This Couple Makes $40K/Month Planning Surprise Vacations

Published: March 2nd, 2019
Roshni & Jeff
The Vacation Hunt
from Washington D.C., Washington, D.C., USA
started May 2017
Discover what tools Roshni recommends to grow your business!
customer service
social media
stock images
Discover what books Roshni recommends to grow your business!
Want more updates on The Vacation Hunt? Check out these stories:

Hello! Who are you and what business did you start?

Hi - we are Roshni & Jeff and we have sent hundreds of travelers on vacations around the world - without them knowing where they were headed!

We started The Vacation Hunt in 2017 and our primary products are surprise vacation packages. Travelers fill out a survey with their trip preferences, choose a vacation package (US, International or All-Inclusive Resort) and we book their trip (flights, hotels & activities).

We send them clues to their destination over social media and they find out where they are headed a few days before they leave. It’s a lot of fun for us and our travelers!

Below is one our recent surprise vacation clues, can you guess where they are going?

Your surprise destination is the birthplace of an iconic government safety campaign! Surprise trip clue #1 for Jennifer, Grayson, & Andrew! #surprisevacation #familytrip #thevacationhunt

What's your backstory and how did you come up with the idea?

The Vacation Hunt was a melding of several ideas actually! Jeff and I often just buy plane tickets to somewhere on a whim when we know we’ll have time off from work and when we see a good deal to a place we haven’t been.

When we came back from the trip, we told a friend about the whole surprise aspect and she asked us to plan a similar surprise vacation for her - and it just kind of went from there!

For his 30th birthday, I surprised him with a trip to Patagonia in Chile! He knew he was going on a trip to celebrate (and he knew that we were going somewhere wild since I had him pack his hiking shoes) but apart from that, he didn’t know much else until the day before the trip!

We had a great time in Chile and during that week-long trip, we visited Patagonia and the Atacama desert (which is on the opposite end of the country so required some logistical coordination and flight connections). When we came back from the trip, we told a friend about the whole surprise aspect and she asked us to plan a similar surprise vacation for her - and it just kind of went from there!

The whole aspect of giving out destination clues so our travelers could try to “guess the destination” came about in a different way. I normally write little riddles and brain teasers on a whiteboard by my desk at work to add a little fun in the office and my co-workers love guessing them!

When I was traveling, I did themed riddles and clues to where I was going. Once we decided to start the surprise travel business, we thought the clues would be really fun for the travelers to share with friends and family to join in on the fun!

We finally got everything up and running in May 2017, and the idea has really taken off since then! Our travelers have had a ton of fun on their trips and we have had a great time planning them!

Take us through the process of building the product.

The whole surprise vacation is built specifically for each traveler based on the answers to their trip survey.

The trip survey itself is an evolving questionnaire. When we first started out we put questions that were important to us like “Where do you want to go?” and maybe more importantly “Where do you not want to go?.”

As we started getting more surveys and the airlines began changing their baggage policies, we also changed our survey to add questions like “Are you willing to fly basic economy to get somewhere great?” Or “Are you willing to upgrade your flight for more legroom?” We expect that we will continue to change it as our business evolves and as travel itself evolves.

We have to balance the cost of the trip for each component, and fulfill as much of their preferences on the survey. We always prioritize destination preferences, meaning that if they have listed some places they really want to go, we’ll try to get them there! The process of picking a destination and planning an entire itinerary is pretty complicated. We book flights, hotels and activities and each itinerary is different.

Part of our responsibility to making sure that we make decisions similar to what our travelers would want, so we’ve learned to kind of “read between the lines” on our surveys.

For example on our shorter trip (3 or 4 days) if we can get direct flights, we usually do, because no one wants to send a ton of time traveling when the trip is so short. If it’s a longer trip (9 or 10 days) then 1 stop flights are probably okay.

Aside from practical considerations like that, there are other considerations we think about to make it a great trip. We like to put people a bit outside their comfort zone and experience something new, so if you’re coming from the Denver area (near Rocky Mountain National Park) we might not send you to Calgary and Banff National Park because the landscapes are similar.

We both work full-time (at other jobs) and have been fortunate enough to be able to travel to a lot of places. We use our own knowledge of what is important to us while traveling to plan surprise trips.

For example, most of our travelers also have full-time jobs so we try to maximize vacation days by using weekends strategically and book direct flights whenever possible.

We also know the importance of a nice hotel on a trip, so we only book 3 star and higher hotels (usually 4 stars). We don’t really book backpacking or shoestring budget trips, because it’s not what we’re familiar doing ourselves.

Describe the process of launching the business.

As I’ve mentioned before, we both work full-time so the hardest thing for us launching the business was finding the time to do everything an online business needed.

We wanted to be nimble and able to update our website or change our products whenever needed, so we decided to build our website ourselves - I would highly recommend this to anyone starting out! We used Squarespace to build our website and it took us about 2 months to get it all where we wanted.


We spent a considerable time brainstorming a name for our business that would be memorable, easy-to-spell for potential customers looking for us, and for which the domain name was still available - a challenge we'd never attempted before! Then, we also had to design a logo and luckily one of our family members came up with an amazing one!

Lastly (this is the part that took the longest) we took a lot of time to research and price our packages. A special challenge for us is trying to balance flight costs from different origination airports as well as hotel room costs in different cities. Smaller airports are usually more expensive to fly out of than larger ones and larger destination cities with well-developed public transit tend to have higher hotel costs. So to help account for all the variability, we decided to make the length of our vacation packages variable (5 or 6 days, etc.) instead of just set lengths.

When we first launched our business in 2017, we started out by telling our family and friends who in turn told their friends. To help spread the word a bit, we did the planning for few surprise trips for free and it was good for both us and for our travelers.

We learned how long it really took to research, plan and write up a trip (way more time than we thought initially!) and that helped us figure out how much to charge. This side business pretty much consumed our nights and weekends in those early days.

It wasn’t until we were featured on the Side Hustle School podcast that summer that we got a lot of customers!

Since launch, what has worked to attract and retain customers?

Word of mouth and referrals from past clients has honestly been the best way to attract new clients for us.

The clues that we post on our own social media account (then often get re-posted by our travelers) really help us spread the word. We also send our business cards in their surprise trip envelope to give an easily shareable promotional item, and we simply ask them to tell their friends and family about their experience. Never hurts to ask!

Another fun thing we include in the envelope is a full-page color sign with their destination printed on it in big bold letters. Travelers going on one of our trips can then share their destination “reveal” on social media using the sign to show off where they're going and tell their friends and family - it’s great for our customers and us - we’ve now had quite a few travelers who decided to trust us after seeing the great time their friends and family had on a their trip!

You can see an example of a couple revealing their destination on our social media, like this link to see Alaina and Sean find out where they were going to celebrate New Year's Eve!: here.

We have also been covered in quite a few news outlets like the Washington Post and the Wall Street Journal - that helps too! We were also featured in The Epoch Times.

We didn’t really do any outreach on our end, they reached out to us (we were a bit to busy planning trips)!

How are you doing today and what does the future look like?

We are doing pretty well these days - the winter holidays were a busy travel period so we are recovering from that still! Spring break and summer travel are also very busy for us so we are trying to stay one step ahead of our trip bookings.

Last year (2018) was our first full year in business and though we were more profitable than 2017 (which was a half year for us), we don’t really have that much data to compare - yet!

Looking ahead - we just added a longer International surprise trip to our package offerings (11 to 14 days) since we had quite a few travelers ask for longer trips. We are also thinking of ways to make the trip survey more fun to fill out. We are constantly looking for ways to take customer suggestions and make them happen!

Through starting the business, have you learned anything particularly helpful or advantageous?

As we mentioned before, we are SO glad that we chose to make our website ourselves rather than pay someone else to do it.

It was a lot of work but it also allows us to monitor analytics and change anything really quickly.

Prior to designing the TVH site, neither of us had made a website before so it was all completely new for us!

We also had to figure out how to use social media for business - we didn’t even have an Instagram account!

What platform/tools do you use for your business?

We use Squarespace to build our site - they have been pretty easy to work with, though it does have limitations. You trade those limitations for the ease of use, though. Most importantly, we utilize Instagram and Facebook for our clues and sharing traveler photos. Travel in general is pretty picture heavy, so Instagram in particular has been a great platform for us.

What have been the most influential books, podcasts, or other resources?

Our friends and family have been super helpful and our best resources. They’ve helped us research destinations, design and edit our website and even come up with destination clues!

We definitely could not have started the business without their help and support. We are also pretty big fans of Side Hustle School and were even featured on an episode after we got TVH up and running!

Advice for other entrepreneurs who want to get started or are just starting out?

It’s super cliche but our advice is: you never know until you try! There are a million reasons to not do something but sometimes you have to just go for it - what is the worst that happens?

To be clear: I’m advocating setting aside a budget (both time & money) and working within that and seeing what happens, not betting the whole house or quitting a good paying job right away if you have one.

While that’s not always an option for everyone, if you are lucky enough to be in a position where you can do it, that is my advice.

Start off doing it on the side and see where it goes. It takes off a lot of the pressure of “being successful” right away!

Where can we go to learn more?

If you have any questions or comments, drop a comment below!