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Settled

Settled pairs agentic AI with human judgment to resolve disputes that are currently not worth the effort of pursuing. Its first product, TripFix, chases compensation for disrupted air passengers. Chris Houston, who founded the consumer VPN SurfEasy, co-founded it.

The people

What they build

TripFixPursues compensation for air passengers whose flights are delayed, cancelled or disruptedProduct page ↗

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Working at Settled

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On the TechTO stage

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About

Settled's argument starts from an asymmetry it states plainly: disputes are getting more frequent and more complex while the mechanisms for resolving them have not kept pace, so for many issues the effort and cost of seeking resolution outweigh the value of the outcome — and the claim simply goes unmade. Its answer is what it calls agentic operating systems for dispute resolution: AI agents doing the work that makes small claims uneconomic, with human judgment kept in the loop where judgment is what is actually required. TripFix, the first product, applies that to air-passenger compensation, a domain with real statutory entitlements, an adversarial counterparty and a claims process most travellers abandon. Chris Houston is a co-founder. He started SurfEasy in Toronto in 2011 and was its chief executive, growing the consumer VPN through QVC television shopping rather than paid search — a story he told on the TechTO Travel Toronto stage in December 2025, in the talk carried on this page.

Backers

No funding round or investor is announced by the company or found in any source read for this page.

Some figures are founder-stated, not independently confirmed

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Quick answers

What is Settled?

An AI dispute-resolution company. It pairs agentic AI with human judgment to make claims worth pursuing that would otherwise cost more effort than they return.

What is TripFix?

Settled's first product. It pursues compensation on behalf of air passengers whose flights are delayed, cancelled or otherwise disrupted.

Who founded it?

Chris Houston is a co-founder. He started the consumer VPN SurfEasy in Toronto in 2011 and was its CEO.

Who from Settled is in this directory?

Chris Houston, who spoke at TechTO's Travel Toronto event in December 2025 on consumer growth strategies — introduced by TechTO as founder of Settled.ai and TripFix.

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Maintained by TechTO · facts sourced and dated · last reviewed Aug 29, 2026