Travel Tech / Founders
David Chait
He found a hotel booked for the wrong dates, and built a company so it would never happen to anyone again.
He found a hotel booked for the wrong dates, and built a company so it would never happen to anyone again.
Ask a travel advisor what runs their day and there is a decent chance the answer is Travefy. The itineraries that arrive looking like a glossy magazine, the proposals that close a trip before the client has finished their coffee, the client portal that quietly tracks who paid for what - that is David Chait's company doing its job in the background.
Chait is the co-founder and CEO. He is not a travel-industry lifer who fell into software, and he is not a coder who fell into travel. He is a former McKinsey consultant and Obama-era Small Business Administration policy advisor who looked at the messiest, least glamorous corner of travel - coordination - and decided that was the interesting part. Today thousands of advisors build trips on the platform, and Chait spends his time arguing, publicly and often, that those advisors deserve better tools than the industry ever gave them.
The unusual part is where he does it from. Not San Francisco. Not New York, where he earned two Columbia degrees. Lincoln, Nebraska - a deliberate choice, and one he will defend at length.
It is worth sitting with how strange that resume is for a travel-software founder. The standard path runs through a coastal accelerator and a hospitality background. Chait arrived instead from strategy consulting and federal policy work, carrying a habit of mind that treats a business as a set of moving parts to be diagnosed rather than a vibe to be chased. When he talks about Travefy, the language is operational - ROI, sustainability, the cost of learning a tool - not the breathless founder-speak that usually accompanies a travel app. That difference is the whole story.
Somewhere around 2012, Chait was helping plan a friend's bachelor party. The logistics sprawled across more than 75 emails. Then someone in the group booked a hotel - for the wrong dates - because they never checked with the groom. The trip survived. The lesson did not let go.
Group travel, he realized, was broken in a way that no amount of enthusiasm could fix. People wanted to go places together and could not agree on a thread, a date, or who owed whom forty dollars. The first version of Travefy was built for exactly that: a consumer tool to coordinate group trips and split the bills without the email avalanche.
It was a clean idea with a stubborn problem. Consumers plan a big trip once or twice a year. They do not build software habits around something they do twice a year. The people who live inside trip logistics every single day were somewhere else entirely - behind desks, selling travel for a living, cobbling together itineraries in Word documents and PDFs.
By 2016, Chait had seen enough. He pointed the whole company at those professionals. It is the kind of pivot that sounds obvious in a sentence and terrifying in a board meeting. It also made the business.
Remember that you're building a business, not a startup. From day one, have a plan for the factors that make a company sustainable.
Chait understands his customer with the precision of someone who has watched a thousand of them work. Travel advisors, in his telling, are not a sales department. They are solo entrepreneurs, and the thing they are most desperately short of is hours.
They're solo entrepreneurs. Their biggest barrier is time. If a tool doesn't clearly deliver ROI, it's not worth the hours it takes to learn.
So much of the magic comes from the 'wow' on the traveler side. The backend efficiency - integrations, automations - that's what makes the 'wow' scalable.
That is the whole product philosophy in two quotes. The client feels the polish - a beautiful, branded itinerary that lands like a gift. The advisor feels the speed - the automation that built it in minutes instead of an afternoon. Travefy lives in the gap between those two feelings, and Chait treats that gap as sacred. A tool that does not pay for the time it costs to learn is, by his standard, a failure.
This is also why the 2016 pivot was not a betrayal of the original idea so much as a correction of who it was for. The coordination problem was real either way. What changed was the recognition that the people willing to build a daily habit around solving it were the professionals, not the once-a-year vacationer. Consumers wanted a magic button. Advisors wanted a workbench. Chait stopped selling the button and started building the workbench, and the company found the durable demand it had been missing.
Before Travefy, Chait advised Fortune 500 companies, governments and nonprofits at McKinsey's New York office, then served as Senior Policy Advisor to the Administrator at the U.S. Small Business Administration - small-business economics, credit, trade. He has, in other words, spent real time thinking about what actually keeps small companies alive. It is not a coincidence that he runs his own like one.
He earned a B.A. in economics-political science from Columbia College and an MBA from Columbia Business School, both with honors. He is also a regular contributor to Entrepreneur, where he writes the kind of advice that sounds like it was earned rather than borrowed.
In August 2017, on a stage at the ASTA Global Convention in San Diego, the American Society of Travel Agents named Chait its Entrepreneur of the Year. He has been candid about what the award actually did for a small company in Nebraska: it opened doors that money alone could not.
Recognition turned into responsibility. He joined The Travel Institute's board in 2024 and was elevated to vice chair the following year - a seat from which he keeps making the same argument he has made for a decade: travel advisors are an undervalued, growing force in the economy, and the tools they are handed should reflect that.
This was a game-changing moment for Travefy. Beyond the cash prize, the exposure let us reach advisors we otherwise might never have met.
Every software company now has an opinion on artificial intelligence. Chait's is unusually disciplined, and it follows directly from how he sees his customer.
We want AI to elevate what advisors uniquely do best, and automate the rest.
The line in the sand is clear. The human craft of a travel advisor - taste, relationships, the instinct for what a particular family will actually love - is the part the software is meant to protect. The busywork around it is the part the software is meant to swallow. He is not building a robot to replace the advisor. He is building one to do their typing.
It is also, characteristically, a roadmap he refuses to own alone. "We're going to keep evolving based on what our users need. The roadmap is driven by them,"
he has said. Investor interest has followed: by his account, the door now gets knocked on daily, in a market that traditional money used to ignore.
The restraint is the interesting part. In a moment when the easy move is to bolt a chatbot onto everything and call it a strategy, Chait keeps drawing the same boundary: automate the rote, protect the human. He has watched advisors win business precisely because they are not an algorithm - because they remember a client's anniversary, or know the one hotel on the island worth the splurge. The software's job is to give them more hours to be that person, not to impersonate them. It is a contrarian bet that the human in the loop is the asset, not the inefficiency, and it runs against a decade of travel-industry conventional wisdom that kept predicting the agent's extinction.
Nebraska, on purpose. A Columbia MBA building travel software in Lincoln - not a coastal accident, a thesis about where good people stay.
6:30 AM, then pedals. Up early, commuting to the office by bicycle. The routine is the strategy.
There is a cat named Sadie. Every founder profile needs one true domestic detail. This is his.
Reads venture, follows travel. Points people toward Skift and Fred Wilson, and cites Jon Meacham on Thomas Jefferson.
Tests on strangers. He hands products to "blind" users who never heard the pitch - if the idea needs a speech, it isn't done.
A personal creed. "Education truly equals opportunity." Two honors degrees later, he still means it.
"Question everything and never stop iterating." The whole company is a long argument with its own assumptions.
"User stories. Nothing brings an idea to life like writing out a narrative." Specs are cold; stories are alive.
"There's been a broader recognition that this is a vibrant and growing market." Travel tech, finally getting its due.