Systems Over Spreadsheets – Technology in Real Estate with Dylan Goren, Co-Founder & CEO of Pillar

This episode of Breaking New Ground, Dylan Goren dives into the future of real estate decision-making and how technology is changing the playbook.


In this conversation, Dylan Goren, Co-Founder & CEO of Pillar, unpacks the site selection problem that continues to frustrate developers and how automation can transform outcomes. He explains why time lost in manual processes is money left on the table, how systems thinking sharpens future project evaluations, and why technology should be seen as an enabler, not a replacement. Dylan also touches on the evolving role of zoning, the rise of open data, and why younger leaders are accelerating the industry’s adoption curve.






Key Takeaways

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The Site Selection Problem: Pillar is tackling one of real estate’s most time-intensive bottlenecks.

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Manual ≠ Modern: Developers still rely heavily on outdated, manual processes.

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Time = Revenue: Automation can meaningfully increase speed, efficiency, and returns.

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Empowering, Not Replacing: Technology should support developers, not sideline them.

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Systems Thinking: Building frameworks for decisions strengthens long-term outcomes.

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Tracking Matters: Documenting decisions improves evaluation of future projects.

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Zoning’s Diminished Role: Less a barrier than before, zoning is no longer the central driver.

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The Power of Storytelling: A strong narrative is essential when pitching stakeholders.
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• Open Data Shift: More accessible data is reshaping how developers analyze opportunities.
• Generational Momentum: Younger leaders are pushing technology adoption forward.

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Chapter Breakdown


00:00 – Introduction to Dylan Gorin and Pillar


02:14 – Why Site Selection Remains a Bottleneck


03:59 – Data Collection: From Manual to Streamlined


06:06 – The Case for Automation in Development


08:28 – Adopting a Systems-Thinking Mindset


09:56 – Why Tracking Decisions is a Strategic Edge


12:38 – The Evolution of Real Estate Processes


13:52 – Technology and Decision-Making Integration


20:29 – The Changing Weight of Zoning


22:55 – Rethinking Development Strategies in Light of Zoning


24:57 – Storytelling as a Development Tool


31:04 – Open Data and Its Impact on CRE


38:46 – Tech Fatigue in Real Estate Organizations


42:37 – How Generational Change is Shaping Leadership






Show Notes & Links


Pillar: https://www.pillar.codes/


Guest: Dylan Goren, Co-Founder & CEO of Pillar


Connect: Dylan Goren on LinkedIn (  / dylan-goren  )