James Harris built his real estate career from scratch after relocating from the UK to Los Angeles. His latest venture is Breezy, an AI tool for real estate agents designed to reduce the administrative load that eats into most agents' days. Breezy recently raised a $10 million pre-seed round led by Ribbit Capital with participation from Fifth Wall, DST Global, and others. Over the past decade he's closed more than $6 billion in luxury residential sales across Beverly Hills and the Platinum Triangle, and appeared on Bravo's Million Dollar Listing LA for seven seasons spanning over nine years before stepping away to focus on his next chapter. He also hosts Rise Above the Ranks, where he talks through the practical side of the business: negotiation, discipline, and how to build something that lasts.

(2:11) - What Proptech Gets Wrong About Real Estate Agents
(6:49) - Realtor Painpoints
(8:54) - What is Breezy
(13:32) - Why Now
(16:26) - Real Estate Agent & Founder Resiliency
(18:31) - Brand, Distribution & Early Traction
(21:42) - AI Agents Enhance and/or Replace Real Estate Agents
(24:20) - First Mover Advantage
(26:36) - What Parts of Real Estate Will Be Human-driven in 3-5 years
(28:24) - The Power of Data & Workflow Platforms
(29:16) - What Changes in Real Estate Over the Next 2-3 Years?
(30:49) - Collaboration Superpower: The Founder Entrepreneur

🏙️ Learn more:
-Visit Breezy
-James on LinkedIn
-James on IG

🏙️ Connect with Tangent:
-Edward Cohen on LinkedIn
-Zach Aarons on LinkedIn
-Tangent on LinkedIn

🏙️ Events coming up:
-AI & Innovation Forum Q2: virtual on 6/10

-Retail & Hospitality Forum: in NYC on 6/18
-Institutional Investors & PE Forum: in NYC on 9/16
-All upcoming events

Disclaimer: Commercial Observer Tangent podcast is for entertainment and informational purposes only, you should not construe any such information or other material as legal, tax, investment, financial, or other advice. Nothing contained on our program constitutes a solicitation, recommendation, endorsement, or offer by Tangent, Commercial Observer, MetaProp, or any third party guest to buy or sell any securities, public or private, other financial instruments or funds.

Dillon Okner is the Founder & Partner of SiteRise, a retail development and construction platform helping brands streamline site selection, store development, and portfolio expansion. With more than 15 years of experience in retail construction and operations, Dillon previously helped support the expansion of major brands including Apple and Tesla. Today, he focuses on helping retailers, restaurants, and franchise operators eliminate development bottlenecks and open locations faster through better data, workflow management, and portfolio visibility.

(01:13) - How Retail Openings Break
(03:36) - Retail Innovation Edge
(05:00) - Store development with SiteRise
(07:38) - Apple & Tesla Lessons
(09:26) - Proprietary Data
(14:07) - Construction Influence on Deals
(15:27) - Working with Brokers
(16:33) - SiteRise's Clients
(17:44) - Getting Buy-in From Stakeholders
(20:50) - Collaboration superpower: Dillon's father and grandfather

🏙️ Learn more:
-Visit SiteRise
-Dillon Okner on LinkedIn

🏙️ Connect with Tangent:
-Edward Cohen on LinkedIn
-Zach Aarons on LinkedIn
-Tangent on LinkedIn

🏙️ Events coming up:
-AI & Innovation Forum Q2: virtual on 6/10

-Retail & Hospitality Forum: in NYC on 6/18
-Institutional Investors & PE Forum: in NYC on 9/16
-All upcoming events

Disclaimer: Commercial Observer Tangent podcast is for entertainment and informational purposes only, you should not construe any such information or other material as legal, tax, investment, financial, or other advice. Nothing contained on our program constitutes a solicitation, recommendation, endorsement, or offer by Tangent, Commercial Observer, MetaProp, or any third party guest to buy or sell any securities, public or private, other financial instruments or funds.

Will Parrish is the Co-Founder and Chief Customer Officer of Lula, a Kansas City-based proptech platform built to streamline property maintenance for property managers and their residents. Will co-founded Lula alongside CEO Bo Lais with a mission to make property maintenance smarter — pivoting the business during the pandemic to focus on property managers in the single-family rental space, a move that fueled rapid growth. Lula recently closed a $28 million Series A round and is expanding from 42 markets to 60, with heavy investment in AI and automation. Before co-founding Lula, Will spent nearly two decades in enterprise sales and business development, including a long tenure at Thomson Reuters.

(00:53) - How Lula Started
(02:34) - Trading Corporate for Startup Life
(03:29) - Is Maintenance Archaic
(05:49) - Where Work Orders Fail
(07:30) - Scaling 100K Work Orders
(12:28) - Building Vendor Trust & Quality
(13:19) - Expanding Markets
(16:16) - Flat Rate Pricing Playbook
(19:15) - Ideal Rental Customers
(21:54) - Integrations
(25:47) - AI In Maintenance
(30:21) - Future of Lula
(32:14) - ROI for Property Owners & Operators
(35:49) - Hardware play ahead?
(39:12) - Collaboration Superpower: MacGyver

🏙️ Learn more:
-Visit Lula
-Will Parrish on LinkedIn

🏙️ Connect with Tangent:
-Edward Cohen on LinkedIn
-Zach Aarons on LinkedIn
-Tangent on LinkedIn

🏙️ Events coming up:
-AI & Innovation Forum Q2: virtual on 6/10

-Retail & Hospitality Forum: in NYC on 6/18
-Institutional Investors & PE Forum: in NYC on 9/16
-All upcoming events

Disclaimer: Commercial Observer Tangent podcast is for entertainment and informational purposes only, you should not construe any such information or other material as legal, tax, investment, financial, or other advice. Nothing contained on our program constitutes a solicitation, recommendation, endorsement, or offer by Tangent, Commercial Observer, MetaProp, or any third party guest to buy or sell any securities, public or private, other financial instruments or funds.