Libsyn Directory

Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event)

Release Date: 04/17/2025

Episode 382: What Investors Need to Know About Built to Rent Opportunities in Chicago

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= What do I need to know to pursue built-to-rent opportunities in Chicago? 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: Email the Show: Guest: Prashanth...

Episode 381: How Chicago’s Powerhouse Lender Renovo Financial Was Built with Kevin Werner

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Kevin Werner, CEO of Renovo Financial, has over 20 years of experience building and scaling successful lending companies! Kevin discusses his start in the lending business including his first company that did not survive the Great Financial Crisis. He shares lessons learned from...

Episode 380: Innovation in Modular Housing With Rory Rubin

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Rory Rubin shows us first hand how S.I. Container Builds is bringing high quality, low maintenance steel dwellings to help solve the housing supply shortage! Rory jumps right with a recap of modular housing and the advantages it brings over traditional brick and wood housing...

Episode 379: Preparing Your Property To Add an ADU

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= How can I prepare my existing property to add an ADU? 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: Email the Show: Guest: Prashanth Mahakali, Link: ...

Episode 378: How Wonderful Togbey Built a 20-Unit Portfolio Against the Odds

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Wonderful Togbey joins us to explain how he’s grinded to build a rental portfolio of 20 doors and is actively scaling! Wonderful shares his start in REI back in Omaha, Nebraska. He breaks down a deal in Bronzeville that closed right at the onset of COVID that came equipped with...

Episode 377: This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Daniel Baker, owner of Teton Properties, explains how he’s built a portfolio with strategic house hacks and value-add renovations. Daniel discusses his move from Memphis to Chicago to get started in real estate. He shares some hilarious stories on househack value-add projects and...

Episode 376: Buy Before You Sell; How To Write Offers Non-Contingent on The Sale of Your Existing Property

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= How Can I buy a new property before selling my existing property, while still not having my offer contingent on the existing sale? 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...

Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Real Estate Nate shares how he has accumulated 26-units with healthy cash flow all while having a demanding W2 job! Nate shares lessons learned from his first few deals and compares small vs large multifamily buildings. He explains how he and his wife leverage their high-income W2...

Episode 374: Taking On Opportunity In Chicago’s Toughest Neighborhoods with Corey Oliver

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Corey Oliver, CEO of Strength in Management, is back three years later to share additional insights on managing in C/D neighborhoods. Corey starts by discussing recent compression of cap rates and investment financials in Chicago C/D class neighborhoods. He gets granular on...

Episode 373: A New Option to Fund Renovations For Chicago 2-4 Properties

Straight Up Chicago Investor

Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= How can Chicago investors fund rehabs for 2-4 unit properties? 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: Email the Show: Guest: Perry Farella of Link: ...

More Episodes

Tom and Mark interview Joe Smazal of Interra Realty and Ann Reilly of Westward360 during NSBC’s Live Event! Conversations range from leasing trends to handling evictions and the state of the multifamily market in 2025. This show is full of valuable insights from two heavy hitters in the Chicago Multifamily 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: [email protected]

Guest: Joe Smazal & Ann Reilly, Interra Realty & Westward360

Link: Joe Smazal's LinkedIn

Link: Ann Reilly's LinkedIn

Link: SUCI Ep 156 - Joe Smazal

Link: Northwest Side Building Coalition (NSBC) Website

Guest Questions

00:30 The State of Chicago’s NW Side Commercial Real Estate.

04:33 Leasing trends and strategies!

10:18 Dealing with evictions in today’s market.