Straight Up Chicago Investor

Latest Episodes:

Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars Aug 07, 2025

Show notes

Kevin Cawley, aka Cost Seg Kev, is a Senior Account Executive at CSSI Services - a firm with over 55,000 cost segregation studies completed since 2003.

Cost Seg Kev starts by reviewing the 101 on cost segregation and how it can be used to offset your tax liability. He dives into the benefits of real estate professional status and recent tax code changes by the presidential administration. He also touches on frequently asked questions on cost segregation studies and closes with how he built his business and reputation!

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

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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Guests: Kevin Cawley, CSSI Services

Link: CSSI Cost Segregation Calculator

Link: SUCI Ep 59 - Cost Seg Kev

Link: James Mahon (CPA Referral)

Link: At Your Command (Book Recommendation)

Guest Questions

02:46 Housing Provider Tip - Go above and beyond to acknowledge tenants after management mistakes.

05:00 Intro to our guest, Cost Seg Kev!

05:43 The 101 on Cost Segregation.

11:37 The benefits of real estate professional status!

25:42 Recent changes to depreciation rules.

32:15 Technical side of cost segregation!

34:23 Cost Seg on smaller properties.

43:43 What is your competitive advantage?

44:42 One piece of advice for new investors.

46:00 What do you do for fun?

46:37 Good book, podcast, or self development activity that you would recommend?

47:52 Local Network Recommendation?

48:55 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 391: Do You Have a Business Continuation Plan? Aug 05, 2025

Show notes

Josh Steigelmann explains the importance of a business continuation plan and provides step-by-step guidance on how investors can set-up a business continuation plan

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Connect 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.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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Guest: Josh Steigelmann, State Farm Insurance

Link: Straight Up Chicago Investor Investor Stories Featuring Sean Morrissey

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Production House: Flint Stone Media

Episode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims Jul 31, 2025

Show notes

Mitch Schoeneman is a Managing Partner at A. Schoeneman & Co. - a top rated Chicago public insurance adjusting firm that has been serving customers for over 55 years!

Mitch starts by explaining the services rendered by insurance adjusters. He breaks down how investors can set themselves up for success with insurance claims and provides tactical steps for handling disastrous situations at properties. Mitch dives deep on insurance coverages, how investors can best protect themselves, and shares some wild insurance stories! This show is full of valuable insurance insights that you will want to put into practice!

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

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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Guests: Mitch Schoeneman, A. Schoeneman & Co | Email Mitch

Link: Jimmy Sarnoff (Tax Appeal Attorney Referral)

Guest Questions

03:14 Housing Provider Tip - Home insurance considerations to improve coverage and pricing!

04:56 Intro to our guest, Mitch Schoeonemen!

08:33 The value of insurance adjusters.

15:57 How investors can prepare for successful insurance claims.

21:17 Properly handling emergency situations at properties!

37:15 General timelines for insurance payouts.

45:00 Wild insurance stories!

53:39 What is your competitive advantage?

54:01 One piece of advice for new investors.

54:08 What do you do for fun?

54:59 Good book, podcast, or self development activity that you would recommend?

55:32 Local Network Recommendation?

55:53 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec Jul 24, 2025

Show notes

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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Sebastian Mysliwiec, founder of The Dream Rentals, explains how he's built a short-term and mid-term rental management company that delivers top guest experiences and maximizes profits!

Sebastian talks about cutting his teeth and eventually thriving at a marketing company that helped build his real estate skill set. He provides tactical advice on underwriting, marketing, and managing short-term rentals (STRs). Sebastian explains how his team manages seasonality, shares a STR horror story, and top amenities for guests. He closes with remarks on refinancing considerations for STR properties and his team's growth strategy.

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

Guests: Sebastian Mysliwiec, The Dream Rentals

Link: The Dream Rentals Instagram

Link: Skyscraper Tom's Instagram

Link: The 12 Week Year (Book Recommendation)

Guest Questions

01:58 Housing Provider Tip - Leverage Freedom of Information Act (FOIA) to request property info during due diligence!

04:25 Intro to our guest, Sebastian Mysliwiec!

08:31 Defining AirBnB arbitrage.

13:28 Underwriting basics of short-term rentals (STRs)!

20:10 Listing platforms for STRs.

26:09 Managing STR seasonality in Chicago to optimize profit.

35:36 STR Marketing Tips!

45:45 AirBnB Horror Story!

47:46 Top STR amenities.

49:23 Mid-Term Rental analysis and expanding to other markets!

55:13 Refinancing STR properties.

56:47 What is your competitive advantage?

57:15 One piece of advice for new investors.

57:42 What do you do for fun?

58:25. Good book, podcast, or self development activity that you would recommend?

58:54 Local Network Recommendation?

59:29 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 388: NBOA 2025 Summer Soiree Update Jul 22, 2025

Show notes

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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What is the NBOA Summer Soiree and how can investors benefit from this event?

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: Mike Glasser & Real Estate Nate, NBOA

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

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Production House: Flint Stone Media

Episode 387: This Is How You Make Money In Chicago In Your Early 20s with Alex Diaz Jul 17, 2025

Show notes

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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Alex Diaz explains how he left his day job as a barber to successfully flip and wholesale real estate for a living at 24 years of age!

Alex starts by sharing how he made the jump from being a barber to wholesaling real estate. He explains how he acquired his first property; a househack sourced off-market! Alex provides tactical advice on marketing directly to sellers to create deal flow. He talks about lessons learned from flipping and gets granular on the real estate market in Aurora and the surrounding suburbs. This is another motivating show with an investor thriving at a young age!

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: Alex Diaz, Bluestone Property Solutions

Link: Alex Diaz's Instagram

Link: SUCI Ep 335 - Aram Ghazaryan

Link: The Art of the Deal (Book Recommendation)

Guest Questions

03:16 Housing Provider Tip - Maintain and understand misusage of water hose spigots!

05:09 Intro to our guest, Alex Diaz!

10:38 Alex's first house hack sourced off-market!

14:24 Jumping into wholesaling and direct-to-seller marketing.

26:20 Marketing strategy and the 101 on Montgomery, IL.

29:11 Benefits of being around like-minded investors.

35:10 Lessons learned from flipping!

39:24 Alex's geographic areas of focus.

44:06 What is your competitive advantage?

44:31 One piece of advice for new investors.

45:14 What do you do for fun?

45:31 Good book, podcast, or self development activity that you would recommend?

46:04 Local Network Recommendation?

46:23 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 386: How to Invest in DuPage County with Katie and Rob Hayes Jul 10, 2025

Show notes

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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Katie and Rob Hayes are investors and realtors with nearly 2 decades of experience acquiring and managing investment properties!

The duo starts by sharing their background including investing in Florida before transitioning to the Chicago Western Suburbs. They share lessons learned from investing in lower cost areas and why they pivoted to higher class assets. Rob and Katie share golden nuggets on marketing to owners for deal flow and on operating short-term rentals. They close out with a positive outlet on Downer's Grove and why investors should be considering it!

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

Guests: Katie and Rob Hayes, Platinum Partners Realtors

Link: Team Hayes Realtors Facebook

Link: Rob's LinkedIn

Link: CAREIA Investor's Group

Guest Questions

03:03 Housing Provider Tip - Utilize Starbucks gift cards to easily express gratitude towards tenants and vendors!

04:33 Intro to our guests, Katie and Rob Hayes!

09:54 Jumping from Florida to local investments!

14:30 Considerations when investing in lower price point areas.

17:45 Investments leading up to the housing crash.

23:47 Getting a real estate license during the housing crash.

29:05 Creating deal flow in a low inventory market.

34:40 Representing and adding value to buyers in this market.

39:17 Dialing back acquisitions and strategizing for retirement!

44:35 Short-term rentals in Chicago suburbs.

54:40 Advice for couples who invest together!

57:15 What is your competitive advantage?

58:31 One piece of advice for new investors.

59:45 What do you do for fun?

60:34 Good book, podcast, or self development activity that you would recommend?

61:42 Local Network Recommendation?

63:05 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 385: What is a Demand Letter and How to Handle Receipt of a Demand Letter Jul 08, 2025

Show notes

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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As an investor, how do I handle receipt of a demand letter?

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: Bibek Das, Das Law

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Production House: Flint Stone Media

Episode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton Jul 03, 2025

Show notes

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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Jake Clopton, President of Clopton Capital, has successfully been running his commercial lending business for over 17 years.

Jake shares how he grinded early in his career to get off the ground, and emphasizes the value of cold calling. He explains the different types of interest rates and provides the current state of rates. Jake speaks about macro-level economics including the stagflationary environment in today's market. In typical SUCI fashion, he closes out with a bullish outlook on Chicago!

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: Jake Clopton, Clopton Capital

Link: Jake Clopton's LinkedIn

Link: Jake Clopton's Instagram

Link: Never Split the Difference (Book Recommendation)

Link: Elevate Energy (Network Referral)

Guest Questions

02:07 Housing Provider Tip - Understand how to prioritize emergency work orders.

04:10 Intro to our guest, Jake Clopton!

12:20 Surviving as a lender during the real estate crash.

19:20 Jake's "tipping point" deal!

20:21 The state of interest rates.

28:56 Rates on residential real estate.

34:04 Jake's predictions on rates and the RE market!

41:53 The 101 on Stagflation.

43:50 Jake's bullish remarks on Chicago!

48:05 What is your competitive advantage?

48:32 One piece of advice for new investors.

49:06 What do you do for fun?

49:17 Good book, podcast, or self development activity that you would recommend?

50:06 Local Network Recommendation?

51:40 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 383: From Chemist to Chicago's "Bow Tie" Attorney w/Mahmoud Faisal Elkhatib Jun 26, 2025

Show notes

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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Mahmoud Faisal Elkhatib is an attorney with vast experience in real estate transactions, development, and litigation allowing him to bring huge value to his clients.

Mahmoud gives his back story including time in the laboratory as a chemist and starting various businesses prior to landing into his current career as an attorney! He breaks down foreclosure defense and how he is going to bat for his clients. Mahmoud explains the roles of attorneys and Title Company personnel in a real estate transaction and how his unique fee structure allows his clients to save on fees. Throughout the show, Mahmoud conveys the importance of having a knowledgeable attorney in your corner in any real estate transaction!

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: Mahmoud Faisal Elkhatib, EV Has

Link: Mahmoud's Instagram

Link: No More Mr. Nice Guy (Book Recommendation)

Link: The Subtle Art of Not Giving a F*ck (Book Recommendation)

Link: Tammie Lester (Loan Officer Referral)

Guest Questions

01:54 Housing Provider Tip - Understand new rules around HVAC to strategically maintain and repair systems!

03:18 Intro to our guest, Mahmoud Faisal Elkhatib!