Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons
Release Date: 11/13/2025
Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs
Straight Up Chicago Investor
Darryl Jacobs, partner at Ginsberg Jacobs, has over 3 decades of experience in tax and corporate law with a focus on tax credit financing transactions. Darryl starts off with a high-level overview of the various tax credits available to investors. He dives deep on opportunity zones and how geographical areas get designated as opportunity zones. Darryl explains how investors can leverage New Markets Tax Credits. Throughout the show, Darryl demonstrates his deep knowledge in Tax Credits and conveys how it can be a super powerful tool for investors who know how to leverage it! If you enjoy...
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Episode 428: Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley
Straight Up Chicago Investor
What are recent legal updates to the 2026 lease and new squatter laws? ============= Connect with Mark and Tom: Guest: Mark Ainley, and Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ----------------- Production House: Copyright of Straight Up Chicago Investor 2026.
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Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon
Straight Up Chicago Investor
Jake Fugman and Mike Scanlon of The Axon Group return to forecast Chicago’s Real Estate Market in 2026! Jake and Mike kick things off by reflecting on their 2025 predictions including office space leasing trends, downtown sales stats, and impacts of the Northwest Side Preservation Ordinance. The duo then make their 2026 predictions with topics ranging from ADU Zone expansion to creative mortgage solutions to help with affordability. Jake and Mike close out with an outlook on interest rates and the future of real estate based on recent brand mergers! If you enjoy today’s episode, please...
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Episode 426: Reshaping Suburban Woodstock with Jessica Erickson
Straight Up Chicago Investor
Jessica Erickson, Director of Economic Development for the City of Woodstock, joins us to discuss development news and opportunities in Woodstock, IL! Jessica starts with her backstory on moving from Denver to Chicagoland and ultimately taking a role in Economic Development for the City of Woodstock. She breaks down Woodstock’s downtown redevelopment plan and also speaks to city corridors with development opportunities. Jessica explains “infill” sites, metrics for successful developments, and strategic planning of developments to allow for future adaptive reuse. Throughout the...
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Episode 425: Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options
Straight Up Chicago Investor
Do you need a HELOC on your investment property? ============= Connect with Mark and Tom: Guest: Benjamin Stef, Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ----------------- Production House: Copyright of Straight Up Chicago Investor 2026.
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Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith
Straight Up Chicago Investor
Ryan Smith, top producing agent specializing in REO properties, returns to provide an update on the state of the Chicagoland foreclosure market heading into 2026! Ryan starts with an overview on the foreclosure process and expectations when getting into a foreclosure transaction as a buyer. He provides tips on positioning yourself as a legit, experienced buyer in the eyes of REO listing agents. Ryan gets granular on latest foreclosure statistics and provides his outlook on the REO market heading into 2026. He closes with his take on Chicago’s crime problem and the neighborhoods that he is...
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Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm
Straight Up Chicago Investor
Jonathan Klemm of Quality Builders returns to discuss refinements in his General Contracting business and investment strategy since his last appearance! Jonathan starts by explaining partnership pitfalls to avoid based on recent changes within his business. He gets vulnerable by discussing a multifamily investment on Chicago’s southside that involved various evictions and a $400,000 fire caused by a problem tenant! Jonathan shares tips on the mindset required to weather business storms and turns to more positive news by discussing some large renovation projects that his company is working...
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Episode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market
Straight Up Chicago Investor
Is now a good time for me to purchase in Chicago? ============= Connect with Mark and Tom: Guest: Mark Ainley, Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1
Straight Up Chicago Investor
Alec Greenberg is the Principal of Base 3 Development and has vast experience developing and stabilizing multifamily assets! Alec explains how he transitioned from the corporate real estate world to a more entrepreneurial position at Base 3 Development. He describes how he “stretched” out of his comfort zone by jumping into a 6-unit gut rehab project off the bat and shares lessons learned! Alec shares insights on large residential development projects including zoning, underwriting, and leasing considerations. He closes with tips on leveraging VAs and off-shore staffing solutions for...
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Episode 420: The Chicago Permitting Process with Tom Shallcross
Straight Up Chicago Investor
SUCI Podcast Co-Host Tom Shallcross is today’s special guest and breaks down everything you need to know about architectural plans and permits in Chicago! Tom discusses when you need plans and permits for a project and when it’s appropriate to engage an architect. He shares the best way to optimize timelines to ensure your plans and permits get approved as fast as possible. Tom discusses lessons learned on design and functionality particularly on luxury redevelopments! He closes with insights on dormer additions and considerations for ADUs and historic district remodels that will add to...
info_outlineLuke Helliker is a buy and hold real estate investor that has leveraged networking, house hacking, and value-add strategies to build a successful portfolio.
Luke kicks things off by sharing how he acquired his first house hack and provides insights on the ADU process that he used to add a third legal unit. He lays out top considerations when converting a basement into a dwelling unit including the top dollar items. Luke talks about getting a 4-unit acquisition to the finish line, despite it involving violations and a difficult seller. Throughout this episode, Luke demonstrates how holding real estate for the long term has built him great wealth and how staying active in the market is the key to success!
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: StraightUpChicagoInvestor@gmail.com
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com
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
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Guest: Luke Helliker
Link: Luke Helliker - DocuSign | LinkedIn
Link: EUBA
Link: SUCI Ep 345 - Joey Turano
Link: SUCI Ep 354 - Jake Fugman & Mike Scanlon
Link: SUCI Ep 389 - Sebastian Mysliwiec
Link: Rich Dad Poor Dad (Book Recommendation)
Guest Questions:
03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up!
05:03 Intro to our guest, Luke Helliker!
13:19 Luke’s first deal: a 2-unit house hack!
20:18 How to leverage the ADU process.
27:20 Funding an ADU project.
41:09 Navigating investing with your significant other.
43:15 Acquiring a 4-unit building in a competitive market!
58:47 Lessons learned on the 4-unit acquisition.
65:30 Luke’s next investment targets.
66:19 What is your competitive advantage?
67:15 One piece of advice for new investors.
67:59 What do you do for fun?
69:19 Good book, podcast, or self development activity that you would recommend?
70:01 Local Network Recommendation?
70:30 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.