Straight Up Chicago Investor

Latest Episodes:

Episode 244: Real Estate Tax Advantages, Short Term Rentals, and Branding, With Ryan Bakke Sep 14, 2023

Show notes

Ryan Bakke is a CPA, real estate investor, and coach who is helping others build wealth via real estate and tax strategy!

Ryan starts by explaining the value a Tax Strategist brings and common mistakes on tax returns. He dives into the power of short-term rentals (STRs), their tax advantages, and how to underwrite STR investments. Ryan shares his philosophy and tips for building a client base and following that have led him to a thriving business! Throughout the show, Ryan hammers home the importance of being a go-giver and delegating tasks to best use your time!

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: Ryan Bakke

Link: The LearnLikeaCPA Show

Link: $100M Offers (Book Recommendation)

Link: The Game (Podcast Recommendation)

Link: Muscle for Life Podcast

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Guest Questions

02:56 Housing Provider Tip: Be ready to recognize and act on a good deal!

04:58 Intro to our guest, Ryan Bakke!

05:29 Tax Preparer vs. Tax Strategist

09:14 Common Tax Returns Mistakes.

10:35 Tax Insights on Short-Term Rentals (STRs)!

17:27 Short-Term Rentals in Chicagoland.

19:21 Automating STRs!

24:58 Underwriting STRs!

31:06 Ryan's approach to building a following!

46:29 Ryan's next 5 years!

50:34 What is Ryan's competitive advantage?

51:16 One piece of advice for new investors.

52:34 What do you do for fun?

53:18 Good book, podcast, or self development activity that you would recommend?

54:20 Local Network Recommendation?

54:55 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 243: A New Chicago Lending Option to Assist With Rehab Funding Sep 12, 2023

Show notes

What is this new lending option that could finance my rehab funds?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guests: Perry Farella, First Community Mortgage

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Production House: Flint Stone Media

Episode 242: From Rookie Status to Seasoned House Hacker, Flipper, and BRRRR Conductor on Chicago's Northwest Side with Manny Escarpita Sep 07, 2023

Show notes

Manny Escarpita is a young Chicago Real Estate Investor and Licensed General Contractor who has built up an impressive real estate portfolio since starting in 2019!

Manny leads by explaining the hungry mindset he cultivated when starting in real estate and the lessons learned on his first deal. After discussing his first couple house hacks, he breaks down a successful BRRRR project that ultimately motivated him to quit his job to pursue real estate investing full time! He dives deep into hard money lending, estimating rehabs, and generating deal flow for his flipping business. Throughout the show, Manny emphasizes the importance of taking action despite fear and attributes his success to his ability to do just 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: Manny Escarpita

Link: SUCI Ep 196 - John Warren

Link: SUCI Ep 229 - Hernandez Roofing

Link: George LaGuardia - A and N Mortgage

Link: Raising Private Capital (Book Recommendation)

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Guest Questions

02:52 Housing Provider Tip: Understand insurance policy coverage as it relates to water damage in basement units!

04:30 Intro to our guest, Manny Escarpita!

05:51 Hungry mindset of a new investor.

13:12 Manny's journey after his first deal!

17:42 Dealing with hard money loans.

24:26 Manny's next deal in West Logan!

28:30 Manny's transition to General Contracting and Flipping!

30:33 Advice for new flippers.

34:25 Manny's long term goals.

39:11 Estimating rehabs.

41:06 What is Manny's competitive advantage?

41:40 One piece of advice for new investors.

42:28 What do you do for fun?

42:55 Good book, podcast, or self development activity that you would recommend?

43:12 Local Network Recommendation?

43:46 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 241: Game-Changing Appraisal Insights with Steve Zidek Aug 31, 2023

Show notes

Steve Zidek has nearly two decades of real estate experience as a broker and appraiser!

Steve kicks off with how he got into the appraising business and breaks down the appraisal process! He gets granular on adjustments that may or may not be considered and speaks to the "art" components of an appraisal. Steve discusses how income factors into residential appraisals and even throws in a crazy appraisal story! This show is loaded with golden nuggets that will help set you up for success during your next appraisal!

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: Steve Zidek, Keller Williams Inspire Realty

Link: Steve's Facebook

Link: Tom Ferry Podcast

Link: Conspiracy (Book Recommendation)

Link: Melissa Steuart (Network Referral)

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Guest Questions

02:45 Housing Provider Tip: Prepare for appraisals to maximize value!

04:05 Intro to our guest, Steve Zidek!

07:36 How did Steve get into appraising?

15:48 Breaking down the appraisal process!

21:33 Quantifying pieces of a property to arrive at a value.

27:53 Contesting appraisals.

36:22 Considering unofficial neighborhood boundaries and expanding criteria when valuing properties.

41:08 Crazy appraisal stories!

43:11 Importance of rents on 2-4 unit property appraisals.

48:00 What is Steve's competitive advantage?

48:50 One piece of advice for new investors.

49:32 What do you do for fun?

50:01 Good book, podcast, or self development activity that you would recommend?

51:08 Local Network Recommendation?

52:14 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 240: What is Going On In the Chicago Multifamily Market? Aug 29, 2023

Show notes

What is Going On In the Chicago Multifamily Market?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guests: Jordan Gottlieb, Essex Realty Group

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Production House: Flint Stone Media

Episode 239: Cook County's New Program To Reduce Your Assessed Value and Maximize Profitability with Cook County Assessor Fritz Kaegi and CIC's Stacie Young Aug 24, 2023

Show notes

Assessor Kaegi and Stacie Young explain how the Assessor's Office and CIC created a program to incentivize affordable housing providers!

To kick things off, Assessor Kaegi explains how properties are assessed in Illinois and Stacie shares the history of the Class 9 Program. They then break down the Affordable Housing Special Assessment Program including how it works, the increased profits for participating housing providers, and the qualification requirements. Our guests share numerous ways to learn more about the program and how the Assessor's Office and CIC can be a valuable resource for housing providers. Immense value is packed into this episode with insights that can potentially decrease property taxes and maximize profitability!

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: Assessor Fritz Kaegi & CIC President Stacie Young, Cook County Assessor's Office & Community Investment Corporation (CIC)

Link: Assessor's Affordable Housing Programs Webpage

Link: Assessor's Affordable Housing Email for Questions

Link: Erik Harmon - Assessor's Director of Commercial Outreach

Link: John McDonnell - Assessor's Director of Multifamily Development

Link: CIC Team

Link: The Power Broker (Book Recommendation)

Link: The Whalebone Theatre (Book Recommendation)

Link: SUCI Ep 151 - Assessor Kaegi

Link: SUCI Ep 94 - Stacie Young

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Guest Questions

03:10 Housing Provider Tip: Don't forget to appeal your property taxes!

05:09 Intro to our guests, Assessor Fritz Kaegi and Stacie Young!

05:47 How are properties assessed for tax purposes in Cook County and Illinois?

09:22 History of the Class 9 Program!

15:00 Who can benefit from the Affordable Housing Special Assessment Program?

21:58 Requirements and process to qualify for the program.

33:19 Interest levels in the program.

36:41 How to stay in compliance once in the program?

39:35 What's next for CIC and the Assessor's Office?

43:56 What is Assessor Kaegi's and Stacie's competitive advantage?

46:31 One piece of advice for new investors.

49:31 What do you do for fun?

50:24 Good book, podcast, or self development activity that you would recommend?

52:04 Local Network Recommendation?

54:33 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 238: Dissecting 20 Years of Real Estate and Lending Experience; Mike Facchini's Journey to a Thriving Portfolio in Chicago Aug 17, 2023

Show notes

Mike Facchini of Fairway Mortgage is a Mortgage Lender and Investor with over 20 years of real estate experience!

Mike starts with insights on the real estate environment leading up to the Housing Crash and compares it to today's market! He drops golden nuggets on indicators by the lending industry that precede and foreshadow what is to come in the economy. Mike shares his investment strategy and his geographical areas of focus centered around neighborhoods with high quality properties and tenants! Throughout the show, Mike emphasizes the importance of getting in the game and time being your biggest asset when it comes to real estate investing and building wealth!

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: Mike Facchini, Fairway Mortgage

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Guest Questions

04:29 Keep up with property maintenance to avoid negative attention!

06:38 Intro to our guest, Mike Facchini!

09:22 Real Estate before and leading up to the Housing Crash!

16:05 Mike's experience with bridge loans.

17:39 Tenant horror stories!

22:33 Lending environment now vs pre-crash.

24:43 Mike's investment strategy!

27:18 Neighborhoods Mike is focusing on!

36:36 Talking New Construction.

44:31 Financing options to create opportunities.

54:13 What is Mike's competitive advantage?

54:48 One piece of advice for new investors.

56:02 What do you do for fun?

56:25 Good book, podcast, or self development activity that you would recommend?

57:00 Local Network Recommendation?

57:54 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 237: Mastering the Maze: 5 Savvy Tactics to Conquer the High-Interest rate, Low-Inventory Real Estate Market with Perry Farella Aug 15, 2023

Show notes

How do you navigate a low inventory & higher interest rate environment?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guests: Perry Farella, First Community Mortgage

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Production House: Flint Stone Media

Episode 236: Grinding and Unlocking Success in Chicago's West Town Neighborhood with Alex Morsch Aug 10, 2023

Show notes

Alex Morsch of Peak Realty is a Commercial Broker and Investor with vast experience in repositioning assets in West Town.

Alex starts by discussing the grind of being a leasing agent and transitioning to brokering real estate! He lays out his experience walking 100 buildings prior to making his first purchase and the valuable lessons gained through that process. Alex breaks down how his "nose to the ground" approach to investment property acquisition has allowed him to add immense value to his clients and succeed as a broker. He also drops wisdom on house hacking, the West Town neighborhood, and creating opportunities in a tight inventory market. Alex closes with a bullish 5 year outlook on Chicago Real Estate!

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: Alex Morsch, Peak Realty

Link: Alex's Instagram

Link: Rich Anselmo (Network Referral)

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Guest Questions

02:24 Housing Provider Tip: Check the faucet aerator when troubleshooting low water pressure!

03:56 Intro to our guest, Alex Morsch!

07:33 The grind of being a leasing agent.

12:52 Transitioning from leasing to a commercial broker!

16:30 Walking properties to gain experience.

26:38 Alex's first investment!

37:57 The reality of House Hacking.

42:25 Breaking down the West Town neighborhood!

49:10 Finding deals and creating opportunities.

54:27 Alex's 5 year outlook on Chicago Real Estate!

55:18 What is Alex's competitive advantage?

55:35 One piece of advice for new investors.

55:53 What do you do for fun?

56:12 Good book, podcast, or self development activity that you would recommend?

57:05 Local Network Recommendation?

57:35 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 235: Exploring Portage Park; An Interview With Special Guest and Straight Up Chicago Investor Podcast Co-Host Tom Shallcross Aug 03, 2023

Show notes

Mark is flying solo as co-host this week as he interviews a very special guest; flipper, investor, and fellow SUCI podcast co-host Tom Shallcross!

Mark takes a different spin to start the show by asking Tom about his childhood and upbringing in Portage Park! Tom talks about the differences between Jefferson and Portage Park. Tom breaks down Portage Park at a street-level including the lesser and more desirable pockets, rents and property values, and schools in the neighborhood! To close the show, Tom shares powerful words on committing to succeeding in real estate and encourages listeners to leverage all the SUCI resources that he and Mark have put out!

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: Tom Shallcross, Straight Up Chicago Investor

Link: The Road Less Stupid (Book Recommendation)

Link: The Ruthless Elimination of Hurry (Book Recommendation)

Link: Chicago's ADU Ordinance - What Investors Need to Know

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Guest Questions

01:00 Housing Provider Tip: Ensure you're adding sewer backup to your insurance policy.

02:51 Intro to our guest, Tom Shallcross!

04:02 What was young Tom like?