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Straight Up Chicago Investor

Straight Up Chicago Investor

By: Straight Up Chicago Investor
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About this listen

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.Copyright of Straight Up Chicago Investor 2021. Career Success Economics Personal Finance
Episodes
  • Episode 377: This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker
    May 29 2025

    Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

    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

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    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!

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    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    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?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    55 mins
  • Episode 376: Buy Before You Sell; How To Write Offers Non-Contingent on The Sale of Your Existing Property
    May 27 2025

    Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

    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

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    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!

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    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Perry Farella of First Community Mortgage

    Link: Perry Farella - First Community Mortgage

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

    Show more Show less
    10 mins
  • Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez
    May 22 2025

    Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

    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: StraightUpChicagoInvestor@gmail.com

    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.

    Show more Show less
    52 mins
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