David Stifter has spent more than two decades at the intersection of real estate, technology, and finance. As Managing Director and functional CTO at Digital Bridge (formerly Colony Capital), he led data architecture, process improvement, and finance transformation initiatives across major acquisitions. In 2020, he co-founded PredictAP with a team of B2B SaaS and AI veterans from Blizzard, Apple, and HubSpot. Since then, the company has grown to serve more than 60 real estate firms and raised an $8 million Series A in 2023. David is based in Lincoln, MA.

(02:20) From Colony Capital to founding PredictAP
(05:11) When a $60B firm couldn't pay bills
(07:23) Why invoice coding is harder than it looks
(09:29) CAM pools, triple net leases, and the permutation problem
(13:43) When institutional knowledge walks out the door
(16:38) How to tell a real solution from a pretty demo
(20:48) PredictAP: From inbox to Yardi in 30 seconds
(24:47) Related Group, Cushman & Wakefield, and what 130 clients taught PredictAP
(27:59) Why integration makes or breaks AP automation
(30:17) Build vs. buy: what CFOs & COOs get wrong
(33:51) Sheriff vs. shepherd: how to manage AI adoption internally
(35:50) AP coding, audit risk, and financial misstatement
(38:44) Collaboration superpower: Richard Feynman

🏙️ Learn more:
-Visit PredictAP
-David Stifter on LinkedIn

🏙️ Virtual Events:
-AI & Innovation Forum: Multifamily: on 9/29

-SFR / BTR Forum: on 10/22

🏙️ In-person Events:
-Institutional Investors & PE Forum: in NYC on 9/16
-South Florida Capital & Development Forum: in Miami on 10/15
-Finance Forum: in NYC on 11/3
-All upcoming Commercial Observer events

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

Jeffrey Havsy is the commercial real estate industry practice lead at Moody's Analytics, where he focuses on combining property fundamentals with economic, credit, climate, and alternative data to help lenders, investors, and operators make better decisions. He has spent his career at the intersection of economics and real estate, including roles at NCREIF and CBRE. Moody's Analytics covers more than 600 million public and private entities worldwide and generated over $7 billion in revenue in 2025. Jeffrey is based in Needham, Massachusetts.

(02:46) From data scarcity to data curation
(03:39) What lenders and investors miss beyond property fundamentals
(05:34) Tenant credit, crime data, and truck traffic as signals
(09:16) Moody's commercial location score explained
(12:52) Cap rates: overrated, underrated, or misused
(15:39) Moody's MCP launch and what it means for CRE decisions
(18:32) Why Moody's stays AI platform-agnostic
(20:44) Where the human stays in the loop
(23:33) Physical risk vs. ESG
(26:11) The hidden risks in industrial real estate
(30:06) How robotics changes what a warehouse is worth
(31:09) The one macro data point CRE ignores: productivity
(33:10) Collaboration superpower: Abraham Lincoln

🏙️ Learn more:
-Visit Moody's Analytics / Moody's CRE
-Jeffrey Havsy on LinkedIn

🏙️ Virtual Events:
-AI & Innovation Forum: Multifamily: on 9/29

-SFR / BTR Forum: on 10/22

🏙️ In-person Events:
-Institutional Investors & PE Forum: in NYC on 9/16
-South Florida Capital & Development Forum: in Miami on 10/15
-Finance Forum: in NYC on 11/3
-All upcoming Commercial Observer events

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

Jamie Borodin is the founder and CEO of Docuverus, a document verification and fraud detection platform purpose-built for multifamily housing providers. With over 30 years in resident screening, Jamie founded Docuverus in 2017 to address a gap no existing tool was solving: authenticating income documents at the metadata level while simultaneously reading and calculating their contents. Docuverus is one of the only platforms with a direct connection to the Social Security Administration for synthetic identity detection. Jamie is based in southern New Jersey.

(02:16) Why standard screening misses income fraud
(05:03) How fraud evolved from COVID to AI-generated documents
(07:13) What a sophisticated fake pay stub looks like today
(09:09) What bad debt files actually reveal
(13:10) Operators don't know how much bad debt is fraud
(14:12) False security: when your PMS fraud tool isn't enough
(18:27) Why bank account linking isn't fraud detection
(19:11) Fraud hotspots: Houston, Atlanta, and why NYC is different
(24:27) Social Security fraud and synthetic identity detection
(25:36) What a CPN is and how it fabricates a credit file
(27:58) Florida's felony law and the limits of regulation
(29:29) Screening compliance: why the liability falls on the operator
(33:27) Where fraud prevention goes as AI lowers the barrier
(35:42) Collaboration superpower: Albert Einstein

🏙️ Learn more:
-Visit Docuverus
-Jamie Borodin on LinkedIn
-Sales line
-Multifamily Applicant Fraud Trends Report: Q2 2026

🏙️ Virtual Events:
-AI & Innovation Forum: Multifamily: on 9/29

-SFR / BTR Forum: on 10/22

🏙️ In-person Events:
-Institutional Investors & PE Forum: in NYC on 9/16
-South Florida Capital & Development Forum: in Miami on 10/15
-Finance Forum: in NYC on 11/3
-All upcoming Commercial Observer events

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

Jordan Hearin is the chief strategy officer at ID Plans, a platform that digitizes the physical reality of commercial real estate assets to support leasing, property management, construction, and asset management across the full property lifecycle. Founded in 1999, ID Plans now covers over 3 billion square feet across the US, with clients including Regency Centers, JLL, Brixmor Property Group, Kite Realty and DLC Management. Jordan is based in Tampa, Florida.

(03:28) Who owns the CRE data problem
(05:02) When leasing and property management diverge
(06:00) How Proptech specialization fragmented teams
(09:25) Data migration for traditional operators
(13:38) Data diligence when buying a shopping center
(16:22) Connecting leasing, ops, & construction
(18:51) From vacancy to signed lease
(22:20) Drone imagery & decision compression
(23:53) Tenant selection strategy
(27:14) Kroger, Amazon & grocery anchors
(32:29) NYC city-run grocery stores
(35:01) Collaboration superpower: Jon Gray

🏙️ Learn more:
-Visit ID Plans
-Jordan Hearin on LinkedIn

🏙️ Virtual Events:
-AI & Innovation Forum: Multifamily: on 9/29

-SFR / BTR Forum: on 10/22

🏙️ In-person Events:
-Institutional Investors & PE Forum: in NYC on 9/16
-South Florida Capital & Development Forum: in Miami on 10/15
-Finance Forum: in NYC on 11/3
-All upcoming Commercial Observer events

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

Rob Whiting is the co-founder and CEO of Boom, a proptech company building the future of rental financial services for residential property managers across single-family rental, manufactured housing and multifamily. Boom's three products — Boom Report for rent reporting, Boom Screen for applicant underwriting, and Boom CRM for agentic leasing and self-showing — serve hundreds of thousands of doors and count American Homes 4 Rent and Manage America among their key partners. Before Boom, Rob founded ventures in healthcare and education, including Haystack Health, a telemedicine company, and a financial aid organization focused on FAFSA access. Rob is based in Austin, Texas.

(02:55) Why Rob built Boom
(05:44) The ROAD to Housing Act, explained
(07:11) The 350-home cap & how institutions keep buying
(14:01) Rent reporting as a compliance path
(16:09) What Boom does & who it serves
(17:44) Is screening a commodity? Data quality & hit logic
(21:51) How to evaluate a tenant screening vendor
(25:47) How the ManageAmerica partnership came together
(30:00) Lessons from partnering with AMH Homes
(32:48) Closing the leasing stack gap with Boom CRM
(35:52) Coexisting with Yardi, RealPage, & AppFolio
(37:40) Collaboration Superpower: Daniel Ek

🏙️ Learn more:
-Visit Boom
-Rob Whiting on LinkedIn
-SFR Leasing Operating System Boom Secures $15M Series A Funding

🏙️ Virtual Events:
-AI & Innovation Forum: Multifamily: on 9/29

-SFR / BTR Forum: on 10/22

🏙️ In-person Events:
-Institutional Investors & PE Forum: in NYC on 9/16
-South Florida Capital & Development Forum: in Miami on 10/15
-Finance Forum: in NYC on 11/3
-All upcoming Commercial Observer events

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

Steven Song is the founder and CEO of Diald, an AI-powered decision intelligence platform for commercial real estate. Before founding Diald, Steven worked on both the investing and development sides of real estate, and built his career across architecture and urban planning, training at Carnegie Mellon and the University of Pennsylvania. He was a founding principal at SCAAA, a global strategy, planning, and design firm, and is a partner at Axle Companies, a family office focused on real estate investment and social impact ventures. Steven is based in Los Angeles.

(02:26) Why CRE Decisions Are Still Judgment-Driven
(04:41) The Signal That Killed an Atlantic City Deal
(07:44) Contextual Drift: The Risk Nobody Models
(10:20) Diald's approach
(11:59) AI Token Costs and Asking Better Questions
(14:27) Tools vs. Workflows
(15:52) Diald's Underwriting
(17:58) Killing Bad Deals Earlier
(19:18) How AI Upgrades the Analyst Role
(20:44) Where General Purpose AI Fails at Underwriting
(24:23) Does AI Make CRE More Efficient or More Competitive
(26:02) What Underwriting Looks Like in 5 Years
(27:14) Where Human Judgment Still Matters
(29:06) The Local Signals Investors Miss
(31:15) Collaboration Superpower: Denise Scott Brown and Reyner Banham

🏙️ Learn more:
-Visit Diald
-Steven Song on LinkedIn

🏙️ Virtual Events:
-AI & Innovation Forum: Multifamily: on 9/29

-SFR / BTR Forum: on 10/22

🏙️ In-person Events:
-Institutional Investors & PE Forum: in NYC on 9/16
-South Florida Capital & Development Forum: in Miami on 10/15
-Finance Forum: in NYC on 11/3
-All upcoming Commercial Observer events

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

Rafael Weiss is the co-founder of Sytes, a marketplace platform that connects commercial real estate landlords, developers, and brokers with tenants actively looking for space in real time. Rafael came to the problem as a developer who lost a deal because tenant demand was invisible until it was too late, and built Sytes to fix the information asymmetry at the core of retail leasing. The platform serves nearly 350 tenants and over 35,000 active site listings across all 50 states, with clients including Kimco, InvenTrust, Church's Chicken, and Dutch Bros. Rafael is based in Boca Raton, Florida.

(01:04) Retail's Demand Visibility Problem
(02:44) Why Sytes
(04:04) A Filtration System for Tenant Demand
(06:24) Getting First Customers to Pay Upfront
(07:24) Why Tenant Demand Data Was Opaque
(08:34) Anonymous Tenant Expansion
(10:14) How a Deal Happens on Sytes
(11:24) Church's Chicken Case Study
(14:54) Kimco & MyEyeDoctor Portfolio Review
(16:34) REITs & Strip Centers
(18:04) The Subscription Model
(19:24) Retail Is Back
(22:44) AI Leasing Agents & the Broker's Future
(24:04) Tenant Demand Index for Developers
(27:24) Bootstrapping vs. Venture Capital Backing
(28:24) Collaboration Superpower: Travis Kalanick

🏙️ Learn more:
-Visit Sytes
-Rafael Weiss on LinkedIn

🏙️ Virtual Events:
-AI & Innovation Forum: Multifamily: on 9/29

-SFR / BTR Forum: on 10/22

🏙️ In-person Events:
-Institutional Investors & PE Forum: in NYC on 9/16
-South Florida Capital & Development Forum: in Miami on 10/15
-Finance Forum: in NYC on 11/3
-All upcoming Commercial Observer events

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

Rowland Hobbs is CEO and co-founder of Stake, a fintech platform that rewards renters with cash back, working to make renting financially rewarding. Before Stake, he led design and innovation at Teneo and served as head of product design for Accenture North America, and he founded Post+Beam, an innovation design firm, and Linea, a computer vision driven photo sharing app. Rowland is based in Dallas, TX.

(04:10) - Why Rent Was Left Out of Loyalty
(06:00) - Loyalty Programs Go Multifamily
(08:30) - Financial Amenities vs. Flashy Perks
(12:20) - Cash back for Delinquency, Retention & Vacancy
(14:40) - Rewarding Renters Instead of Punishing Them
(15:50) - Bilt Rewards
(24:50) - Stake's Cash back Business Model
(27:10) - Cash back by Property Type
(28:50) - UMoveFree Acquisition in Texas
(31:10) - Vertical Integration in Multifamily
(32:20) - Rising Housing Costs & Renter Churn
(36:50) - Renter Loyalty's Next 25 Years
(38:50) - Collaboration Superpower: Barack Obama & Loyalty Program's Inventor

🏙️ Learn more:
-Visit Stake
-Rowland Hobbs on LinkedIn

🏙️ Virtual Events coming up:
-AI & Innovation Forum: Multifamily: on 9/29

-SFR / BTR Forum: on 10/22

🏙️ In-person Events coming up:
-Institutional Investors & PE Forum: in NYC on 9/16
-South Florida Capital & Development Forum: in Miami on 10/15
-Finance Forum: in NYC on 11/3
-All upcoming events

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

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.