How I Started A $450K/Month Travel Agency That Curates Surprise Vacations

Published: March 14th, 2021
Lillian Rafson
Founder, Pack Up + Go
Pack Up + Go
from Pittsburgh, PA, USA
started January 2016
Discover what tools Lillian recommends to grow your business!
social media

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

Hi! My name is Lillian Rafson, and I’m the founder + CEO of Pack Up + Go. We’re a travel agency that plans curated getaways around the United States. The catch? Your destination is a surprise until the day you depart! Since launching in 2016, we have sent 25,000+ travelers to 100+ destinations nationwide.


Our mission is to encourage the pursuit of wonder, spontaneity, and exploration by planning surprise getaways that champion the traveler experience, promote responsible tourism, and create community. We believe that travel can build bridges and that vacations should be stress-free, fun, and exciting! We work to make the world a better place by supporting as many small businesses as we can in our destination cities.

We offer four different types of vacations:

  1. Plane/Train Trips
  2. Road Trips
  3. Outdoor Road Trips
  4. Staycations

Each of our trip types includes reservations at a top-notch hotel, curated itineraries full of recommendations for things to do, see, and eat in the destination, and 24/7 in-house traveler support.

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

I started Pack Up + Go when I was 23 years old, having no experience running a business or in the travel industry. I went to school in New York and was working at a startup after graduating, and was already feeling burnt out from working in sales.

Leap, then work really, really hard to make it work once it’s up and running. You’ll thank yourself later!

I decided to quit that job to take time off and travel, embarking on a 3-month journey with no set plans. My goal was to figure out what I actually wanted to do with my life, what really sparked my interest, and what I would feel passionate about showing up to do every day for the rest of my life.

I was in Riga, Latvia talking to two women in the lobby of my hostel, who was there on a surprise vacation with a European surprise travel agency. As soon as they finished explaining why they were in this seemingly random city, I went to the shared hostel computer, did a quick search to see if there were any surprise travel agencies in the United States, and discovered that there were not.

I emailed my parents to tell them I was moving home to Pittsburgh, PA, and I was going to become a surprise travel agent. I don’t typically believe in fate, but this felt like the stars were aligning. Only 24 hours before this interaction, I had decided to give up my apartment lease in New York and fell asleep hoping I would have some sort of lightbulb moment to give my life some direction. The rest is history, and I haven’t looked back since!

Take us through the process of designing, prototyping, and manufacturing your first product.

After that fateful day in my Riga hostel, I still had about 6 weeks remaining in my travels. As I wandered around the Baltic coast, I kept a notebook with me and constantly took notes about ideas that I had related to the business. It was an invigorating process, and I remember constantly challenging myself with the question, “Why?” The first major decision I made was to limit departures and destinations to the United States. Why? I couldn’t shake the idea that I was walking around small villages in Slovenia brainstorming this business, but I had never been to Savannah.

Why, I kept asking myself, did I feel the impulse to take short-haul trips every weekend of my year studying abroad, but those impulses stopped when I returned to New York? Why is it that Americans don’t typically see the places within the United States as leisure vacation destinations?

I was raised in Pittsburgh, PA, which I know has a negative connotation for many Americans, but I love the city. It occurred to me that surprise travel could be a conduit for change by encouraging Americans to learn more about the hidden gem cities that they have never thought to visit before.

Surprise travel could give a city like Pittsburgh the opportunity to surprise and delight. As I brainstormed and traveled, I realized the potential economic benefit a company like this could have on smaller markets in the United States. After all, when you travel, you’re so much more likely to support local businesses. This could be huge, I realized.

All I needed to do was create a website, and convince total strangers to let a 23-year-old with no industry experience plan their vacation to an unknown destination. Easy enough!

Describe the process of launching the business.

The hardest part of launching a business is deciding on a name. I remember thinking of dozens, if not hundreds of name ideas, only to discover that the domain was taken or that it was already trademarked. When I finally landed on Pack Up + Go and discovered that the domain was available, I was sitting in my grandmother’s living room. She handed me her credit card and said, “Please, buy the domain immediately so we can all move on from this brainstorming.” That $50 investment in the domain marked the official start of Pack Up + Go!

When recounting the story of starting their business, many founders fail to mention the nitty-gritty details. After deciding on a name, the next several weeks were spent combing through government websites, understanding how to register a business, securing an EIN, setting up bank accounts, email addresses, phone numbers, and insurance policies. There’s a lot of groundwork that must be done before the fun can begin.

Once all of that was squared away, I applied for a local pitch competition. I had only talked to friends and family about the business idea and had never pitched any type of business before, but I won first place! This came with a small cash prize, but more importantly, the win gave me the confidence I needed to move forward with launching Pack Up + Go. If this panel of three judges thought surprise travel was a solid idea, that was enough encouragement for me.

After winning that pitch competition, I secured an interview at Pittsburgh’s local NPR radio station. I shared that interview on my Facebook page, and a friend of a friend happened to see it. That friend was a reporter for Business Insider, who wrote a story about us that was published a month later on February 8, 2016. By the end of that fateful day, Pack Up + Go had received a handful of orders - real trip orders! - and I had taken calls from NBC Nightly News, Shark Tank, and The Travel Channel. It was completely surreal.

Although it was the best possible scenario, it also filled me with anxiety. Real, paying customers had placed orders. Now, the pressure was on to live up to their expectations, and the real work began.

Picture from that initial pitch competition!

We were featured on NBC Nightly News a few short months later!

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

As a bootstrapped business, we’ve never had a big marketing budget, but I knew that word of mouth and real traveler testimonials could be huge for us. When our very first travelers returned home from their vacations, I sent them an email asking for photos from their trip. I was surprised when they happily obliged, and one of the photos I received was of the traveler holding up her sign that said, “You’re Going to Washington, D.C.!” I shared it on the Pack Up + Go social media accounts, and it quickly became a trend.

After every trip, travelers started sending me the same photo of them holding up the sign that revealed their destination, so I kept sharing them on social media. How, I thought, could this single piece of paper become our biggest marketing strategy? But its success is multifaceted:

It’s authentic!

We only share images of our real travelers on social media, not stock images. This traveler-generated content shows prospective travelers how their trip might unfold. Sometimes, that means the quality of the photos isn’t top-notch, but that only adds to the authenticity. We aim to showcase all of our travelers - all ages, races, genders, types of trips, solo travelers, families - and a wide range of their experiences.

It builds anticipation!

Truthfully, when I launched Pack Up + Go, I imagined mailing these physical envelopes was just going to be a placeholder as my MVP. I imagined that as soon as we had the funds saved, I would replace those physical envelopes with an app that would reveal the traveler’s destination. But in a world where so much of e-commerce is digital, having a literal physical touch goes a long way. It feels like receiving a gift in the mail and only heightens the traveler experience.

Tearing apart the envelope to reveal your destination on the morning of a vacation is exciting! Every time I watch a traveler video, I still get goosebumps and hold my breath.

It’s fun!

In a world where travel has become commoditized as a luxury product, I love that Pack Up + Go Surprise Vacations remind us to have fun on vacation. How often are we, as adults, genuinely surprised? Many of our travelers tell us the only other surprise they can remember experiencing is discovering the sex of their baby.

Vacation is supposed to relieve stress, allowing us to discover a new place, but instead, it has become an Instagram-worthy-experience-seeking opportunity. I love that our “You’re Going To…!” piece of paper encapsulates how fun, silly, and exciting traveling can and should be.

Aside from this unintentional marketing strategy, we have enjoyed great success from partnerships with larger brands. Whether it is planning Road Trips in partnership with Ford, partnering with HotelTonight to plan vacations for influencers, or raffling off trips for newly engaged couples with WeddingWire, we know that the best way to promote ourselves is to help other brands succeed in tandem. As long as we stay true to our mission and our values are aligned with the co-sponsor, I am a strong proponent of partnerships.

We also stay engaged with our travelers after they return from their getaway! I’ve always thought it was silly that the conversion funnel ends with the conversion. What is supposed to happen after that? We believe that the conversion funnel reopens after ‘conversion,’ into a new category that I call, ‘Community.’

We have a private Facebook group for Pack Up + Go, alumni, where our travelers can engage with one another, ask questions, share stories and pictures, and we can stay in touch with them. We offer exclusive discounts to this group, and we also ask them questions! We know that our travelers are a valuable resource and have amazing firsthand experience using our services, so we want to make sure that we stay in touch with them as we work to develop new products.

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

Like so many businesses, the pandemic posed immediate challenges that we had never seen before. Before 2020, the travel industry was growing annually, and we were happily riding on that success. Pack Up + Go is inherently profitable since our travelers prepay for their trips in full, and our only overhead is our payroll. We take a 20% service fee for planning our trips, and we earn commission on hotel reservations. It’s a really straightforward business model, which has always served us well.

However, when travel came to a screeching halt in March 2020, we had to get creative, quickly. For the first four years of our business, we coasted on the success of our two hero products: Plane/Train Trips and Road Trips. To respond to changing traveler needs, we quickly launched Staycations before all stay-at-home orders were in effect.

Later in the summer, we pivoted again to launch Outdoors trips, where travelers can travel to nature-centric destinations and stay in off-the-beaten-path accommodations. Our Outdoors trips buoyed our business through the fall, accounting for nearly 25% of our total annual trip volume in 2020, and we expect to see them continue to grow in 2021.

Although both of these new trip types were born out of necessity and pivoting, they ultimately strengthen our brand as a whole. Now that we offer a wider variety of vacations, we can attract a wider range of travelers. We understand that a surprise vacation isn’t the best fit for everyone, so our Staycation option, offered at a lower price point, is an approachable point of entry to our brand.

In 2021, we will continue to diversify and grow. We have had many travelers ask for a standalone itinerary product, without the travel planning services, for when they know they are traveling to a specific destination to visit friends or for a work trip. We are launching Pack Up + Go Picks to offer our expertise as a package of recommendations for things to do, eat, and see in our destination cities! Our Picks will be offered at a static cost and will work to extend the lifetime value we can provide to our travelers.

If there’s one thing that the pandemic taught us, it’s that we should not be afraid of growth or change. Although it was hard to see Pack Up + Go have its first year operating at a loss in 2020, I like to think that we seized the opportunity to come back stronger than before.

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

I’ve learned that you can’t understate the value of customer service. At Pack Up + Go, our very first core value is to Hold the Traveler Experience Above All Else, and we mean it. Although we’re a small team, we offer in-house 24/7 traveler support, no matter what. We always say that our travelers come for the surprise, but stay for our service. As a digitally-native company, it’s easy for our travelers to assume our team is much larger than we actually are.

When I first launched the business as a 23-year-old working out of a coworking space, I made the decision, to be honest with our travelers about who the person was behind the website. Early on, when skeptical potential customers called, I would offer to put them in touch with a recent traveler so that they could ask questions directly. I gave out my cell phone number and took calls at all hours of the night. Although this level of support can be exhausting and doesn’t scale as easily as outsourcing CX, it is one of our strongest assets.

As the pandemic tore the travel industry apart, we saw record numbers of repeat travelers and referrals from past travelers. Our travelers know that they can trust us to keep their best interests at heart, and know that we will do everything in our power to plan them a safe, fun surprise vacation, even during a global pandemic.

Although prioritizing customer service came naturally to me, I’ve come to learn and appreciate that it’s the best investment you can make for your business and ultimately leads to creating an engaged, thankful community.

What platform/tools do you use for your business?

Until recently, Pack Up + Go was a low-tech, high-touch company. As a bootstrapped business, finances have always been tight, and we have been diligent in our saving strategy. Much of our website is still hosted on Squarespace, and we use Google Drive for team collaboration and Quickbooks for accounting.

Over the past year and a half, we worked to build proprietary software to streamline our back-office management and processes to help ourselves scale and improve our traveler experience. This technology was the outcome of years of manual processes and understanding exactly what we would need to develop to set ourselves up for success. It’s amazing to me how far we were able to go using existing tools and resources for small businesses!

There’s a big trend for startups to raise a lot of capital early on and to build proprietary technology, which passes up the opportunity for organic, sustainable growth. I wanted to make sure that Pack Up + Go could survive and be self-sustaining without relying on outside capital, which meant that we sometimes had to get creative with piecing together various free platforms. In the end, I’m proud of our journey, and I would recommend it to any other founder.

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

The most influential book I read before launching Pack Up + Go was The Lean Startup by Eric Ries. When I started telling people about my idea for the business, I got a lot of mixed feedback. Some advisors told me to keep it lean and work with free or existing tools and platforms, while others told me to raise capital and invest in technology. Reading The Lean Startup helped me to understand the benefit of starting small, working with free and low-cost resources, and improving the business as I grew and could afford it.

I’m so thankful that I heeded the advice in the book because it turned out that Pack Up + Go could make it pretty far using free software and services. This allowed me to save money, invest in branding and public-facing materials that improved our traveler experience, all while gaining a better understanding of what technology we would need to build when the time came.

For the first three years of the business, we made small changes here and there, and kept a running log of our tech wishlist, diligently saving our money. Finally, we were able to self-fund a fully proprietary tech stack that is perfect for our use case. Had I invested the money and energy in developing technology early on, it would have not been nearly as useful. Remember, your product doesn’t have to be perfect to start, it just has to work!

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

My motto in life is “If not now, when?” I say it all the time when people tell me they’re considering starting their own business. It’s easy to think of a million reasons not to take the leap or make a list of a dozen things you need to do before launching, but I say just go for it.

There’s always going to be more work to do, and your product or service will never be perfect. But if you never launch and put it in front of real customers, you’re never going to be able to improve. Leap, then work really, really hard to make it work once it’s up and running. You’ll thank yourself later!

Are you looking to hire for certain positions right now?

We’re hoping to rehire and rebuild our team in the coming months! Be sure to check out our Careers Page to learn more!

Where can we go to learn more?

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