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

On the podcast Breaking New Ground venture into the world of commercial real estate with entrepreneurs who challenge the status quo, and create innovative paths with bold approaches. In conversations with John and Rachel, explore the stories of real estate trailblazers who are reshaping the industry.

Breaking New Ground - Conversations with entrepreneurs who are innovating and redefining real estate is a business podcast hosted by John Pugh and Rachel Walters, with 31 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

John Pugh and Rachel Walters hosts Breaking New Ground - Conversations with entrepreneurs who are innovating and redefining real estate, a business show with 31 episodes published.

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  Episode #18

  Why Zoning Isn’t Enough: Jonathan Berk on the Real Barriers to Housing

  Jan 14, 202648 minS2

  <p>In this episode of Breaking New Ground, Rachel Walters and I sit down with Jonathan Berk, a placemaker, urbanist, and founder of Remain, a new platform designed to help municipalities and small developers actually deliver housing. Jonathan has spent the last decade working at the intersection of policy, development, and placemaking, including leading partnerships at Patronicity and serving in housing advocacy and local planning roles across Massachusetts.</p><p>We dig into why missing middle housing has become so hard to build, how permitting risk quietly kills small projects, and why zoning reform alone won’t solve the housing crisis...

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  Episode #17

  The New Operating Playbook: Lillian Chen on AI-Enhanced Underwriting and Analyst Capacity

  Dec 3, 202546 minS2

  <p>In this episode of Breaking New Ground I sit down with Lillian Chen, founder of Proptimal and one of the most thoughtful minds working across real estate, financial analysis, and technology. Lillian’s path from grinding through underwriting to learning how to build software offers a rare look at how modern analysts are developed and why capacity and clarity matter as much as technical skill.</p><p>We dig into the realities of financial modeling and why analyst work is so difficult to scale. Lillian describes the challenges of training teams, the limits of templates, and the importance of judgmen...

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  Episode #16

  Why Personal Branding Matters More Than Ever in Commercial Real Estate

  Oct 30, 202550 minS2

  <p>In this episode of Breaking New Ground, I sit down with with Rachel Walters to explore the evolving role of personal branding in commercial real estate—and how authentic visibility is translating into real deal flow.</p><p>From newsletters to podcasts to Substack, we unpack how consistency, storytelling, and clarity of message are reshaping how professionals connect with investors, partners, and peers. The conversation moves from strategy to execution—covering lessons learned, common pitfalls, and why credibility and authenticity matter more than production value.</p><p>Whether you’re a developer, capital allocator, or marketing lead, this discussion offers...

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  Episode #15

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

  Sep 17, 202546 minS2

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

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  Episode #14

  Bridging Institutional Real Estate and Personal Wealth: A Conversation with Isabela Carrasco

  Jul 9, 202532 minS2

  <p>Show Notes</p><p>In this episode, John Pugh sits down with Isabela (Bela) Carrasco, Assistant Vice President of Investor Relations at Origin Investments, founder of WealthOps, and host of the podcast How Do You Know. Bela shares her perspective on the current state of multifamily real estate, how she helps investors navigate uncertainty, and her mission to empower professionals and athletes to achieve long-term financial freedom through alternative investments.</p><p>With a background spanning private equity, family offices, and entrepreneurship, Bela brings both professional expertise and personal passion to the conversation. She discusses market tailwinds in multifamily, the...

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