Driving Disruption: Jay Schwartz Of Once Upon a Time Hospitality On The Innovative Approaches They Are Taking To Disrupt Their Industries

An Interview With Cynthia Corsetti

We’re building bespoke AI engines that leverage images and brand standards we define for some our clients, so we can avoid trademark and copyright implications.

In an age where industries evolve at lightning speed, there exists a special breed of C-suite executives who are not just navigating the changes, but also driving them. These are the pioneers who think outside the box, championing novel strategies that shatter the status quo and set new industry standards. Their approach fosters innovation, spurs growth and leads to disruptive change that redefines their sectors. In this interview series, we are talking to disruptive C-suite executives to share their experiences, insights, and the secrets behind the innovative approaches they take to disrupt their industries. As part of this series, we had the pleasure of interviewing Jay Schwartz.

Jay Schwartz is the Executive Creative Director and CEO at Once Upon a Time Hospitality. Renowned for his expertise in brand development and creative direction in the hospitality sector, and with a career spanning over 25 years, his collaborations include icons such as Ian Schrager and Jean-Georges Vongerichten. Schwartz is known for his immersive approach to branding, involving extensive research and stakeholder engagement to craft compelling identities for his clients. His work reflects a deep commitment to enhancing the guest experience through innovative design and storytelling.

Jay founded Ideawork Studios in 1999, which was acquired by Once Upon a Time in 2019, and he’s worked on hotel, resort, and luxury projects around the globe.

Thank you so much for joining us in this interview series. Before we dive into our discussion about disruption, our readers would love to “get to know you” a bit better. What brought you to your specific career path?

Good question. My background is as a fine artist — I have always been active in making art — and after I got disillusioned by the business side of the art world, I decided to get a formal training in graphic design. I started my own agency in the late 90s and then things all sort of aligned; a lot of right place/right time and proving myself.

What do you think makes your company stand out? Can you share a story?

Many of our clients seek us out and continue to work with us because of our deep expertise in the hospitality sector. Our senior team have deep roots in hotels, and hotel marketing. We know what it takes to successfully open and run a hotel, both from the marketing side and from the operations side. This deep understanding allows us to approach projects from multiple perspectives: as a guest, as a marketer, and as a key stakeholder (owner or operator) so we can provide solutions that are not only beautiful and memorable, but they get done on time and we’re mindful of budgets.

Working at this level for so long, we’ve had the privilege to know and work with, and learn from, many visionaries in hospitality like Ian Schrager, Aby Rosen, and Jean-Georges Vongerichten. Those icons set the standard for not only innovation, but for the high level of expectation that comes with continued success.

Another key aspect that sets us apart is that we don’t have a single visual style, in terms of design and how things look. As the lead creative on all our brand projects, I can work in all different styles — from luxury to resort to urban, across different geographies and cultures.

Jay Schwartz

You are a successful business leader. Which three-character traits do you think were most instrumental to your success? Can you please share a story or example for each.

  1. Foremost, and this is what I try to impart on every member of my team, I do what I said I was going to do, when I said I would do it. If I said I’ll have something done by Wednesday at 2pm, it’s done Wednesday by 2pm. I was trained at a very early age to be punctual — if you’re on-time you’re late — and I can’t seem to shake that. That seems like a low expectation threshold, but I see it as a baseline for excellence.
  2. I hear voices — mostly the voices of art teachers that were instrumental in my formal art education. They tell me to, “stop noodling” and to, “stop futzing” when I’m obsessing over a design or illustration and going down rabbit holes. Other voices scream at me to, “let your soul out” when I’m being too cautious on a project and not going with my instinct. It’s funny how the smallest lessons can have the biggest impact on who we become and what we carry with us. I’m sure those instructors had no idea I’d still be listening to them all these years later.
  3. I don’t watch the clock or count beans. I pour all of myself into my projects — each is one of my ‘babies’ and needs the time and attention it deserves. At this stage of my career, I’m fortunate in that I can be extremely selective about taking on new work — the project needs to align with what I want to be working on and needs to afford a level of creative freedom, or it’s not worth the time.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Building and running a creative business has never been an easy road. I did not major in Business or sit down one day and decide, “tomorrow I’m going to start an agency and we will specialise in hospitality”. These things were born out of necessity and agile (and constant) decision-making. One of the biggest decisions I made during my career was to have my agency acquired by Once Upon a Time. It wasn’t about sailing off into the sunset — I work just as much/hard now as I did before — but it was more of a strategic decision to expand our (ONCE Hospitality’s) global presence and to add extremely valuable services that we couldn’t have done on our own without being part of a much larger team.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page.

Disruption is about taking a current/traditional business model and approaching the solution from a different perspective, adding to the end-user experience in such a way as to overtake the traditional model, and become the norm.

How do you perceive the role of ‘disruption’ within your industry, and how have you personally embraced it? Is it a necessity, a strategy, or something else entirely in your view?

I don’t believe it’s our place, as a creative agency, to necessarily disrupt any particular business model. Within hospitality, however, the traditional models are constantly being disrupted by our clients. Most notably by brands like PUBLIC, SIXTY, and CIVILIAN Hotels, who have all changed how we define, “luxury” by looking at what guests actually want out of their urban travel experiences and changing how the hotel spaces are designed to deliver.

What lessons have you learned from challenging conventional wisdom, and how have those lessons shaped your leadership style?

My key takeaway is things can always be done better. The better solution may take some time to catch on but once it does, that will become the new normal. In terms of how this has shaped my ideas on leadership — I look at things through the same lens: how can we solve this problem more efficiently? What can we learn from this situation that we can do differently? Whilst none of what we do is templated, there are patterns that continue to emerge across every project that we can find ways to problem-solve through simple solutions.

Disruptive ideas often meet resistance. Could you describe a time when you faced significant pushback for a disruptive idea? How did you navigate the opposition, and what advice would you give to others in a similar situation?

As mentioned, i don’t feel it’s the role of a creative agency to be disruptors, per se. The thing i see time and again, by way of disruption, is that disruption is intentional. We encounter new technologies all the time that aim to disrupt, but oftentimes they’re ill-conceived or they cause more problems than they solve. It’s usually time most simple situations that are the most susceptible to disruption in any industry.

What are your “Three Innovative Approaches We Are Using To Disrupt Our Industry”?

1 . We’re using data to challenge what we think we know about luxury markets, and pushing the boundaries of how to craft meaningful and informed brands. This may not sound terribly disruptive, but we’re thinking beyond what the data is telling us and anticipating the next iteration, in order to craft brands that will continue to push boundaries well into the future.

2 . We’re building bespoke AI engines that leverage images and brand standards we define for some our clients, so we can avoid trademark and copyright implications.

3 . In the current age of AI-everything, we’re continuing to take genuine and thoughtful approaches to how we build brands. We’re not allowing ourselves to take the easy road of having ChatGPT write brand books, like many of our competitors. We’re continuing to keep personal touches in everything we do. This may seem like the antithesis of disruption, but we see it as disruption because we’re not allowing ease to dilute quality. We are utilizing AI as a tool, but largely for repetitive tasks — not allowing it to take over our creative vision.

Looking back at your career, in what ways has being disruptive defined or redefined your path? What surprises have you encountered along the way?

One example, from long ago, is when I directed a photo shoot for a prominent Las Vegas Hotel & Casino. The shoot itself was fairly risqué, as the property was geared toward a younger/hip crowd (which was in and of itself disruptive) and the accompanying copy had pushed the envelope even further. Turns out we pushed the envelope too far with the combination of image and copy, and we were levied a fine by the Gaming Commission, which wound up putting our ad creative on the front page of the New York Times, who covered the story about the fines. I arrived on-property expecting to be fired but was lauded for getting press coverage that far exceeded the value of the fines we incurred. Sometimes it pays to take risks.

Beyond professional accomplishments, how has embracing disruption affected you on a personal level?

Aside from the obvious use of disruptive technologies in my daily life, I think just overall risk-taking and never being satisfied with status quo. I do look at things from a lens of curiosity and am generally not complacent doing things as they’ve always been done.

In your role as a C-suite leader, what thoughts or concerns keep you awake at night? How do this guide your decisions and leadership?

Nothing keeps me up at night. I know that all of tomorrow’s challenges will be solvable.

How can our readers further follow your work online?


(21) Once Upon a Time Hospitality: Overview | LinkedIn

Once Upon a Time Hospitality (@onceuponagency_hospitality) • Instagram photos and videos

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.