Trippy
Building a Zero to One Local-First Discovery & Booking Ecosystem for a Startup
My Role
Lead Product Designer
Product Strategy
End-to-End UX/UI
Design System
User Research
Beta Testing
Team
C-level Executives
Technical Team
Marketing Team
Timeframe
2024 - 2026 (Ongoing)
Tools
Figma
Github
Notion
OVERVIEW
Trippy is an AI-powered travel platform designed to bridge the gap between "tourist-trap" planning and authentic local discovery. As the lead UX designer, I led the product from a blank canvas to a high-fidelity beta, transforming a fragmented planning process into a consolidated experience for Hong Kong locals and travelers.
PROBLEM
Fragmented, Tourist-Centric Planning
Travel planning today is a "Frankenstein" workflow. Users juggle Instagram for inspiration, Google Maps for navigation, and spreadsheets for scheduling.
For Hong Kong locals, this is particularly frustrating because existing platforms fail to surface:
AUTHENTICITY
Recommendations are often generic and tourist-heavy.
FLEXIBILITY
Rigid 5-day itineraries don't match the need for short, spontaneous weekend outings.
CONTEXT
Tools lack "vibe-based" discovery (e.g., "Where is a good date spot near me right now?").
PROBLEM
Fragmented, Tourist-Centric Planning
Travel planning today is a "Frankenstein" workflow. Users juggle Instagram for inspiration, Google Maps for navigation, and spreadsheets for scheduling.
For Hong Kong locals, this is particularly frustrating because existing platforms fail to surface:
SOLUTION
The All-In-One Travel Companion
Trippy streamlines the entire travel lifecycle by consolidating discovery, community, and booking into one seamless journey. By treating every part of your trip like a modular "Playlist," we replace fragmented app-hopping with a single, intuitive platform.
AUTHENTICITY
Recommendations are often generic and tourist-heavy.
FLEXIBILITY
Rigid 5-day itineraries don't match the need for short, spontaneous weekend outings.
CONTEXT
Tools lack "vibe-based" discovery (e.g., "Where is a good date spot near me right now?").
REFLECTION
End to end design
Building Trippy taught me that great travel experiences aren't about adding more features—they’re about removing the noise. As the sole lead designer, I had to take the high-anxiety chaos of planning and distill it into a modular "playlist" that feels as intuitive as listening to music.
This role wasn't just about the pixels; it was a constant masterclass in collaboration. I worked closely with our CEO and CFO to align the vision with business goals, coordinated daily with the tech team to ensure my designs were feasible, and managed expectations across all our stakeholders to keep the project moving forward.
This project pushed me to balance AI automation with human agency, ensuring the technology handles the heavy lifting while the user stays the author of their own adventure. I’m walking away with a new standard for simplicity: if a tool doesn't turn a complex task into a single, effortless tap, it’s not finished yet.
CORE COMPONENTS
Design System
The design system for Trippy is a comprehensive toolkit that ensures consistency and efficiency across all user interfaces. It includes a set of reusable components, style guidelines, and design patterns that maintain a cohesive look and feel throughout the app.
EMPATHY INTERVIEWS & BETA TESTING FEEDBACK
Instant TripList
We analyzed feedback from over 200 beta testers to identify friction in the travel planning process and validate our curated "vibe-based" discovery model.
200+
active participants joined the
beta launch
50
in-depth interviews
were conducted to
identify UX friction
52.8%
day 1 retention
rate recorded
during the
testing period
RESEARCH & STRATEGIC INSIGHTS
Iterative Evolution
I mapped out every user flow and refined the wireframes through multiple iterations, simplifying the navigation based on direct feedback and usability testing.
LLM Driven Travel
Itinerary Generator
Interactive community
Simple Design
Summary
Triple Korea is our gold standard for high-integration planning. Built-in route navigation eliminates the need to exit the app for Google Maps. Triple keeps users in-app by managing reservations natively.
LLM Driven Travel
Itinerary Generator
Interactive community
Simple Design
Summary
Real-time 'Google Docs-style' collaboration for groups. However, broken booking UX—users are often redirected to external 3rd-party sites, breaking the mobile experience.
LLM Driven Travel
Itinerary Generator
Interactive community
Simple Design
Summary
Trip.com, Klook, Tripadvisor, and Agoda all suffer from information overload and identity crisis. Agoda's AI Review Summarization reduces due diligence time but UI is cluttered. Tripadvisor's booking features are hidden within content.
Instant TripList
Instantly discover the best local spots tailored to your mood. Customize your quick-access themes and dive into community-vetted recommendations with a single tap.
AI Generated TripList
The "Playlist" for Places: Transform your preferences into a complete, actionable journey. Let the AI handle the logistics and build modular itineraries while you maintain full creative control.
Community Hub
Connect with travelers to share insights and coordinate adventures. This space allows you to tap into local knowledge or find companions for your next excursion with ease.
Let's collaborate & create something together!
I'm always up for a chat, especially about design related topics : )
Let's collaborate & create something together!
I'm always up for a chat, especially about design related topics : )
Trippy
Building a Zero to One Local-First Discovery & Booking Ecosystem for a Startup
My Role
Lead Product Designer
Product Strategy
End-to-End UX/UI
Design System
User Research
Beta Testing
Team
C-level Executives
Technical Team
Marketing Team
Timeframe
2024 - 2026 (Ongoing)
Tools
Figma
Github
Notion
OVERVIEW
Trippy is an AI-powered travel platform designed to bridge the gap between "tourist-trap" planning and authentic local discovery. As the lead UX designer, I led the product from a blank canvas to a high-fidelity beta, transforming a fragmented planning process into a consolidated experience for Hong Kong locals and travelers.
PROBLEM
Fragmented, Tourist-Centric Planning
Travel planning today is a "Frankenstein" workflow. Users juggle Instagram for inspiration, Google Maps for navigation, and spreadsheets for scheduling.
For Hong Kong locals, this is particularly frustrating because existing platforms fail to surface:
AUTHENTICITY
Recommendations are often generic and tourist-heavy.
FLEXIBILITY
Rigid 5-day itineraries don't match the need for short, spontaneous weekend outings.
CONTEXT
Tools lack "vibe-based" discovery (e.g., "Where is a good date spot near me right now?").
COMPETITOR’S ANALYSIS
Before diving into the design phase, we began by breaking down the problem into key pain points. We then selected and evaluated popular travel planning and booking platforms apps to understand how they addressed these issues.
LLM Driven Travel
Itinerary Generator
Interactive community
Simple Design
Summary
Triple Korea is our gold standard for high-integration planning. Built-in route navigation eliminates the need to exit the app for Google Maps. Triple keeps users in-app by managing reservations natively.
LLM Driven Travel
Itinerary Generator
Interactive community
Simple Design
Summary
Real-time 'Google Docs-style' collaboration for groups. However, broken booking UX—users are often redirected to external 3rd-party sites, breaking the mobile experience.
LLM Driven Travel
Itinerary Generator
Interactive community
Simple Design
Summary
Trip.com, Klook, Tripadvisor, and Agoda all suffer from information overload and identity crisis. Agoda's AI Review Summarization reduces due diligence time but UI is cluttered. Tripadvisor's booking features are hidden within content.
*Only key insights are shown for simplicity.
Before diving into the design phase, we began by breaking down the problem into key pain points. We then selected and evaluated popular travel planning and booking platforms apps to understand how they addressed these issues.
RESEARCH & STRATEGIC INSIGHTS
Expert-led curation could unlock authenticity
From the competitors analysis, we saw a potential opportunity: if you could combine expert-led local recommendations — like marketplace platforms do for services — with a travel planning workflow, you might deliver higher-quality, authentic travel discovery that travelers couldn’t get from existing products.
Integrated itinerary tools make planning easier, but recommendations are generic and lack local perspective.
(Wanderlog, Triple)
Booking platforms prioritize listings and deals, overwhelming users with options instead of helping them decide what actually fits their vibe.
(Trip.com, Klook, Tripadvisor)
Successful marketplaces prove users value trusted local experts, but this model hasn’t been applied to travel discovery.
(Soomgo)
01 — Planning Without Local Context
02 — Discovery Overloaded by Bookings
Potential Opportunity
Combine expert-led local recommendations with travel planning workflow to deliver higher-quality, authentic discovery
03 — Experts Exist, Just Not for Travel Planning
What broke when we tried to make it real
To evaluate this hypothesis, we explored what it would take to operationalize a consultant-led model through early research, stakeholder discussions, and feasibility analysis. Early research, stakeholder conversations, and feasibility checks revealed structural challenges.
01 - INITIAL APPROACH
Verified local experts curate recommendations for a fee
Consultant Mode for _____
HIGH ONBOARDING FRICTION FOR EXPERTS
Verification processes, resume requirements — too much friction for consultants to join
MARKETPLACE COMPLEXITY SLOWED LEARNING
Two-sided marketplace payment infrastructure would delay MVP by months
SLOW TO SHIP
Complex overhead preventing us from validating core assumptions
PIVOT
Strategic Shift
01 - INITIAL APPROACH
Reddit-style crowdsourcing for real-time local insight
Community focused ____
LOW FRICTION
Anyone can contribute instantly — "Is it raining in Sai Kung now?" gets answered in real-time
TECHNICAL DEBT
Achieves the same authenticity goal through community trust, not payment processing
SLOW TO SHIP
No marketplace overhead means we can validate core assumptions immediately
OUTCOME
Same authenticity goal,
70% less complexity
, and validated in
weeks instead of months
FLOWCHART & WIREFRAMES
Comprehensive flow of the app and the iterative evolution
AI-Generated TripList — Primary Beta Flow
This was the core planning flow shipped in beta, allowing users to generate, review, and refine a TripList based on preferences.
Translated the flow into low-fidelity wireframes, iterating on hierarchy and navigation to reduce cognitive load during multi-step planning.
Instant TrippySpot — Added After Beta Feedback
Beta feedback revealed a need for faster, low-commitment planning. Instant TrippySpot supports spontaneous decisions without heavy filtering.
Designed as a shortcut that trades precision for speed, allowing users to act first and refine later.
Community Discovery — Validated Direction
While still in development during beta, user feedback consistently validated the need for real-time local context, reinforcing our shift toward community-driven discovery.
Translated the community flow into low-fidelity wireframes, prioritizing low-pressure interaction through filters, contextual posts, and optional DMs rather than forced participation.
EMPATHY INTERVIEWS & BETA TESTING FEEDBACK
Instant TrippySpot
We analyzed feedback from over 200 beta testers to identify friction in the travel planning process and validate our curated "vibe-based" discovery model.
200+
active participants joined the beta launch
50
in-depth interviews were conducted to identify UX friction
52.8%
day 1 retention rate recorded during the testing period
Key Insights: Planning Needs to Be Fast, Flexible, and Uninterrupted
1
Planning Isn’t One-Speed-Fits-All
Users wanted two speeds of planning: deep planning and instant decisions
A single, filter-heavy flow failed to support both mental modes
Momentum Dies Outside the App
Context switching (leaving the app to Reddit or Google) broke momentum
Re-explaining their trip context each time felt repetitive and exhausting
2
3
Too Many Choices Slowed Spontaneity
Over-filtering created friction during spontaneous planning moments
Users often didn’t know exactly what they wanted upfront
SOLUTION
The All-In-One Travel Companion
Trippy streamlines the entire travel lifecycle by consolidating discovery, community, and booking into one seamless journey. By treating every part of your trip like a modular "Playlist," we replace fragmented app-hopping with a single, intuitive platform.
REDUCE FRICTION
We make finding hidden gems as easy as adding a song to a playlist.
END APP HOPPING
Consolidate discovery, community, and booking into one ecosystem.
SUPPORT LOCAL CONTEXT
Prioritize "vibes" (Dating, After Work) over traditional landmarks.
Instant TrippySpot
Instantly discover the best local spots tailored to your mood. Customize your quick-access themes and dive into community-vetted recommendations with a single tap.
AI Generated TripList
The "Playlist" for Places: Transform your preferences into a complete, actionable journey. Let the AI handle the logistics and build modular itineraries while you maintain full creative control.
Community Hub
Connect with travelers to share insights and coordinate adventures. This space allows you to tap into local knowledge or find companions for your next excursion.
CORE COMPONENTS
Design System
The design system for Trippy is a comprehensive toolkit that ensures consistency and efficiency across all user interfaces. It includes a set of reusable components, style guidelines, and design patterns that maintain a cohesive look and feel throughout the app.
REFLECTION
End to end design
Building Trippy taught me that great travel experiences aren't about adding more features—they’re about removing the noise. As the sole lead designer, I had to take the high-anxiety chaos of planning and distill it into a modular "playlist" that feels as intuitive as listening to music.
This role wasn't just about the pixels; it was a constant masterclass in collaboration. I worked closely with our CEO and CFO to align the vision with business goals, coordinated daily with the tech team to ensure my designs were feasible, and managed expectations across all our stakeholders to keep the project moving forward.
This project pushed me to balance AI automation with human agency, ensuring the technology handles the heavy lifting while the user stays the author of their own adventure. I’m walking away with a new standard for simplicity: if a tool doesn't turn a complex task into a single, effortless tap, it’s not finished yet.
Triple Korea is our gold standard for high-integration planning. Built-in route navigation eliminates the need to exit the app for Google Maps. Triple keeps users in-app by managing reservations natively.
Let's collaborate & create something together!
I'm always up for a chat, especially about design related topics : )