Upside raises $50 million as Priceline founder-fronted discount service goes live

Huge investment sum to the tune of $50 million going into Upside – on the day Jay Walker officially unveils the site.

The startup (TLabs here from June 2016) has been in beta testing for months but used today’s launch to disclose that it has raised the money from a group of investors including Red Ventures and Leucadia National Corporation.

Upside works by rewarding business travellers with gift cards (typically $100 or $200), if they are willing to be flexible in their travel plans and save costs (typically 15%) for their companies by buying flight-and-hotel packages.

Walker is best known for his role in creating Priceline and the name-your-own-price model for hotels in the late-1990s.

Upside negotiates opaque discounts from suppliers. It only sells packages, so the customer doesn’t know whether, say, the hotel or the airline is the supplier doing the discounting off of publicly available rates.

But the traveller can select which airlines and hotels it is willing to use.

Unlike with the original blind-bidding model of Priceline, Upside reveals the name of the hotel and airline prior to asking a customer to purchase, enabling the customer to vet its quality via TripAdvisor, Routehappy, or another source.

The company’s data analytics system ingests 500 million records a night from Sabre and Expedia to provide a comprehensive shadow system of price-comparison data via a mobile app and website.

The gift cards cover purchases in US retailers such as Amazon, Nike, Home Depot and Target.

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Kevin May

About the Writer :: Kevin May

Kevin May was a co-founder and member of the editorial team from September 2009 to June 2017.



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  1. Martin Cowley

    Great Idea, Great Team= Great company. Watch this space. The 50 will be 500 in no time!!!!!


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