Episode 450: Alderman Bennett Lawson & The 44th Ward

from Straight Up Chicago Investor · host Mark Ainley and Tom Shallcross

Alderman Bennett Lawson discusses historical developments in his 44th Ward and how that success can be applied across the City of Chicago! Alderman Lawson jumps right in by explaining the successful development in Wrigleyville including partnering with the Ricketts family! He breaks down successful developments including Advocate Masonic Hospital in Lakeview and across the 44th Ward. Alderman Lawson gives practical advice for developers to help increase the chance of having aldermanic support on potential projects! He dives deep on the ADU Pilot Program, its city wide expansion, and how it can best be leveraged to bring much needed housing supply to the city. This show is full of golden insights on Zoning and Development that you won't want to miss! 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 Bennett Lawson, City of Chicago 44th Ward Link: Alderman Lawson's Instagram Link: Chicago ADU Program Link: Chicago's Great Fire (Book Recommendation) Link: Tom Moore (Zoning Attorney) Guest Questions: 01:55 Housing Provider Tip - Leverage rent payment services to allow tenants to build their credit history! 03:38 Intro to our guest, Alderman Lawson! 10:55 The development history of Wrigleyville! 18:20 Previous developments in the 44th Ward. 23:30 Advice for developers seeking support from aldermen. 27:18 The background of the Chicago ADU Program! 31:41 Lessons learned from the ADU Pilot Program. 44:08 Potential solutions for the housing supply issue. 48:50 What is your competitive advantage? 49:11 One piece of advice for new investors. 49:35 What do you do for fun? 49:48 Good book, podcast, or self development activity that you would recommend? 50:48 Local Network Recommendation? 51:15 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.

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This episode is 54 minutes long.

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This episode was published on May 7, 2026.

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