Straight Up Chicago Investor

Ryan Bakke turns to discuss the power of smart business acquisitions and tax strategy to skyrocket returns and keep more money in your pocket! Ryan starts by reminding us the tax benefits of short-term rentals and real estate professional status. He explains the process of buying businesses including defining a buy box, identifying opportunities, and improving operations upon acquisition. He dives deep on lessons learned from operating businesses and tips on how to improve efficiencies through off-shore staffing. The show closes with great insights on assessing return on equity and investment to ensure your capital is working as hard as possible. 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guests: Ryan Bakke, Tax Strategy 365 Link: SUCI Ep 244 - Ryan Bakke Link: Ryan's Instagram Link: Influence (Book Recommendation) Link: SUCI Investor Meetups Page Guest Questions: 01:24 Housing Provider Tip - Understand the maintenance and life span of hot water heaters. 03:34 Intro to our guest, Ryan Bakke! 06:42 Leveraging short-term rentals for tax benefits. 11:26 Efficiently delegating to grow your business. 22:37 How to hire off-shore employees. 28:32 The process of buying a business. 32:03 Defining a "buy box" for a business. 39:07 Lessons learned from buying businesses. 46:08 Ryan's take on ROI and Chicago's future! 53:28 What is your competitive advantage? 53:37 One piece of advice for new investors. 53:46 What do you do for fun? 53:59 Good book, podcast, or self development activity that you would recommend? 54:17 Local Network Recommendation? 54:35 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Adam Friedberg, CEO of Mavrek Development, joins us to discuss the ins and outs of large-scale developments in Chicago. Adam starts by explaining how he started in real estate and hustled early on to learn development and value-add construction. He breaks down pitching development deals to investors and various methods for raising money. Adam talks about projects during COVID and how his team pivoted given the unforeseen circumstances. He gets granular on how to most efficiently cut construction costs without negatively impacting the quality of the final product. In typical SUCI fashion, Adam explains why he is doubling down on Chicago investments and why you should too! 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guests: Adam Friedberg, Mavrek Development Link: Adam's LinkedIn Link: SUCI Ep 421 - Alec Greenberg Link: Abundance (Book Recommendation) Link: Crain's Chicago Guest Questions: 01:50 Housing Provider Tip - Simplify property management by setting expectations! 03:16 Intro to our guest, Adam Friedberg! 06:41 How to learn value-add construction in real estate. 10:35 Taking down commercial projects in Oak Park. 23:18 Pitching large development deals to investors! 27:10 Lessons learned from developments in 2020. 30:53 Acquiring The Saint Grand development. 37:20 Getting lean on construction costs. 44:14 Upcoming Mavrek developments! 55:31 Adam's bullish outlook on Chicago! 57:53 What is your competitive advantage? 58:00 One piece of advice for new investors. 58:15 What do you do for fun? 58:53 Good book, podcast, or self development activity that you would recommend? 59:34 Local Network Recommendation? 60:33 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

What is the process for assuming a VA or FHA loan? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Scanlon, The Axon Group (EXP Realty) Email the Show: [email protected] Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Josh Bandoch is the Head of Policy at the Illinois Policy Institute, TED Talk Speaker, and Author who joins to discuss his new book, How to Get What You Want! Josh jumps right in by explaining the concept of his book and the neuroscience of persuasion! He shares insights on how the brain works as it relates to persuasion and gives tactical negotiation tips. Josh describes the process of writing his book and the impact that artificial intelligence and technology are having on communication. This show is full of golden nuggets to leverage on your next real estate negotiation and to help create more win-win situations in business! 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guests: Josh Bandoch, Illinois Policy Institute Link: How To Get What You Want (Josh's New Book) Link: Josh's LinkedIn Link: SUCI Ep 347 - Josh Bandoch Link: GC Realty Maintenance Blog Link: Mike Glasser - NBOA Link: How to Stop Worry and Start Living (Book Recommendation) Link: Thinking, Fast and Slow (Book Recommendation) Guest Questions: 02:37 Housing Provider Tip - Have contacts to efficiently solve all maintenance requests! 04:37 Intro to our guest, Josh Bandoch! 06:48 The neuroscience of persuasion. 11:52 Understanding persuasion to get deals done! 16:27 Tactical negotiation tips. 24:10 The process of publishing a book. 36:20 The impact of AI on communication. 38:45 What is your competitive advantage? 39:04 One piece of advice for new investors. 39:34 What do you do for fun? 39:41 Good book, podcast, or self development activity that you would recommend? 41:14 Local Network Recommendation? 41:28 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Jay Patel and Tedi Nati of JP Acquisitions join us to explain how they've leveraged mentors and discipline to build a sizable multifamily portfolio on Chicago's West Side! Jay and Tedi explain how they networked and built their team to set themselves up for success when starting in real estate! They break down raising money and setting up a syndication to acquire their first multifamily building in Austin. The duo discuss their next 16-unit building acquisition and lessons learned on that deal. Jay and Tedi close by sharing their motivative business plan hammering home their go-getter attitude which has led to their great 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guests: Jay Patel & Tedi Nati, JP Acquisitions Link: Jay's LinkedIn Link: Tedi's LinkedIn Link: Frank Jaffe (Attorney Referral) Link: Eric Kogan (Network Referral) Guest Questions: 01:08 Intro to our guests, Jay and Tedi! 09:20 Learning how to execute a real estate deal! 16:34 Jay and Tedi''s first syndication deal. 22:45 Software and tools for asset management. 27:07 Mistakes on an 8-unit acquisition. 33:38 The importance of an experienced team. 38:04 Acquiring a 16-unit building in Austin. 44:35 How to make money when starting a syndication? 49:58 2-Year outlook for Jay and Tedi! 56:10 What is your competitive advantage? 56:30 One piece of advice for new investors. 56:40 What do you do for fun? 56:55 Good book, podcast, or self development activity that you would recommend? 57:32 Local Network Recommendation? 58:20 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

What do investors need to be aware of when taking on a 203k or Homestyle Renovation loan? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Jonathan Klemm, Quality Builders Email the Show: [email protected] Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Samuel Pavlovcik of the Pavlovcik Architecture returns to explain opportunities brought by the expanded city-wide Additional Dwelling Unit (ADU) Ordinance! Samuel jumps right in by explaining the process and expectations on obtaining a Zoning Change without leveraging the ADU ordinance! He dives deep on various Zoning and Building Code requirements when looking to build and/or legalize a basement ADU. Samuel breaks down various requirements on coach house ADUs and ground-level commercial ADU conversions. He closes with tips for successful ADU projects and shares top pitfalls to avoid when leveraging the program! 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guest: Samuel Pavlovcik, Pavlovcik Architecture Link: Pavlovcik Architecture's Instagram Link: SUCI Ep 97 - Samuel Pavlovcik Link: SUCI Ep 264 - Samuel Pavlovcik Link: Chicago Zoning Map Link: Tom Moore (Zoning Attorney Referral) Link: The Toyota Way (Book Recommendation) Guest Questions: 03:08 Housing Provider Tip - Optimize your rental listings to attract tenants and avoid vacancy! 05:35 Intro to our guest, Samuel Pavlovcik! 06:10 The 101 on Chicago Zoning changes. 13:34 Building Department considerations for legalizing an ADU. 23:03 Easiest ways to improve building efficiency. 23:25 City wide expansion of Chicago's ADU Ordinance. 32:42 Nuances on coach house ADUs. 38:55 Ground-level Commercial vs Basement ADUs! 44:37 Top mistakes when leveraging the ADU program. 46:31 What is your competitive advantage? 49:16 One piece of advice for new investors. 49:28 What do you do for fun? 49:48 Good book, podcast, or self development activity that you would recommend? 50:00 Local Network Recommendation? 50:57 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Joe Konopacki, Founder and CEO of Insight Property Services, is a seasoned home inspector with various professional certifications on Building Performance and Efficiency! Joe starts with a story on acquiring a mixed-use building to establish his business and invest simultaneously! He breaks down his background of growing up in a real estate family and transitioning into the business. Joe gets granular on causes for building inefficiencies and means for improving building performance. He explains top considerations for heating system options and closes out with some wild inspection stories! 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guest: Joe Konopacki, Insight Property Services Link: Joe's LinkedIn Link: Modern Wisdom (Podcast Recommendation) Link: The E-Myth Revisited (Book Recommendation) Guest Questions: 02:24 Housing Provider Tip - Understand the benefits of lease agreements over month-to-month agreements! 04:15 Intro to our guest, Joe Konopacki! 10:16 Advantages of mixed-use buildings. 12:02 Growing up in a real estate family and transitioning into the business. 23:03 Easiest ways to improve building efficiency. 31:12 Understanding the efficiency of boilers! 43:05 Considerations for electric heating systems. 52:03 Cost analysis of switching from boilers to central HVAC! 60:27 Incentive opportunities for solar energy systems. 67:13 Wild inspection stories! 71:37 What is your competitive advantage? 73:27 One piece of advice for new investors. 73:38 What do you do for fun? 73:54 Good book, podcast, or self development activity that you would recommend? 74:40 Local Network Recommendation? 75:12 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

What are the upcoming elections that every investor should be aware of, and what's this dinner with Rahm Emanuel I heard about? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Glasser & Aron Borstein, NBOA PAC | An Evening with Rahm Emanuel ⭐⭐Get your tickets today!⭐⭐ Email the Show: [email protected] Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Gil Villegas is the alderperson of Chicago's 36th ward and has focused on generating opportunities for economic and business development to best serve the constituents of his ward! Alderman Villegas starts by discussing how zoning changes can be utilized to create win-win situations for investors and members of a community or ward! He talks about how he and his fellow members of City Counsel were able to influence the city's approved budget with the needs of their constituents at the forefront. Alderman Villegas breaks down why he chose to withdraw his Ward from the Northwest Housing Ordinance. He closes with an extremely bullish outlook on Chicago leaving us motivated to continue doubling down on our great 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guest: Alderman Gil Villegas, City of Chicago's 36th Ward Link: Alderman Villegas' Facebook Link: Alderman Villegas' Instagram Link: The 48 Laws of Power (Book Recommendation) Link: NBOA Chicago (Network Recommendation) Guest Questions: 03:31 Housing Provider Tip - Understand lease renewal notices to remain compliant! 05:28 Intro to our guest, Alderman Villegas! 07:19 Zoning changes to create affordable housing. 18:48 City council's involvement with the city's approved budget. 25:45 How Aldermen work together to make positive impacts! 35:05 Drawbacks of the Northwest Housing Ordinance. 43:34 How Aldermen utilize facts and community input to make decisions. 45:39 Exciting developments in the 36th ward! 48:28 Alderman Villegas' outlook on Chicago. 51:41 What is your competitive advantage? 52:11 One piece of advice for new investors. 54:26 What do you do for fun? 55:46 Good book, podcast, or self development activity that you would recommend? 56:08 Local Network Recommendation? 56:31 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

What are the common mistakes made when handling lease renewals? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor and GC Realty Email the Show: [email protected] Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Zack Limbaugh of the Limbaugh Law Firm returns to dive deep on code violations including top pitfalls to avoid! Zack starts by explaining the 101 on buying properties with building code violations! He discusses top lending considerations when attempting to finance a property with violations. Zack dives deep on common code violations, how owners get notified, and how to mitigate your risk! Throughout the show, Zack provides insights on handling various code violation scenarios to give you an edge against the competition! 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guest: Zack Limbaugh, The Limbaugh Law Firm Link: Zack's LinkedIn Link: SUCI Ep 333 - Zack Limbaugh Link: SUCI Ep 79 - Gary Davidson Link: Essentialism (Book Recommendation) Guest Questions: 02:35 Housing Provider Tip - Understand the true costs of not allowing pets in your rentals! 04:44 Intro to our guest, Zach Limbaugh! 10:23 Buying a property with code violations. 16:48 Lending considerations for violations exist. 23:52 Protecting yourself against fines for code violations! 31:03 Ensuring violations are found during due diligence. 43:15 Common violation tickets to watch out for! 50:35 Crazy code violation stories! 51:17 What is your competitive advantage? 51:32 One piece of advice for new investors. 51:39 What do you do for fun? 51:51 Good book, podcast, or self development activity that you would recommend? 52:03 Local Network Recommendation? 52:18 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career! Zach starts off by detailing the acquisition of his first house hack and the hurdles that came almost immediately after closing. He talks about purchasing an oversized 4-unit building, seeing value-add potential, and executing a renovation strategy to create equity! Zach gives property management insights for house hackers which are centered around doing right by tenants and people in general. He explains the ins and outs of acquiring a property by assuming a VA loan. Throughout the episode, Zach demonstrates that growing a portfolio as a busy professional is doable and that the financial reward far outweighs the work that is required! 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: [email protected] Properties for Sale on the North Side? We want to buy them. Email: [email protected] 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 ============= Guest: Zach Posey, Chicago Multifamily Club Link: Chicago Multifamily Club Meetup Link: Wisdom Takes Work (Book Recommendation) Link: SUCI Ep 52 - Aaron Zimmerman Link: SUCI Ep 326 - RJ de Leon Guest Questions: 01:58 Housing Provider Tip - Understand easy fixes for malfunctioning garbage disposals! 03:57 Intro to our guest, Zach Posey! 07:38 Starting off with a 4-unit house hack. 17:25 Acquiring a second house hack in Roscoe Village. 26:28 Property Management tips for house hackers! 28:44 Leveraging assumable loans to make the numbers pencil. 34:41 The value of networking events. 37:40 Zach's REI goals and outlook on Chicago! 42:42 What is your competitive advantage? 43:13 One piece of advice for new investors. 43:35 What do you do for fun? 43:50 Good book, podcast, or self development activity that you would recommend? 44:40 Local Network Recommendation? 45:39 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.