Ari Segal

I help real estate investment teams think more clearly about risk, using data and AI

I am the co-founder and CEO of Caps for Sale, a predictive analytics platform built for retail and net-lease real estate investors. My work sits at the intersection of real estate, applied machine learning, and how real teams actually make decisions.Over the last decade I have led organizations through periods of stress, growth, and reinvention. I have turned long-running deficits into operating surpluses, built multi-million-dollar endowments, and led capital campaigns from idea to execution. That experience shaped how I approach technology. I care less about hype and more about whether a tool actually helps people do better work.Today I spend my time advising investment firms, REITs, and lenders who know the old playbook is breaking down. I help them surface risk earlier, understand tenant behavior more deeply, and use data in ways that complement human judgment rather than replace it.


This quarter I am focused on three things:

1. Expanding Caps for Sale’s tenant renewal and void-analysis models.
2. Working closely with mid-sized REITs and investment funds as an AI and analytics advisor.
3. Building partnerships with institutional data providers and real estate platforms.


Experience highlights

• Co-founder and CEO, Caps for Sale, a machine-learning analytics platform for retail and net-lease investors
• Former CEO and Chief Strategy Officer of a $60M+ organization, leading a turnaround from $18M in debt and recurring deficits to sustainable operating surpluses
• Led creation of a $10M endowment and a $20M capital campaign including tax-exempt bond financing
• Founder of a real estate micro-fund achieving a 33 percent IRR
• Executive advisor and board coach to education and nonprofit organizations in the U.S. and Israel
• Speaker and writer featured in The Times of Israel, The Jewish Journal, The Forward, and industry podcasts


Links


Writing & Talks

Big Data Comes for Net Lease Real Estate

A deep dive into how data and machine learning are changing how investors predict tenant renewals and value single-tenant real estate.

Lessons in Peace from an RV Park

A reflective piece on unexpected lessons in understanding community, empathy, and leadership learned from time spent in an RV park.

Guest Lecture on Data, AI, and Real Estate

A recap of my guest lecture where I explored how data and machine learning are influencing real estate investment and strategy.