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

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.

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. Jonathan brings a grounded, operator-informed perspective on what’s broken—and what needs to change if we want walkable, affordable neighborhoods to function again.

Key Takeaways

• Remain is designed to support missing middle housing by partnering with municipalities, property owners, small developers, and aligned capital.

• The missing middle is missing because small projects face the highest uncertainty, the most politics, and the least tolerance from capital.

• Zoning reform is necessary, but it won’t scale housing production on its own without permitting, code, and process reform.

• Permitting uncertainty is a tax on housing—more boards, more discretion, more delays means fewer builders willing to try again.

• Many Massachusetts communities have zoning frameworks that wouldn’t allow their existing neighborhoods to be built today.

• The “developer” label is too blunt—there are bad actors, but many builders are mission-driven and want to build great communities.

• Misinformation thrives in big public meetings; one-on-one conversations and clearer language often change the temperature.

• Language matters: “eliminating single-family zoning” creates fear, while “allowing more housing choices” reflects reality.

• Transportation and land use must be aligned—low density around commuter rail stations undermines the value of major transit infrastructure.

• Beyond zoning, reforms like building code updates, elevator cost dynamics, condo insurance constraints, and modular code friction can materially unlock production.

  
  

Chapters

00:00 Introduction to Jonathan Berk and Remain

01:32 The impetus for Remain and why housing became the core issue

05:06 Balancing private developers and government realities

07:35 Is this generational, political, or structural?

10:37 The real regulatory barriers to missing middle housing

12:27 Why approvals become political and why small projects stop penciling

15:06 The zoning contradiction: neighborhoods “illegal” under today’s code

16:51 Education, misinformation, and why meetings devolve

21:30 Why zoning isn’t enough: permitting, code, insurance, and cost drivers

24:35 The chaos of layered boards and discretionary power

30:12 Training gaps and the need for permitting reform

32:21 Infrastructure and transit: land use patterns vs. transportation goals

36:30 Learning from other places: Kelowna, Vermont, Montana, and beyond

39:12 Social media as an education tool and why language matters

43:57 What’s next for Remain and who should reach out

46:12 Where to follow and connect

Show Notes & Links

Listen now on ⁠Spotify⁠, ⁠Youtube⁠, or ⁠Apple⁠

Remain: ⁠remainplaces.com⁠

Guest: Jonathan Berk, Founder of Remain

Connect: ⁠Jonathan Berk on LinkedIn⁠

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.

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 judgment when translating assumptions into sound underwriting. She also shares how her real-world experience shaped the creation of Proptimal and why small and midsize developers need access to better data, better tools, and higher quality analysis.

What stood out most is Lillian’s approach to AI. She explains how AI can expand productivity, improve workflows, and give analysts more mental bandwidth, but only when it is paired with responsible use and a strong foundation in financial principles. For her, technology is a force that strengthens good thinking rather than replacing it.

Whether you are an analyst, developer, operator, or anyone curious about how real estate and technology are converging, this episode offers a practical and forward-looking perspective on how smarter tools and stronger workflows can elevate the entire industry.

Key Takeaways

• Proptimal was created to bring better financial analysis to real estate professionals who often don’t have analyst teams behind them.

• Becoming a strong analyst requires persistence, real-world reps, and navigating complexity.

• Training analysts is difficult because underwriting isn’t plug-and-play—templates alone don’t cut it.

• AI can streamline repetitive processes and expand analyst capacity.

• Financial modeling tools can democratize knowledge and increase access to institutional-quality insights.

• Learning to code helps bridge the gap between analysis and scalable software.

• AI can accelerate both underwriting and software development when used intentionally.

• Mental bandwidth is one of the most important variables in good decision-making.

• Responsible AI use requires understanding limits, risks, and ethical considerations.

• Closing the information gap empowers small developers with better financial modeling, clearer assumptions, and stronger deals.

00:00 Introduction to Proptimal and Lillian Chen

02:55 Lillian’s Journey in Real Estate

05:57 Challenges in Training Analysts

08:45 The Role of AI in Financial Modeling

11:59 Building a Financial Modeling Tool

14:44 Learning to Code and Building Software

17:46 Using AI for Software Development

20:38 Strategizing Technology Transformation

24:17 Defining Roles in AI Interactions

25:30 Establishing Clear Objectives for AI Engagement

27:53 Utilizing AI for In-Depth Research

30:14 Learning and Adapting to AI in Workflows

32:01 The Dual Nature of AI: Enhancing or Diminishing Intelligence

34:20 Ethics and Personal Growth Through AI

36:04 Proptimal: Bridging the Gap in Real Estate Analysis

39:23 Understanding the Market Needs of Small Developers

Show Notes & Links

Listen now on Spotify, Youtube, or Apple

Proptimal: ⁠proptimal.com⁠

Guest: Lilian Chen, Founder & CEO of Proptimal

Connect: ⁠⁠⁠Lilian Chen on LinkedIn⁠⁠⁠

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.

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.

Whether you’re a developer, capital allocator, or marketing lead, this discussion offers a practical roadmap for building a brand that compounds into opportunity.

Key Takeaways

• Personal branding in CRE isn’t about fame—it’s about trust and access.

• Consistency across platforms builds credibility and recognition.

• Authentic storytelling beats overproduced marketing every time.

• Newsletters and podcasts can directly generate deal flow.

• Substack success depends on clear audience focus and sustained cadence.

• Video accelerates trust by showing personality and professionalism.

• Authenticity matters—AI can refine your message, but it can’t replace your voice.

• Building a brand is a long game; consistency compounds over time.

Chapter Breakdown

00:00 – Why personal branding matters now in CRE
03:32 – How values drive credibility and long-term relationships
08:23 – Turning content into measurable deal flow
10:40 – Clarity through marketing: defining who you serve
15:08 – Moving beyond “influencer culture” to real business outcomes
18:58 – The cost of being invisible in commercial real estate
24:06 – Building an authentic Substack and audience growth
36:23 – The power of video and authentic presence
38:39 – Lessons learned: start small, stay consistent, keep it real
43:43 – Storytelling as the foundation of a meaningful brand

Show Notes & Links

🎧 Listen now on Spotify or Apple Podcasts
Guest: Rachel — Marketing Strategist & Branding Advisor
Connect: Rachel on LinkedIn

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.

Show Notes

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.

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 challenges of raising capital in today’s environment, and the importance of building community in wealth creation.

• The Multifamily Outlook

  • Why Origin Investments has gone “an inch wide and a mile deep” into multifamily.

  • Tailwinds shaping the sector: affordability gaps, suppressed construction starts, and rent growth projections.

  • How Origin’s proprietary AI tool, Multilytics, drives more accurate rent growth forecasting.

• Capital Raising in Uncertain Times

  • Current challenges for investors amid tariffs, liquidity constraints, and capital calls from prior vintages.

  • Why deal selection and timing are critical—and how Origin balances funds with single-asset opportunities.

  • Examples of distressed and opportunistic deals that investors have quickly rallied around.

• Preferred Equity & Lending Strategies

  • Why Origin is focusing on preferred equity, whole loan lending, and development in the current cycle.

  • Typical deal sizes ($10–30M) and focus on Sunbelt growth markets.

  • How Origin builds a margin of safety and structures returns.

• WealthOps: Building a Community of Investors

  • The importance of surrounding yourself with the right people—on the field and in finance.

  • WealthOps as a platform to educate, connect, and empower accredited investors.

  • Helping tech professionals, athletes, and executives architect portfolios for long-term freedom.

• How Do You Know Podcast

  • Why Bela started a show on decision-making in investing and entrepreneurship.

  • Guests ranging from attorneys to entrepreneurs, breaking down due diligence, risk, and opportunity.

  • The mission: give people confidence and conviction in their investment choices.

• Mindset and Takeaways

  • Community as a shortcut for learning—avoiding mistakes by sharing knowledge.

  • The shift from ownership to rental housing as a generational trend.

  • Why “no one cares about your money as much as you do” should guide investor education.

• LinkedIn: Isabela Carrasco 

• WealthOps community & free monthly webinars

• Podcast: How Do You Know

This episode of Breaking New Ground explores the YIMBY movement.

Courtney Porcella⁠ shares how YIMBY Action empowers the local community to engage with planning decisions, push for zoning reforms, and work alongside developers—not against them. We get into the real-world barriers to new housing, from financing challenges to NIMBY resistance, and highlight success stories that prove collaboration works. Her career path, from PR to PropTech to housing advocacy, offers a unique perspective on why open dialogue and local partnerships are key to solving the housing crisis.

This conversation matters if you’re a housing developer who wants to navigate the politics of housing and actually get projects built.

Episode Highlights

• Why grassroots power is the most important—and overlooked—tool in solving the housing shortage

• How developers can work with pro-housing advocates to build trust and momentum

• Real-world case studies showing how policy changes unlocked new housing supply

• The listening skills every developer needs to win community support

Time-Stamped Show Highlights
⏱️ 00:00 – “Housing is still a local game.”
Courtney explains why local voices—not just national policy—drive housing outcomes.

⏱️ 05:02 – “We need you to keep building.”
How YIMBY Action partners with developers to counter anti-housing narratives.

⏱️ 07:48 – “You need the local community power.”
Why grassroots advocacy changes the conversation around development.

⏱️ 12:13 – Financing headwinds in today’s market.
Courtney shares how rising costs and interest rates are stalling projects.

⏱️ 15:59 – Success stories from the front lines.
Case studies where community support helped get projects approved.

⏱️ 21:10 – From real estate to PropTech to advocacy.
Courtney’s personal journey and what she’s learned across sectors.

⏱️ 25:43 – The art of listening to a community.
How developers can engage without alienating neighbors.

Show Notes + Links
🎧 Listen now on Spotify, Apple, or wherever you get your podcasts

🔗 ⁠YIMBY Action: ⁠yimbyaction.org⁠
👤 Guest: ⁠Courtney Porcella, YIMBY Action⁠
📱 Connect: ⁠Courtney on LinkedIn⁠

Title: Placemaking Through Art: How Fine Art Elevates Real Estate with Killian Repasky

In this episode of Breaking New Ground, John Pugh and Rachel Walters sit down with Killian Repasky, Founder of Fresh Kills Fine Art, to explore how fine art is shaping the future of real estate development.

Killian shares her unique approach to curating and commissioning large-scale art installations, emphasizing the transformative power of public art in creating iconic destinations, boosting community engagement, and driving financial value.

With experience working with artists like Daniel Popper and referencing monumental works like Ugo Rondinone’s Seven Magic Mountains, Killian offers behind-the-scenes insights into the logistics, creative collaboration, and placemaking strategies that turn buildings into cultural landmarks.

📄 Show Notes

Episode Highlights:

• The cultural and commercial value of integrating fine art into real estate

• How art influences placemaking, branding, and community engagement

• The challenges and logistics behind large-scale art installations

• Working with artists: balancing creative freedom and business constraints

• Case studies: Thrive by Daniel Popper, Seven Magic Mountains by Ugo Rondinone, and Seattle’s Sculpture Park

• The evolving role of art consultants in real estate development

• Social media’s impact on visibility, foot traffic, and ROI

Guest:
Killian Repasky, Founder of Fresh Kills Fine Art
Follow on Instagram: @freshkillsfineart
Connect on LinkedIn: Killian Repasky

This episode of Breaking New Ground dives deep into a platform—and a mindset—that’s reshaping commercial real estate.

Rafael Weiss is a real estate developer and entrepreneur who built SYTES to solve a problem we’ve all experienced: the inefficiency of site selection and leasing in a fragmented, opaque market. His AI-powered platform does what brokers and landlords have struggled to do for decades—it reveals where tenant demand actually exists, and filters the noise from meaningful opportunities.

This conversation matters if you’re a developer, broker, landlord, or investor trying to move faster and smarter in today’s market. Rafael breaks down how SYTES works, what’s changing in commercial real estate right now, and how AI is starting to reshape the way deals get done. His journey—from hiking the Appalachian Trail to producing music for Call of Duty to running a family real estate portfolio and a racehorse stable—makes this a fun and wide-ranging episode you don’t want to miss.

Episode Highlights

• Why Rafael believes AI agents will eventually negotiate leases with each other—and what that means for brokers

• How SYTES uses AI to automate site screening and save tenant reps hours of tedious work

• The critical data partnerships (Placer.AI, SitesUSA, Leasecake) that make SYTES even more powerful

• Rafael’s blunt take on the current market freeze, cap rate expectations, and what buyers/sellers need to face in 2025

• How his background as a DJ and producer influences his creative approach to development and technology

• Why horse racing, community building, and CRE all share more overlap than you’d think

Time-Stamped Show Highlights

⏱️ 01:14 – “Will AI leasing agents negotiate with each other?”
Rafael imagines a near future where tenant rep and landlord rep AI agents broker deals directly.

⏱️ 04:38 – “Rio reads every site submission—and filters the junk.”
How Rafael’s AI agent (named after his dog) parses deal docs and flags the best sites instantly.

⏱️ 08:25 – “I was tired of guessing where tenants wanted to be.”
The origin story of SYTES—and why Rafael knew tenant reps were the underserved key.

⏱️ 11:13 – “We know where tenants want to be. That’s powerful.”
Why SYTES adds a layer of demand data that complements existing location analytics tools.

⏱️ 12:10 – “Nobody wants a new product—until they can’t live without it.”
Lessons learned from early adoption struggles—and how SYTES overcame them.

⏱️ 13:45 – “LinkedIn exploded for us—it’s 90% of our business.”
How Rafael built traction through organic CRE engagement on LinkedIn.

⏱️ 21:38 – “Sellers are stuck in 2021. Buyers are in 2025.”
Rafael’s take on the bid/ask disconnect—and what really needs to change.

⏱️ 27:00 – “Real estate development is like producing a track.”
What music production taught Rafael about timing, creativity, and managing complexity.

Show Notes + Links

🎧 Listen now on Spotify, Apple, or wherever you get your podcasts

🔗 SYTES: sytescre.com
👤 Guest: Rafael Weiss, Founder of SYTES and Managing Partner at JW Advance
📱 Connect: Rafael Weiss on LinkedIn

In this conversation, Shree Kulkarni, a dynamic real estate executive and entrepreneur, discusses his journey in real estate development and technology. He shares insights on current projects, the role of technology in the industry, and the challenges faced in real estate development. Sri also introduces his PropTech innovations, including Roov.ai and Realty Dynamics, and explores the future of real estate amidst regulatory changes and market dynamics.

In this episode of Breaking New Ground, John Pugh and Rachel Walters sit down with Nick Jones, Founder of Alakai Capital, to unpack the evolution from hands-on real estate technician to company builder and venture investor. Nick shares how the rebrand to Alakai Capital reflects his shift to leadership, systemization, and team culture—and why that’s been essential to scaling his platform.

We explore how his team implements standard operating procedures (SOPs), project management tools like Asana, and AI-powered workflows to boost efficiency and performance. Nick also dives into Alakai’s LP investments in tech and hospitality startups and how AI is transforming lease abstracting, investor communication, and portfolio reporting.

He closes by sharing where he sees commercial real estate opportunities in the current market—especially around inflation-driven rent growth in under-managed assets.

🧭 Key Topics & Timestamps:

00:00 – Intro & Alakai Rebrand
Nick discusses the mindset shift from investor to company builder and why a rebrand was necessary to embody their values of trust, expertise, and community leadership.

03:00 – Scaling with Systems
Why hitting 5+ employees forced him to systematize—and how checklists, SOPs, and Asana transformed operations.

07:00 – Culture as Strategy
Nick shares how predictive indexing helps build a performance-focused, authentic culture, and why he views team members more like athletes than family.

12:30 – Celebrating Wins
Why high-performing teams need to take time to recognize achievements to reinforce vision and morale.

15:30 – Tech + AI in Real Estate
How Nick's team uses AI (ChatGPT and others) to handle communications, lease abstracts, and investor reporting—and why human oversight still matters.

21:00 – Investing Beyond Real Estate
A look at Alakai Ventures: LP investments in fintech, online marketplaces, and AI startups—and why Nick believes some of these bets can return 50–100x.

26:00 – CRE Market Outlook
Nick discusses where he’s finding opportunity in CRE today—including value creation via rent growth in overlooked industrial and retail assets.

🔗 Connect with Nick Jones:

🌐 Website: www.alakai-capital.com
💼 LinkedIn: Nick Jones Real Estate
📩 Investor Portal: Available via website