Straight Up Chicago Investor

What do investors need to know about the current Chicago market? ============= Guest: Jason Wagner, Greystone Realty , Real Life Investing with Jason Rachel Wagner Link: SUCI Build Your Team C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail...

Oscar Medina of AMG Realty joins us to discuss his journey from wholesaling to a thriving fix-and-flip business at only 23 years old! Oscar starts by explaining how transitioned into real estate after serving time in the military. He gives a super thorough explanation on subject-to deals including pros, cons, and top considerations when pursuing these kinds of deals! Oscar shares why he transition...

Bill Powers, who first joined us back in Episode 6, returns with his daughter Shannon Powers to share how their real estate business has evolved since 2021! Bill and Shannon discuss how they've scaled their portfolio over the last several years, jumping into ground-up development in Florida, and lessons learned from investing in a declining market! They dive deep into short-term and mid-term renta...

What simple steps I can take to find more deals in this market? ============= Guest: Mark Ainley of  GC Realty and Co-host of Straight Up Chicago Investor Podcast Link: SUCI Build Your Team C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail....

John Bradford, founder of PetScreening.com , joins us to discuss pros, cons, and mitigating risks associated with having pets in rental properties! John jumps right in by sharing the top misconceptions that landlords have on pets and the opportunity costs of a no-pet policy! He gives a detailed breakdown on how to screen pets, spot fraudulent activity around pets and support animals, and how PetSc...

Miguel Chacon, 25th Ward Aldermanic candidate and seasoned investor, joins us to discuss the past, present, and future of Pilsen and Chicago Housing Policy as a whole! Miguel shares how Pilsen has grown over the last couple decades and the challenges that the neighborhood faces today! He breaks down limitations caused by Zoning and Ordinances and explains changes that tremendously help bring housi...

What are the different financing products I can leverage as a Chicago investor? ============= Guest: Chris Puleo, Puleo Group Link: SUCI Build Your Team Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We...

Mark Myers of Kiser Group joins us to share insights from over three decades of experience in senior housing investments and brokerage! Mark starts with how he got involved with senior housing and the evolution of the asset class over the last 30 years! He shares the basics of senior housing underwriting and compares the operations and returns to multifamily investing. Mark gives a detailed breakd...

David Shifrin of Elite Properties Chicago returns to share how he has scaled his portfolio since his last SUCI podcast appearance in 2024! David opens up by summarizing his portfolio and how he created cash flow in premier Chicago neighborhoods! He breaks down how a 1031 exchange works and gets granular with an example that led to the acquisition of a great multifamily asset in Avondale. David sha...

What do investors need to know regarding the proposed legislation for both the Road To Housing and Move Act? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Chris Puleo, Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chica...

Arthur Barkan of Barkan Realty joins us to share how he rapidly scaled his multifamily portfolio to 80 units! Arthur breaks down the ins and outs of investing in North Chicago, current market deal flow, and evaluating troubling tenants and potential evictions! He also shares strategies for scaling faster, tools to improve property management operations, and lessons learned from working with villag...

Jake Rome, co-founder of Backflip, joins us to share the wild journey from institutional real estate private equity to building a vertically integrated lending platform for fix-and-flip investors! Jake breaks down the return-on-equity math that makes single-family flips so powerful, then digs into the leverage and risk decisions that separate successful investors from those who blow up their portf...

How can Property Sentinel help me as a Chicago building owner? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Jim McMahon, Property Sentinel Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vac...

We're taking Straight Up Chicago Investor on the road for a special live episode from the NBOA Summer Soiree ! We catch up with some of Chicago's most active real estate professionals to get their takes on what's happening across the market right now. Jeff Weinberg breaks down a 65-unit 1031 deal, Nate Fernandez shares his latest western suburban acquisition, and Mike Glasser and Brie Schmidt disc...

Pablo Gonzalez of Vendoroo joins us to discuss how AI is changing the way real estate investors and property managers operate and scale their businesses! Pablor shares insights on raising capital and building communities before diving into how AI can be implemented in real estate operations. He breaks down how Vendoroo uses AI to coordinate maintenance, understand tenant sentiment, and help proper...

How do I evaluate and fix a Chicago porch? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Frank Knight, Mr. Porch Link: Understanding the Cost and Maintenance of Chicago Porches with Mr. Porch Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. E...

Mark Skowron of Festival Properties joins us to share top insights from his real estate journey which began back in 2010! Mark explains how he got started in real estate and pitfalls to avoid when building a wholesaling business! He shares how he got scrappy to find deals and eventually vetted and leveraged virtual assistants to scale. Mark dives into out of state investing including buying busine...

Hart Turner joins us to share how he went from a career in Los Angeles to building a Chicago multifamily portfolio through house hacking and partnerships! Hart dives into how he got started investing and how house hacking allowed him to get in the game! He shares real numbers behind his deals, discusses navigating financing challenges, and reflects on costly mistakes that shaped his investing appr...

What is Builders risk insurance and as an investor when do I need this policy? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Josh Steigelmann, State Farm Insurance Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInves...

Eric Field of Big Door Home Buyers joins us to share how he has successfully built his real estate wholesaling business! Eric jumps right in by explaining how he got into wholesaling and how he scaled his business! He provides tactical advice on marketing, wholesaling overhead expenses, and estimating rehab costs. Eric shares wholesaling horror stories and his biggest lessons learned from underwri...

SUCI Co-Host Mark Ainley gives a presentation on his deals over the last 30 months at the WSBOA meetup!  Mark shares details on various deals including flips, BRRRRs, and even short-term rentals. He  explains how he sourced, financed, and stabilized these deals. He discusses biggest wins and top lessons learned. Mark closes the presentation with the biggest REI takeaways and a Q&A session that you...

Can the government stop my insurance claim? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Josh Steigelmann, State Farm Insurance Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We ca...

Newly elected Cook County Assessor Pat Hynes joins us to share his plan for bringing fair, accurate, and predictable property assessments! Pat starts by discussing the flaws in the current property assessment system and his plan to improve and simplify the system! He shares an emotive story on why he decided to take on the county assessor role. Pat gets granular on common mistakes made on tax appe...

SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down a fraud story on a West Town property that he purchased! Tom dives deep into a recent purchase in West Town that involved ownership fraud when transferring title. He explains how the fraud was detected and how he navigated the process to reach a resolution. Throughout this show, Tom emphasizes the importance of being due...

More Tenant Protections... Less Housing? Breaking Down Chicago's New RLTO ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Glasser, NBOA Link: Amendment of Municipal Code Chapter 5-12 regarding Residential Landlord and Tenant Ordinance Link: Oppose Mayor Johnson's Proposed Ordinance Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Strai...