14 October 2026International edition
Vol. I · No.
14 October 2026
AI in Fashion
DAILY
The daily briefing on AI in the fashion business
Where fashion meets artificial intelligence.
Journalists and editors

Cale Weissman

Managing editor, New York, The Real Deal

Cale Weissman is managing editor for New York at The Real Deal, the real estate news publication. He was previously editor in chief of Modern Retail, which he left in February 2025.

Facts
RoleManaging editor, New York
OutletThe Real Deal
Based inNew York
BeatReal estate, business
PreviouslyEditor in chief, Modern Retail; Fast Company; Business Insider

Who is Cale Weissman?

Cale Weissman is a New York based business journalist and editor. He is managing editor for New York at The Real Deal, which covers the real estate industry. Before that he led Modern Retail, Digiday Media's publication on retail and e-commerce, as editor in chief.

Career

Weissman joined Modern Retail as a senior reporter, was promoted to editor in April 2020 and later became editor in chief. He departed in February 2025 for a new role. Earlier he was a staff writer and associate news editor at Fast Company, covered cybersecurity and tech politics and culture for Business Insider's tech section, and reported for PandoDaily. As a freelancer he wrote about technology, entrepreneurship, culture and media for outlets including Vice, Atlas Obscura and Mic. He is a graduate of Reed College.

Coverage

At Modern Retail he oversaw coverage of how brands and retailers adapt to digital commerce. His career has covered:

  • Direct-to-consumer brands and retail strategy
  • Technology companies and startups
  • Real estate and property markets in New York

At The Real Deal he now edits coverage of the New York property market, from landlords and policy to major deals.

Frequently asked questions

Who is Cale Weissman?

Cale Weissman is managing editor for New York at The Real Deal and the former editor in chief of Modern Retail.

What did Cale Weissman cover at Modern Retail?

He led coverage of retail, e-commerce and direct-to-consumer brands, having earlier reported on technology for Fast Company and Business Insider.

All people