Straight Up Chicago Investor

Latest Episodes:

Episode 154: Scaling From a Duplex to a $100 Million Portfolio in Chicago's North and Northwest Side with Jeff Weinberg Jul 21, 2022

Show notes

Jeff Weinberg of Drexel Properties joins us to discuss the importance of systems and relationships when scaling a large Chicago Real Estate portfolio.

Jeff kicks things off by talking about his start in real estate and leaving his W2 job to pursue his passion full time. He jumps into the mindset and strategies that will help in scaling a portfolio. Jeff drops street level knowledge on the North and Northwest side and explains why he is bullish on Chicago. Throughout the show, Jeff emphasizes the importance of cultivating long term relationships with brokers, contractors, and other vendors, and attributes much of his success to implementing this principle!

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: Jeff Weinberg from Drexel Properties

Link: The Splendid and the Vile (Book Recommendation)

Link: Jeff Weinberg's LinkedIn

Sponsors: The Axon Group (EXP Realty) and Appeal.tax

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Guest Questions

03:55 House Provider Tip: Remember to have a baseline for utilities to identify irregular bills!

06:04 Intro to our guest, Jeff Weinberg!

07:22 How did Jeff get started in real estate?

09:52 At what point did Jeff decide to leave his W2 job?

11:47 Jeff talks about how he scaled his portfolio.

15:32 In hindsight, what would Jeff change about his investing career?

17:46 What attracted Jeff to investing in the Northwest side of Chicago?

26:11 Why does Jeff choose to buy-and-hold and why is he continuing to scale an already large portfolio?

29:04 Why is Jeff still bullish on Chicago?

30:50 How is Jeff's portfolio setup?

38:12 How do you develop relationships with brokers and vendors?

Wrap Up Questions

42:14 What is Jeff's competitive advantage?

42:42 One piece of advice for new investors.

44:37 What do you do for fun?

46:27 Good book, podcast, or self development activity that you would recommend?

49:05 Local Network Recommendation?

50:55 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

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Production House: Flint Stone Media

Episode 153: Building Wealth via Long-Term Real Estate Investments in Chicago with Bill Himmelstein Jul 14, 2022

Show notes

Bill Himmelstein of Tenant Advisory Group drops in to share great insight on long-term investing and reminds us that real estate is not a "get rich quick" but rather a "get wealthy slowly" investment.

Bill starts by talking about his start in real estate and his experience with multi-family investing. He gets granular by speaking to the effect of rising interest rates on the market and also explains investing with partners. Bill emphasizes the importance of living below your means and adapting the long-term investor mindset to build generational wealth. This episode is full of golden nuggets around having a long-term outlook to keep growing your real estate portfolio!

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: Bill Himmelstein, Tenant Advisory Group

Link: Willam Himmelstein - Tenant Advisory Group

Link: The Secret of Shelter Island (Book Recommendation)

Sponsors: The Axon Group (EXP Realty) and Appeal.tax

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Guest Questions

02:44 House Provider Tip: Be mindful of timelines when planning turnovers with Section 8 tenants!

05:13 Intro to our guest, Bill Himmelstein!

08:03 How did Bill get started in real estate?

11:23 How do you balance having capital on hand with investing that money into long-term investments?

17:50 How did Bill begin buying multi-family real estate with partners?

22:31 Bill talks about a previous deal.

29:31 How are rising interest rates affecting cap-rates?

34:50 How does Bill handle his limited partnerships?

43:02 How does someone with little capital get started?

Wrap Up Questions

46:31 What is Bill's competitive advantage?

47:50 One piece of advice for new investors.

48:25 What do you do for fun?

49:22 Good book, podcast, or self development activity that you would recommend?

50:28 Local Network Recommendation?

51:33 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

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Production House: Flint Stone Media

Episode 152: Straight Up Tues Tip 32 Jul 12, 2022

Show notes

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

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Mike Glasser of NBOA

Link:https://www.straightupchicagoinvestor.com/podcast/episode-37-the-nboa---your-ally-and-voice-as-a-chicagoland-housing-provider

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Production House: Flint Stone Media

Episode 151: Dissecting Property Taxes on your Chicagoland Properties with Cook County Assessor Fritz Kaegi Jul 07, 2022

Show notes

Ever wonder how your Cook County properties are assessed and how taxes are calculated? Cook County Assessor Fritz Kaegi presents valuable info on property taxes and the overall mission of his office!

Fritz starts by sharing his background and how it allowed him to seamlessly step in and improve processes as the Assessor. He talks about his office's responsibilities and some of the common misconceptions the public may have. Fritz elaborates on the massive amount of data involved with assessing 1.9 million properties and gives tips on making your case if you believe your property's assessed value is inaccurate. Tremendous value packed in this episode that can potentially lead to decreased property taxes and increased NOI!

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: Fritz Kaegi, Cook County Assessor's Office

Link: Capital Allocators (Podcast Recommendation)

Link: Hacks on Tap (Podcast Recommendation)

Link: Power Broker (Book Recommendation)

Link: Samir Mayekar (Network Recommendation)

Link: Michael Fassnacht (Network Recommendation)

Sponsors: GC Reality and The Axon Group (EXP Realty)

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Guest Questions

02:29 House Provider Tip: Do not overpay for a property simply to complete a 1031 Exchange - weigh out all options!

05:43 Intro to our guest, Fritz Kaegi!

06:24 What attracted Fritz to the position of Cook County Assessor?

08:34 How are property taxes calculated?

18:20 What is the process for establishing assessed values?

25:29 How is the massive amount of data managed by the Assessor's office?

29:01 How many PINs are there in Cook County?

29:44 Why is a majority of the property tax burden put on the housing providers (i.e. owners of apartment buildings)?

33:32 How are property taxes impacting affordable housing?

35:45 What are some common misconceptions about the Cook County Assessor?

Wrap Up Questions

41:20 What is Fritz's competitive advantage when compared to his predecessors?

43:04 One piece of advice for new investors.

45:29 What do you do for fun?

45:51 Good book, podcast, or self-development activity that you would recommend?

47:46 Local Network Recommendation?

49:04 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

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Production House: Flint Stone Media

Episode 150: Mastering Multi-Family to Propel Your Chicagoland Investments with Rod Khlief Jun 30, 2022

Show notes

As many may already know, Rod Khleif is a multifamily real estate investor, business consultant, and high-performance coach. In today's show, Rod focuses heavily on being prepared to take action as opportunities arise during a changing market like the one we are in today!

Rod starts off by speaking about the huge loss he experienced during the last housing crash and how he was able to bounce back stronger. He elaborates on the anticipated recession and on what investors should be doing to capitalize on upcoming opportunities. Rod emphasizes the importance of real estate being a team sport and gives his take on single-family vs multi-family investing. This episode is loaded with empowering words on taking action and embracing a mindset to succeed in real estate and life in general!

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: Rod Khleif of Rod Khleif Multifamily Mastery

Link: The 5 Love Languages (Book Recommendation)

Link: Turning Pro (Book Recommendation)

Link: The One Thing (Book Recommendation)

Link: The Lifetime Cashflow Podcast

Sponsors: Kiser Group and Appeal.tax

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Guest Questions

02:47 House Provider Tip: Focus on retaining existing tenants to prevent costly turnovers!

05:23 Intro to our guest, Rod Khleif!

06:07 The rise and fall of Rod Khleif!

09:07 What is Rod doing to prepare for the anticipated recession?

16:23 How do you balance being patient with continuing to strive towards goals in this market cycle?

19:09 What is step one in preparing for a market turn?

25:07 What would you say to new investors who want to start with single-family homes and then transition into multi-family?

27:05 What is EOS?

28:47 What mistakes do investors make when vetting people for their team when trying to scale?

31:42 How will Rod be changing his asset management during this changing market?

33:07 What is Rod's competitive advantage?

Wrap Up Questions

33:48 One piece of advice for new investors.

34:32 What do you do for fun?

34:51 Good book, podcast, or self development activity that you would recommend?

36:26 Local Network Recommendation?

37:14 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

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Production House: Flint Stone Media

Episode 149: Revitalizing the "Land of Lincoln" with Aurora Mayor (and potential IL Governor) Richard Irvin Jun 23, 2022

Show notes

Mayor of Aurora and gubernatorial candidate Richard Irvin discusses his plan to create jobs, lower crime, and attract businesses if he were to be elected Governor of Illinois.

Richards speaks on hot-topic issues including affordable housing, taxes, and crime. He dives deep into his tenure as Mayor of Aurora and how he can translate Aurora's successful revitalization to the rest of the state as governor. Innovative concepts on reforming the educational and police system are among other nuggets dropped in the episode. Richard closes with empowering words on his vision of making Illinois the "Land of Lincoln" again and bringing pride back to our state!

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: Richard Irvin from the City of Aurora

Link: SUCI Episode 30 (Investing in Aurora)

Sponsors: Kiser Group and Prime Lending

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Guest Questions

03:28 Intro to our guest, Richard Irvin!

04:28 What does Richard consider to be his greatest accomplishment?

06:40 What can be done to create more affordable housing in Illinois?

10:42 What is the sequence of events to create affordable housing and bring businesses to Illinois?

12:48 How can Richard transfer what he's done in Aurora to the rest of the state?

Wrap Up Questions

17:27 What are the first steps to solve the crime issues in Illinois?

22:55 How can we get the community to buy into this plan of redeveloping Chicagoland?

27:30 What is the one thing Richard wants to be remembered for?

28:45 Chicago/Illinois Fact!

That's our show! Thanks for listening!

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Production House: Flint Stone Media

Episode 148: Acquiring Distressed Real Estate by "Beating the Streets" in Chicago with Joe Sevcik Jun 16, 2022

Show notes

Are you struggling with deal flow in this market? Joe Sevcik drops in to share how Networth Realty is acquiring distressed properties and wholesaling to add value to their investors.

Joe covers how his company is grinding it out by hitting the streets to get in front of motivated sellers. He talks about the mindset required to succeed in this space where rejection is commonplace. Joe dives deep into how his company is adding value to their investor clients by project values and construction costs to name a few things. This episode is full of nuggets on deal acquisition and things to keep in mind when looking for your next off-market, distressed property!

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: Joe Sevcik from Networth Realty

Link: Rich Dad Poor Dad (Book Recommendation)

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

Link: Illinois Transfer Tax Info

Sponsors: Kiser Group and Appeal.tax

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Guest Questions

03:22 House Provider Tip: Be mindful of pest control and account for associated expenses!

06:35 Intro to our guest, Joe Sevcik!

07:30 What/who is Networth Realty?

08:02 What is Networth Realty doing to acquire deals?

10:42 How do Joe and his team stay motivated when marketing to sellers is unsuccessful a large portion of the time?

12:20 How is Networth Realty adding value to their investors?

14:50 How is estimating rehab costs different in Chicago compared to other locations?

19:06 What are some tips for investors looking for off-market deals?

21:40 How are Joe and his team following up with sellers?

25:27 Any cool or funny stories when acquiring these distressed homes?

26:15 What is an example of a deal that was difficult to close on?

27:27 How has the hot market impacted the business?

29:02 Who are the ideal clients/investors for Networth Realty?

32:56 What does the future look like for Networth Realty?

35:15 For someone interested in joining Networth Realty, what skills/qualities should they bring?

Wrap Up Questions

37:15 What is Joe's competitive advantage?

38:00 One piece of advice for new investors.

38:18 What do you do for fun?

38:47 Good book, podcast, or self-development activity that you would recommend?

39:40 Local Network Recommendation?

39:57 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

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Production House: Flint Stone Media

Episode 147: Straight Up Tues Tip 31 - Perry Farella Breaks Down HUD 203k Loan Options Jun 14, 2022

Show notes

What is a HUD 203k loan, when does it make sense for investors to leverage this loan, and where do 203k loans fall apart?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Perry Farella of Prime Lending

Link: ttps://perryfarella.com/blog/

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Production House: Flint Stone Media

Episode 146: How To Manage Your Rehabs and What to Look For In a Chicagoland General Contractor with RJ DeLeon Jun 09, 2022

Show notes

RJ Deleon is all things real estate, as he wears the hats of a contractor, investor, and mentor. In today's show we focus almost exclusively on RJ's experience as a GC and how investors can best partner with contractors.

RJ covers some of the most frequently asked questions investors have for GCs and how he handles different requests from investors. He showcases how his personal investing experience is a huge value-add to his clients and explains how to approach, vet, and manage contractors. Throughout the episode, RJ drops numerous jewels of wisdom on building quality relationships with contractors so that you can successfully take down your next rehab!

If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! Also check out RJ's previous episode with his wife Nicky - https://www.straightupchicagoinvestor.com/podcast/episode-43-househacking-scaling-and-large-multifamily-deals-with-one-of-chicagos-best-power-couples

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: RJ DeLeon, EJC Partners

Link: Book Recommendation

Link: Brie Schmidt (Network Referral)

Link: Jason Wagner (Network Referral)

Link: Quality Builders (Network Referral)

Sponsors: Kiser Group and Appeal.tax

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Guest Questions

03:10 House Provider Tip: Be more specific in texts/emails to avoid miscommunication!

05:07 Intro to our guest, RJ DeLeon!

06:09 What is the one thing that contractors get asked most frequently?

08:30 What is RJ's strategy when estimating a construction job?

10:14 How does RJ consult investors on their construction scopes to get the best ROI?

13:28 How is RJ marketing his consulting services?

16:25 How does RJ handle requests to walk properties?

19:14 How can an investor most-effectively approach a contractor when requesting services?

23:26 What questions should an investor ask contractors to vet them?

31:07 How can an investor effectively keep tabs on a project to ensure progress is being made?

34:55 How can draw schedules be set up to protect both the investor and the contractor?

40:45 What is a mechanics lien?

42:40 How is RJ tracking scopes, schedules, and other elements of the project?

Wrap Up Questions

44:59 What is RJ's competitive advantage?

45:50 One piece of advice for new investors.

46:47 What do you do for fun?

47:35 Good book, podcast, or self development activity that you would recommend?

48:36 Local Network Recommendation?

49:35 How can the listeners learn more about you and provide value to you?

That's our show! Thanks for listening!

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Production House: Flint Stone Media

Episode 145: NFL Tight End Turned Chicago Real Estate Investor with Matt LaCosse Jun 02, 2022

Show notes

Ever wonder how professional athletes are investing to set themselves up for life after their sports career? NFL Tight End Matt LaCosse joins us to shine light on this exact journey.

Matt starts off by talking about how the skills required to be a professional NFL player translate to real estate investing. He explains why he came back home to Chicago to start his investing career. Matt dives into the lessons learned on his first C- class investment and how that changed his investment strategy. Mr. LaCosse talks about his current Naperville investments and closes with golden nuggets on building a team and setting yourself up for success as a new investor!

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: Matt LaCosse

Link: Book Recommendations

Link: Bibek Das (Network Recommendation)

Sponsors: The Axon Group (EXP Realty) and Appeal.tax

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Guest Questions

02:25 House Provider Tip: Consider other ways Real Estate makes you money aside from cash-flow during this tight inventory market!

05:01 Intro to our guest, Matt Lacosse!

06:30 How do skills required for the NFL translate into Real Estate investing?