The AI Experience Economy: How Pintours Is Reimagining Travel with Lou Chatta
On this episode of The Covert Code Podcast, I sat down with Lou Chatta, founder of Pintours, to discuss the AI Experience Economy and how artificial intelligence is transforming the way people travel, explore, and connect with places around the world.
Lou’s company is building an AI-powered orchestration layer for travel experiences, combining transportation, attractions, restaurants, local knowledge, and personalization into one seamless journey. Instead of forcing travelers into generic group tours or expensive private guide experiences, Pintours is using AI to make personalized, guided experiences more accessible, scalable, and affordable.
From Apple Special Projects to AI-Powered Travel
Before launching Pintours, Lou worked at Apple Special Projects, where he helped develop health-focused products and technologies. That experience showed him how to turn subject matter expertise into powerful technology.
The inspiration for Pintours came from something much more personal: his father was a tour guide. Lou saw firsthand how much knowledge local guides carry in their heads and how difficult it is to scale that kind of expertise.
That became the central idea behind Pintours: what if the knowledge of local guides could be digitized and used to create personalized experiences for anyone, anywhere?
Why Generic Travel Experiences Fall Short
One of the biggest problems Lou identified is that most travel experiences are generic. A group tour may work for logistics, but it often fails to meet the needs of individual travelers.
Some people want history. Some want food. Some want romance, adventure, shopping, family-friendly experiences, accessibility, or a very specific pace. A private guide can personalize the journey, but that kind of experience is often expensive and difficult to scale.
Pintours is trying to solve that gap.
How Pintours Works
Lou described Pintours as an AI orchestration layer. In simple terms, it acts almost like a best friend who knows your preferences and can plan the experience for you.
A traveler might say they have only one hour in a destination, want to learn about history, need transportation, and want food afterward. Pintours can then help coordinate the transportation, tickets, storytelling, restaurant reservation, and timing into one connected experience.
The experience can also be adapted for each person. A parent, child, and grandparent could all be in the same location but receive storytelling tailored to their interests.
That level of personalization is where AI becomes especially powerful.
Empowering Local Guides
One of the most important parts of the Pintours model is that it does not simply replace local guides. It creates a way for guides to turn their knowledge into a scalable income stream.
Pintours works with local guides by interviewing them, gathering their expertise, and building AI-powered experiences based on their knowledge. When people use those experiences, guides earn money from the content and expertise they contributed.
This is a powerful example of how AI not only automates but also empowers people with deep local knowledge.
AI, Trust, and the Future of Travel
We also talked about trust and safety, especially as Pintours expands into more global destinations. Lou explained that the platform can help travelers feel more secure by coordinating transportation, tracking experiences, offering support, and creating a more structured journey.
That is especially meaningful in unfamiliar destinations where travelers may not know which vendors to trust or how to navigate the area safely.
AI can help personalize the experience, but it can also help create confidence.
The FIFA World Cup Opportunity
One of the most exciting parts of the conversation was hearing how Pintours is working with FIFA World Cup host cities. The opportunity is not just about what happens inside the stadium. It is about what visitors do before and after the match.
Travelers coming into host cities will need restaurants, transportation, attractions, local experiences, and personalized recommendations. Pintours is building experiences that extend beyond the stadium and help visitors explore each city in a more intentional way.
That is a major shift in how destinations can think about tourism, events, and economic impact.
AI Is Already Powering More Than We Realize
Lou also pointed out that many people may not realize how much AI is already powering the apps, services, and experiences they use every day.
From customer service to logistics, reservations, recommendations, and operational efficiency, AI is increasingly working behind the scenes. Pin Tours is bringing that intelligence into the live experience itself, helping people navigate the real world with greater personalization and ease.
This connects directly to many of the AI and digital transformation conversations I explore through AnnaCovert.com and The Covert Code.
A New Revenue Stream for Guides and Creators
For people who know a city, a neighborhood, a park, a food scene, or a cultural experience deeply, Pin Tours creates an opportunity to turn that expertise into income.
Lou invited people from anywhere in the world to apply as guides or drivers through Pintours.com. Even if someone does not live in a specific city, they may still be able to contribute knowledge about places they know well.
This opens the door for a new kind of experience creator economy.
The Future of Personalized Exploration
This episode was a fascinating look at how AI is moving beyond screens and into real-world experiences. Travel is no longer just about booking flights and hotels. It is about designing meaningful moments.
Pin Tours is showing what happens when local expertise, artificial intelligence, transportation, reservations, and storytelling come together in one personalized journey.
The future of travel may not be about choosing from a fixed itinerary.
It may be about having the experience built around you.
Listen to the Full Episode
Watch the full episode of The Covert Code Podcast featuring Lou Chatta and learn more about the future of AI-powered travel.
You can also connect with Lou on LinkedIn or explore Pin Tours at pintours.com.
And if you’re interested in conversations around AI, authority, innovation, leadership, and the future of digital transformation, explore more episodes and articles at:
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Transcript: The AI Experience Economy with Lou Chatta
Episode: The Covert Code Podcast
Host: Anna Covert
Guest: Lou Chatta
Anna Covert [00:00:04]: Aloha. My name is Anna Covert, and I’m coming to you from my battleship here on the beautiful island of Oahu. This week on The Covert Code, the topic is the AI Experience Economy.
Anna Covert [00:00:14]: My very special guest is Lou Chatta, founder of Pin Tours, who’s building an orchestration layer behind a $1.5 trillion market combining travel, transportation, events, and leisure into a seamless personal shopping experience with partners like Uber and GetYourGuide, as well as working with FIFA World Cup host cities.
Anna Covert [00:00:37]: Today, we’ll be diving into how AI is transforming experiences as we know it. I’m so excited to be having this conversation. Thanks so much for being here today.
Lou Chatta [00:00:53]: Thank you. Thank you for having me. I’m really excited to dive in and tell you more about how Pin Tours is transforming experiences all over the world.
Anna Covert [00:00:59]: Let’s jump in. I like to begin with the CliffsNotes version. Where did you start, and how did you get to where you are right now?
Lou Chatta [00:01:11]: Before launching Pin Tours, I was at Apple Special Projects, working with the R&D team that creates new products behind what Apple ships. I was on the health team, and any product in health that you see today, my team touched.
Lou Chatta [00:01:35]: We worked with subject matter experts and built new technologies around what they knew, specifically doctors and what they had seen in their industry. I spent seven years there and launched a lot of products, including EKG, journals, and many others.
Lou Chatta [00:01:55]: My dad was a tour guide, and I started thinking about how the same things we were doing with doctors could apply to travel. Guided experiences are the most luxurious and best type of experience because someone who knows you personally can show you around and turn something generic into something meaningful.
Lou Chatta [00:02:40]: The problem is that it is expensive and does not scale. Private guide experiences are usually reserved for more luxurious travelers. Most businesses and experiences either do not offer them or offer generic headsets and group guides.
Lou Chatta [00:03:28]: We wanted to solve that. We found that guides have immense knowledge of the world and the places they know, but all that knowledge exists in their heads. We leverage the knowledge they have built over years and build AI around it.
Lou Chatta [00:04:00]: Pin Tours AI works with locals in different areas and digitizes their experience into an AI that works for anyone. Now anyone in the world can use our technology and have a personalized experience anywhere they go.
Lou Chatta [00:04:35]: We are powering drives with Uber, attractions, parks, pop-up experiences, tours, and some really cool work with World Cup host cities. When people come to the U.S. for the World Cup, we are building out experiences in the stadium, outside the stadium, and into the cities, making it fully personalized.
Anna Covert [00:05:19]: That’s amazing. Living in Hawaii, which is all about experience, I really resonate with what you’re saying. Give me an example. If I’m on a cruise and want a private tour in a historical location, how would that customer journey work with Pin Tours?
Lou Chatta [00:07:03]: Let’s say you’re going on a cruise. We partner with cruise lines, so you may see it in the app you booked through. We ask what you’re looking for because everyone wants something different. Maybe you want to dive deep into history, but you only have one hour and you’re hungry.
Lou Chatta [00:07:45]: We take all of that into consideration, including budget and restrictions. We can get you a chauffeur, reserve tickets, build out your tour, personalize the storytelling from pickup to the site, and even book a restaurant afterward.
Lou Chatta [00:08:20]: The experience is personalized to your language, your travel style, and what you care about. Some people want deep history. Some want photos and fun. Whatever kind of traveler you are, we build the journey around that.
Anna Covert [00:09:14]: If I have my daughter and my mom with me, and we all have different interests, can we each have our own custom experience?
Lou Chatta [00:09:39]: Absolutely. Everyone can have their own device and build their own personal experience. We can also create a group experience that ties everyone together, calling out different people’s interests while you are listening together.
Anna Covert [00:10:00]: How are you getting this information? Are you sitting down with experts in each location?
Lou Chatta [00:10:19]: We work exclusively with local guides. We interview them for one or two hours and dive deep into the locations they know, what is special, and what they recommend. Then we build tours and experiences from that data.
Lou Chatta [00:10:40]: The best part is that we are empowering guides. Anytime an experience is used, the guides make money. They own their knowledge, and we are giving them a new way to share it without having to be physically there.
Anna Covert [00:11:13]: That makes me think about people who cannot travel because of age or injury. Is this something that could eventually include virtual experiences?
Lou Chatta [00:11:30]: Today we are focused on real-life experiences, but down the line, we could absolutely explore VR, videos, and immersive storytelling for people who cannot physically be there.
Anna Covert [00:11:58]: Where are you launching right now?
Lou Chatta [00:12:11]: We launched in San Francisco last year and tested the app. Now we are in growth mode, expanding into Honolulu, New York, and LA. Then we want to reach all 11 World Cup host cities.
Anna Covert [00:12:31]: What are your thoughts on AI and the future of experiences?
Lou Chatta [00:12:57]: AI is going to come everywhere. It is not something we should be afraid of. We should look at ways to use it to our advantage. In San Francisco, we already have self-driving cars and AI-powered experiences. AI is here.
Lou Chatta [00:13:35]: We are careful about how we introduce it. We focus on personalization and empowering tour guides. It is the same experience you would have with a human tour guide, just more scalable.
Anna Covert [00:14:10]: What about AI hallucinations or feedback loops? How do you improve the system?
Lou Chatta [00:14:29]: After every experience, we ask customers to review it. Every time we get feedback, the system gets better. We learn what you like and don’t like, so the next experience is better. We
