AskMike.ai
AI-powered event and travel planner that generates personalized itineraries based on user preferences.
Role
Founder / Product Manager
Key Skills Used
AI product design • User workflow design • SaaS monetization • Automation systems
The Problem
People planning events or trips must search across multiple apps for venues, schedules, transportation, and budgets. This fragmented process is time-consuming and frustrating. There was no single tool that could take someone's mood, preferences, and location and turn it into a complete, ready-to-execute plan — leaving most people either over-planning for hours or defaulting to the same places every time.
The Solution
AskMike uses AI to generate complete event or travel itineraries in seconds, combining venue discovery, scheduling, budgeting, and transportation into a single plan. Users tell Mike their preferences once, and from that point forward they get personalized recommendations that improve over time — with 3 curated options at every stop, real-time weather, parking info, and shareable/exportable plans built in.
Planning Time
Hours across 5+ apps
Seconds with one prompt
Personalization
Generic search results
Profile-based AI recommendations
Coverage
Local only
Worldwide with 100+ languages
Product Strategy
- AI itinerary generation as the core value — not search, not listings
- Personalized user preference profiles to improve recommendations over time
- Event discovery engine powered by real venue data (Google Places + Ticketmaster)
- Integrated transportation and logistics intelligence (weather, parking, travel times)
- Budget-aware planning across all tiers (Budget Friendly to Luxury)
- Freemium monetization: 2 free experiences → Starter ($9.99/mo) → Unlimited ($19.99/mo)
- B2C and B2B coverage: personal nights out, group events, full business event management
My Role
As founder and product lead, I:
- Defined the product vision and identified the market gap in fragmented event planning
- Designed all AI workflows — from preference capture to itinerary generation to refinement
- Created the feature roadmap and prioritized by user impact vs. build complexity
- Built the complete user experience flow from onboarding to export
- Designed the subscription monetization model and freemium conversion funnel
- Integrated real-time data sources: Google Places, Ticketmaster, weather APIs
- Shipped and iterated based on real user feedback
Product Decisions
Why AI itineraries instead of search?
Users want recommendations and a complete plan, not just a list of venues. Search puts the burden back on the user. AI removes it entirely.
Why 3 options per stop?
One option feels limiting; unlimited options create decision fatigue. Three is the sweet spot — enough choice without overwhelming the user.
Why user preference profiles?
The AI improves recommendations over time based on user behavior and preferences. Profiles transform AskMike from a one-time tool into a sticky, personalized companion.
Why a freemium model vs. subscription-only?
Letting users experience 2 full itineraries for free removes friction and builds trust before asking for payment — critical for a new AI product.
Screenshots & UI
Scan to try it live
Additional UI screenshots coming soon.
What I Would Improve Next
Future improvements for AskMike:
- Deeper personalization models — AI that learns from past itinerary ratings and behavior
- Improved venue data integration with real-time availability and reservation booking
- AI-generated event themes and mood boards for parties and celebrations
- Group collaboration planning — shared itineraries with voting on options
- Native mobile app for seamless on-the-go planning
- Social sharing — let users share and discover itineraries from others