134 episodes

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.

Straight Up Chicago Investor Straight Up Chicago Investor

    • Business
    • 5.0 • 211 Ratings

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.

    Forty-Six Years of Chicago Real Estate Knowledge with Pioneer Vince DePaul

    Forty-Six Years of Chicago Real Estate Knowledge with Pioneer Vince DePaul

    Vince begins by talking about his previous career as a rockstar manager (Styx)! He shares stories about Roseland and Humboldt Park in the 60s and 70s. Vince transitions into his journey as both a real estate broker and investor. He dives deep into the pros/cons of getting a broker’s license as an investor and the requirements to get licensed. Throughout the episode, Vince speaks to the power of real estate as a wealth generator and the importance of education!
    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: Vince DePaul, Your House Real Estate Academy
    Link: Chicago Heat Ordinance
    Link: Frank Zappa (Network Recommendation)
    Sponsors: Appeal.tax and State Farm
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    Guest Questions
    03:08 Housing Provider Tip: Provide temperature sensors to tenants to document heating and cooling issues!
    06:30 Intro to our guest, Vince DePaul!
    10:03 Did any of the skills Vince learned in his previous career of managing entertainers translate to real estate?
    11:50 Vince talks about Roseland and surrounding neighborhoods in the 60s/70s!
    17:40 What was Humboldt Park like back in the day?
    18:50 How were Vince’s first couple years in real estate?
    21:43 Vince talks about his journey from real estate broker to investor!
    26:44 Should real estate investors get a real estate broker’s license?
    33:43 What are the costs and requirements to get a real estate license?
    40:30 Vince talks about his real estate school’s offerings!
    42:16 What is Vince’s outlook on real estate brokers given advances in technology?
    Wrap Up Questions
    46:36 What is Vince’s competitive advantage? 
    48:03 One piece of advice for new investors.
    48:54 What do you do for fun?
    49:33 Good book, podcast, or self development activity that you would recommend? 
    50:10 Local Network Recommendation?
    50:57 How can the listeners learn more about you and provide value to you?
    That’s our show! Thanks for listening!
    That’s our show! Thanks for listening!
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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 54 min
    How to Vet Contractors For Your Chicago Rehab

    How to Vet Contractors For Your Chicago Rehab

    What are the steps I should take to vet my Chicago contractors?
    Connect with Mark and Tom: StraightUpChicagoInvestor.com
    Email the Show: StraightUpChicagoInvestor@gmail.com
    Guest: Bolanle Ogunmakin, Quality Builders

    Link: Straight Up Chicago Investor Episode 76
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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 15 min
    Million Dollar Batavia 5-Flat From Networking to Closing (POV)

    Million Dollar Batavia 5-Flat From Networking to Closing (POV)

    Return guests Bibek Das, Eric Workman, and Matt LaCosse join us to discuss a 5-unit deal with a lot of hair on it!
    Matt (buyer on this deal) starts by talking about how our very own Mark Ainley (buyer’s agent) brought this 5-unit property in Batavia to his attention. Eric (the lender on this deal) dives into the lending aspect of this deal and the group discusses the offer formulation and negotiation process. Bibek (the buyer’s attorney) explains the meaning of appraisal waivers and “AS-IS” offers. Navigating a plumbing leak the day before closing and escrow holdbacks are also topics of discussion on this show. The episode is closed out with lessons learned from this “hairy” but ultimately amazing deal!
    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: Bibek Das, Eric Workman, and Matt LaCosse, Das Law & Renovo Financial
    Link: SUCI Ep 145 - Matt LaCosse
    Link: SUCI Ep 17 - Bibek Das
    Link: SUCI Ep 19 - Eric Workman
    Sponsors: Appeal.tax and GC Reality
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    Guest Questions
    04:14 Housing Provider Tip: Utilize the main water shut off valve on vacant properties to prevent plumbing issues related to cold weather.
    05:55 Intro to our group of return guests: Bibek Das, Eric Workman, and Matt LaCosse!
    08:15 Matt introduces the deal that will be discussed in this episode!
    14:04 What happened after Matt’s initial walk through?
    20:02 Matt talks about his initial conversation with the lender on this deal, Eric Workman.
    22:30 Matt and Mark talk about the offer and negotiation process!
    30:24 Eric weighs in on waiving an appraisal as part of an offer.
    32:42 What does it mean to make an “as-is” offer?
    36:23 Mark talks about the multiple PIN situation on this deal.
    39:27 What did the loan structure look like on this 5-unit property?
    40:43 How did the inspection and attorney review process go?
    49:47 Matt talks about closing day and reflects on the deal as a whole!
    That’s our show! Thanks for listening!
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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 1 hr
    From Prison to Real Estate Profits; A Transformational Chicago Journey Against All Odds with Mike Biker

    From Prison to Real Estate Profits; A Transformational Chicago Journey Against All Odds with Mike Biker

    From a rough upbringing to a successful REI career in Chicago, Mike Baker joins us to discuss his journey and his vast knowledge on wholesaling, flipping, and consulting. 
    Mike begins by outlining his troubled past involving drugs, gangs, and prison. He shares some of the lessons learned in prison and the mindset shift required to get started and to succeed in real estate. Mike, Mark, and Tom share shocking stories about rehabbing in distressed neighborhoods. Mike closes by explaining how his experience gives him a competitive advantage and how he’s leveraging it to offer hourly, a la carte consulting services to investors looking for support and resources!
    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 Baker of A La Carte REI
    Link: Mike Baker's Blog
    Link: SUCI Episode 89
    Link: SUCI Episode 146
    Link: Michael Kevorkian (Network Referral)
    Link: 48 Laws of Power (Book Referral)
    Link: Brie Schmidt (Network Referral)
    Sponsors: Appeal.tax and Essex Realty Group
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    Guest Questions
    03:23 Housing Provider Tip: Be sure you are cleaning and maintaining your fireplace!
    05:40 Intro to our guest, Mike Baker!
    06:50 Mike talks about his troubled past!
    08:44 What did Mike learn from his time in prison that has been applicable in his real estate journey?
    11:29 Mike talks about his start in real estate working for a wholesaler.
    17:08 Mike shares stories about rehabbing in distressed neighborhoods!
    24:05 What are some advantages of having experience in multiple facets of real estate like Mike does?
    26:18 How can newer investors utilize joint-ventures and resources like A La Carte REI?
    30:27 What is Mike’s motivation for starting A La Carte REI?
    Wrap Up Questions
    37:44 What is Mike’s competitive advantage? 
    38:18 One piece of advice for new investors.
    39:04 What do you do for fun?
    39:45 Good book, podcast, or self development activity that you would recommend? 
    40:37 Local Network Recommendation?
    41:10 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
    Copyright of Straight Up Chicago Investor 2022.

    • 44 min
    How to Reduce the Cost of your Chicago Lawn

    How to Reduce the Cost of your Chicago Lawn

    What are my options to remove maintenance costs on smaller pieces of lawns?
    Connect with Mark and Tom: StraightUpChicagoInvestor.com
    Email the Show: StraightUpChicagoInvestor@gmail.com
    Guest: James Galvin, Chicago Lawn To Garden

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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 12 min
    Rising Rates, 2/1 Buydowns, and The Foreseeable Future of Investing and Lending with Rock Star Lender (and Drummer!) Sam Sharp

    Rising Rates, 2/1 Buydowns, and The Foreseeable Future of Investing and Lending with Rock Star Lender (and Drummer!) Sam Sharp

    Sam Sharp has over 20 years experience in the Mortgage Industry and joins us to discuss rising interest rates.
    Sam begins by talking about his vast experience in the mortgage industry and the lending environment during the last housing crash. He shares tips that have helped him be a top-producing loan originator and provides advice for professionals trying to build their brand. Sam gives his take on the million-dollar question: WHERE ARE RATES GOING AND IS NOW A GOOD TIME TO BUY?! He explains interest rate buy-downs as a strategy that can benefit both buyers and sellers. Sam closes by talking about his approach to investing and how it has worked out for him!
    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: Sam Sharp, Guaranteed Rate
    Link: Never Split the Difference (Book Recommendation)
    Link: Harley Rosenthal (Network Recommendation)
    Sponsors: Pentwater Cabinetry and Essex Realty Group
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    Guest Questions
    03:00 Housing Provider Tip: Be sure your floor drains are free of debris to avoid flooding!
    05:12 Intro to our guest, Sam Sharp!
    06:38 Sam talks about his start in real estate!
    11:30 How does Sam succeed and do business with integrity in an industry where many others do not operate with integrity?
    13:50 Sam talks about the lending environment during the last housing crash.
    23:13 What advice would Sam give to real estate professionals trying to build their brand?
    26:32 Where are interest rates going and is now a good time to buy?
    36:20 Sam explains interest rate buy-downs!!
    47:58 How can investors and other real estate professionals leverage rate buy-downs?
    52:50 Sam talks about his investing strategy!
    Wrap Up Questions
    56:42 What is Sam’s competitive advantage? 
    57:05 One piece of advice for new investors.
    57:44 What do you do for fun?
    58:08 Good book, podcast, or self development activity that you would recommend? 
    59:30 Local Network Recommendation?
    60:05 How can the listeners learn more about you and provide value to you?
    That’s our show! Thanks for listening!
    -----------------
    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 1 hr 4 min

Customer Reviews

5.0 out of 5
211 Ratings

211 Ratings

R. Stader ,

Local flavor

It’s great to listen to a show about RE and be local also. It makes it more relevant

zach6710 ,

Great Podcast

This show provides incredible insight not only into Chicago RE but also RE in general. Tom and Mark are both stand up guys and are willing to drop everything they are doing to help fellow investors. Great show!

Christi Avelar ,

Amazing!

Love the show! I am a Realtor, property manager and investor, and I find value in every single episode. I look forward to listening to you guys and your guests weekly! Keep up the amazing work!

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