Our Surprise Travel Agency Surpassed $7M Revenue In 2022 [Update]

Published: May 23rd, 2023
Lillian Rafson
Founder, Pack Up + Go
Pack Up + Go
from Pittsburgh, PA, USA
started January 2016
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Hello again! Remind us who you are and what business you started.

Hello again! My name is Lillian Rafson, and I’m the Founder + CEO of Pack Up + Go.

We plan curated getaways around the United States, but the catch is that our travelers don’t know where they’re going until the day they depart!

We’re a bootstrapped business, and since launching in 2016, we’ve sent 40,000+ travelers to 300+ destinations around the country. I started the company when I was 23 years old, and today we’re 30 full-time team members.

We’re on a mission to become the best US travel service and offer four types of surprise vacations: Plane Trips, Road Trips, Outdoors Trips, and Staycations. We provide 24/7 in-house traveler support, and offer Peace of Mind Refund Assurance, an in-house alternative to traditional travel insurance to our travelers to make sure their experience with us is the easiest – and most exciting! – a trip they’ll ever take.

In 2022, we surpassed $7 million in annual revenue, up 30% from 2019 and our pre-pandemic numbers. But perhaps the metric I’m most proud of is our Net Promoter Score, 92.

This number proves to me that we’re constantly upholding our first core value: hold the traveler experience above all else. With that core value in mind, we’ve been able to scale without compromising our traveler experience.

Curious how we got here? Here’s our first Starter Story, and here’s our last update!


Tell us about what you’ve been up to. Has the business been growing?

Our biggest update that I’m incredibly excited to share is that we made our first acquisition! I’m proud to say that Pack Up + Go has acquired Have Fun Do Good, a domestic group travel company.

Have Fun Do Good plans group trips that give back, and each trip incorporates a volunteer opportunity, which is perfectly aligned with our core value of inspiring positive change.

Even though more than 60% of Americans do not hold passports, Pack Up + Go and Have Fun Do Good remain two of the only travel brands to service domestic travel. The US has such a wealth of destinations to explore, and we’re excited to further spread the economic benefits of tourism to lesser-visited destinations, while our travelers enjoy fun and stress-free trips. This is a big step towards our goal of becoming the best US travel service.

The two brands will continue to operate independently but Have Fun Do Good will be powered by the Pack Up + Go team and technology. It’s been a really exciting challenge to navigate the acquisition process as a founder, and a unique opportunity for our team.

Our marketing team has been navigating and managing two brands and working to align our key messaging and branding as much as possible. Operationally, group travel is new to us, so it feels like we’re back in the nitty-gritty building phase.

It’s an interesting exercise to start something from scratch when you’re armed with seven years of experience in building another brand!

Whether you’re just starting out or growing your business, some things that you try are just going to fall flat. That’s okay!

Picture of me taken just after the closing on the acquisition!

Aside from the acquisition, the last few years have been a whirlwind! We experienced incredible growth in 2021 and 2022 coming out of the pandemic. Our trip volume was at an all-time high in both years, and we were able to reap the benefits of the return to travel by investing in both our tech stack and our team.

When I started Pack Up + Go, the entire trip planning process was manual and managed in Google Drive. Today, our incredible travel planners still read through each Pre-Trip Survey to plan each trip individually, but our proprietary tech stack then curates completely personalized recommendations for each traveler’s hobbies + interests, dietary restrictions, and mobility restrictions. Then, our travel planners review the tech's work to put our hands-on finishing touches on each trip.

This tech has allowed us to scale, ensure accuracy, and enabled us to personalize our experiences even more than before. We are always looking for ways to improve our trips and leverage tech to do so.

Since launching, we’ve been unbelievably fortunate to have grown organically and never invested in marketing. However, we’ve begun investing in marketing since 2022 to buoy our pipeline and ensure we can withstand a potential economic downturn.

To increase traffic and sales we launched our Influencer Ambassador Program, and we are launching our first paid ads this quarter. Social media is our biggest referral source after repeat travelers and referred travelers, so we’re focusing on Meta and TikTok.

All in all, the last year has felt like a mix of growing and improving what we’re already doing and looking for new adventures.

What have been your biggest challenges in the last year?

I’ve learned that leading a thirty-person team is very different from a team of ten or fifteen people. As a fully remote company, navigating the best ways to share company information and build internal systems has been a growing pain.

We realized that storing all company information on Google Drive was no longer manageable and migrated all general company docs and resources to a centralized platform, which was a huge undertaking. This process taught me that change management only gets harder, but also more important as the company grows.

When you’re a small, scrappy startup, everyone expects things to be constantly in flux. Then, structures are built and things begin to feel more stable. When changes become a company-wide need but not an individual want, it can be challenging and frustrating for team members to change their daily processes to adapt to a new system that they didn’t necessarily ask for.

I learned a lot about communication through this process and realized that is an ongoing area of growth for me as a leader.

The other major challenge our team is up against is burnout. We were all in survival mode from 2020-2022, first trying to stay afloat, then trying to keep up with demand. With ongoing economic uncertainty, a growing team, and new product launches to stay ahead of the curve, we’ve never really had a chance to slow down and catch our breath.

Each time we think we’ll have a little bit of downtime, it seems like there’s an external force at play that keeps us on our toes and moves us into overdrive. It’s hard as a leader to know that your team is experiencing fatigue without having a clear solution.

Something that works for someone else might not work for you! Stay true to who you are, keep your eye on the prize, and keep building.

What have been your biggest lessons learned in the last year?

No matter how much you prepare or plan, there are always going to be factors that are out of your control. Whether it’s social media algorithms changing the way they display content to your followers, or the potential onset of a recession, you can only control what’s truly in your control.

For us, that has meant improving our internal processes, engaging with our existing audience, and always looking for new opportunities to grow creatively and sustainably.

I’m an eternal optimist, and the past few years have been a rollercoaster. The highs have felt very high, and the lows have felt exceptionally hard. Throughout all of it, I’ve learned that optimism and always looking for a solution or path forward are key.

Understanding what we can’t control but embracing what we can with optimism has never been more important for me as an individual, a leader, and a CEO.

What’s in the plans for the upcoming year, and the next 5 years?

For the upcoming year, we plan to launch and manage the new business we acquired, Have Fun Do Good! Learning to balance both brands while entering a new market will certainly take up a lot of our bandwidth.

Meanwhile, we’ll never stop actively working to improve our core product, Surprise Vacations through Pack Up + Go. Whether it’s streamlining our internal processes, building new partnerships to support our Trips, adding new destinations, or eventually launching new trip types, I don’t think our work will ever be done!

Over the next five years, we will continue inching closer to becoming the best US travel service. We’ve set high benchmarks for ourselves to improve our traveler experience, expand our product offerings, and continue growing our services.

No matter how or where you’re traveling around the US, we want to offer a solution for everyone in the future. We’re not there yet, but we’re excited to continue exploring more + enjoying the ride. In the meantime, whether you’re taking a surprise vacation with Pack Up + Go or embarking on a group trip that gives back, we’re excited to send you somewhere soon!

What’s the best thing you read in the last year?

The Making of a Manager by Julie Zhuo has transformed the way I think about management. Our Director of Marketing recommended it to me, and now every manager on our team is reading it. There are so many times when I feel like I don’t know what I don’t know as a manager, and this book provides such useful tips and tricks to grow as a person and professional.

Whether you’re just starting to manage your first team member or have been managing a team for years, I can’t recommend it highly enough!

Advice for other entrepreneurs who might be struggling to grow their businesses?

At Pack Up + Go, we embody what we call a test + learn mentality. We’re constantly trying new things, measuring how they perform, and adjusting for the future.

Whether you’re just starting out or growing your business, some things that you try are just going to fall flat. That’s okay! Now you know what doesn’t work, which will bring you one step closer to building something that will resonate with your audience. Be patient with yourself, and never lose sight of your end goal.

It’s also important that you don’t let your planning become procrastination. I sometimes see entrepreneurs planning so much that they never really dive in. Don’t get me wrong - planning is important!

But when you embrace the test + learn mindset, you stay agile and work quickly towards creative solutions. Remember that something that works for someone else might not work for you! Stay true to who you are, keep your eye on the prize, and keep building.

Where can we go to learn more?

Be sure to also check out our new brand, Have Fun Do Good - havefundogood.co!

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