The Odyy App – Don’t show me options, show me a plan.

Leverage AI/ML to create unique travel plans while seamlessly integrating multiple recommender systems and drastically reducing booking and payment friction.

Vision & Value Proposition:

Leverage AI/ML to create unique travel plans while seamlessly integrating multiple recommender systems and drastically reducing booking and payment friction.

The Problem:

Most people love to travel, love to find new experiences, and love to see their friends & family… but most people also hate to plan.  It typically comes down to either:

  1. There are so many available options and so many niche service apps that “choice overload” sets in and nothing ends up happening; or,
  2. There are too many cooks in the kitchen and so many opinions that a group cannot come to a consensus; or,
  3. One person ends up taking on the time intensive (and thankless) role of researching, proposing, and coordinating all aspects of a trip – many times resulting in a suboptimal experience.

Target Market & Opportunity:

Digital travel sales in the US passed $200B in 2019 and were (in 2019) forecasted to increase to ~$220B in 2021.  Of course, the global pandemic has shaken up everything travel-related, which makes now the exact right time to assemble a team, formulate a strategy, and streamline the travel planning process.  Building a AI/ML-centric platform from the ground up, while taking into account how the next generation will travel is a market opportunity that may never come again.  This could be a chance to emerge from the pandemic haze with a product that appeals to the digital-native generations that trust technology and don’t want to waste their free time researching, scheduling, and arranging itineraries that an algorithm can do for them.

Personalized search results from AI for travel sites is already in use; however, there’s an opportunity to implement even more advanced capabilities at a deeper and more personal level for the user.

The target market consists of millennials and older Gen-Zs that love to travel, love to eat, and truly value an experience more than material goods.  The early adopters are likely young professionals that live in cities away from friend-groups and family.  The solution could also target any type of group booking scenario – weddings, reunions, conferences, events.

The Solution:

  1. An application (“Odyy” for “odyssey”) that gathers as much data as possible from travel/tourism websites, events, maps, accommodation, transit, recreation, social media, restaurant, and weather websites to build extensive and up-to-date database on what’s new, what’s available, and when things are happening.
  2. Users input detailed preferences, past experiences, available dates (calendar sync), budget, trip type, loyalty programs, etc. (educating the user that the more data they input, the better the results is key).
  3. Algorithms compile and match inputs with the database to create start-to-finish unique travel itineraries for users.
  4. Then, the interface allows users to tag aspects of the initial plan that they like, dislike, or what to see more about, and then refresh to iterate further on their agenda.  Think Airtable/Asana had a baby with Kayak, TripAdvisor, Resy, and Bandsintown.
    1. Instead of a vertical list of options for dozens of flights or hotels or restaurants, the platform provides an easily digestible proposed timeline that allows the user to visualize each element of the plan, chronologically.
    2. A user sees when they have to leave the house to get to the airport, when their flight takes off, when they land, when/where they check in, where they’d be booked for 1st night’s dinner, and so on.
    3. As the user scrolls through the timeline, they have the option to click on an individual element and iterate (change restaurant rec or hotel location) by either asking to find the next best option and/or answering additional preference questions.
    4. Could set up preferred apps to link to agenda & only show relevant options (e.g. California, from 12/1-12/7, only show options from Delta, Lyft, Marriott, & Resy).
  5. Once the itinerary is set, the application can enable one button booking for all reservations.  This is a key aspect of the platform – seamless integration of payment and reservation technologies (a hybrid FinTech & Travel planning app).

Additional features could include:

  • Share your agendas with friends and have them opt-in.  Rates automatically adjust based on confirmed participants (either from group-rates or splitting costs).
  • Partner with insurance companies to provide discounted travel insurance based on fully book itineraries.
  • Reminders for cancellation deadlines, new booking opportunities during the trip (agenda audibles), etc.
  • Highlight special events with easy one-click itineraries (Super Bowl, Macy’s Day Parade, NYE, San Fermin, etc.).
  • Build speech activated feature so that you can log, revisit, and bounce ideas off of the application to continue planning as ideas pop into your head.  “ODYY, add Frenchette to my next New York trip.” or “ODYY, where and when is the next chance for me to go camping for a weekend with John & Jane?”
  • Users create a repository to store & track all of their travel history in a single place.  Past itineraries are easily shared with friends, family, or other community members.

Create user value with a library of unique data points (examples):

  • What’s the most carbon-neutral agenda?
  • Only show me vegetarian restaurants.
  • Only show me minority-owned businesses.
  • Only show me local businesses.
  • Only show me COVID-19 certified safe agenda.

Non-booking user engagement:

  • Even when not looking to immediately book a trip, or not actively planning with dates in mind, users can store wishlists for destinations, restaurants, experiences, and events.  The platform can then learn from their wishlists and other detailed preference inputs when to propose a new trip,
  • The platform will learn from social media and traditional influential travel sites (Lonely Planet, Travel+Leisure, etc.) about what destinations or experiences are trending or “hot.”  Introducing new ideas to users will create value.


  • Need for a highly technical product individual experienced with building apps and/or platforms with AI/ML integrations.
  • Need for an experienced travel industry individual
  • Need for an experienced FinTech/InsurTech individual
  • Need for an experienced DTC design & marketing individual


There are tons of booking apps for all aspects of the travel experience, but not many utilizing AI for custom itineraries that can be easily manipulated or iterated upon by a group, and none that I’ve seen with one button reservation for transit, accommodation, and food.  In 2019, an AI travel recommender app, Utrip, abruptly stopped operations amidst many challenges including stiff incumbent competition from big travel sites (TripAdvisor, Expedia, etc.) and tech giants with travel planning capabilities (Google, Airbnb, etc.), as well as having success measured against other AI-specific startups.  Learning from Utrip, the focus of such a DTC play should appear to be a travel app to consumers, but present as a FinTech app to investors.  As important as the AI/ML features, the integration of seamless booking & payment is key.


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Participant comments on The Odyy App – Don’t show me options, show me a plan.

  1. I really like this idea, Ryan, but my knee jerk reaction is to point out the incredible amount of integration and api work that would need to be done. You’d really need to have a very talented group of tech people with you to pull this off. How would you go about getting companies like Delta, Hilton and Lyft to work with you?


  2. Thanks for the feedback, Christina!

    I absolutely agree – full integration with tier 1 partners would be a beast to pull off, and would likely be the last piece of the value-offering for the product. Before that stage, I would absolutely need highly proficient co-founders/team members to help develop the system, as well. This is admittedly a high-level and ambitious idea but I can envision a prototype that works with minimal integrations (maybe even dummy data) that can demonstrate the idea and the technology backing it up. I would want to show investors an app/site that makes the planning process intuitive, easy, and visual. Then, hopefully, with investor backing and a team, take that to a few key partners to integrate their data into the system. Pilot it with small groups, first, then open to a larger population, etc.

    Still – it’s a half baked idea, and I’m 100% sure there are many aspects that I’m not thinking of or not considering, but that’s what I need feedback & mentors for!

    Thanks, again,

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