Ginger Dhaliwal didn’t plan to end up in coworking—or in tech at all. Her journey from social work to startup founder spans continents, industries, and a through-line of solving human-centered problems. As co-founder of Upflex, she’s now at the intersection of workplace experience, real estate tech, and the flex ecosystem.

In this episode, we cover:

• Ginger’s global path from social impact to launching R&D labs, tech startups, and eventually, Upflex.

• The core challenges of aggregating coworking inventory—and why brokers and operators have been slow to adapt.

• Upflex’s unique strategy: white-label partnerships with brokerages, airport lounge operators, and the U.S. government.

• How Ginger thinks AI will reduce booking friction, improve workspace recommendations, and drive industry-wide transformation.

• Why coworking is evolving from access-based models to experience-driven destinations—and what that means for operators.

Ginger shares her vision of a future where space is dynamically allocated, demand is driven by intelligent systems, and coworking plays a key role in restoring human connection.

Resources Mentioned in this Podcast:

Ginger on LinkedIn

Upflex website

Connect with your Hosts:

Connect with Giovanni on LinkedIn

Connect with Jamie on LinkedIn

Find Jamie on the Everything Coworking Podcast

What happens when a designer trades luxury bars and boutique hotels for coworking spaces—and ends up helping shape WeWork’s global footprint? You get Dean Connell: design veteran, creative provocateur, and someone who’s not afraid to say what coworking needs most right now.

In this episode, Dean shares his personal story of stumbling into WeWork, building over 2 million square feet of flexible workspace around the world, and why coworking still has a culture problem. We dig into what’s missing from today’s flex space design and how operators can bring purpose, creativity, and—yes—a little rebellion back into the process.

This one’s part inspiration, part challenge to the status quo, and a must-listen for anyone trying to build spaces that matter.

We cover:

• Dean’s unexpected journey from bar designer to creative director at WeWork, and how it changed the trajectory of his life.

• Why so many coworking spaces feel soulless—and what to do about it.

• The tension between creativity and repeatable models in coworking design.

• How to build spaces that reflect culture, not just brand palettes.

• Dean’s call for operators to stop playing it safe and start building the future, not just repackaging the past.

If you’ve ever looked at your space and thought “there has to be more to this,” you’ll want to hear what Dean has to say.

Resources Mentioned in this Podcast:

Dean on LinkedIn

I-AM.D.C website

Wesley Edmonds on LinkedIn

Connect with your Hosts:

Connect with Giovanni on LinkedIn

Connect with Jamie on LinkedIn

Find Jamie on the Everything Coworking Podcast

What if the future of work isn’t about scaling bigger offices—but building better relationships?

In this episode, we dive deep with Arian Lewis, founder of Kiln and former head of global partnerships at Barclays, to unpack the evolution of flex from “startup scrappiness” to a full-on solution for enterprise clients. Arian has one foot in the VC-backed world and the other in the day-to-day of running flex spaces—and he’s got thoughts.

This isn’t a rah-rah “flex is the future” hype fest. It’s a grounded convo about what actually works—and what doesn’t—when it comes to designing spaces people want to work in.

We cover:

• Why flex isn’t just about desks and square footage—it’s about culture, community, and control.

• What it’s really like raising VC money for a flex workspace brand (spoiler: it’s not for everyone).

• The one key metric Kiln uses to track whether members are actually getting value.

• A behind-the-scenes look at Kiln’s operating model, including how they select cities and sites.

• Arian’s honest take on why landlords and flex operators still struggle to trust each other—and what needs to change.

If you’re thinking about how to scale your space, attract bigger clients, or just survive the next shift in work trends—this episode’s for you.

Resources Mentioned in this Podcast:

Arian on LinkedIn

Kiln website

Connect with your Hosts:

Connect with Giovanni on LinkedIn

Connect with Jamie on LinkedIn

Find Jamie on the Everything Coworking Podcast