Breaking New Ground - Conversations with entrepreneurs who are innovating and redefining real estate

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


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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

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

  • Manual ≠ Modern: Developers still rely heavily on outdated, manual processes.

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

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

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

  • Tracking Matters: Documenting decisions improves evaluation of future projects.

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

  • The Power of Storytelling: A strong narrative is essential when pitching stakeholders.

    • Open Data Shift: More accessible data is reshaping how developers analyze opportunities.
    • Generational Momentum: Younger leaders are pushing technology adoption forward.


  • 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

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    Breaking New Ground - Conversations with entrepreneurs who are innovating and redefining real estateBy John Pugh and Rachel Walters