development activity that you would recommend? 48:14 Local Network Recommendation? 49:05 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.


