Lola.com

» see lola.com as it lived, on the wayback machine

~ the goodbye ~

Paul English sold Kayak to Priceline for 1.8 billion dollars in 2012 and started Lola three years later with Bill O'Donnell, who had been Kayak's chief architect. The pitch in 2016 was almost a rejection of what Kayak had been. Kayak returned four hundred itineraries and left you to sort them out. With Lola you opened an app and typed at a travel agent who was an actual person on an actual shift, and they came back with a hotel.

Investors liked it enough to put in twenty million dollars in April 2016 behind General Catalyst and Accel, then a larger round that December with Charles River Ventures leading and both GV and Tenaya Capital writing five million dollar checks. The consumer version never found the volume it needed. By the time the Series C landed in March 2019, thirty-seven million dollars with General Catalyst and Accel back in, Lola had turned itself into corporate travel software sold to small and mid-sized companies, which is a business with contracts in it rather than a business with tourists in it.

That worked until March 2020, when business travel stopped existing. Lola's revenue was a percentage of trips that were no longer being taken, and no amount of runway fixes a product whose category is closed.

The response was a pivot that read well in a press release. If the company already sat inside the corporate spending flow, it could handle all employee spend rather than just the travel part, so Lola rebuilt itself as expense software over 2020 and formally declared the fintech turn in February 2021. Mike Volpe, a HubSpot veteran, was running it as chief executive by then.

~ the chronicle ~

~ from trips to receipts ~

A travel company becoming an expense company during a pandemic is a reasonable move on paper and a very hard one in practice, because the buyer is different. Travel software gets bought by whoever owns the travel policy. Expense software gets bought by finance, which already has an incumbent, usually one it hates but has integrated with its general ledger.

The partnership layer went first. On 23 September 2021 Skift reported that American Express Global Business Travel had broken out of its arrangement with Lola, which for a company of that size is less a setback than a diagnosis.

~ whose tool it was ~

I have never once chosen the expense tool. Nobody on the engineering side of any company has. It arrives as an email saying that from the first of next month receipts go in a different place, and you learn the new one badly, and three years later another email arrives. Lola's whole existence sat on the other side of that email, in a procurement conversation I was never in and would not have been invited to. The honest distance here has nothing to do with Turkey. It is that I was the thing being administered.

~ the two september dates ~

The wind-down had a schedule. Lola Spend went dark on 15 September 2021 and the travel product followed on 17 September. The office near South Station closed and the corporate contracts were wound up, with refunds going to clients who were owed them, which is a more orderly exit than most startups of that size manage.

Capital One announced the acquisition on 8 October 2021, three weeks after the products were already off. Fifty-seven people moved across and ended up in Kendall Square alongside about 250 existing Capital One staff. Volpe went to work on the bank's business-to-business payment products and English became an entrepreneur-in-residence. The terms were never published, which usually means there were not many.

~ the second lola ~

In April 2026, Booking Holdings bought lola.com and lola.ai from Paul English, and English is now building a new Lola there with Steve Hafner, his Kayak co-founder. It is an agentic travel and dining assistant: you describe what you want in a sentence and it comes back with places and live prices. Which is, allowing for twenty years of hardware, the 2016 pitch again with the human taken out of the chair.

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