Like many Westporters, Oona Robinson’s life was filled with travel and adventure.
The South Africa native’s management consulting career took her to Toronto, then New York. She met her future husband on a Roosevelt Island tennis court.
They married, had kids, and migrated from the Upper East Side to Westchester, then Westport. Robinson was deputy CFO of Webster Bank, then joined Capital One as CFO of their commercial bank division just before COVID.
Oona Robinson
In 2022 their oldest son graduated from Staples High School. On a trip to South Africa shortly thereafter, her husband had a seizure. He was diagnosed with glioblastoma — an aggressive brain tumor.
She left her job, to care for him. Two years later, he died. She was an empty nester, a widow, and exhausted.
During her husband’s illness, Robinson had reflected on her many roles — including trip planner.
She told her husband about a business idea: an app that takes some of the burden off of the people (usually women) who plan family journeys.
He loved it.
After his funeral, she mentioned the concept to a friend. Encouraged, Robinson began developing it.
She spent much of 2025 creating a prototype, getting feedback and tweaking it. Eric Shapiro — CEO of app developer ArcTouch, paired with Robinson through StartUp Westport‘s mentorship program — helped immensely.
“He gave me courage to lean in, and trust my own voice,” she says.
Pivoting from Wall Street to the web has been eye-opening — and exhilarating.
“My whole career had been spent in aggressive competition,” Robinson says. “There’s a wariness there about who you bring into any conversation.
“This is the exact opposite. Very successful people have been available for always, for nothing in return. They just want me to succeed.”
In July, Robinson launched FliFlo. It’s “a private space for friends and family to plan, experience and remember” every vacation.
Or any other event — a family reunion, baby’s christening, etc. — that requires planning, coordination and communication.
Robinson had not thought of other group activities, like a youth sports tournament. But that’s another opportunity.
People will continually discover their own uses for FliFlo, she says.
(And those who are not going on a trip — someone who is busy or ill, say — can also use the app. They’ll see what they’re missing, and afterward what they missed, hopefully without too much envy.)
Sharing photos and comments.
Despite little promotion, it’s growing organically. Word of mouth has been good. “People try it, they like it, and they tell people,” Robinson says.
That’s the whole idea. If you’re going on, say, a family vacation, one person sends a link to the others. Together, everyone helps plan activities, adding suggestions and comments far beyond a text-based group chat.
As an itinerary is built, details — including confirmation emails and PDFs — can be manually or automatically added in.
Creating a shared itinerary.
“It takes the burden off the uber-planner,” Robinson notes. “It makes the process simpler for everyone, and captures the essence of the experience.”
During the event, everyone can upload comments.
Afterward, the site is a great way to relive the experience.
Right now, the site has no ads. There are no subscriptions either, though that may happen down the line.
But for now, it’s free. (Unlike probably any other part, of any trip.)
Sounds like a plan!
(For more information, and to download FliFlo for an iPhone or Android, click here.)
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