The Chicago travel app that plans your trip using the people you trust - friends, family, the influencers you follow - instead of a wall of anonymous stars.
Here is a fact about travel planning that everyone knows and nobody says out loud: the reviews are mostly useless. Not because they're fake - though some are - but because a five-star rave and a one-star meltdown are sitting right next to each other, written by two strangers whose taste you have no way to evaluate. You are being asked to average the opinions of people you would never let plan your Saturday. This is the central, quietly absurd condition of modern travel, and it is the thing Out of Office was built to fix.
Out of Office - OOO to its users, reachable at the pleasingly on-the-nose domain takemeoutofoffice.com - is a Chicago travel app founded in 2020 by Jan Seale and Coabi Kastan. The pitch is simple enough to fit on a luggage tag: plan your trip using recommendations from the people you actually trust. Friends. Family. The specific influencer whose taste happens to match yours. You browse the spots those people vouch for, build an itinerary, share it, book a hotel, reserve a table, and go. The anonymous crowd never enters the room.
The origin story is the kind of thing that sounds invented but isn't. Seale and Kastan were on a trip to London, planning across the usual battlefield of spreadsheets, email threads, and screenshots, and they missed a high-tea reservation because the detail was buried somewhere in the mess. That is a small failure. It is also, if you think about it, the entire travel-planning experience in miniature: good intentions, scattered across too many tools, quietly falling through the cracks. Most people would grumble and move on. These two started a company.
About that pandemic. The timing looks, on paper, like a punchline. They committed to building a travel company right as travel itself went to zero in March 2020. The conventional read was that this was insane. The founders' read was the opposite, and more interesting: travel wasn't dead, it was compressed. Demand was coiling. When it released - and it would - people would want their trips organized, social, and trusted, not cobbled together from a dozen browser tabs. This is the part worth sitting with. The moment everyone flees a category is sometimes exactly the moment to build in it, precisely because nobody else is. They were right. The app launched in August 2021, straight into the surge that got nicknamed “revenge travel.”
To understand why OOO looks the way it does, it helps to know where its founders came from. Both Seale and Kastan were executives at Trunk Club, the personal-styling company that Nordstrom acquired. Trunk Club's whole business was a single idea executed well: a trusted human tells you what to wear, so you don't have to wade through infinite options. Seale spent six and a half years there, arriving as one of the first twenty employees; before that, seven years at Gap and, later, a stint as VP of revenue at Havenly. Kastan came from film and television production - HBO, NBC, Warner Bros. - before pivoting into tech at Trunk Club, then Cameo, where she ran talent relations.
Twelve years in consumer tech before OOO - Gap, Trunk Club, Havenly. Among the first 100 Black women to raise more than $1M in venture capital, a statistic that is impressive and indicting in equal measure.
Came up in film and television production, then moved into tech at Trunk Club and Cameo. Runs operations at OOO, turning the trusted-recommendation idea into a working product.
If you squint, OOO is Trunk Club pointed at travel. Both companies answer the same question - who do you actually believe when there are a million options? - and both answer it the same way: a trusted source, not a crowd. That's not a coincidence. It's a worldview the founders carried from one product to the next, and it explains why OOO didn't try to build the biggest review database. It tried to build the most trusted one.
Stripped of the framing, OOO is a trip-planning app that does four things in one place. It lets you discover curated spots - hotels, restaurants, things to do - across more than 3,500 cities, filtered through recommendations from your network rather than strangers. It lets you build and share itineraries, which matters because nobody actually plans a trip alone; you plan it in a group chat with three friends and a screenshot of a reel. It lets you book - hotels directly, restaurant tables via an OpenTable integration - so the plan and the reservation live together instead of in different apps. And more recently, it added an AI trip generator on both web and mobile.
Curated places across 3,500+ cities, surfaced by the friends and influencers you follow - not an anonymous star average.
Build itineraries and share them with your travel group, so the whole trip lives in one place instead of a dozen tabs.
Reserve hotels and restaurant tables inside the app via OpenTable, with direct flight booking on the roadmap.
Describe the trip you want and get a plan back - grounded in OOO's network of trusted recommendations, not the internet's average.
The AI piece is easy to misread, so it's worth being precise. The interesting thing about OOO's trip generator is not that it uses AI - everything uses AI now, and a generic model will happily hand you the average of the entire internet, which is to say the tourist trap. The interesting thing is that OOO has a network of real, trusted recommendations to feed the model. AI without a point of view gives you a bland consensus. AI grounded in people whose taste you trust gives you something closer to a plan. The moat was never the model. It was the trust the model gets to draw on.
OOO is venture-backed, and its funding history is short and legible. A pre-seed round of $1.6 million in 2021, backed by former colleagues from Cameo and Havenly plus a few travel-world names - The Points Guy founder Brian Kelly, Cameo CEO Steven Galanis, and former Orbitz chief product officer Chris Brown. Then a $3.5 million seed round in April 2022, led by Chicago's Hyde Park Venture Partners. That's roughly $5 million total, raised, it bears repeating, into and through a pandemic that had temporarily deleted the entire travel industry.
Backed by former Cameo and Havenly colleagues, plus Brian Kelly (The Points Guy), Steven Galanis (Cameo CEO), and Chris Brown (ex-CPO, Orbitz).
Led by Hyde Park Venture Partners, the Chicago firm. The round that pushed total funding to roughly $5 million.
The business model behind all this is refreshingly boring, which in venture terms is a compliment. OOO makes money on commission: when a user books a hotel or reserves a table through the app, the platform takes a cut from the provider. No ad auction, no selling your attention to the highest bidder. The company's revenue rises when its users actually use it - a rare case where the incentives of the business and the interests of the traveler point the same direction. It is not glamorous. It is just aligned.
One detail keeps surfacing in coverage of OOO, and it deserves to be stated plainly rather than buried in a founder bio. Jan Seale is among the first 100 Black women to raise more than $1 million in venture capital. Read that again. Not the first 100 this year. The first 100, full stop. That number is small in a way that says less about the founders who cleared the bar than about the bar itself - who gets funded, who gets the benefit of the doubt, and, downstream of all that, what kinds of products get built and for whom. Seale cleared it, raised roughly $5 million, and built a travel company through a pandemic. The statistic is an achievement and an indictment at the same time, and both readings are correct.
Who is OOO for? Leisure travelers, mostly younger and more social, the sort of people whose jobs went remote and whose weekends filled up with road trips and getaways they now had the flexibility to take. The kind of traveler who already plans in a group chat and already saves reels of places they want to go - people, in other words, who were doing OOO's core behavior manually before OOO existed. That's the tell of a product built on observation rather than invention. The company didn't have to teach anyone a new habit. It just had to remove the friction from one they already had.
Put it all together and Out of Office is a small company making a specific, defensible bet: that in a travel market drowning in options and stranger opinions, the scarce and valuable thing is trust. Not scale, not the biggest database, not the flashiest AI - trust. It's a hard thing to build and an easy thing to underestimate, which is probably why the founders had to hear “you're insane” before they got to hear anything else. The bet isn't fully settled. But the logic is clean, the incentives are aligned, and the product does the one thing it set out to do: it gets you a trip planned by someone you'd actually listen to. For most travelers, that has quietly always been the whole point.