• Episode 381: How Chicago’s Powerhouse Lender Renovo Financial Was Built with Kevin Werner
    Jun 19 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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    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 lending through the Housing Crash and how those insights coupled with great relationships lead to the inception of Renovo Financial. Kevin gives the philosophy that has led to Renovo’s explosive growth the last decade including thriving through the uncertainty of COVID. Throughout the show, Kevin drops powerful outlooks on business, customer service, and relationships that you’ll want to remember and implement!

    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: Kevin Werner, Renovo Financial

    Link: Kevin's LinkedIn

    Link: All-In Podcast

    Link: King of Capital (Book Recommendation)

    Guest Questions

    01:51 Housing Provider Tip - Understand the power of being decisive and taking action!

    03:18 Intro to our guest, Kevin Werner!

    10:44 Getting a loan business off the ground in the 90s.

    15:28 Lending through the Housing Crash!

    34:21 The business model of lending business.

    45:27 Renovo’s explosive growth through COVID into 2025!

    60:18 Kevin’s parenting philosophy and outlook on Chicago!

    63:24 What is your competitive advantage?

    64:20 One piece of advice for new investors.

    64:53 What do you do for fun?

    66:04 Good book, podcast, or self development activity that you would recommend?

    66:53 Local Network Recommendation?

    68:38 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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    1 hr and 11 mins
  • Episode 380: Innovation in Modular Housing With Rory Rubin
    Jun 12 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

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

    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 structures. She shares lessons learned after 7 successful years of leading S.I. Container Builds. Our video viewers get to see an awesome container building constructed for Navy Pier and Rory breaks down some complex projects. This episode showcases the innovation within modular housing and Rory makes it clear that container builds are quality housing stock that everyone should strongly consider!

    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: Rory Rubin, S.I. Container Builds

    Link: The Art of Happiness (Book Recommendation)

    Link: Tim Swanson (Network Referral)

    Link: SUCI Ep. 351 - Richard Koenig

    Guest Questions

    03:11 Housing Provider Tip - Communicate your move-out procedure and expectations to your tenants!

    04:41 Intro to our guest, Rory Rubin from SI Container Builds!

    06:46 Recapping the 101 on container builds!

    09:45 Advantages of container builds.

    17:30 Lessons learned from 7 years of modular building!

    21:30 Complex container builds!

    25:25 Navy Pier Container and Affordable Housing!

    28:09 What is your competitive advantage?

    28:33 One piece of advice for new investors.

    29:21 What do you do for fun?

    29:33 Good book, podcast, or self development activity that you would recommend?

    29:55 Local Network Recommendation?

    30:21 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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    33 mins
  • Episode 379: Preparing Your Property To Add an ADU
    Jun 10 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

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

    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: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    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.

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    12 mins
  • Episode 378: How Wonderful Togbey Built a 20-Unit Portfolio Against the Odds
    Jun 5 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

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

    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: StraightUpChicagoInvestor@gmail.com

    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?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    57 mins
  • 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

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

    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: 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

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

    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: 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.

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    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?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    52 mins
  • Episode 374: Taking On Opportunity In Chicago’s Toughest Neighborhoods with Corey Oliver
    May 15 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

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

    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 the process for placing and managing CHA tenants. Corey breaks down how he sets investment return expectations for out of state investors looking to invest in lower income neighborhoods. Corey closes with exciting news about his upcoming development project which includes city grants and tax credits!

    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: Corey Oliver, Strength in Management

    Link: NBOA Chicago (Network Referral)

    Link: Corey's Original Episode 175

    Guest Questions

    02:38 Housing Provider Tip - Understand the risks of hydro-jetting old sewer lines!

    04:07 Intro to our guest, Corey Oliver!

    09:49 Cap rates and expense ratios in challenging neighborhoods!

    15:16 Rent increase on subsidized housing tenants.

    17:55 Managing CHA tenants.

    32:00 Setting expectations on C/D class investments!

    42:18 Corey’s upcoming development project!

    61:21 What is your competitive advantage?

    61:37 One piece of advice for new investors.

    62:02 What do you do for fun?

    62:43 Good book, podcast, or self development activity that you would recommend?

    63:48 Local Network Recommendation?

    64:08 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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    1 hr and 7 mins