3 Trips I Booked for Strangers Last Week (and Why I’d Do It Again)
Every week, I help people trade points for bucket-list travel—sometimes friends, sometimes clients, and sometimes total strangers. Why? Because watching someone go from “I didn’t think this was possible” to boarding a lie-flat flight is the best dopamine hit in the world.
The Mission That Outpaces the Model
UpNonStop is a business. But sometimes, the mission comes first.
Every so often, someone shows up with a battered suitcase of points, a dose of desperation, and a glimmer of potential—and that’s when I know it’s time to jump in. Because nothing beats the satisfaction of taking someone from chaos to calm, from couch-bound daydreams to champagne in first class. Especially when the whole thing costs them nothing out of pocket and drops them in a seat worth five figures.
This past week, three redemptions reminded me why I keep showing up. They’re proof that points aren’t just currency—they’re keys. To adventure. To healing. To relationships. To freedom.
Let’s break them down...
The Honeymoon That Almost Didn’t Happen
Who They Are
A couple in their 30s—working professionals who just threw a modest wedding and were about to skip a honeymoon. They had budget fatigue. They felt like indulging would be irresponsible. So they stayed home and poked around on the Amex Travel Portal. It offered them coach seats to Cabo and a budget hotel.
Their Points Situation
They had 240,000 Amex Membership Rewards points. Not bad. But also not enough if you don’t know how to use them.
What I Did
I transferred 170,000 of their Amex points to ANA, one of the best ways to book Star Alliance business class, and locked in two lie-flat seats from the U.S. to Bali, routed through Tokyo to Jakarta.
Then I booked them 7 nights in Ubud at a stunning Hyatt Category 6 property using 180,000 Hyatt points. They didn’t have those Hyatt points, but a friend did. A quick referral and a bit of coordination made it happen.
Retail Value
Roughly $17,000 between flights and hotel.
Why It Mattered
They were ready to trade their honeymoon for savings. I gave them both. They clinked glasses at 35,000 feet and sent a video from their lay-flat seat, grinning with disbelief. That’s not just a redemption—that’s a memory they’ll talk about for decades.
The Freelancer’s Escape
Who She Is
A solo creative who joined a TikTok Live. She was emotionally wiped, professionally burned out, and convinced her points weren’t worth using.
Her Points Situation
She had ~90,000 Capital One Venture miles. She’d never transferred a single one. She thought they were worth “maybe $900” if she cashed them out. She’d never left the country on her own.
What I Did
I spotted availability on TAP Portugal, transferred her CapitalOne miles to Avianca LifeMiles (an underrated but powerful transfer partner), and booked her a roundtrip lie-flat seat from JFK to Lisbon.
She left three days later.
Retail Value
About $3,400.
Why It Mattered
She messaged me from a rooftop in Alfama, glowing. “No one in my family has ever traveled solo,” she said. “I didn’t think I could.”
When she boarded that plane, she wasn’t just taking a trip. She was rewriting her story. That’s why I help. That’s the magic.
The CEO Who Had No Time to Plan
Who He Is
A busy entrepreneur with a 12-person company. He spends about $70,000 a month on his credit cards, yet had never redeemed a single point. His wife was planning their 20th anniversary, and he was too overwhelmed to help.
His Points Situation
He had 900,000 Chase Ultimate Rewards. Every single one untouched. He’d only used points for 1.5% cash back and had no idea what they were really worth.
What I Did
I transferred points strategically: first from Chase to British Airways—one of the lesser-known but most powerful workarounds for premium flights.
I booked first-class flights to Tokyo on Japan Airlines—arguably one of the best ways to cross the Pacific. Then, seven nights at the Park Hyatt Tokyo, which is luxury on another level.
Retail Value
North of $28,000.
Why It Mattered
When he got back, he told me, “This felt better than my year-end bonus.” He didn’t just wow his wife—he experienced true luxury, felt like a travel wizard, and finally saw what all that business spend could unlock.
Now? He’s a client. And a convert.
Why I Still Do This—Even for Free Sometimes
Because most people are taught to treat points like coupons.
They use 100,000 points to get a $1,000 domestic flight—or worse, they cash them in for $750. They don’t realize those same points can put them in a $10,000 seat to Asia or a villa in the Maldives.
Because the points game is stacked against the average user. It's designed to confuse you. And because I remember what it felt like to think travel like this was out of reach.
I do this because I’ve seen what it means to someone to realize they can. That a dream doesn’t have to be delayed. That first-class travel isn’t reserved for influencers and finance bros.
I do it because it’s a skill I’ve built that actually helps people. And every once in a while, when someone shows up with the right mix of need, hustle, and trust—I drop everything and help.
Because this is more than a business. It’s a mission.
Where We’re Headed Next
Yes, UpNonStop is growing. Our B2B clients get this level of concierge redemption at scale. Small businesses, founders, and remote teams are finally turning spend into reward—with clarity, not confusion.
But I’ll always make time for the late-night DM. For the freelancer who needs a lifeline. For the burned-out bride who’s about to give up on the honeymoon. Because those are the stories that matter most.
They remind me why I started. Why I’ll never stop.
And why your points—yes, yours—are worth more than you think.
Want Your Own Redemption Story?
If you’ve got points, I can tell you what they’re worth. I can show you how to stop settling and start flying further, sleeping better, and collecting memories that don’t cost your savings.
Reach out. DM your balances. Join a Live. Or just keep reading.
Because next week, the redemption story I write might be yours.
