New Travel Booking Site Upside Will Give You Back At Least $150 Per Trip

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Free VIP Pass for Upside

Upside is a new travel booking site that will help you save money and gives you back gift cards for business travel. It’s brought to you by the founder of Priceline, it was just announced today, and it debuts in September.

    Sign up today as a pre-launch VIP and you’re guaranteed $150 back on every trip through the end of the year. You just provide your email address and answer a few multiple choice questions and your VIP status is locked-in.

About a week and a half ago I had breakfast with Priceline’s and Upside’s founder, Jay Walker, to talk about the new idea. And I agreed that my blog would be one of a handful of places where you can get a free early ‘VIP pass’ to the site which special benefits.

That Business Trip May Get a Bit Better

Upside is aiming at unmanaged business travelers; people who book their own business travel can save their companies money and benefit personally at the same time by monetizing their flexibility.

With Upside, business travelers can turn flexibility on their flights and hotel into 100s of dollars in free Gift Cards to leading national retailers of their choice — and companies get 5% to 15% in immediate travel savings — on every trip!

Business travelers book the flights that make sense, and stay wherever makes sense, without respect to cost as long as their trip is ‘within policy’. And business travelers game that, too.

Say they have to book the least expensive airfare, and their preferred airline is more expensive. “The meeting isn’t quite confirmed yet,” wait a few days to book so you’re within 7 or 3 days of travel, and the price of all options has gone up but your preferred airline isn’t more expensive anymore.

Upside turns this on its head. It provides a financial incentive to travelers to choose less costly options — paying you in gift cards for your flexibility.

  • How much would it be worth to you to take a late night flight instead of the one after your meeting?

  • What if you flew into a different airport?

  • How much would it be worth to fly the night before a trip? Or to stay the weekend after a business trip and explore the city — if it didn’t cost more, in fact even put money back in the traveler’s pocket?

  • How much would it be worth to stay at a nearby hotel instead of your conference hotel or the one closest to your meeting — since you can Uber anyway?

Maybe you’re not flexible along any of these dimensions on a given trip. But most of us have flexibility at some price. Would you fly into a different airport for a million dollars? Sure. For $1? Absolutely not. The amount you’d take though would likely change based on the circumstances.

These are decisions business travelers wouldn’t usually make. And maybe they still won’t. But the Upside mobile app will prompt you with questions about your flexibility along with how much they’ll pay you to choose the more flexible option. So you can figure out the margin at which you’re flexible and monetize it.

All of the trips they sell are air and hotel packages. Nothing is opaque. You see the full itinerary before you book.

By selling packages they’re able to provide better deals: they aren’t displaying just the price of the hotel so they aren’t bound by requirements not to undercut a hotel’s own pricing.

  • You specify flight-time windows
  • You pre-approve which travel providers you’re willing to use
  • You see full travel plans in advance. You can buy what they suggest. You can make changes before you buy. Or you can change your mind and walk away. So why not try it out?

You add up the flexible choices you’ve made for total savings on a trip. They’ll provide backup to give your finance department showing the company saved, too. And you pocket gift cards — if you sign up as a pre-launch VIP you are guaranteed a minimum of $150 per trip through end of year. They make business travel rewarding, not just grueling.

How it Usually Feels

What’s more, these aren’t opaque “you’re stuck with it” bookings. Priceline was great for leisure travel but business trips change. They’ve got 24 hour customer service to make changes or cancel a trip.

Upside expects to offer pre-launch VIPs a referral program to earn gift cards when the people they refer book trips through the site as well. This is my referral link, I’m told people who sign up now with it may get their own once the site goes live.

If this works as promised, you’re going to be looking to take more business trips and your employer will be happy to send you too.

There’s literally no reason not to sign up to lock in the chance of a great payout come September.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. […] New Travel Booking Site Upside Will Give You Back At Least $150 Per Trip by View From The Wing. Interesting concept, but usually my work wants me taking direct flights/staying at the closest hotel as it gives me more time to actually work and I’m better refreshed when I do have to work – don’t think they would go for this idea but it’s difficult to tell. Not a big fan of signing up for things I can’t actually see in action, but the $150 offer might be enough to get me over the line. […]


  1. Do you still earn points & miles within your respective loyalty programs, since this would still be a 3rd party booking?

  2. “They make business travel rewarding, not just grueling.”

    So I suppose you could use the gift card to enroll in TSA Pre?

    I do think the implication that this program will allow one to have a better airport experience is a bit misleading…

  3. My main question is how great is their support service going to be when something goes bad. We’ve all heard about bad experiences trying to rebook canceled/delayed/missing hotel reservations or flight reservations when they were booked through an OTA like Expedia and not directly through the company.

  4. @Juno that’s a great question and I’m not prepared to claim to know the answer until we see it in action. Jay tells me, however, that he’s investing in real customer support because the lifetime value of a customer making business travel bookings is high. That means the business model allows high touch support, and demands it since it’s too costly to lose someone that’ll book a few trips a year through him.

  5. @Jeff Note I said reward not JUST (ie only) grueling, I did NOT say rewarding INSTEAD OF grueling.

    It wasn’t my intention to suggest the travel experience itself gets better. I don’t say travel gets LESS grueling.

    Instead what I mean (and I think I said) is that you’re willing to suck up business travel when there are additional benefits for it. I’m sorry I wasn’t clear enough for that message to come through to you more crisply.

  6. @Ritz you definitely still earn airline miles, this isn’t an opaque priceline booking. I don’t think you’re going to earn hotel elite credits because you are booking through an OTA. So if you’re hotel chain-loyal and status-dependent this may not be the solution for every trip. But it could still be the solution for trips where you aren’t going to stick to your preferred chain.

  7. If he is reading this, they definitely need to figure out a way to make the hotel bookings elite qualifying. With matches, I have status in several chains, so *which* chain isn’t particularly important as long as I’m getting my elite benefits.

  8. @Justin both Hyatt and Marriott recognize elite status on OTA bookings, they just do not provide credit towards elite status in my experience.

    For me this won’t make sense on Hyatt and Starwood stays. But I’d be open to it on Marriott/Hilton/IHG stays. I’ve had ~ 5 stays this year outside my preferred chains. I need a strong value proposition to do this still. But I’d be willing to go to the Upside app and price that.

  9. @Gary, did Jay mention which retailers the Upside gift cards would be redeemable at? I’m mostly an Amazon shopper nowadays, and some retailers don’t move the needle for me. On the other hand, the very fact that shoppers have moved online probably presents a good opportunity for Upside to buy these gift cards (from retailers) at a decent discount, so perhaps this is a win-win opportunity for everyone. Anyways, sounds like it’s worth a shot, thanks for the link.

  10. I just signed up through your link and within 5 minutes from signing up, I got a robodial call, soliciting my business for a $200k loan. Not cool.

  11. Gary, could you contact them about it? I’m picky about who I give my number to and I hadn’t received a solicitation like that before — particularly as it was referring to “my business” being eligible for the loan.

  12. @gnutello if i had even two people reporting this, or if i had gotten this myself, i might have a theory that this was somehow linked but it seems exceedingly unlikely.

    besides i don’t know of any lists that get exported and sold in real-time like that. has to be unrelated.

  13. Looks like a way to use a Priceline model to get the hotel and give you part of the savings in someone’s gift card

  14. The site gets stuck “loading” at the first welcome screen where you enter your email address. Perhaps the VIP offer is expired and the landing page is still visible (yet disabled)?

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