Straight Up Chicago Investor

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**Straight Up Chicago Investor**

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.

Latest Episodes:

Episode 304: What Are the Different Items Holding Up Closings in 2024? Jun 25, 2024

Show notes

How are local Chicago real estate transactions different than they were a year ago?

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 303: How Two Teachers Found Financial Independence Through Real Estate with Blaine and Lily Kosek Jun 20, 2024

Show notes

Want to hear an inspirational story about two teachers leaving their W2 and amassing over 20 rental units over a few short years? If so, then this show is for you!

Blaine and Lily talk about their decision to leave their jobs as educators to become full-time real estate agents and investors! They discuss specific suburb markets that they target along with pros and cons of the BRRRR strategy. Lily and Blaine share their vast experience with short-term rentals and dive deep on top considerations to set yourself up for success. Through the show, the duo provides repeated examples of how they just took action and let experience be the best teacher and largely attribute their success to that!

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

Guests: Blaine and Lily Kosek, The Blaine Kosek Team

Link: Krush It With The Koseks (TikTok)

Link: Rich Dad Poor Dad (Book Recommendation)

Link: Atomic Habits (Book Recommendation)

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Guest Questions

02:11 Housing Provider Tip - Perform preventative maintenance on gutters and downspouts to be prepared for rain season!

03:58 Intro to our guests, Lily and Blaine Kosek!

05:32 Leaving teaching to pursue real estate!

19:27 The Kosek Meetup Group!

24:16 The Pitfalls of the BRRRR strategy.

29:32 Opportunity in DeKalb.

35:10 Ins and outs of short term rentals!

43:45 Considerations for lake-front AirBNBs.

50:50 Best suburbs for short term rentals.

60:20 The Future of the Koseks!

62:52 What is your competitive advantage?

64:06 One piece of advice for new investors.

66:00 What do you do for fun?

66:21 Good book, podcast, or self development activity that you would recommend?

67:12 Local Network Recommendation?

67:48 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 302: Strategies for Acquiring Off Market Real Estate with Dain Laverty Jun 13, 2024

Show notes

Dain Laverty is a Managing Partner of Property Pals; a company that specializes in acquiring off market real estate through a variety of methods!

Dain shares his start in real estate including his first deal on Chicago's south side sourced from Craigslist! He discusses finding his business partner and how he identified their complementary skill sets. Dain discusses different strategies for acquiring off market properties including Subject to and gives pointers on approaching potential sellers! Throughout the episode, Dain drops great insights on transitioning from corporate America to real estate and emphasizes the importance of having a "take action" mindset!

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

Guests: Dain Laverty, Property Pals USA

Link: SUCI Ep 64 - Frank Montro

Link: All-In Podcast

Link: The Go Giver (Book Recommendation)

Link: Dain's Instagram

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Guest Questions

02:37 Housing Provider Tip - Build and keep rapport with your residents to make your life easier!

04:32 Intro to our guest, Dain Laverty!

13:50 How Dain found his business partner!

17:48 Keys to scaling.

26:03 Starting a conversation with a potential seller.

28:54 Expanding beyond Chicago Real Estate.

32:37 Sub2 Financing!

40:35 The Due on Sale clause.

47:49 Dain's outlook on Chicago!

53:50 What is your competitive advantage?

54:07 One piece of advice for new investors.

54:29 What do you do for fun?

54:46 Good book, podcast, or self development activity that you would recommend?

54:24 Local Network Recommendation?

56:23 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 301: How to Maximize Showing Value by Professionally Decluttering With Karen Welch Jun 11, 2024

Show notes

What is the easiest way to declutter a home to maximize it's showing value?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Karen Welch, Moovers Chicago

Link: Build Your Team | Straight Up Chicago Investor Podcast

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Production House: Flint Stone Media

Episode 300: 300th Episode Celebration - Answers To Burning REI Questions Amongst Chicago Investors with Mark and Tom Jun 06, 2024

Show notes

Straight Up Chicago Investor Podcast celebrates its 300th Episode! To celebrate the huge milestone, Mark and Tom answer questions from guests on all things Chicago REI!

If you enjoy all the value the SUCI podcast brings, 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

Guests: Mark Ainley and Tom Shallcross, Straight Up Chicago Investor

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Guest Questions

03:55 How to maximize rent in a hot market?

08:00 Biggest wins and losses in REI!

18:19 Changing REI strategies to promote progression!

21:00 BRRRR'ing single family homes vs multifamily rentals.

24:03 Advice letter from your 20-year old self!

26:16 Brick vs Frame Buildings.

31:15 Pros and Cons of CHA Tenants.

35:12 Chicago's new "Express Permit".

37:56 Best property management softwares.

39:55 Is rental arbitrage worth it?

42:45 Build-to-Rent in Chicago!

45:07 Managing security deposits.

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Production House: Flint Stone Media

Episode 299: The Top 25 Lists to Find Motivated Sellers with DealMachine's David Lecko May 30, 2024

Show notes

David Lecko is an investor and CEO of DealMachine; a software that helps investors streamline the process of off-market property lead generation!

David starts by discussing the genesis of DealMachine He does a deep dive on the 25 motivated seller lists that can be found on DealMachine or other applications. He emphasizes the importance of being persistent and putting in the reps as off-market lead generation is a numbers game. David closes with great tips on the importance of taking action and building a network to set yourself up for 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: David Lecko, DealMachine

Link: David's Instagram

Link: The DealMachine REI Podcast

Link: My First Million Podcast

Link: Nick Gray (Network Recommendation)

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Guest Questions

01:39 Housing Provider Tip - Perform a usability check during your turnovers to ensure everything is functioning appropriately!

02:34 Intro to our guest, David Lecko.

06:14 The Genesis of DealMachine.

10:04 DealMachine's Lists!

30:16 How new investors can start utilizing the lists.

33:02 Scripts for sellers and call-back expectations.

36:50 What is your competitive advantage?

37:13 One piece of advice for new investors.

38:07 What do you do for fun?

38:29 Good book, podcast, or self development activity that you would recommend?

38:54 Local Network Recommendation?

40:20 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 298: How To Fund Renovations with Larry Baszynski and Scott Hodgden May 23, 2024

Show notes

Larry Baszynski and Scott Hodgden of Finance of America Commercial are seasoned lenders who have helped their investor clients build tremendous real estate portfolios and wealth.

Larry and Scott discuss the products that their company offers including Fix and Flip loans, Construction Loans, and Long-Term loans for stabilized properties. They share common pitfalls and root causes of failed renovation projects. The duo explains how hard money loans are underwritten and what a borrower needs to know to set themselves up for a successful loan! This show is full of golden nuggets with emphasis on the importance of building your team and buying your next investment property sooner!

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: Larry Baszynski and Scott Hodgden, Finance of America Commercial

Link: The Success System That Never Fails (Book Recommendation)

Link: SUCI Ep 79 - Gary Davidson

Link: SUCI Ep 50 - Andrew Holmes

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Guest Questions

02:57 Housing Provider Tip - Ensure windows are properly caulked to prevent leaks!

04:34 Intro to our guest, Larry and Scott!

13:41 FOA Commercials' transition after being bought out.

15:06 FOA Commercials' products.

18:57 DSCR loans for stabilized properties.

25:44 Common causes of failed investments!

29:03 How interest rates are impacting lending!

35:25 Where are hard money funds sourced from?

36:49 Taking back a property on a failed project.

40:53 How aggressive can FOA Commercial get?

44:18 What happens if interest rates hit 10%?

46:02 What is your competitive advantage?

46:43 One piece of advice for new investors.

47:57 What do you do for fun?

48:23 Good book, podcast, or self development activity that you would recommend?

49:33 Local Network Recommendation?

51:00 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 297: How to Pay Less in Taxes Via Tangible Property Regulations with Brenten Blakeman May 21, 2024

Show notes

What are tangible property regulations and how can investors leverage this IRS code to pay less in taxes?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Brenten Blakeman, Tangible Property Tax Methods

Link: Build Your Team | Straight Up Chicago Investor Podcast

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Production House: Flint Stone Media

Episode 296: How to Crush RE Investments on Chicago's South Side with Moses Hall May 16, 2024

Show notes

Moses Hall is a top producing commercial real estate broker and leads a brokerage that serves investors, landlords, and tenants.

Moses discusses his start in real estate, taking the plunge to start his own business, and the challenges that came with that. He dives into his geographical areas of focus in Chicago and his investment strategy. Moses sheds light on the Chicago Association of Realtors (CAR), his leadership position on the board, and the value that CAR brings to all its members. Moses closes with a bullish outlook on Chicago emphasizing why we are and will continue to be a world class city!

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: Moses Hall, MoHall Commercial & Urban Development

Link: Kevin Rocio (Network Recommendation)

Link: Moses' LinkedIn

Link: SUCI Build Your Team

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Guest Questions

02:00 Housing Provider Tip - Make yourself visible for CHA and City Inspections!

04:00 Intro to our guest, Moses Hall!

10:10 Biggest unforeseen challenge when starting a business!

11:49 Drama with Tiffany Henyard.

13:53 Moses' areas of focus.

16:16 Chicago Association of Realtors (CAR) and their mission!

23:39 Benefits of being a CAR member.

25:43 How is CAR working with NAR on the recent settlement?

37:27 Other areas of focus for CAR!

40:47 Efforts to make adding affordable housing easier.

41:55 Moses' outlook on Chicago.

43:33 What is your competitive advantage?

44:07 One piece of advice for new investors.

44:38 What do you do for fun?

44:55 Good book, podcast, or self development activity that you would recommend?

45:26 Local Network Recommendation.

49:59 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 295: The Ultimate HACK to Long-Term Wealth with Brian Tibbs May 09, 2024

Show notes

Brian Tibbs is an investor and best-selling author who teaches others how to thrive financially!

Brian starts by sharing how he hit the ground running by house hacking multiple properties and scaling up to 10-units before the age of 30! He explains how he saved money for down payments and the setbacks he experienced during his early REI days. Brian explains "The HACKER Method" - a wealth-building system to "hack" your lifestyle to grow great wealth. He breaks down each part of the system and reveals the practical steps to save more, invest more, and build wealth. Throughout the show, Brian emphasizes the importance of strategically budgeting and investing for anyone looking to thrive financially!

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: Brian Tibbs of The Unexpected Investor

Link: The Unexpected Investor Calculators

Link: All-In Podcast

Link: The 21 Irrefutable Laws of Leadership

Link: Brandon Turner Instagram

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Guest Questions

03:11 Housing Provider Tip - Understand HOA rules if you're considering changing flooring!

05:15 Intro to our guest, Brian Tibbs!