Straight Up Chicago Investor Podcast

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4.1K - 6.9K listeners Male 5.0 rating 276 reviews 381 episodes USA
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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.

Producers, Hosts, and Production Team

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Emails, Phones, and Addresses

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Emails
  • Email the Show: st***@gmail.com
  • Contact for accessibility issues: st***@gmail.com
Phone Numbers
  • General enquiries: 630.587.7400
Addresses
  • Office Address: 219 E Irving Park Rd., Roselle, IL 60172
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A contact form is available on this page. You can fill out the form at this link.

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  • st***@gmail.com

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  • st***@gmail.com
  • ns***@gmail.com

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Recent Hosts, Guests & Topics

Here's a quick summary of the last 5 episodes on Straight Up Chicago Investor.

Hosts

Previous Guests

Prashanth Mahakali is a professional involved in architecture and permits, with expertise in Chicago building regulations, permits, violations, and nonconforming or illegal units.
Wonderful Togbey is a real estate investor who has built a 20-unit rental portfolio, starting his investing journey in Omaha, Nebraska. He has experience with gut renovations, managing tenants, and scaling his property holdings despite challenges such as the COVID-19 pandemic.
Daniel Baker is the owner of Teton Properties, with a background in building a real estate portfolio through strategic house hacks and value-add renovations. He moved from Memphis to Chicago to pursue real estate and has experience with projects during the COVID-19 pandemic, emphasizing perseverance and scrappy strategies.
Perry Farella is associated with First Community Mortgage, likely a mortgage professional specializing in real estate financing and lending.
Nate Fernandez is an experienced real estate investor who has accumulated 26 units with healthy cash flow while maintaining a demanding W2 job. He shares lessons learned from his initial deals, compares small versus large multifamily buildings, and discusses leveraging high-income W2 jobs to propel real estate investments. Nate also runs a consulting business focused on CRM system implementation, and provides tips on financing 5+ unit buildings and building a strong team to succeed in real estate investing.

YouTube Channel

Channel Info

Straight Up Chicago Investor Podcast
@straightupchicagoinvestor

Channel Stats

Subscribers: 2,230
Total Videos: 1,628
Total Views: 300,448
Joined: May 6, 2020
Location: United States

Description

Welcome to the only podcast that specifically focuses on Real Estate investing in and around Chicago. Are you ready to become a Straight Up Chicago Investor? In our podcast, we'll share information on our winning strategies, success stories, and the obstacles we've had to overcome along the way. We will also discuss what has and hasn't worked in the market as well as best practices and pitfalls to avoid. You ready?

Additional Info

Content Rating: None

Instagram Profile

Instagram

Profile Info

@sucipodcast
Straight Up Chicago Investor 🎙

Account Stats

Followers: 1,328
Posts: 1,207

Account Status

Account Type: Business
Privacy: Public

Biography

Join us as we share our winning strategies, success stories, obstacles, & most importantly, lessons learned
#SUCIpodcast

Episodes

Here's the recent few episodes on Straight Up Chicago Investor.

0:00 12:25

Episode 379: Preparing Your Property To Add an ADU

Hosts
Mark Tom
Guests
Prashanth Mahakali
Keywords
ADU Chicago real estate property management investment strategies building permits illegal units

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

=============

How can I prepare my existing property to add an ADU?

If you enjoy todays 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: Prashanth Mahakali,PMPC

Link: Episode 21: Leveraging an Architect for Chicago Permits, Building Violations, & Nonconforming and Illegal Units, with Prashanth Mahakali

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Production House:Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

0:00 56:57

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

Hosts
Mark Tom
Guests
Wonderful Togbey
Keywords
real estate investing Chicago real estate property management rental portfolio gut renovations Bronzeville COVID-19 impact long-term investing tenant management

Properties for Sale on the North Side?  We want to buy them. Email: [email protected]

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

=============

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 non-paying tenants! Wonderful reflects on lessons learned from gut renovations including considerations on layouts to maximize rents. He has multiple examples of pivoting while under, and even getting a second job to get deals done. This episode is a motivating one with countless stories showcasing perseverance and grit.

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: Wonderful Togbey

Link: Wonderful's Instagram

Link: How to Win Friends & Influence People (Book Recommendation)

Link: Eric Workman (Network Referral)

Guest Questions

02:17 Housing Provider Tip - Leverage Google Earth and other tools for measurements and floor plans!

03:55 Intro to our guest, Wonderful Togbey!

09:21 Starting real estate investing in Omaha, NE.

13:40 Challenging Bronzeville Deal with COVID looming!

19:51 The power of long term investing and dealing with non-paying tenants. 

30:16 Wonderful’s first gut rehab project and buying another property simultaneously!

36:38 Cultivating perseverance in real estate.

41:56 Lessons learned from redeveloping a building.

47:41 Wonderful’s long term investing goals.

50:36 Management systems for small investors.

52:14 What is your competitive advantage?

52:50 One piece of advice for new investors.

53:34 What do you do for fun?

53:45 Good book, podcast, or self development activity that you would recommend? 

54:23 Local Network Recommendation? 

54:52 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

0:00 55:27

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

Hosts
Mark Tom
Guests
Daniel Baker
Keywords
Chicago real estate house hacking value-add renovations property management COVID-19 impact on real estate investment strategies neighborhoods in Chicago

Properties for Sale on the North Side?  We want to buy them. Email: [email protected]

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

=============

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 getting extremely gritty to get projects to the finish line. He then breaks down a deal that closed right at the onset of COVID in 2020. Throughout this episode, Daniel gives numerous examples of how getting scrappy and persevering can be a competitive advantage that pays huge dividends. 

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: Daniel Baker, Teton Properties

Link: How to Win Friends and Influence People (Book Recommendation)

Link: Snowball (Book Recommendation)

Link: Jen Fritzshall (Attorney Referral)

Link: SUCI Ep 22 - Matt Fritzshall

Guest Questions

02:08 Housing Provider Tip - Consider making professional carpet cleaning a move-out requirement for tenants!

04:23 Intro to our guest, Daniel Baker!

07:35 Getting started in real estate with Marcus & Millichap.

18:46 Purchasing a Lincoln Square 4-Flat after a few house hacks!

26:48 Daniel’s top lessons learned after his first few projects!

29:41 Jumping into a deal with COVID looming.

39:33 Closing a deal while getting laid off!

44:40 What’s next for Daniel?

47:48 Daniel’s outlook on Chicago!

50:43 What is your competitive advantage?

51:11 One piece of advice for new investors.

51:30 What do you do for fun?

51:51 Good book, podcast, or self development activity that you would recommend? 

52:22 Local Network Recommendation? 

49:10 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

0:00 10:20

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

Hosts
Mark Tom
Guests
Perry Farella
Keywords
real estate investing Chicago real estate buy before you sell non-contingent offers property management tenant placement

Properties for Sale on the North Side?  We want to buy them. Email: [email protected]

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

=============

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 Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: [email protected]

Guest: Perry Farella of First Community Mortgage

Link: Perry Farella - First Community Mortgage

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

0:00 52:05

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

Hosts
Mark Tom
Guests
Nate Fernandez
Keywords
Chicago real estate multifamily investing W2 income property management risk hedging financing multi-unit buildings team building in REI

Properties for Sale on the North Side?  We want to buy them. Email: [email protected]

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

=============

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 jobs to propel their real estate investments and hedge associated risks. Nate dives into his consulting business involving CRM system implementation. Nate closes with tips on financing 5+ unit buildings and emphasizes the importance of building a great team to set yourself up for REI success!

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: Nate Fernandez, Optimum Process Partners

Link: Nate's Instagram

Link: Nate's LinkedIn

Link: NBOA Chicago

Link: West Suburban Building Owners Association

Link: Extreme Ownership (Book Recommendation)

Link: SUCI Ep 196 - John Warren

Guest Questions

02:51 Housing Provider Tip - Power through difficult deals and keep the end goal in mind!

04:48 Intro to our guest, Nate Fernandez!

09:06 Lessons learned from Nate’s first deal!

16:17 Comparing 2-4 unit vs 5+ unit buildings.

20:16 Hedging risk with proper planning.

23:33 Setting up a property management system.

27:02 Nate’s system implementation consulting business and areas of focus.

30:43 Navigating pre-sale inspections.

35:57 Nate’s goals by 40!

38:05 Leveraging a W2 job to propel real estate investments!

40:55 How to finance 5+ unit buildings.

45:11 What is your competitive advantage?

45:53 One piece of advice for new investors.

46:19 What do you do for fun?

46:57 Good book, podcast, or self development activity that you would recommend? 

47:50 Local Network Recommendation? 

49:10 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

Ratings

Global:
5.0 rating 276 reviews

USA

5.0 ratings 275 reviews

Australia

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UK

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Canada

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Ireland

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New Zealand

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Singapore

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