What The Hotelier Next To Google Sees

with Dipesh Gupta, Shashi Group

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If you want a glimpse into the future, there are few better to learn from than Dipesh Gupta, the founder and CEO of Shashi Hospitality Group and Shashi AI. I discovered Dipesh’s work in a Wall Street Journal article, “Make Yourself at Home in the Hotel of the Future,” and for today’s story, drove down to one of their properties, the Shashi Hotel in Mountain View, to see it for myself.

Dipesh shared his journey from engineer to investor and hotelier, the changes he's seeing in the market as an owner and operator, and what he's doing about them. Regardless of where you live and work, there are insights about what it will take to stay relevant and engaging in a changing world that I think you’ll find useful.


The “funnel” offers a roadmap for understanding a guest's journey from dreaming about travel to booking a stay at your hotel. It is broken down into four key stages: Discovery, Planning, Booking, and the Guest Experience. Learn how this framework can guide you in effectively attracting, engaging, and delighting guests at each stage.

What The Hotelier Next To Google Sees

Dipesh Gupta, Founder & CEO, Shashi Group

Dipesh Gupta is the Founder and CEO of Shashi Group, and today joins us to share what he’s seen building a hotel company in the heart of Silicon Valley. You can listen to us here on the podcast, and I’ve summarized some of my top takeaways below.

Disruption Is Coming

With a front-row seat to the quickly changing landscape of traveler preferences in Silicon Valley, Dipesh observed how technology has disrupted many industries - and that he believes hospitality is next.

When the rate of change in a customer's life is more than the rate of change in an organization, the end is in sight.

Takeaway: Hospitality providers must act now to stay relevant with quickly changing customer behavior and expectations driven by technology.

Put this in action:

  1. Regularly assess how technology and customer expectations are advancing.

  2. Invest in scalable, cloud-based solutions that can be easily updated and integrated. (Some of our tech episodes may be helpful in showing how other hoteliers have done this.)

  3. Develop partnerships with tech companies to integrate cutting-edge innovations into hotel operations.

Anticipate What’s Coming to Stay Relevant

Dipesh emphasized the importance of focusing on the customer and their behavior and preferences to anticipate where things are going.

You have to focus on the customer. And if you don't do it, someone else will.

Takeaway: Staying close to your guests and customers is key to meeting their needs - both spoken and unspoken.

Put this in action:

  1. Talk with your guests and customers! It sounds basic, but I see this all too rarely, especially in corporate roles.

  2. Collect and process feedback through a wide variety of channels to learn as much as you can. (Andy Chabot shared how they do this at Blackberry Farm last week - and it’s helped them reach #1)

  3. Use data analytics to identify and interpret changes in behavior and opportunities for your organization.

  4. Encourage a culture of continuous improvement and flexibility among teams.

Today’s Guests Have High Expectations for Technology

Over and over across his portfolio, Dipesh sees how tech-savvy and demanding today’s guests are. They want their personal preferences to be seamlessly integrated into their hotel experience.

People today want to be empowered with the ability to hyper-personalize, control, and manage every aspect of their journey from anywhere, anytime, and from any device.

Takeaway: The traveler of today wants personalized and convenient experiences that align with their tech-driven lifestyles.

What Dipesh Has Built at the Shashi Hotel to Help His Guests Personalize Their Stay

Dipesh is developing his own technology - Shashi AI - to allow guests to customize their room settings and overall experience to match their personal preferences.

Guests unlock a door into their own [temporary] living room with their family portrait on a 75-inch TV with the background music of their choice... and the lights in the room are exactly the way they want to have them.

Takeaway: Personalization enhances guest satisfaction and loyalty by making them feel at home, even when traveling.

Put this in action:

  1. Think about how you might offer a “living room in a box”-type experience where guests’ preferences are pre-set in their rooms.

  2. Offer the ability for guests to control room settings (temperature, lighting, entertainment) digitally.

  3. Offer amenities like a sleep concierge to cater to guests’ increasingly high expectations around wellness in travel.

  4. Constantly gather and analyze guest preferences to refine and enhance the personalized service you offer.

And that’s a wrap! This email was handmade for you—it took me 52 minutes to write this. If you found it helpful, I’d be very grateful if you could forward it to a friend or colleague who might also enjoy it.

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A few final things:

  • If you have any thoughts, ideas, questions, or suggestions for Hospitality Daily, please reply to this email. I’d love to hear from you.

  • If you’d like a private community where you can discuss things like this and ask other hotel operators and investors questions that you can’t just Google or ask ChatGPT, the Hospitality Daily Huddle might be a good fit.

  • If you have a product or service that would benefit the hospitality professionals who read, listen to, and watch Hospitality Daily, let’s work together to help you help more people.

Thank you for reading, and I’ll see you here tomorrow.


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