Podcast Summary

Episode Overview

Podcast: The TreppWire Podcast: A Commercial Real Estate Show
Episode Title: WeWork CEO John Santora on the Power of Flexibility & Real Estate Cycles
Date: November 18, 2025
Host(s): Hayley Keane (B), Lonnie Hendry (C)
Guest: John Santora (A), CEO of WeWork

This episode features an in-depth conversation with John Santora, WeWork’s CEO (since June 2024), about his career, WeWork’s restructuring journey post-bankruptcy, the evolving landscape of commercial real estate, and why flexibility is key for occupiers and landlords in a cyclical market. Santora shares lessons from nearly 50 years in the industry and details how WeWork is positioning itself as an agile, profitable partner for corporate and entrepreneurial tenants alike.

Main Topics & Insights

John Santora’s Career Journey and Perspective on Industry Cycles

• Serendipitous Start: Santora began his real estate career in 1977, taking a summer job at Cushman & Wakefield when plans to join the FDNY fell through due to a city hiring freeze. He started as an engineer’s helper in boiler rooms, eventually moving through property management, global leadership, and top executive roles.

  • Quote (John Santora, 01:28): “Real estate was really happenstance to me...47 years later [after Cushman & Wakefield], joined WeWork. It was a great run.”

• Industry Evolution:

  • Shift from owning headquarters and long-term leases to flexible, global footprints.
  • Emphasis on data, technology, and hybrid work models.
  • “Real estate is cyclical. Its down cycles may be driven by real estate itself, overbuilding...or it may be driven by different economic conditions...But whatever it is, it's a cycle. And you know, shortest cycle might be four years. The longest might be 10.” (Santora, 04:22)

• Recent Market Trends:

  • Despite negative headlines, office assets in NYC are trading again, a sign of office resurgence.
  • “There was a headline...‘Who would want to own a New York office building?’ ...in the last three months there’s probably been 15 out of traded hands, right, of significant scale.” (Santora, 05:17)

WeWork’s Post-Bankruptcy Transformation

• Real Estate Core Identity:

  • “At the end of the day, I said, this is a real estate company. You lease space and you sublease it to your members...Technology enables you, but you're a real estate business.” (Santora, 08:05)

• Restructuring After Bankruptcy (2024–25):

  • Debt cleared, a new focus on operational discipline and profitability.
  • Relocated from public company compliance to a leaner, more nimble structure.
  • “Nothing was going to be...at a loss. It's not how much space you own, it's how profitable it is...” (Santora, 08:46)

• Restoring Trust:

  • Engaged with landlords and corporate clients to “polish up” the WeWork brand and reestablish WeWork as a credible partner post-crisis.

Flexible Workspace & the Power of Hybrid

• Hybrid Opportunity:

  • “The hybrid model does create some more opportunity for us. It comes with its own challenges for anybody that owns real estate, right? How much do you need? How many people are actually going to be in the office?” (Santora, 11:06)
  • Employers rethinking space demand—shift from 100% office to 3–4 days/week average occupancy.
  • WeWork bridges the gap for companies reconfiguring, downsizing, or growing.

• Interim Solutions for Corporates:

  • 60- to 90-day turnaround on customizable space, minimal paperwork, rapid deployment.
  • “We can be the fast solution before they get to their long term...We sign the lease pretty quick and then do whatever limited work you need for a couple year period of time.” (Santora, 13:39)

Misconceptions, Brand, and the WeWork Value Proposition

• Not Just a Tech Company:

  • Santora reiterates WeWork’s identity as a tech-enabled real estate firm, with strong hospitality elements.
  • “WeWork is just probably misunderstood more than anything else...There was so much hoopla at the beginning of this disruptor and kind of this tech startup in real estate...You guys are at your core a real estate company.” (Hendry, 16:21)

• Hospitality Focus:

  • WeWork invests in service: staff trained with Ritz Carlton Leadership Center, frequent events, and plug-and-play amenities.
  • “There’s always something to engage people and bring people together. We think that's an important component of why you go to the office.” (Santora, 18:26)

Financial Discipline, Growth Outlook, and New Business

• Measured Expansion:

  • WeWork now operates about 45 million square feet globally (“down about a third from its peak”) and future growth will be selective, highly strategic, and data-driven.
  • “We think this is the right footprint for us. There will be some adds in key markets...the analysis that goes into that...is just as any developer or any owner would be leasing their space, we go through that same discipline.” (Santora, 21:50)

• Multiple Revenue Streams:

  • Small entrepreneurs, regional firms, major enterprise clients, on-demand and subscription-based access (“All Access” card), short-term sublets, and even build-to-suit for Fortune 100 firms.
  • “Like 47 of the Fortune 100 sits in our spaces....We’ve also started to do some five years, ground up, build, full build out for some clients.” (Santora, 24:38)

Relationships with Landlords and Industry Stakeholders

• Rebuilding Trust Post-Bankruptcy:

  • Santora leveraged decades-old relationships, credibility, and candor to reopen landlord dialogues.
  • “Every landlord has been in that same conversation with their banker...If you've got a relationship and you've been through some, you've met the person before, they know who you are, you've built some credibility and trust. When you have that crisis, you can usually work through it.” (Santora, 27:25)

• Financial Health as Core Message:

  • No debt, multiple billions in revenue, and transparent communication are now central to WeWork’s pitch.

Personal Reflections & Purpose

• Still Energized and Engaged:

  • “I'm excited by it. I get to deal with a lot of people that I knew in an industry...that I love, and I'm working with a bunch of really talented young professionals here. So that's energizing in itself.” (Santora, 30:08)

• Giving Back:

  • Santora remains connected to his family’s fire service roots by raising funds for the FDNY Foundation.
  • “Yeah, I sit on the fire department board today, the foundation board, and we raised lots of money for the FDNY...” (Santora, 31:24)

Future of Real Estate & WeWork

• Predictions for Market & Assets:

  • Quality assets with abundant amenities will remain in demand.
  • Cities like SF and NYC will rebound despite downturns—talent and infrastructure remain key.
  • “The move first is always to the best assets. Those assets today have to have lots of amenities.” (Santora, 32:16)

• Ongoing Investment:

  • WeWork will reinvest $80–$100 million/yr into refreshing existing spaces (finishes, technology, and amenities) to stay competitive.

Notable Quotes & Moments

• “Real estate is cyclical...the shortest cycle might be four years. The longest might be 10. But we know in that ten-year period something's going to happen. And I've lived through all of those...” (John Santora, 04:22)

• “At the end of the day, I said, this is a real estate company...Technology enables you, but you're a real estate business.” (Santora, 08:05)

• “The office is a grounding piece for brand, for learning, for mentoring, for creativity. And you need to have people in, but those spaces need to be exciting.” (Santora, 12:09)

• “The hybrid model does create some more opportunity for us...We can be the fast solution before they get to their long term [space].” (Santora, 13:18)

• “Our community associates are...the lifeblood. They're the people that our 550,000 members meet every day when they walk in the office...the Ritz does. When you go to one of their hotels, you know, they're sharing that. So it's been...the start of a game changer.” (Santora, 18:46)

• “WeWork is just probably misunderstood more than anything else.” (Hendry, 16:21)

• “I'm still first one in the office at, you know, quarter to seven in the morning, seven o' clock. And, you know, if I didn't wake up with a smile and happy to get here, that might be the time that it’s, you know, I decide it's enough. But right now, I'm having a blast.” (Santora, 30:19)

• “We will continue to invest back in our spaces...I see that on into the future, both in its, the furnishings and finishings and the paint and carpet, but also the technology we have in it. And I think that's important for any firm is to continue to invest back in your product.” (Santora, 32:52)

Timestamps for Key Segments

| Time | Topic / Segment | |-----------|---------------------------------------------------------------------------------------------| | 01:28 | Santora’s accidental start in real estate | | 03:47 | Major shifts in industry: globalization, cyclical markets, hybrid work | | 05:17 | NYC office asset resurgence and cyclicality of the industry | | 08:05 | Defining WeWork: Real estate business, post-bankruptcy discipline | | 11:06 | Hybrid work opportunities and WeWork’s positioning | | 13:39 | How WeWork delivers interim solutions for corporate clients | | 16:21 | Misconceptions about WeWork; host’s personal experience with spaces and brand | | 18:26 | Hospitality model and Ritz Carlton training for staff | | 21:50 | Operational discipline, right-sizing footprint, and approach to growth | | 24:38 | Diverse customer base: entrepreneurs to Fortune 100 firms, flexible offerings | | 26:39 | Landlord conversations, rebuilding trust, and financial health | | 30:08 | Personal energy, engagement, and connection to industry and family roots | | 32:16 | Final thoughts: quality assets, amenities, market resilience, and ongoing reinvestment |

Conclusion

This episode delivers rare insight into WeWork’s current state and future trajectory, guided by a seasoned industry leader with a pragmatic, cycle-savvy view of real estate. Santora outlines not only WeWork's renewed operational discipline and hospitality emphasis, but also offers a broader industry perspective on asset quality, city resilience, and the enduring need for flexibility in commercial real estate.

Listeners gain a fresh appreciation for WeWork’s real estate DNA, strategic reinvention, and commitment to creating meaningful, energizing spaces—while also understanding the cyclical, relationship-driven nature of commercial real estate at large.