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.
Three vectors converged in the last twelve months. Twelve months ago, this stack didn't exist. Twelve months from now, the default agent will be picked.
Sonnet 4.5 + Opus 4.6 cleared the trust threshold for multi-step tool calling. Booking-grade reliability on $4K transactions finally works. We route Haiku/Sonnet/Opus per query.
Search, book, hold, change, cancel, seats, bags. 300+ carriers including AA, Aeroplan, Lufthansa, through one API. Last year the rails were partial; today they're complete.
Free Account Access tier across 609 loyalty programs. Real-time balances + status without per-user scraping. Without this, every points agent was DOA on cost-of-data.
Four verbs, one chat. The flow below is a single transaction: ask, route, score, book, no tab-switching, no expertise tax.
Premium travel cohorts (18–35, Bilt generation) are creator-led and AI-search-first. We own both surfaces while OTAs burn SEM on the old one.
Real before/after redemptions on TikTok, YouTube, Instagram. Every video is a product demo. Flight-review creators (the new MrBeast lane) seed launch.
Travel creators demo Upway with their real portfolios. Authentic, verifiable, shareable. Harry runs the program (8 yrs B2B partnerships).
stack.upway.travel — 15+ cabin pages live with Schema.org JSON-LD. When ChatGPT, Perplexity, Google AI Mode answer points questions, we become the cited source. OTAs can't compete here without cannibalizing SEM.
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 clone the chat; the tool layer takes years.
Duffel for cash + NDC (300+ carriers). AwardWallet OAuth for live balances (609 programs). Seats.aero for award space (30+ programs). Nobody else has all three. Layla and Mindtrip have none; Point.me only has Seats.aero.
Airlines, aircraft, loyalty rules, transfer maps, cabin configs, card benefits, IRROPS recovery, secret phone numbers. Structured data LLMs can't learn from the open web.
"Don't book now. 85% probability seats drop Tuesday." Predictive intelligence no one else can build , 6+ months of our own award-space data required.
Every interaction deepens the moat. The agent learns your portfolio, your destinations, your risk appetite. Switching cost climbs daily.
Business class MEL→NRT: Upway finds the 100K-point door, not the 1M one. Real-time comparison across every program.
Every search returns the cheaper currency — today. Not what an affiliate publisher earns commission on.
“Fly Tuesday, save 30K points.” The agent recommends when to move, not just where.
Book a flight, Upway creates the trip. The agent then suggests neighborhoods, restaurants, transit, accommodation , aware of your spend & balance.
“For Tokyo, run AmEx on groceries: 5x MR → SQ KrisFlyer transfer window opens Friday.” Cross-card, cross-program reasoning.
“Maddie just booked LAX→TYO biz for 95K points.” Friends see it, ask how, sign up. The social proof IS the marketing.
Every adjacent player owns one slice. We're the only one wiring cash, points, and trip management under one chat that executes.
| Player | What they do | Fatal flaw | Result |
|---|---|---|---|
| Layla.ai | Chat recommendation engine | Doesn't execute | Hands you off to OTAs |
| Mindtrip | AI travel agent ($22.5M raised) | Cash-only, OTA-routed | Booking.com with a chat skin |
| Hopper | Consumer travel + B2B | Retreated to B2B (90% of rev) | Consumer business gutted ex-NA |
| Point.me | Manual award concierge | $200/pax, award-only, slow | Expert-required, doesn't scale |
| The Points Guy | Ad media | Conflict of interest | Recommends highest-paying cards |
| ChatGPT / general AI | General-purpose chat | No live booking rails | Fabricates flights, can't transact |
| Upway | Agentic OS for travel | None | Plan, book, redeem, manage. One chat. |
Cash fares via Duffel. Commissions cover servers, LLM, APIs , CAC effectively zero.
Every points result, transfer paths, agentic execution, stack optimization. vs. point.me's $200/pax concierge , "$10 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 , $10 to save $400 is an impulse, not a decision.
Bonus: the $10 sub keeps Upway on the home screen between trips. Solves the OTA deletion problem , we still earn the cash commission six months later.
Three revenue engines stacked: Pro subscriptions compound, card affiliate kicks in at scale, B2B licensing finishes the curve.
$10/mo, ~100% margin, compounding monthly cohorts.
$150–250 per approved card. $2B+ X-factor at scale.
Banks & issuers. $5–20M ARR per top-10 contract.
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.