Jan Seale

A company named after the email you dream of sending.

Jan Seale runs Out of Office, a Chicago travel app built on a stubborn little idea: the best recommendation you will ever get does not come from a stranger with five stars and a grudge. It comes from the friend who already went, already ate there, already knows which room to ask for.

The app collects those recommendations - from your own circle, and from people whose taste you actually trust - and turns them into something you can browse, save, and book. Hotels. Tables. The high tea you would otherwise forget to reserve. It now spans more than 3,500 cities, and Seale is the CEO and co-founder steering it.

The mechanics are the whole argument. Instead of scrolling a firehose of anonymous reviews, you follow the people whose taste you already trust - friends, family, a handful of tastemakers - and their picks become a map you can act on. Restaurants tie into reservation tools like OpenTable. Places you love get saved into lists you can share back. The pitch is small and human: your next great trip is probably already sitting inside someone else's memory, and nobody had built a clean way to pull it out.

Here is the part that makes people lean in. She started it in 2020, in the exact moment the travel industry was told to sit down. Airports empty. Borders closed. Every reasonable person shelving their trips indefinitely. That is when Seale and her co-founder Coabi Kastan decided to build a travel company.

The idea itself was older than the pandemic. Seale and Kastan first sketched it in 2016, back when they worked together at Trunk Club, the Chicago menswear startup. They shelved it. Life moved. Then, in March 2020, stuck at home with nowhere to fly, the idea came back with a vengeance and a very specific origin story.

Picture a trip to London. Two friends trying to run a full itinerary out of spreadsheets and forwarded emails - restaurants here, a note there, a screenshot somewhere. Somewhere in the chaos, a high tea reservation slipped through the cracks and was simply missed. A small failure. But the kind that lodges in a founder's brain and refuses to leave.

Twelve years of somebody else's company first.

Seale did not arrive at founder overnight. She is a Cornell graduate who spent roughly seven years at Gap's corporate headquarters in San Francisco, moving through finance, planning, and merchandising - the unglamorous machinery of how a large consumer brand actually runs.

Then came Trunk Club, where she was an early employee and helped guide the company through its 2014 acquisition by Nordstrom, eventually running as Head of Sales. After that, Vice President of Revenue at Havenly, the online interior design platform. By the time she bet on her own idea, she had put in about twelve years across consumer technology. She knew how revenue is built, not just imagined.

Her co-founder brought a different toolkit entirely. Coabi Kastan came out of film and television - an HBO intern turned NBC production assistant turned Emmy-winning producer for Warner Bros., with later stops running sales at Trunk Club and talent relations at Cameo. One founder who understood commerce and operations, one who understood story and influence. Travel, it turns out, needs both.

Their partnership is not incidental to the story - it is a subject Seale talks about openly. Building as two people rather than one means splitting the emotional weight of a company, but it also means constantly aligning on the hard calls: who to hire before there is money to pay them, which investors to let in, how to keep a small team pointed the same direction. Both founders came up through Trunk Club, so they had already watched a Chicago startup scale, get acquired, and keep moving. When they finally started their own thing, they were not guessing at what growth costs.

Often the only one in the room. Now the one who sets it.

Seale is direct about what those corporate years looked like from her seat. She was frequently the only woman at the leadership table, and often the only Black woman in the room, full stop. It is not a complaint she dwells on. It is context for a decision she made deliberately: to build Out of Office as a company where that would not be the default.

When Out of Office raised its pre-seed round, Seale became one of the first 100 Black women in the United States to raise more than a million dollars in venture capital. Read that number again. Not the first hundred this year. The first hundred, period. She then pushed past it, closing a $3.5M round led by Hyde Park Venture Partners and stacking the company's first-year total to more than $5 million.

Her work and her company have since turned up in Fortune, Bloomberg, Forbes, Inc., Entrepreneur, and The New York Times. Fortune slotted Out of Office into its "Startup Year One" feature as a summer travel app worth watching - which, for a company that opened its doors mid-pandemic, is its own quiet punchline.

What makes the fundraising number land harder is the timing behind it. Seale was pitching a travel product to investors at the precise moment travel looked like the worst bet on the board. She has said the reception often came with a look that translated roughly to "are you serious." She was. The bet was not that the pandemic would last, but that it would end - and that when it did, people would be desperate for a better way to plan the trips they had spent two years dreaming about. Every dollar raised was a vote that she had read the moment correctly.

Ten things, before the coffee.

Ask Seale how she keeps going through the founder gauntlet and the answer is almost disarmingly simple. Every morning, no matter the mood, she names ten things she is grateful for - written down, typed into her phone, or just said quietly in her head.

It is not decoration. For a founder who launched into the worst possible market, ran a company as the only Black woman at more than one table, and raised millions anyway, a daily practice of counting what is good is less a nicety and more an operating system. Out of Office is, in the end, a company about noticing where you want to be. Its CEO practices that before breakfast.

The roadmap points outward from here: more direct booking inside the app, hotels and flights handled without ever leaving it, and a company that keeps growing without losing the thing that started it - a recommendation from someone you trust, about a place you have not been yet.