Jan Seale is a small town girl with sky-high dreams. She is the CEO and co-founder of Out of Office, a disruptive travel app that allows you to plan your dream vacation with personalized recommendations and tips from friends and community. With her innovative company, Jan is on a mission to shake up the travel space and help put more stamps on your passport.
Jan grew up in Overland Park, Kansas, a conservative suburb of Kansas City that was named Best Place to Raise a Family in 2019. “Most people who are where I'm from stay in Kansas City, go to college in Kansas, and come back and raise their kids in the same place,” says Jan. “I knew from the time I was young, that wasn't for me.”
Jan was sure she needed to see the world, and her parents — who emigrated to the US from Barbados — armed her with considered confidence, an entrepreneurial spirit, and a taste for the unknown. She left Kansas for New York to study at Cornell University, then spent time working at Gap’s corporate HQ in San Francisco. After five years on the West Coast, Jan settled in Chicago, serving as Head of Sales for the apparel subscription service Trunk Club. It was there that she met friend (and fellow Hall of Femme honoree!) Coabi Kastan, and in 2020, the two united their love for travel and tech to co-found Out of Office.
The Out of Office platform aggregates top destinations, hotels, restaurants, and experiences, customized to your preferences and based on suggestions from the friends and influencers you follow within the app. It also lets you browse and save your friend’s travel wishlists and past trip experiences to inspire your own getaway. With another year of post-pandemic “revenge travel” on the horizon, OOO is definitely here at the right time.
Jan is also dedicated to increasing venture capital access to BIPOC founders. For OOO’s pre-seed round of funding, Jan was in the first 100 Black women to raise over a million dollars. “While it sounds like an accomplishment, with billions of venture dollars being deployed each year, it's unfortunate that that number is so small,” Jan has said. Both she and Coabi are “committed to changing that dynamic and ensuring that more marginalized groups get access to venture capital.”
Here, Jan opens up about the most surprising thing she’s learned as an entrepreneur, the powerful role gratitude plays in her life, and the travel spot she’s itching to visit next.
Where did you grow up and how has it impacted who you are today?
I grew up in Overland Park, Kansas, which was a great place to grow up. I think I had your idyllic childhood. It is in the suburbs of Kansas City. I got a great education. I think it impacted me the most in an interesting way, which is, most people who are where I'm from stay in Kansas City, go to college in Kansas, and come back and raise their kids in the same place. I knew from the time I was young, that wasn't for me. My parents encouraged me to go out and explore the world and experience other places. They weren't from Kansas, originally — my parents were from Barbados, so they're immigrants, and they wanted us to get out of our comfort zone. That's what I was encouraged to do. It taught me that it's a great thing to have a great childhood, but there's so much more to the world. I went away to college, and then I lived a ton of other places, as well.
When you were a young girl, what were the narratives you were exposed to about women and women's rights?
My parents probably exposed me to the most. Kansas is a very conservative state. I was one of the only Black kids in my entire school, my brother and I. We were very sheltered from any progressive notions. From the time I was young, my parents told me I could be anything: "Go out and figure out whatever you want to do. If you're going to do it, you’ve got to be good at it. And go figure out how to be good at something if you're not."
That is so instilled in me. That's why I'm an entrepreneur today. I knew I could figure it out. I worked hard. I was an athlete my whole life. I got into an Ivy League school. And then, I started my own business. As it relates to women's rights in particular, I was really sheltered from what that meant until I went away to college, and [learned] in a real way.
Tell us about a woman who has inspired you to see new perspectives.
I have been so fortunate to have amazing women in my life who have taught me, guided me, inspired me, and challenged me through every part of my life. My mom is my biggest inspiration. She came to the US, didn't know a soul, and created a life — then, she made sure that the life she created for my brother and I was amazing. It was an inspiration to me.
I’m also really fortunate to have close friends in college who opened up my eyes to the world. I've had amazing mentors. Emily Arelle is a woman that I met while I was working at Gap in my first job at corporate headquarters. She was someone that I liked from the very beginning, and she didn't fit the mold of every other person that worked there. She challenged me to try different things, like go after that job that maybe I wouldn't get. “Go do a job that is complicated and really hard, and learn how to grow and be better.” I look to her often. She is a friend of mine to this day, she’s an investor of mine to this day, and she's someone that has changed my perspective on how you build a career. I'm very fortunate for her.
What’s the most surprising thing you’ve learned as an entrepreneur?
Do I have all day? It's what everyone says. People tell you what it's like to build a company and be an entrepreneur, but it’s not until you're in those shoes that you understand what it's like to feel literally every single emotion on any given day. You go from having the biggest win of the day, having a great meeting, a great call, great business traction… to, something breaks, someone is unhappy, something goes wrong. You go through all these emotions every single day.
My dad has always told me, "Never get too high, never get too low." But it's hard. That is something that I try to take with me every single day. I'm going to wake up saying, “I might feel great, but at the end of the day I might feel awful.” The next day, you have to start over. Remember to take those small wins, those little things that were really important, and latch onto those, because those are the things that really matter.
Where is your favorite place to travel?
The place I love to go the most is Italy. There's something about that country that I have fallen in love with from the first time I went. You can do so many different things there. I'm a big wine person, red wine in particular, so I love to go to Tuscany. The Amalfi Coast is beautiful. Rome and Florence have so much culture. I love that you can have a great experience with all the great food, great people, and great wine, but then also have culture and history. I feel like I'm in a different world when I'm there.
If you had an unlimited budget to plan a dream vacation for you and your girlfriends, where would you go and what would you do?
The dream vacation that I'd love to go on is Africa. It's where I'm from, it's where my roots are, and I know that there's so much in that country and it's supposed to be amazing. I'd love to go on safari and experience Cape Town. There's all these things that I have on this bucket list. It would be really amazing to fly private, maybe, with an unlimited budget, with all of my girlfriends, and really just enjoy ourselves.
What's a ritual in your life that you swear by?
I wake up every single morning and no matter how I'm feeling, I either write down — or put notes on my phone, or even just say in my head — 10 things that I'm grateful for that day. I think gratitude is really important. It goes back to my earlier point: it’s really easy to get bummed out by all of the minutiae, the bad things that can happen, or the stress that’s happening in your life. I don't like to start my day that way. So, I try to say, "What am I grateful for today?" It can be something as small as, "I'm glad my dog slept in this morning."
I'm just glad that I have an amazing family and friend group to support me. It runs the gamut. Sometimes it's silly things. “I'm just glad that I only have two meetings today.” But it's a ritual that I have, and I've stuck to it every day. It helps me start my day with a little bit of perspective.
What's your favorite way to celebrate a win (big or small)?
With red wine and maybe a nice dinner. Obviously, I've started a travel company, so restaurants and travel are so important. I'm always a fan of pouring myself a glass of wine, going to a nice restaurant, having a nice meal, and enjoying the company around me.
You can follow Jan on Instagram.