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Straight Up Chicago Investor

Straight Up Chicago Investor

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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 importa ...
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Kevin Schnell of Concord Capital has amassed a portfolio of over 400 rental units and has vast experience repositioning multi-family and mixed-use real estate investments! Kevin hits the ground running with how he grinded early in his real estate career to learn his markets and efficiently prospect to generate deal flow. He discussed the valuable k…
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Michael Kaplan is a real estate broker and investor who has grinded to become a top broker at 24 years of age! Michael starts by explaining how he realized that college was not for him and pivoted to an entrepreneurial route in real estate! He explains the mindset required to start real estate investing and how he was able to acquire a 4-unit prope…
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What's Different in Today's Lending Environment and How do Chicago Investors Capitalize? ============= 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] Guest: Eric Workman…
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Erik Swanson, owner of Fernweh Property Group, explains how he’s developed a track record with investors that has allowed him to build a Tap Room business and an impressive real estate portfolio! Erik starts with very cool stories about his days in the music industry including working alongside some legendary bands! He dives into his first couple r…
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Tom and Mark interview Joe Smazal of Interra Realty and Ann Reilly of Westward360 during NSBC’s Live Event! Conversations range from leasing trends to handling evictions and the state of the multifamily market in 2025. This show is full of valuable insights from two heavy hitters in the Chicago Multifamily Real Estate market! If you enjoy today’s e…
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How do I incentivize and optimize renewals? ============= 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] Guest: Jeff Weinberg, Drexel Properties Link: Jeff Weinberg Shar…
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Jeffrey Ma joins us to share his experience as a real investor, broker, and wholesaler including various creatively structured deals! Jeffrey starts by discussing his upbringing, start in real estate, and how he established a focus on wholesaling. He dives deep into “creative” deals including one deal where he was able to close on a property minute…
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Wyatt Simon, owner of Full Circle Real Estate, discusses the successes and lessons learned in his journey to building a $20 million real estate portfolio! Wyatt starts by talking about how a successful BRRRR deal allowed him to gain momentum early on in his investing career. After a homerun deal, he shares lessons learned from a bad deal that invol…
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How does credit effect DSCR loans? ============= 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] Guest: Eric Workman, Renovo Financial Link: Workman Lending Team - Renovo…
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John discusses his start in real estate over a decade ago and reflects on missed opportunities, lessons learned, and success stories! He shares practical advice on simply structuring partnerships and talks about Forte Properties’ plan for growth in the western suburbs. John dives into starting a property management company along with building and r…
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Scott Henry, Founder of Celadon Partners, joins to discuss the ins and outs of Affordable Housing Development including tax credits, grants, and construction considerations. Scott starts by sharing his experience working at JPMorgan’s Low Income Housing Tax Credit investment group and his transition to developing affordable housing! He provides a c…
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What actionable steps do I need to take for the Northwest Side Preservation Ordinance? ============= 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] Guest: Brie Schmidt, …
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David Lanciotti and Del Denney of The Land Trust Company explain why all real estate investors should understand and consider utilizing Land Trusts! David and Del jump right in by explaining the basics and complexities associated with land trusts. They dive into the challenges that may arise when transferring properties into land trusts. The duo pr…
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Tom Raleigh, Founding Attorney of Halsted Law Group, returns after being on Episode 40 to talk evictions! Tom jumps right in by breaking down the eviction process and the timelines in 2025. He gives great tips on getting ahead of the process and emphasizes the importance of staying on top of tenants and not waiting too long to file the eviction cas…
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What can I do to maximize my tax returns? ============= 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] Guest: Michael Procaccio, Pro Financial Services Group Inc. Link: …
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Tom and Mark interview some of Chicago’s Real Estate Heavy Hitters during Kiser Group’s 20 Year Anniversary Celebration! Conversations range from condo deconversions, the attorney review side of a commercial deal, and the origins and evolution of Kiser Group. This show is full of wisdom from Kiser Group’s top brokers and business partners so prepar…
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Frank Montro, the King of Chicagoland, returns to share how he and his real estate team have remained top producers during recent years of high interest rates and prices. Frank explains how he coaches buyers to understand monthly payments as opposed to being scared off by rates and pricing. He discusses the keys to getting off the ground as a new b…
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What Can I Write Off as a Chicago Househacker? ============= 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] Guest: Michael Procaccio, Pro Financial Services Group Inc. L…
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Jake Fugman and Mike Scanlon of The Axon Group return to discuss Chicago’s REI market performance, predictions, and exciting developments! Jake and Mike kick things off by assessing their 2024 predictions regarding mortgage rates, appreciation, and cap rates! They then break down the impacts of the Northwest Side Housing Preservation on landlords i…
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Mike Bednarz, an accomplished real estate investor and HVAC business owner, joins us to share his inspiring trajectory of growing a real estate portfolio and overcoming a scary accident! Mike explains how he lived frugally to save a down payment and buy his first multifamily investment property in Edison Park. He discusses the discipline he used to…
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What are the current political issues Chicago investors need to be aware of and how can the NBOA help? ============= 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] Guest…
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Richard Koenig is HODC’s Executive Director and has led the development of over 600 units of affordable housing! Richard starts with how he found his “Why” and discovering that he wanted to dedicate his career to helping solve the lack of affordable housing. He gets granular on the financing and approval process on these types of developments. Rich…
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Mike Tenerelli not only has a background in Reality TV, but also in construction, management, and sales which have propelled his explosive growth in real estate! Mike discusses his journey from flipping homes to helping others find the right property. He breaks down analyzing remote markets to find lucrative deals, growing a brokerage business, and…
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When Does a 5 Day Notice Become a 30 Day Notice? ============= 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] Guest: Mark Ainley, Straight Up Chicago Investor Podcast Li…
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Sam Patterson is a successful Commercial Real Estate Broker, Investor, and Restaurant Owner with vast experience in renovation and property management! Sam opens with his experience in commercial real estate receiverships and his start in investing! He touches on structuring and leveraging partnerships to scale a real estate portfolio. Sam discusse…
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Josh Bandoch is the Head of Policy at the Illinois Policy Institute where he works to spread awareness on improving housing policies to promote affordability and social mobility. Josh starts by describing how he got into housing policy and the mission of the Illinois Policy Institute. He explains some of the prohibitive policies in Illinois that re…
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What IL rules changes do investors need to be aware of in 2025? ============= 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] Guest: Mark Ainley, Straight Up Chicago Inve…
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Joey Turano is real estate broker and investor who has leveraged partnerships and low down payment loans to quickly build his multifamily buildings portfolio! Joey starts by describing his “soul searching” journey in Europe and realizing that real estate would be his career path in life! He explains how he got scrapy to bring value to a Top Produci…
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Boyan Salha is a seasoned General Contractor and the leader of his company Best Fit Homes. He joins us to share how he learned to source and renovate deals from working with a large investment group. Boyan starts by explaining the investing lessons learned by working with a large investment group alongside previous guest Kirby Atwell! He breaks dow…
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What do investors need to know about the new tenant credit report law? ============= 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] Guest: Mark Ainley, Straight Up Chica…
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Pete Neubig joins us to discuss how he built and sold a 7-figure property management company and started VPM Solutions; a platform designed to help property management and real estate professionals with staffing to improve efficiencies and profits! Pete starts by explaining how he went from IT to building and selling a 7-figure property management …
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Susan Tjarksen is the Managing Director at Cushman & Wakefield and has led the development of residential and commercial across the country! Susan discusses her time in hotel management and shares some funny/horror stories! She explains how receiverships work and how investors can capitalize on this opportunity. She breaks down the nuances of large…
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What is an enterprise zone and how can investors benefit from these areas? ============= 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] Guest: Tom Shallcross, Straight U…
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Jeff Weinberg returns to the show after two years to share the impressive growth of Drexel Properties! Jeff explains how Drexel Properties has grown from 600 units to over 1000 units over the last 2 years. He discusses how his team leverages technology to streamline their property management business. Jeff dives deep on how to find deals in a compe…
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Andy Friedman is a Senior Director at Kiser Group and has a proven track record of success in Chicago Multifamily Real Estate. Andy shares his experience as a stock trader and brewery owner, including how the skills he obtained in those endeavors translated to real estate! Andy explains the grit required to get off the ground in commercial real est…
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What are the appropriate steps to take to raise capital from investors? ============= 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] Guest: Aram Ghazaryan, AMG Realty Li…
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Michelle starts by explaining both Chicago’s RLTO and Cook County’s RTLO, and the differences between the two ordinances. She gets granular on disclosures required from Housing Providers to remain in compliance with the ordinance(s) and breaks down security deposits and move-in fees. Michelle dives deep on the eviction process and shares resolution…
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Aram Ghazaryan returns to explain how he transitioned from a successful RE broker to a flipper executing over ten profitable flips per year. Aram starts by discussing his first multifamily investment which was a 7-unit building. He explains his decision to stop being an agent and jump into flipping properties full time. Aram shares tremendous lesso…
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What can you cancel a contract for after all contingencies have passed? ============= 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] Guest: Chance Badertscher of Lavelle…
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Zack Limbaugh of the Limbaugh Law Firm provides his clients with legal representation and strategy to remedy Building Code Violations and other matters associated with Chicago Buildings! Zack starts by explaining how he got his foot in the door with the City of Chicago before becoming an attorney and leveraged those relationships to build a niche i…
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Joey Halperin is a real estate broker and developer with vast experience in ground up development and renovation projects across Chicago! Joey starts by explaining how he left the corporate world to jump into general contracting and real estate brokerage! He gets granular on difficult renovation projects and the importance of having skilled contrac…
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Which South Side neighborhoods have been the biggest surprise and which neighborhoods have the most potential? ============= 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]
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James Erwin has decades of experience practicing Real Estate Law and is a board member of the NSBC! James starts by breaking down the legal ins and outs for condo deconversions. He dives deep on the process for clearing building violations on properties including tips to keep the City and lenders happy. James explains the Corporate Transparency Act…
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Sean Douglas of the Axon Group discusses his adventurous start to his real estate journey! Sean began his investment career when he inherited his grandparent’s home, which after numerous setbacks, he eventually flipped! He breaks down how he jumped into the deep end by doing construction himself. After having a contractor steal $7000 from him, Sean…
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What should I focus on in negotiating a multifamily transaction? ============= 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] Guest: Noah Birk, Kiser Group Link: Kiser G…
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Luke Blahnik returns to educate us on the new Northwest Side Preservation Ordinance. Luke jumps right in by explaining the ins and outs of the expansion of the Predominance of the Block (606) District under this new ordinance. He breaks down the increased fees to demolish a multi-unit building, limitations on building single family homes, and requi…
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RJ de Leon returns to the show to tell us about his most recent investments and how he’s managing his portfolio remotely as he and his family spend most of the year traveling! RJ starts by discussing how he and his wife Nicky set up their investments and businesses to be able to manage them remotely and travel the country for months at a time! He g…
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What are the construction costs associated with building out a new ADU unit? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: [email protected] Guests: Jonathan Klemm, Quality Builders Link: SUCI Episode 264: Unlocking Zoning Secrets: Your Guide to Chicago Zoning, ADUs, and Other Essential Information -----…
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George McCleary is a real estate investor and developer with two decades of experience. He is also the creator of courses that teach investors to protect themselves from Squatters and Deed Fraud! George starts by discussing his viral “I Stole a House” video which explains how sophisticated squatters are able to steal a property owner's equity. He d…
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Horacio Tristan is a born and raised Chicagoan and full-time government employee who has built an impressive real estate portfolio and brokerage business! Horacio starts by discussing his upbringing and his first few real estate deals on Chicago’s South Side. He explains how he built and maintained his real estate brokerage business during the hous…
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