WeWork 2.0

Ken sits down with John Santora—CEO of WeWork and longtime real estate industry leader—for a candid look at WeWork’s evolution, its post-bankruptcy comeback, and the future of flexible workspaces.

Drawing from nearly five decades at Cushman & Wakefield, Santora brings a real-world perspective on what it takes to rebuild a company, reimagine workspaces, and rethink how businesses adapt to change.

This episode unpacks the real dynamics behind WeWork’s turnaround: how the company stabilized after historic restructuring, why flexibility is shaping the future of work, and how WeWork’s service-driven model stands out in an increasingly crowded flex office landscape. With grounded leadership and a clear vision, Santora challenges outdated assumptions about coworking—and makes the case for investing in people, spaces, and simplicity.

Key Takeaways from the Conversation:

From Bankruptcy to Rebirth
Santora shares how WeWork executed one of the largest real estate restructurings in history, emerging as a private company with no debt and a right-sized global portfolio of 45 million square feet.

Flexibility for Every Stage of Growth
WeWork isn’t just for startups anymore. Santora breaks down how the company now serves small businesses, AI firms, and even 47 of the Fortune 100 companies, offering flexible solutions for businesses at every stage.

Real Estate Meets Hospitality
With his roots in commercial real estate, Santora explains why WeWork succeeds where others struggle: blending professional space management with a hospitality mindset that drives community, culture, and convenience.

Post-Pandemic Work Trends
As companies reassess their office strategies, WeWork’s plug-and-play model offers an attractive alternative. Santora highlights how businesses are using WeWork to stay agile without the burden of traditional long-term leases.

A Culture Built for the Future
Beyond sleek design, Santora is reinvesting in technology, refreshing WeWork spaces, and creating a service culture that meets the needs of today’s workforce—without losing the vibrant, collaborative spirit that defined WeWork’s origins.

Why This Conversation Matters:

• John Santora brings unmatched experience from both the legacy real estate world and the new era of flexible work.
• This episode cuts through the noise to show how workspaces—and leadership—are evolving post-crisis.
• Leaders will walk away with a clearer view of how flexibility, community, and simplicity are reshaping the future of work.
• If you’re in business, real estate, or thinking about how the future workforce will operate, this conversation is essential listening.

“We want to be the easy button—the place that just works, wherever you are.”

Whether you’re an entrepreneur, a corporate leader, or simply curious about how work is changing, this episode will reframe how you think about office space—and what it takes to build a company built to last.