Allison Kobasky

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Allison Kobasky is the owner and co-founder of Over The Moon Vacations, which she owns with her loving husband named Josh and playful pup, Buddy. Having traveled to more than 30 countries, this dynamic duo uses their personal experiences to custom curate luxury vacations and honeymoons across the globe.

What inspired you to join the travel industry as a travel advisor?
Back in college, I took a summer job as a counselor on teen tours—this means that I got to travel the world for free as a glorified chaperone for a group of high school kids. Luxurious 6-week programs in Europe eventually led me to volunteer-based programs, most notably when I was afforded the opportunity to live and volunteer in a small West African Village for about two months. These combined experiences made me a better person—they taught me to be more humble, kind, compassionate and understanding—traits that have shaped me into who I am. I became so passionate about the magic of travel that I decided that nothing could be more rewarding than giving these opportunities to others by planning their travel.

How long have you been in the travel industry?
It’s been just over 10 years since my first teen tour, but about three years since I’ve owned my own travel planning business.

Where do you see yourself as a travel advisor five years from now?
I’d like to build out a self-sustaining e-commerce platform that gives travelers the tools and resources they need to plan their own trips. I’d like to oversee that operation as an onsite travel expert, finalizing and tweaking trips to perfection. If you know anyone in travel tech, send them my way!

What do you think Millennial-age travel advisors have brought to the industry?
Fresh perspective! Destinations are constantly evolving—the best restaurants, buzz-worthy places for Instagram pics, the coolest hotels to stay at are not the same now as they were 20-30 years ago. They might not even be the same as they were TWO years ago. Millennial advisors are savvy, fast-learners with the ability to quickly adapt to new trends.

How do you think the industry can continue to attract younger travel advisors?
Wait, more people want to do this? I thought it was just us! Kidding—young travelers are definitely interested in becoming advisors—they just don’t know how to get started. There’s something so attractive about a flexible work schedule, and it’s not a bad situation to dream about travel all day. We’ve had so many clients come back from their trips asking how to get started in this field; so maybe writing a few articles on how easy it is to become an independent agent and pushing them out on social media to a highly targeted audience of travelers would empower young travelers to take the plunge into this awesome industry.

How do you find your Millennial-age clients?
We actually don’t do any marketing currently, so all of our business comes from organic social media activity and word-of-mouth referrals—since 95 percent of our clients are millennials, they typically refer other millennials.

What motivates Millennial travelers and do you think there’s a tendency for Millennial-age travelers to seek out Millennial-age travel advisors and if so, why?
In our experience, most millennial travelers are motivated by price—they are researchers who want to know that they’re getting the absolute best price for something vs. being value-driven. They’re also motivated by social media—being able to post that drool-worthy Instagram photo in the perfect spot or being able to say they’ve been somewhere has become a huge motivator for travel. Unless someone is wealthy, well-traveled and already armed with a family travel agent, we find that most millennials haven’t really used an agent before. With this in mind, they appreciate an advisor who is relatable, that can speak their language—someone who knows what is trendy and current, who is flexible in their planning style, who knows how to find the best prices in the market, and who is able to curate trips that offer a mix of popular destinations with unique cultural experiences.

How does the form in which you communicate with your Millennial-age clients differ from how your older counterparts communicate?
All of our planning is virtual and over the phone—we work out of google docs so that clients can see changes as they’re being made in real time, and also can contribute comments, feedbacks and edits in one living document. Millennials LOVE this planning this way, as it works best for their busy schedules. This is very different from how older travel agents work out of brick and mortar offices, planning with their clients in person. We find that our older clients are more accustomed to this in-person approach, and prefer to get together to plan since they’re not usually as technologically inclined.

Are you starting to sell to the Gen Z demographic (those in their early 20s) and if so, how is that different from how you sell—in terms of their expectations—to the Millennial demographic?
We haven’t sold Gen Z just yet—since our business is geared towards honeymooners and luxury travel, this generation just isn’t there yet.

If you do sell to the Gen Z crowd, what is the key differentiator you are finding between the Millennial traveler and the Gen Z traveler?
I’d say the biggest difference between these travelers is budget. Millennial travelers tend to be more established in their careers with more disposable income, while Gen Z travelers are going on smaller-budget trips with friends, or even solo backpacking trips.

And one more Millennial vs. Gen Z question: Are you seeing the Gen Z crowd more influenced by what they see on social media than Millennials and how is it affecting where they choose to travel?
Honestly, I think both generations are similarly motivated by social media—most travelers under the age of 30 are excited by snapchat and Instagram stories, and want to be able to highlight their travels through these platforms.

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