Hall of Femme Honoree: Coabi Kastan on the Importance of Changing Your Mind

If you’re tired of scrolling through random reviews, booking hotels blindly, or collating group plans in a Google spreadsheet, Coabi Kastan has you covered. She’s the COO and co-founder of Out of Office, an app that allows you to plan your dream vacation with personalized recommendations and travel tips from your inner circle. With more than a decade in consumer tech and an ocean-deep love of travel, Coabi is the perfect woman for the job. 

The Hall of Femme honoree grew up “a really big tomboy” in Ann Arbor, Michigan, a cozy college town that exposed her to different types of people and points of view. Her mother took the lead at home, setting an example that Coabi carries with her to this day. “I saw her exhibiting what it looks like to be a strong, working woman,” she says. “I always knew I wanted to have a big career or do something important.”

Coabi studied at the University of Colorado, Boulder and UCLA, along with a stint abroad at Griffith University on the east coast of Australia. She started her career in film and television, racking up roles at Warner Bros., NBCUniversal, and HBO before pivoting to the consumer tech industry. She served as VP of Talent Relations at Cameo and VP of Clubhouse Sales at Trunk Club, an apparel subscription service that was acquired by Nordstrom in 2014. 

Now based in Chicago, Coabi linked up with her former Trunk Club colleague, Jan Seale, to found Out of Office in June 2020. It’s a user-generated content platform with over 200,000 recommendations that’s partnered with brands like Penguin Random House, Wander Vacation Homes, and OpenTable, which allows users to book reservations at 60,000-plus restaurants directly in the app. 

Not only did Coabi’s mother inspire her to be a working mom (her kids are 6 and 3!), but she’s also responsible for spreading the travel bug. “I think travel is so important — understanding people, and different cultures, and seeing the world through that lens is so important,” says Coabi. “I definitely learned that from my mom.” Along with revamping the travel industry, Coabi is also co-founder of One/Third, a DTC women's jacket company focused on "third pieces” at accessible price points. 

Here, Coabi opens up about shattering glass ceilings, changing your mind, and the most beautiful place she’s ever traveled.  

Where did you grow up and how has it impacted who you are today? 

I grew up in Ann Arbor, Michigan. It's where the University of Michigan is, and I think it was a great place to grow up. It's not a big city; you're surrounded by college. There are a lot of interesting people who moved there to work at or attend the university. It’s a bit insular in Michigan, in that people are really open-minded, and you get exposed to a lot of diversity in origin and thought. It definitely informed my ability to think about things holistically and exposed me to so many different types of people and points of view. It allowed me to be more flexible in my viewpoints as an adult.

When you were a young girl, what were the narratives you were exposed to about women and women's rights? 

My mom is a very strong woman and my dad sort of takes the passenger seat. It was the status quo for me. Being a working mom was always important to me, because that's how my mom modeled it. I was a really big tomboy growing up — I had a lot of friends that were boys, and there were times when, if they got around some other guys who didn't know me, they'd be embarrassed to have brought me along, the girl. I’ve felt from a very young age like I had to prove that I could be in those rooms with them. Being an equal was always something I strived for.

Working in consumer tech for the last 12 years, there was a bit of a glass ceiling. I’d be in positions where my female peers and I were greatly contributing to the growth of the company, but in the boardroom, or the C-suite, no one looked like us. There were no women making real decisions on how to run the business. Growing up the way I did, it was important to me to change that dynamic, or be in that room, and not be someone who is impacting the business but not getting a voice in how it can grow and evolve and scale.

You've contributed to the growth of numerous startups. What part of the business and brand-building life cycle gets you most excited, and why? 

With Out Of Office, it’s the earliest I joined a company as one of the founders, starting it from nothing. That part has been really interesting because you're dictating what the brand is, how you want it to show up, who it should be resonating for, and how you ensure it fills a space for that demographic. That’s been really fun.

In my previous positions, I enjoyed starting really early, before there was this big inflection point, and helping get the business to that point. Then putting processes or strategies in place that really allow for scale.

What’s a key learning you’ve had since starting Out of Office?

When I was at Trunk Club, we had a value: “Hold strong ideas loosely.” Honestly, I don't know if it resonated as much with me then as it does now, but it's so true. It's obviously important to have a strong point of view, but it's equally as important to change your mind. Sometimes, you don’t want to be wrong so you dig your heels in. I think that can do a lot of harm, because things change. A business decision you make one day could be the right one, and then the next week it could be the wrong one. Having the confidence to admit that you were wrong is really important.

Tell us about a woman who has inspired you to travel.

My mom is from Newfoundland, which is a smaller island in Canada, and she's one of eight. They're from this little town with no traffic lights, and she always had a hunger to see the world. When my mom was growing up, she wanted to go to Europe. She ended up moving to the US after meeting my dad, who's American. And while all of her seven siblings lived within an hour of each other, she was three plane rides away in Michigan. She really has impacted me. My parents are retired now, and they just spent six weeks in Europe.

I think travel is so important — understanding people, and different cultures, and seeing the world through that lens is so important. I definitely learned that from my mom.

Where’s the most beautiful place you’ve ever traveled? 

When I was in college, I studied abroad in Australia. There is a chain of islands called the Whitsunday Islands, and they are really, really beautiful. I think that's definitely up there. Bali is also amazing. I mean, our world is so beautiful. To be able to travel and see all these places is such a gift.

What's a ritual in your life that you swear by?

I am really not on top of my game when I don't get enough sleep. Sleep is so important to me, so I practice sleep hygiene. What that looks like for me is, I stop looking at screens at 9:00pm. Generally, I go up to my room and do a bit of meditation practice and breath work. I do legs up the wall to relax, and then I read a book and use that as a way to let my mind unwind. I think that's crucial to making sure I show up as the best version of myself.

What's your favorite way to celebrate a win (big or small)? 

With my family. Being a working mom is important to me, but it also takes me away from my kids sometimes. When something happens that I'm proud of or that I want to celebrate, being able to share and show them what that looks like is really important to me.

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