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Orli Q&A: Founders Hailey and Max on the Transformation of a San Diego Landmark

September 19, 2022

Travelers all of their lives, Orli Co-Founders Hailey and Max Waitt grew to recognize the range of what’s possible, and most desirable, in a hotel experience.

They saw a need to create a novel hospitality brand that delivers unfettered independence and profound experiences artfully guided by design and technology. This led them to the concept for Orli and, ultimately, the debut of the brand’s first location in La Jolla. After a two-year restoration and transformation of a 1910-era private residence originally designed by Irving Gill, the father of California modernism, the siblings are excited to share a new kind of travel experience for discerning travelers that blurs the line between a 5-star hotel and homestay. One that allows guests to customize their entire stay pre-arrival or at any time during their stay, arrive and depart on their own terms, and effortlessly enjoy hyper-local discoveries — all while experiencing elevated design and tap-away convenience.

luxury hotel orli la jolla founder hailey and max waitt

In celebration of the launch, Hailey and Max reflect on their journey to create Orli, their best – and worst – sibling moments, and more. 


What are you most excited for guests to experience at Orli La Jolla?

H: I am so excited to see Orli through the eyes of our guests. When you’ve worked so hard and long on a project, you can get caught up in the minutiae and it’s difficult to step back and truly appreciate something. I’m also really excited for the interpersonal aspect: speaking with guests, helping them curate their perfect stay, and making their time at Orli one they will never forget. 

M: I am most excited to welcome guests in an entirely new and exciting way to stay; one that gives them the freedom to create their perfect travel experience. I am also thrilled to see guests’ reactions to the detail and design incorporated into every aspect of Orli. 


What was the origin of the idea behind Orli?

M: I wouldn’t say there is a singular origin story behind Orli, but rather years and years of traveling. I have had the privilege of being our family’s designated travel agent, and I can say with absolute certainty that there have been countless pain points with high-end accommodations – whether that’s encountered through lackluster design, antiquated room technology, or a friction-filled guest experience. We saw an opportunity for something different, and Orli was born.

H: For me, it happened organically, born of years of traveling and open discussions with friends and family about the je ne sais quoi that would put a trip over the top. When you look at La Jolla, you see one of the most gorgeous places in the world, but the accommodations have remained the same for as long as I can remember. There isn’t the variety of options there should be given the locale. We couldn’t have found a better place to open Orli’s first location. 


Why is Orli unlike anything else in the hospitality space?

H: We’ve always been avid travelers, but as I got older and began to travel on my own, I constantly felt torn between staying in a traditional hotel versus a more modern homestay. Hotels felt secure – with amenities, concierge services, and a communal feel – yet they often felt outdated. On the other hand, homestays often felt more modern, accessible, and affordable, and came with a sense of ease. In reality, it shouldn’t have to be a trade-off. You should be able to get the ease and accessibility of a modern homestay with the comfort and concierge of a hotel. To me, Orli is that perfect blend.

M: Orli is unique as we are small but mighty. It’s rare to find this level of high-design matched with such a unique and small property. It’s also unusual that one sees this level of design with a strong focus on automation and technology. Incumbents in the space focus their attention on one or the other, while Orli focuses on both.

Hailey, you’re a bit of an architectural buff and Max, you work in the real estate industry — can you each share with us what you love about the landmark building in which you’re launching Orli?

H: When Max and I first stepped foot on the property, we instantly knew it was the one. Irving Gill was a pioneer of the modern movement in architecture, and championed the idea that form should follow function, an idea you can see clearly in his clean lines and swooping arches. It’s hard to say what, exactly, is the most important aspect of the historic building. Perhaps it’s because Gill made such a mark on San Diego, or perhaps because his cubist architecture instantly draws forth inspiration. Or, perhaps it’s just the energy you feel standing on such a historic property that has been through so many lifetimes and seen over a century of love and life – either way, I’m all but certain our guests will love it too.  

M: There’s something very special about the property that almost feels like you’ve time traveled back to a simpler day without the craze of any trends or neon signs. I love the courtyard as it evokes the charm of something you’d find in a small boutique hotel in Europe.


Orli hotel books and interior decorations


Tell us about the team you assembled to restore and reimagine this 1913 landmark into a modern day Boutique hotel?

H: The team started small but it very quickly grew into a solid crew of young local professionals who are all passionate about hotels, travel, design, history, and most importantly, creating something beautiful that will hopefully have a positive impact on the world for years to come. Axon Architecture painstakingly restored our landmark building, updating it while also maintaining the integrity of historic design elements. For interior design, we partnered with Maddie Lord,  principal designer with ML Design Co. Maddie fused elements of Parisian Art Deco with design inspiration from the building’s historic architecture and La Jolla’s storied, coastal setting.

M:The core team at Orli, meaning those that have been with us since day one, are all under 35 and local, which I think is a tremendous advantage as the team brings forth innovative and creative ideas that could’ve been overlooked had we gone with big firms. Beyond the core team, we have had the opportunity to work with some of the best artisans, builders, and restoration companies we could find in La Jolla. 


Drawing of the Orli hotel exterior


Any favorite stories about the building’s past that you’ve learned about?

H: The building has a storied history. Built by one of San Diego’s most prominent architects, landscaped by famed horticulturist Kate Sessions, re-imagined multiple times over the decades – from a single family home to a lovely Bed and Breakfast and now to its most modern interpretation – Orli. I’m sure the building has incredible stories of Sessions and Gill, even if we’re not privy to them, but I’m also sure that some of the best stories are yet to come.  

M: The exciting thing about launching the Orli brand with an established historical property is that so many people have experienced the property first hand and will share these stories with us when they return. Orli also plans to hire back some of the establishment’s previous employees which will allow us to fuse the old and new together. 


What is it like being business partners with your sibling?

M: I never envisioned working with one of my siblings, as all of us forged our own paths from a young age and had different interests. It has been a great opportunity – lots of learning, laughing, and the occasional passive aggressive text. 

Being business partners with your sibling does come with its own set of challenges though, as we’re never not working. On vacations, I love to bother Hailey with work emails which she notes and then takes another sip of a watermelon margarita. Productive!

H: It’s honestly the best…and worst. But mostly the best. You understand your sibling more than any other person, so it’s really easy to guess what the other’s needs are or how they may respond in a given situation. The great thing about working with your sibling is you can say exactly what you mean, you never have to sugarcoat anything, and even if we get annoyed with each other, an hour later we’re discussing where to get lunch. The hardest part of working together is that it’s difficult to truly ever turn work “off.” I mean, I can’t ever just sip my watermelon margarita in peace.


Hailey, can you tell us a fun fact about Max?

H: Max has the best style of anyone I know, hands down. Every person we know – from my husband to our friends to my sisters (and me) – turns to him for fashion advice, home decor, etc. Be careful though, if you’re going to ask his advice, you’re going to get his honest opinion. Unless he tells you “actually, it’s okay” – then it is very, very much not. 


Max – your turn! What’s something we should know about Hailey? 

M: I’m not sure how it all fits up there, but Hailey has a history book stored in that head of hers. Ask her anything from the Middle Ages to present day politics and socio-economic issues and she will have all the facts and figures ready for you.


What’s it like to see your vision take form?

M: It’s similar to Christmas morning. Much of the design and furniture was selected 18 months ago, but the pandemic, supply chain issues, as well as the complexity of the historical restoration severely delayed the project’s completion. With that said, seeing all the FF&E appear over the past few weeks has been a bit of a dream, with the occasional nightmare. 

H:It’s surreal. I’ve never done anything even close to this magnitude and sometimes I can’t even believe that we’ve accomplished something like this. There are so many stunning elements that truly bring a smile to my face every time I see them, and I can’t wait for others to finally experience it. 


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