This is a follow up story for Pack Up + Go. If you're interested in reading how they got started, published over 3 years ago, check it out here.

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’re a travel brand that specializes in Surprise Vacations. In case you’re unfamiliar with surprise travel, we plan curated getaways around the United States. The catch is that our travelers don’t discover their destination until the day they depart!

We launched in January 2016 and have sent over 25,000 travelers to 300+ destinations around the country. Our goal is to help Americans experience the country in a new way by exploring destinations they wouldn’t think to visit on their own - all with a sense of spontaneity, ease, and excitement!

We’re a bootstrapped business, and I launched the brand on Squarespace. At first, it was just me planning the trips, doing all the research for our curated recommendations, and offering 24/7 in-house traveler support.

We launched with two core products: Plane/Train Trips and Road Trips and grew organically from there. During the pandemic, we launched two new types of trips: Staycations and Outdoors Trips.

The company took off pretty quickly early on, largely thanks to how sharable the concept of Surprise Travel is! Our early travelers became brand ambassadors, and I’m so grateful for how much our travelers share their experiences with their communities. It’s so fun for us to see travelers’ videos of them opening their Surprise Envelopes, sharing pictures of their vacations, and encouraging their friends to leap, as well.

Our travelers come from all over the country, but are typically in their 30s, have a sense of adventure, and appreciate top-notch customer service and personalization.

Although the pandemic has been tough for the entire travel industry, we finished 2021 with our strongest numbers ever with over $7 million in revenue, a 20% increase from 2019. Our team more than doubled in size, growing from 10 at the start of the pandemic to 24 full-time team members today. We’re on track for an even bigger year in 2022, and I couldn’t be more proud of the company’s progress.

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

I’m an eternal optimist and saw the pandemic as an opportunity for us to strengthen our brand, expand our product offering, improve our tech, and come out stronger than we were before.

Since we last spoke, our primary focus has been rebuilding the company. It’s incredible to think that this time last year, we were just a team of 10 people full time - I am proud to say that we are now a team of 25+! It’s amazing what a difference a year can make.

In 2020, we added two new Trip types: Staycations and Outdoors Trips. Adding these new product offerings allowed us to solve more problems for our travelers and opened our minds to what other problems we could help solve.

The biggest pain point that we were seeing for our travelers was trip protection and travel insurance. We saw firsthand that more than ever, there was a need for complete flexibility with travel, but traditional travel insurance companies weren’t stepping in to solve that problem for our travelers.

If you have to pay customers, get on the phone with them! Be open and honest with them that you’re a new business trying to get off the ground, and ask them for their insight.

So, we decided to take matters into our own hands! On March 31, 2021, we launched Peace of Mind Refund Assurance, our way of promising our travelers the flexibility they need, allowing them to protect their travel investment. If you had asked me in 2019 whether I thought I would launch a fintech product, I would have laughed! But when it came to solving a real need for our travelers and knowing that we were able to help by creating an innovative solution, it was a no-brainer.

Peace of Mind (or POM, as we call it) has truly transformed Pack Up + Go. It’s been really rewarding to see our Traveler Support Team help our travelers in so many scenarios without having to loop in a third-party insurance agency. It’s resulted in higher traveler satisfaction and greater team ownership, and it’s also opened up a new revenue stream for the company. A win-win-win, if you ask me!

Launching POM couldn’t have come at a better time. In early April 2021, we saw the travel floodgates open as cities reopened their businesses, the weather warmed up, and vaccines became widely available. Because we proudly offered four ways to travel domestically, we were equipped to plan a vacation for any type of traveler with any level of comfort during the pandemic.

Our summer was busy, to say the least. We saw record-breaking numbers of Surprise Vacations, and we began to rehire and restructure our team to allow our current team members to grow into new roles and become specialized in the new products and services that we had launched.

We expanded our Marketing Team to dive into our data and expand our social media reach. We’ve seen huge engagement on TikTok, which now accounts for nearly 10% of all new customers referrals.

Another big initiative was building out a structure for how we work with influencers. Instead of one-off transactions, we wanted to build relationships with a diverse range of content creators, so we launched the Flight Crew, our Influencer Ambassador Program.

We’ve also found new ways to nurture our relationship with past travelers, including launching a podcast to share additional insight and information with our audience and interview past travelers and external partners.

We launched a formal loyalty program, The Cloud 9 Club, as a way to thank our past travelers for being such incredible brand ambassadors, which has exceeded our expectations in performance.

Since launching six years ago, we’ve always loved building the brand through partnerships. Last summer, we were fortunate to work with Chase/United on a major partnership to promote their new Quest Card! This partnership was especially exciting for us because it delivered an amazing opportunity for our travelers and allowed us to streamline the way that we work with third parties on big promotions moving forward.

All the while, the new revenue from Peace of Mind allowed us to start rebuilding our savings and invest in technology. Being so busy after a really difficult year presented challenges, but we kept track of all the ways that we could improve internally to be prepared for our next busy summer season.

We’re launching some very exciting updates to our tech stack in the next couple of weeks that I think will help take Pack Up + Go to the next level!

All that to say, it was a really busy and exciting year, and I can’t wait to see where this year takes us.

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

There have been so many lessons learned in the last year. Truthfully, this time last year, I was still very cautious about the company surviving - optimistic, but still very cautious. Now that the team is so much bigger, I am confident that we will survive, but there are new types of stress and anxiety that come with the responsibility of providing for a larger team.

Perhaps the biggest lesson I’ve learned is that there are always ways to grow - personally, professionally, and as a company. The past year, and last summer in particular, really pushed my team to the limits of our capacity. It was sometimes hard for me to accept how close everyone was to burning out. I was grateful to have travelers booking trips again and excited that we were going to survive.

So when signs of frustration and burnout started popping up across the team, I wanted to respond, “Yes but what great problems to have! This is what we’ve waited more than a year for!” Instead, making space to listen to the team and understand their pain points was critically important.

Realizing that when members of my team were upset or at the end of their rope and venting to me wasn’t an attack on me personally but an ask for help, was a big mindset shift for me as a leader. In the height of our crazy summer of 2021, I drew out a plan to completely restructure the team in an attempt to alleviate some of the pain points I was hearing.

If you’re just getting started, don’t let your planning become procrastination. Whatever you’re building will never be perfect, so you just have to start somewhere. Commit to a deadline, and hold yourself accountable.

We’re still really (really) busy, but we’ve put systems in place to help all three of our teams (Operations, Marketing, and CX) feel more supported. We’re not perfect, but we’re in a much better place now than we were before.

Some of the changes required a significant investment in our technology, which was hard for me to stomach since we lost all of our savings during the pandemic, but knowing how much this tech will support the team and fuel our growth meant taking a professional risk and making the investment.

Shifting from a mindset of fear and caution from the pandemic back into a growth mindset was a major change for me as a leader and a lesson I’m still working to implement daily.

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

We have a lot of big plans in the works! As I mentioned, we’re working on building out a really exciting piece of technology that will open a lot of new doors for us as a brand. We’ve spent the last year launching so many new initiatives, so I’m excited to see how those continue to grow and develop with time.

Without giving too much away, we’re actively working on ways to expand our reach to create a more well-rounded experience for our travelers and work with locals nationwide.

Ultimately, I want to ensure we’re evolving as a brand and staying in touch with our travelers to make sure we’re always helping them solve a problem and providing the best possible solution. Be sure to follow us on social media and subscribe to our newsletter for future announcements.

Have you read any good books in the last year?

I try to alternate reading business-centric books with novels and books on other topics to help keep me centered and remember that there’s more to me (and my brain!) than just running a business.

Here are some of the books that I read or reread this past year and loved:

High-Performance Habits by Brendan Burchard was a really important book for me to read coming out of our crazy summer season last year. I was burnt out and found my energy and focus waning. This book helped me form habits in my personal life to revitalize my ability to deliver professionally. I’m not normally big on ‘self-help books,’ but I appreciated the tangible pieces of advice and reminders that Burchard offers.
This is Marketing by Seth Godin is a classic and one that I revisited earlier this year. It was great to reconnect with this book after a really busy year of working on so many new initiatives to reconnect with the core of our audience and strategy.
Radical Candor by Kim Scott is a book I’d heard a lot about but had never read. As our team more than doubled in size, our projects grew, and team members grew into management positions, this was a really helpful book for me to read. I’ve always considered myself conflict-averse but learning practical tools to support open communication and actionable feedback was useful.
It’s About Damn Time by Arlan Hamilton was one of the most inspiring books I’ve read in a long time. Outside of running Pack Up + Go, I’ve started doing business coaching to help entrepreneurs get their businesses off the ground. I’ve realized a passion of mine is to help as many people pursue their dreams as possible. Hamilton’s story is incredible, as is their drive to support other underrepresented founders. Hopefully, I’ll be able to write a similar book someday!

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

So much of business is testing + learning, so stay creative, stay agile, and keep your finger on the pulse.

If you have to pay customers, get on the phone with them! Be open and honest with them that you’re a new business trying to get off the ground, and ask them for their insight. It can be really hard to get feedback directly, but it’s important to help you figure out what might need to change.

If you feel like your business is stagnant because of factors outside your control, figure out what is in your control, and make changes there. There are (unfortunately) always going to be factors outside of your control - whether it’s a global pandemic, issues with suppliers, natural disasters, etc. - so you can’t use that roadblock as an excuse! If going that path feels like a dead-end, figure out another route.

If you’re just getting started, don’t let your planning become procrastination. Whatever you’re building will never be perfect, so you just have to start somewhere. Commit to a deadline, and hold yourself accountable.

Every single thing in business is malleable, and you can always make changes as you learn and grow. The most important thing is putting yourself out there and being open to change.

Most importantly, reconnect with your why. Why did you start your business? What is the impact that you want to have on the world? If there’s another way that you can deliver that impact and enact positive change, go that route. Trust that your impact is possible, and find a way to make it happen. Stay positive, and stay engaged.