Chase to Hyatt? Bilt to Aeroplan? Amex bonus 30% this month?
Award seats are scarce, airlines hide their charts, dates shift hourly.
Same plane, different airline, totally different seat. No one tells her.
Plan. Book. Redeem. Manage. The Adviser is the canonical surface; Intelligence and Loyalty are read-strategies over the same 39 chat tools.
Chat is the product. Every capability ships as a tool the agent reasons across , transfer paths, route intelligence, cabin quality, live availability, portfolio analysis. 162 routes, 210 components, 37 PG tables under the hood. The user sees one conversation.
Every recommendation verified against live data. No claims without a source. Trust is the product.
"Your Chase points" not "UR balance." "Lie-flat bed" not "J-class." Zero jargon, zero learning curve.
Deals, devaluations, transfer bonuses , personalized to YOUR portfolio. The value finds you.
Know before programs change their charts. Transfer your points while they're still worth more.
Amex, Chase, and Citi run 30-40% transfer bonuses. We surface them instantly so you never miss one.
See the real dollar value of every point across all your cards and programs. Updated in real-time.
Trip delay insurance, purchase protection, lounge access , benefits you're paying for but not using.
How well you're using your portfolio. Gamified progress toward unlocking your full potential.
Tool-using LLMs crossed the accuracy bar for $4K transactions inside the last 18 months. Chat-native commerce went from demo to default. We have an 18-month window to be the consumer surface before the rails crystallise.
Sign-up bonuses at all-time highs. More points in circulation than ever. The problem grows faster than solutions.
Tool-using models (Sonnet, GPT-5) just crossed the accuracy bar for $4K transactions. Chat-native commerce became viable in the last 18 months , we're the consumer surface.
Premium travel demand is up; the search experience hasn't kept pace. Reasoning over structured data is finally possible.
Card issuers have a burn problem. $150B sits unredeemed on their balance sheets as ASC 606 liability. We're the consumer-facing fix , and the obvious white-label.
Four verbs, one chat. The flow below is a single transaction: ask, route, score, book, no tab-switching, no expertise tax.
Show someone their 80K points are worth $1,800 instead of $400, they text three friends. That's the whole TikTok.
TikTok / YouTube / SEO. Real "before & after" optimizations. Every video is a product demo.
Travel creators demo Upway with their real portfolios. Authentic. Verifiable. Shareable.
Free tool. Passively captures data. Seeds the flywheel. Converts to paid.
Any competitor can clone the chat. The moat is the four layers underneath, each one taking years to build, every one of them deepening every day a user is on the platform.
Chat is the product. 39 tools the agent reasons across , portfolio, availability, transfers, cabin quality, route economics. Every dashboard is a render of the same tool layer. Competitors can copy the chat; the tool layer takes years.
Airlines, aircraft, loyalty rules, transfer maps, cabin configs, card benefits. Structured data LLMs can't learn from the internet.
Chrome extension captures award availability passively. Building toward real-time global award inventory index.
"Don't book now. Our data shows 85% probability seats drop Tuesday." Predictive intelligence no one else can build.
| Player | Model | Fatal Flaw | Result |
|---|---|---|---|
| The Points Guy | Ad media | Conflict of interest | Recommends highest-paying cards |
| NerdWallet | Comparison | Not award-travel focused | Optimizes sign-ups, not usage |
| AwardLogic | Manual search | Requires expertise | 80% of users can't use it |
| Card Issuers | Proprietary | Single ecosystem | Will never cross-optimize |
| ChatGPT | General AI | No live data | Fabricates flights |
| Upway | Adviser + booking | NONE | Personalized. Grounded. Trusted. |
Cash fares via Duffel. Commissions cover servers, LLM, APIs , CAC effectively zero.
Every points result, transfer paths, agentic execution. Half of point.me's price , "$5 to save $500" is an impulse, not a decision.
Free user sees the $450 cash fare. Below it: a blurred “I also found this for 20K points + $45.” The math is undeniable , $5 to save $400 is an impulse, not a decision.
Bonus: the $5 sub keeps Upway on the home screen between trips. Solves the OTA deletion problem , we still earn the cash commission six months later.
Kyle Fitzsimmons
CEO · Tech · Product. Bootstrapped Cosmo to $2–3M ARR (5,000+ guests, 10-person team) over 7 years. Board roles at ASTRA + Bendigo Health Foundation. Associate Degree Aviation · RPL pilot · plane-obsessed.
Harry Fiske-Kealy
Brand · Creative · Commercial. $200K commission at Fuji Xerox in a dying B2B market, no university. Founded Toke Collective. Owns brand identity, design, social, and commercial GTM.
kyle@upway.travel
BUILDING THE OPERATING SYSTEM FOR TRAVEL.