Lessons Learned 3 Years After Building My Travel Business

Hi everyone! My name is Jalisa Whitley and I am the Founder of BOOKED Trips. I am a world-builder and experience curator reshaping the travel landscape by creating an ecosystem where stories come alive in physical spaces around the world, generating positive impact for destinations, driving revenue for local artists and entrepreneurs, and enabling people to connect, be entertained, and inspired.

I specialize in curating book-inspired, small group travel experiences that seamlessly weave together literature, history, culture, and exploration. Since launching in October 2022, the company has welcomed travelers from across the U.S., Canada, Germany, Kenya, Trinidad and Tobago, and South Africa. I believe storytelling can be both dangerous and disruptive in the best possible ways by transforming perspectives and fostering connection. As we come to the close of the year I wanted to share 5 things I learned after 3 yeas running this travel company and over 10 years as a self-employed entrepreneur.

1. You don’t need a large following to be successful. You just need people who care deeply about what you are selling and can be champions for your work. We sold 85% of our total trip spots this year amidst one of the hardest years in travel since the pandemic. This year we made over $197,000 in revenue a 159% increase since our first full year in business in 2023. Over 20% of BOOKED Trips travelers this year were returning travelers. We have 779 newsletter subscribers with an average open rate of 65%. We have under 4,000 Instagram followers but the majority of new travelers say they found out about us on Instagram or through word of mouth. I don’t have a background in sales, marketing, or advertising. We did no paid advertisement this year. We were still featured in Essence and Success Magazines. It just shows that you don’t have to be the biggest or most well known in the room to have an impact. 

2. Intentional welcomes and openings matter. Having a pre-trip information session so people can meet each other and our on the ground staff before arrival to feel more confident and clear about the trip. Making sure there are included airport pickups with signage and clear communication. Writing personalized welcome cards and having them at the hotel desk at check-in. An intentional opening dinner and book discussion with personalized name cards, tables capes that connect to the book and the country we’re in, and an opening prompt that shows people that they already have commonalities that can provide the basis for connection.

We start each opening dinner with the question “Who are your people? Who are the people that make you feel most like your best self?” We hear how people enjoy other readers, curious women, kind women, passionate people, givers, etc. and at the end of each dinner our travelers find that the women at this table are their people. Building trust early allows for relationships to build and makes travelers more likely to give you grace later in the trip if changes or mishaps happen (because it’s travel after all, if nothing else things will change!)

3. Curation is care. The most common feedback we get about our trips is that our travelers appreciate how intentional and curated they are. How each meal and experience is connected to the book and the place we visit. How special our experiences are because of the local partners we work with. How surprised people are by the community of women they meet on these  trips and how these relationships extend beyond the trip. All of these things are intentional. Before each trip I do a research trip to personally try out our experiences, restaurants, and try out a few potential partners to ensure there is values alignment and deep local connections that keep our tourism dollars in the communities we visit. 

All of our travelers fill out a trip interest form before being sent the booking link so that we can ensure that what we offer meets traveler expectations and that we’re bringing together a group of women with enough diversity of age, geography, and experiences to stretch each other and have interesting dialogues while having enough in common to feel safe to connect. 

4. Nothing sustainable is built alone. YOU NEED PEOPLE. I have felt like quitting so many times this year but was able to push through because of the collaborations I’ve built with other people and the support of this community of travelers. Destinee Hodge has served as BOOKED Trips Partnerships & Engagement consultant for two years and has been a huge champion behind the scenes, got signed books from Trevor Noah, hosted IG Lives with Cristina Henriquez and Lauren Francis-Sharma, and played co-pilot on the BOOKED Trips Morocco experience sharing the whole experience in our IG highlights. She is also the person I go to in order to bounce ideas off of because she sees possibilities where I see road blocks. 

None of this work would be possible without our on the ground partners El Trip de Jenny, CURIOCITY, Sorted Chale, and Impulse Travel. Special thanks to Juliana and the whole Impulse team for holding me through one of my biggest griefs of the year with such tenderness while ensuring we could offer our travelers the experience they deserve.

With that said, be very discerning about partnerships. The biggest misstep I’ve had this year was because I moved forward with a partnership that didn’t feel right in my gut and kept me up at night. Those feelings of trepidation absolutely played out on the trip and I spent the whole trip recovering from changes, miscommunications, and undermining behavior. Alternatively, I chose the right partner for another trip and it helped me navigate one of the biggest life challenges I’ve ever had with grace feeling supported. 

When going into partnership it’s very important to ask: Do you have aligned goals and approaches? Is this something that feels exciting/ like a hell yes?  Would this benefit you as much as it would them? What would be the monetary, emotional, and mental costs of this engagement? Do you meet your minimum monetary benchmarks if you engage? Is this a sustainable partnership that can be ongoing or a one off? 

5. Revenue is great but margins matter more. This year we made over $197,000 in revenue a 159% increase since our first full year in business in 2023. This is the first year I took a small salary of $25,000 and I reinvested the rest back into the business. Many people don’t know that I have to make deposits of 25% or more into the next year’s trips to hotels and vendors so I prepay large amounts before travelers even sign up for trips. Having the margins to actually get paid for my work, hire the support I need to be sustainable, and make those pre-payments is vital for longevity. 

I’m excited to put my learning into practice next year as we launch trips to South Africa, Kenya and Zanzibar, and Vietnam. You can find out more and join us at www.bookedtrips.com