The Black travel movement is bigger now than it’s ever been before. Following the COVID-19 pandemic, there’s been an uptick in travel — family reunions, destination weddings, squad trips, and more. Black entrepreneurs Darrien Watson and Stevon Judd are revolutionizing how travel agents, small businesses, and trip organizers plan and curate travel experiences with their platform SquadTrip.
Hailing from Brooklyn, the entrepreneurs met in college where they pledged for historically Black fraternities — Kappa Alpha Psi (Watson) and Phi Beta Sigma (Judd). Together, they created SquadTrip, a tool that makes travel planning as easy as 1,2,3.
SquadTrip is also a part of the inaugural program for Techstars Build in Tulsa, which sits in Black Wall Street of Tulsa, Oklahoma. Techstars is a top tier tech accelerator program and only 1% of companies get accepted. As part of the program, Watson and Judd have received $120k in venture funding to date.
We had the opportunity to sit down with Darrien Watson where he walked us through conceptualizing SquadTrip and how the platform came to life to help plan hundreds and thousands of travel experiences.
Jouviane: Official Black Wall Street is not only about introducing our readers and community to Black-owned businesses, but also providing them with some insight into the entrepreneurs themselves. To start, could you share a bit about your background — both personally and professionally — and how you feel it led you to this point?
Darrien: I’ve always had a passion for entrepreneurship, especially technology. I have a background in product management and an interest in connecting people through events and experiences. I used to host events in high school and college, and that myriad of skills — product management and software building — plus my interest in connecting people led me to build software for travel organizers.
"So that’s what drove us — knowing that at the end of this was a Black entrepreneur who had a vision for doing something that he was passionate about."
Jouviane: And what do you think led you or put you on the path of travel? What inspired you to start this?
Darrien: I was actually running a web development shop with my best friend from college. We were both Black men in technology, and we were able to attract a lot of other small businesses who wanted to use our services. Plus, I wanted to work with Black-owned businesses.
What I think was one of the catalysts for us was trying to solve a problem for a friend of ours. He was also a client of ours, and he wanted help growing this travel experience he was building. And he had a vision of becoming an entrepreneur himself and doing this full-time, but he was struggling with the pains of automating the process of collecting money and building out his website. What drove us was the fact that if we could help solve this problem for him, he’s going to be able to grow his business, quit his job, and employ more people who look like him.
Ultimately, we could use that same tool and give it to others who have an interest in travel and want to connect other people through events and experiences. Just as a small business, you can either hire a developer or hire somebody else to do some of the manual labor of sending out emails, receipts, and reminders for your travel group. Or you can use a platform that essentially enables a small business. So that’s what drove us — knowing that at the end of this was a Black entrepreneur who had a vision for doing something that he was passionate about. It was knowing that we could use technology to help him scale his business and then give that to others as a playbook so that they can also live a life of financial freedom in doing something they are passionate about, but in this case, travel.
Jouviane: And maybe it’s just me, but I feel like after the COVID-19 pandemic, travel seems to be booming a lot more. So for all the people who are interested, what is SquadTrip, and how does it work?
Darrien: SquadTrip is a turnkey SAS platform for travel organizers to build a trip page to market it while offering payment plans so that they can collect money in minutes.
"Black people across the globe are creating amazing travel experiences. They’re promoting them on social media. And what they’re finding is that hosting a trip, let alone a group trip, is a lot of work."
Jouviane: Excellent. And like I mentioned with the uptick in travel, what do you think sets SquadTrip apart from the competition?
Darrien: In the last couple of years, the term “Black travel movement” has surfaced. I think that it comes together at a time where we have access to social media. Black people are increasingly making more money and want to share experiences. I think in the history of Black folks, we want to go places where we know we’re going to be safe and so that pushes us to travel in groups.
And so SquadTrip, we created this as a solution to something that people were already doing. Black people across the globe are creating amazing travel experiences. They’re promoting them on social media. And what they’re finding is that hosting a trip, let alone a group trip, is a lot of work. There’s planning, organizing, collecting money, and communicating with the vendors and everyone who is attending.
So imagine a travel organizer who is planning an experience for 200 people. They have to collect installment payments for six months for hundreds of people. And they’re using all these tools to put together this beautiful, curated experience. What we found is that there are tools to help you plan and organize. You can make some tools if you put together a Wix or Squarespace landing page with a PayPal button. You can use Zelle to collect money. There are also tools to communicate. Some might use WhatsApp or others use GroupMe. There are many tools, but there’s no tool that brings all of these pieces together.
And again, group travel is a movement. It’s something that’s growing, something that’s new. It wasn’t possible to do at scale 20 years ago. And so now, it’s becoming easier and more people are doing it. Ultimately, the competition, they’re all focusing on one part of the experience, but they’re not focusing on the person who’s creating it. We want to enable more people to create these amazing experiences so that more people can attend.
The bottleneck in part is the access to tools that help them to do so without breaking the bank or hiring a large team. And that’s what separates us from the competition — we’re focused specifically on software for travel groups.
"Anybody who has an experience that they want to curate and bring friends and family together can do so through SquadTrip."
Jouviane: I think it’s clear to see that this platform would work exceptionally well not only for travel organizers but even for someone who is planning a one-off trip, like a family reunion. For you, who would you say is the ideal client of SquadTrip?
Darrien: I think the demand for curated experiences is driving this renaissance in the travel agent business. I remember when I was growing up having to go to a travel agent office with my grandmother to get tickets to go to Honduras for the summer. Travel agents themselves are hosting corporate retreats and destination weddings, but the platform is easy enough for anybody to use.
We have an influencer on our platform who has over 100,000 followers on social media in wellness, health, diet, and meditation. And so she’s built this online community, but as humans, we still crave these in person experiences and she wants to connect in person with her audience. And now she uses SquadTrip to host group trips 4 times a year. And even though she has thousands of followers, she’s able to host 40 women for a wellness retreat.
Those are some of the folks we have using the platform. And much like you mentioned, there’s always that organizer, who’s part of a family/friend group or sorority, who’s putting together a reunion for family or chapter sisters. SquadTrip makes it really easy to build that trip landing page so that people know all the information about the trip — the who, what, where, when — and they are able to have an FAQ section on what is and is not included.
It also makes it really easy to offer payment plans and collect money at ease. So now anybody who has an experience that they want to curate and bring friends and family together can do so through SquadTrip.
Jouviane: I’m sure you’re aware of that meme where someone is planning a trip, and while everyone is so excited at the beginning, once it’s time to start paying and making plans, everyone falls through. I’m positive SquadTrip would help with situations like those.
Darrien: Definitely. I think one of the biggest reasons why is access to financing. So we offer payment plans through the platform. Once they say they’re in, they can put $150 down and get charged automatically each month. It’s like they set it and forget it. And it’s a lot easier for them to sign up and say that they’re going.
I think another important part is that when you put together a travel itinerary, it’s this four or five day list of things. People want to know all this information so they can use it to book and get their flights. Because it’s easy to build a trip landing page with all that information in one place, it’s easier to corral an entire group.
"The most fulfilling part is watching some of our customers grow their business. It’s watching them have the ability to quit their job and dedicate their time to doing what they love."
Jouviane: I think it’s clear that you’re pretty passionate about your business and enabling others to use your tools to curate travel experiences. Throughout this entire journey, what would you say has been the most fulfilling part of starting this business and expanding it?
Darrien: By far, the most fulfilling part is watching some of our customers grow their business. It’s watching them have the ability to quit their job and dedicate their time to doing what they love. And what I really love is that this is a product that anybody can use. This is a product that’s spreading via word of mouth, and the majority of the trip advisors on our platform are Black entrepreneurs.
Jouviane: In the same vein, what would you say has been the most challenging aspect of starting this business?
Darrien: The most challenging part is raising capital. We’re actually trying to raise capital right now. Just two months ago, we raised $120,000 from TechStars, which is a premier startup accelerator program. That was great, but we understand how big this can be. We understand how many other small businesses we can help. And ultimately, to do that, we’re going to need capital to continue to build out our product and our team. And that’s probably one of the biggest challenges.
I know how to build products and how to build things that people need and use. It’s easier when you actually talk and listen to them. And that’s what I’ve sort of done, but breaking into venture capitals is a relationship business so it’s taking a bit more time.
"So we want to make it easy for anybody to build and execute a group travel experience whether they’re an influencer, a coworker planning a corporate experience, or a friend trying to connect with other friends or family."
Jouviane: As you continue to build, help entrepreneurs, and secure more capital, what would you say is the ultimate goal for you and your business?
Darrien: If you want to go on a trip, most of us are going to go to booking.com or Priceline. That’s because booking.com is the largest travel agency in the world, but 30 years ago, that wasn’t the case. COVID has caused a lot of people to move out of inner cities or move away from their families. We’re not spending as much time with family or friends. We’re not going into the office as much. Additionally, remote work is here to stay.
And so there’s always people who want to put together family reunions or even a friendsgiving. Even destination weddings are really on the rise right now. People are using the opportunity to meet up and travel together. At SquadTrip, we want to make it easy for anybody to host a large-scale travel experience. Today, if you want to put together an experience for your destination wedding or family reunion, you have to go through a travel agent because you can’t go to booking.com to block off 30 rooms. You can’t go to booking.com to find 30 flights, transportation, access to excursions and events at scale. You have to go through a travel agent.
So we want to make it easy for anybody to build and execute a group travel experience whether they’re an influencer, a coworker planning a corporate experience, or a friend trying to connect with other friends or family.
Jouviane: So that’s where you hope to see SquadTrip down the line. What’s up next for SquadTrip right now?
Darrien: We’re currently building out an AI itinerary building. In the next year, we’re going to launch that in alpha. It’s going to be a private launch to SEMrush-led private users. Essentially, a user will be able to enter in the information and the preferences for the trip they want to put together — the number of people, the time of year, the type of experiences. The tool will then build out a multi-day itinerary with suggested experiences. And then it’s as easy as them clicking “accept” to book all those separate experiences in one place. It cuts out needing to use a collective team of websites like hotels.com, TripAdvisor, Yelp, or OpenTable.
Jouviane: We’re down to the final question. How can our Official Black Wall Street readers support you and SquadTrip?
Darrien: Share our story with the people it might resonate with. That could be an angel investor or venture capitalist. It might be an entrepreneur who is our next customer. It could be a travel agent, destination wedding planner, or a yoga instructor who wants to put on quarterly events. It’s as easy as sharing our story with people who might want to listen to it.