This week I speak with the co-founder and CEO of Squadtrip, Darrien Watson about how he managed to think of everything when developing his platform.
1 Month Free of SquadTrip Premium Plus $20 off each month for the first year using code TNS.
I’ve put together an itinerary pack that includes five different weekend friendly roadtrips hours from NYC. Take the stress of planning and packing off the table and focus on the road. https://travelnshitpodcast.com/travel-resources/roadtrip/
Never miss a Travel N Sh!t beat! Keep up with guest updates and all things Travel N Shit. Sign up for the mailing list: http://bit.ly/3miJJWu
If you enjoyed this week or any week’s episode, please take a second to subscribe and rate Travel N Sh!t on the platform you listen. If you’re REALLY feeling froggy, please take this quick listener survey so I can get to know you better! https://travelnshitpodcast.com/listenersurvey
Guest: Darrien Watson https://squadtrip.com/
salutations and shit folks welcome back to another episode of your favorite travel podcast travel and shit where are your hosts D Carrie have an experiential conversation about the nuanced ways that travel intersects with regular life and jumping right to the point if you are watching the podcast you already know but you can either watch or listen to the podcast it is available on the YouTube's but you would see that I have a guest joining me today so my guest if you would please introduce yourself
Darrien | SquadTrip (00:31.411)
Hey, what's up everybody? My name is Darren Watson. I'm the co-founder and CEO of Squad Trip, and we help you manage group trips like a pro.
Thank you so very kindly for joining me. I've actually seen your platform around the interwebs and I don't know how your brain works, but my brain kind of works in like Post-It notes. Like I've got a lot of Post-Its going on up here, or there are a lot of tabs. And there was a tab where it was just like, you know what, I'm gonna circle back to that. I don't do the group trips. And I generally have people of color, black people.
on the show. So when I saw that there was a platform that absolutely fostered and made more easeful the experience of a group trip, it came to mind. So I am very happy to be having this conversation starting there. But what was the impetus for your company? How did you come up with this and why?
Darrien | SquadTrip (01:33.739)
Sure, always get that question. For me, just as a black male, to be honest, always seeking connections and experiences of people who look like me. And I remember when I graduated from college and went back home, I felt really disconnected. All my friends that I had met and spent time with who were down the hall from me, they were all across the country. So I decided to take it for myself, start feeling bad for myself, host a group trip. I did the planning, I did the organizing.
I had to collect money, PayPal, Cash App, Venmo, checks, whatever, and communicate with all my friends in a group chat and then all the vendors. It was a headache, I won't lie. But we had a good time. And I just really had that aha moment. I was just like, so if I'm having issues with payment collection, tracking who's paid what and who owes what for a group trip, and I want to do it again.
And we plan to do 50 people next year. What's it like for a travel agent who's doing not one per year, but dozens a year, and not 10 people, but 70, 100 people. They have this problem at scale and we could find a solution to help them with their business. And that's how the business got started.
So what was your travel mode or like, what was your travel lifestyle like prior? Had you gone on group trips beforehand or was this the first group trip that you had embarked upon when you decided, you know what, this is wild. Why are we doing it this way? Let's make a difference.
Darrien | SquadTrip (03:15.791)
Okay, I gotta take it, I gotta really take it a step back to probably when I was like two years old, ever since I was two years old, I would go on, I wouldn't even call trips. I would go with my mom or she would send me to go visit my grandparents in Ratan, Honduras. And I spent a lot of summers there. And then when I got older, I realized by the time I was like 20 years old, I was like, okay, outside of like driving down to like DC or like Miami or like Atlanta.
Darrien | SquadTrip (03:45.267)
for like, spell house, homecoming, or something like that. I hadn't left the country except for to go to Rattan. So I made like a conscious decision to start like traveling more. And those trips started with friends. And those are group trips. And then I've gone on other group trips as well. And ultimately I just really wanted to kind of just like really focus on experiences. And, cause I was realizing I could meet people.
Darrien | SquadTrip (04:14.055)
try new foods, culture, connect the dots, especially across the diaspora, wherever we are, whether it's the Caribbean, whether it's in South Africa, the continent, oh, I'm sorry, South Africa, South America, the continent of Africa itself, or even in Europe, there are black folks all over the place. And I wanted to just sort of connect the dots in my head and meet people who look like me, but maybe spoke a different language.
So before we dive into more of like the nuance of the discussion, in a nutshell, what does Squad Trip do? What does it facilitate and what can people, before I say what can people expect from it, how would someone know that they are in the market for what Squad Trip actually does?
Darrien | SquadTrip (05:01.643)
Sure. Now, if you're a travel brand, you're a tour operator, if you're a travel agent, and you're hosting group trips of 10 or more people, and once you get into the groove, you plan the experience, you've got the people reaching out and asking you questions. And then when it comes times to pay, you're taking credit card authorizations. People are asking to pay in installments. And then they're sending payments
via PayPal, Cash App, Venmo, and you've got to track all these different payments in a spreadsheet, you probably know the pain of this experience. And especially if you're doing this for business and you're trying to grow that travel business. And what I do know is that there's always a spreadsheet at the end of this process, and there's always a frustrated person, because people don't pay on time, even when you tell them upfront. And so if you have that sort of problem...
Darrien | SquadTrip (06:01.695)
hosting group travel experiences, then Squad Trip is a solution for you. We allow you to build a trip landing page within minutes that has all the information so that people don't have to go on the back and forth and what's included or when are we leaving or what vaccinations do I need? And if you're short tempered, then that's really what you need to, I guess, in your stack. And then you can check out...
Darrien | SquadTrip (06:30.323)
Your customers can choose payment plans and by default it's auto billing. So if they make their deposit with like Apple pay, they're going to get billed each month automatically without you having to remind them and check up on see if they paid. And so Squad Trip streamlines that whole payment collection and booking operations. And now we've recently launched a number of marketing features to help you grow your travel business.
Now, I immediately had a rush, a wave of, oh shit, because quietness is kept. And shout out to maybe some of my cousins if y'all was listening. The family reunion. So, yeah, I heard that. Right, understood and felt. My cousin, love you T, truly do.
Darrien | SquadTrip (07:17.951)
um, volunteered us to host the next family reunion as the younger demographic. Um, we're not a company, but we're a large group. Would squad trip be appropriate for say individuals who aren't necessarily business people, but have just a shit ton of people that we're trying to pull together for a trip, like a family reunion or even just like a girl's trip, um, bachelorette.
getaways or bachelor party getaways? Like is this also a space where someone like myself or another listener who may not be a travel agent but would like to establish some type of organization in a large trip, would that also be something that, would Squad Trip be something that we could step into?
Darrien | SquadTrip (08:15.775)
Absolutely. At any given time, there's dozens of birthday parties, 40th, 50th. I've even seen 70th birthday party group trips. Family reunions, link up for college buddies, bachelor parties, birthday parties, you name it. They're all on squad trip. And it really comes down to seamlessly organizing everything, making sure.
Darrien | SquadTrip (08:45.183)
Payments are easy and you're not getting into fights because people didn't pay on time.
What about if somebody starts paying and then they decide to pull out or they're like, actually something came up, I can't afford this anymore. Is there anything in place to help facilitate refunds or is there a way to say, hey, listen, these numbers are based on group accommodations for whatever in particular it is we're doing. Is there something in place for those kind of sensitive money negotiations that sometimes happen down the line, whether it's someone needs a refund
We don't know how to, you know, have that conversation. Is there already a feature in there that someone as the person paying can step into and say, I'm gonna take myself out? Or as a person that is facilitating all of this, they can say, well, we're gonna cut you out because you're not following up with whatever needs the group is requesting at this time. Oh, beautiful. Ooh.
Darrien | SquadTrip (09:45.115)
Yes, yes, and yes, we got it all. We've thought through it all. Before launching Squad Trip, we actually were building travel websites. We did 4,000 bookings, 5 million in sales, and then we launched it. So we had the secret sauce and all the data points to understand what was needed. So yes, to answer that question, when like, so for your family reunion, right, if you're heading it up,
Darrien | SquadTrip (10:11.015)
Maybe you already called a hotel, you've got a room block, 40 rooms or something like that, they sent you a contract, you know what it will cost, you probably owe 10% upfront and then the bulk of it 60 days before, right? But everybody wants to pay month to month for the next 10 months or something like that. You already know what the contract information entails. You can add that contract information, copy it and paste into our platform. You can either use our terms and conditions, the cancellation and refund policy.
Darrien | SquadTrip (10:40.091)
or you can make up your own. And then once that's in there and you publish that trip, when the traveler, so now when your cousin goes to book, again, there's a level of separation between you and the family. So when they go to the website to book, they choose the four day stay or the double room or whatever it is. They know it's $1,900, they check out, they make that deposit with Apple Pay. Before they can even do that, they're gonna have to read the terms and conditions and they're actually gonna have to sign electronically.
with like a DocuSign feature. And so they already know what the deal is before you accept their money. And then of course, if they need to change their credit card, if they didn't wanna pay extra, if they wanna cancel, they can log in to their profile page, change their credit card. Maybe they said they were vegan, they changed it, they're not vegan anymore, whatever it is, right? We all have been there. And then...
I've been there. I've been there. Things happen. And by things, I mean wings. But continue, please.
Darrien | SquadTrip (11:40.087)
So yeah, when it comes down to like if they need to cancel, they hit that cancellation button, they're going to be confronted with the terms that they signed. So they understand canceling means you get 50% back, you get the deposit back, you get nothing back, whatever it is that you put in to the system, they're beholden to those terms. And then it's up to you as the organizer to go and issue that refund. If you want to like override the term.
I don't know, it's a sob story, they're getting deployed, whatever it is, and you have full control over that. But like, we give you the guardrails that you need and the tools and the separation so that nobody's feelings is hurt.
Business is business.
listening to this and side note, excuse me, Darian, but I already told them people that I was not going to be on this committee, but this is actually a game changer. I might step my toe back into that conversation with the cousins. This is at wow. So throwing a wow in there early. You know what I'm gonna ask? What does the platform not do?
Darrien | SquadTrip (12:53.223)
It doesn't plan the experience for you yet. So you still have to do the research and where you want to go. You still have to get that hotel contract. Maybe book the 80 person catamaran tour or the safari, or the, you know, maybe it's a family reunion. So maybe y'all are going on a history tour or a wine tour, something like that. But like, you have to go through the process of booking everything. But once you book it, like, so.
Darrien | SquadTrip (13:21.119)
Think about how, like, if you're an event organizer, what Eventbrite looks like. They're not going to book the DJ the venue. They're not going to bring the alcohol, the flyer. You have to come prepared with all that information. And then you're just typing in what the experience is because you're the curator yourself. And then we basically allow you to build out that inventory and say that there's only 20 rooms available, king size, whatever it is. There's only 30 seats on the bus for the Apple picking tour.
Darrien | SquadTrip (13:50.591)
Um, and, um, so we don't know what it is, the experience that you want. And so we don't plan it for you. Um, but, and I said yet, because we're actually working on that. We're actually working on bringing in hotels, airlines, experiences into the platform. So now, um, give us a couple of months. You'll be able to actually just say where you want to go, how large a group trip is, how much you want to spend per person. And then just say what the, like the general interests are. And we'll be able to build that itinerary.
book directly with the hotels and experience for you. Right now, that's the stuff that you have to do outside of the platform.
Okay, so taking another step back, what is your background? Like this sounds so like freaking revolutionary. Like do you have like a engineering background or... What are the skills? This seems like very, not just a labor of love, labor intensive, but like in a very professional sense, like this is very detailed.
Darrien | SquadTrip (14:51.679)
Thank you, I appreciate that. So funny enough, when I went to college, I took one engineering course and I failed it. But yeah, it's funny. And then I was like, I'm not gonna need this. And anyways, yep, yep. Actually after I graduated from college, so I worked as a product manager, software product manager.
Okay, life happens.
Now look at you.
Darrien | SquadTrip (15:21.015)
long road, but I ended up basically helping to write the requirements for how the software was going to work, talking to the customers and seeing what they needed, testing it to make sure it worked properly, helping with the designer to bring it to life and the engineers to bring it to life. So like, it's the quarterback of this, any software that you build. That's essentially what the product manager does. And then I went to, because I was working at this company, I actually, they paid for me to take some courses.
Nice, you some people money.
Darrien | SquadTrip (15:50.447)
um, to kind of brush up myself. And, um, so I have that background. And then ultimately before I actually built squad trip, my co-founder and I, we built an event ticketing platform. So, um, outside of just working at our jobs and he, he has a background as a tech architect and a developer himself. So like we knew experiences. Stevan. Yep. Shout out to Stevan Joe. We knew experiences. Um, he had the technical expertise to pull it off.
Nice. Shout out to you too, co-founder. Gang gang.
Darrien | SquadTrip (16:19.383)
I had the experience working with designers, developers, to bring it to life. And then we had that one experience where we built something from the ground up ourselves outside of our jobs. And so I think all of that experience gave us the tools that we needed to sort of get this off the ground. And then of course, like perseverance, we wanted it to happen, we had a vision. And so we kept pushing even when we made mistakes.
So what can someone expect the user interface to look like? Do I need a tech degree to do this? Because my little communications major, baby, I wanted to get in and out. I didn't really focus on how to learn to do anything, if you will. So is this something that someone who says, I can figure out my way through Excel, I can bullshit through some Google Sheets, is this going to be something that I need to have established experience using certain
platforms and softwares to be able to actually make this platform useful for me? Or is this something that, okay, well, I could Google, I could, you know, figure out what I want to do and answer simple questions.
Darrien | SquadTrip (17:28.051)
Yeah, I think if you can fill out a Facebook profile and publish that profile, then you're good to go. If you know your way around an Excel spreadsheet, then you're more than qualified. Like, I mean, don't want to throw some people under the bus, but you know, we've got some people celebrating some 70th, 80th birthday parties, and they figured it out on their own without interacting with me.
Okay, there we go. Nice. Do you have a customer care or like a customer assistance feature or anything? If someone did have a concern or ran into a roadblock where something that they wanted to input didn't go through or for some reason if something went wrong, is there an aspect of the platform where someone could reach out for assistance or to have a question answered or something?
Darrien | SquadTrip (18:13.319)
Absolutely. So on our website, there's a chat feature. You just click on the button. I've got two team members who actually work in different time zones. And then it's me, my co-founder. There's always somebody online, and we get the messages. I'm like, do I have one right now? We get the messages to our cell phone. And so there's always somebody available. And it just really depends on the medium. Like, some people just want to text. Some people want to jump on a call.
Darrien | SquadTrip (18:43.431)
And in that case, you can book some time with us and we'll do a face to face. And the reason why we do that, I guess, it's like, me and Stavon, we always use an example, like Master P being like the blueprint. You've got to be willing to sell CDs out the back of your trunk. And if you're doing that, then you know what people like, what they don't like, what's hot, what's not. You're in the streets. And so we're in the streets.
Darrien | SquadTrip (19:13.019)
So you send a message, your email, it's going to be like the face of the company picking up or jumping on a call with you. And hey, sometimes things don't work. But then sometimes I'm like, maybe it doesn't work how you thought and you have an idea. And now I could write that down. That's how we get better. I got to listen to all the feedback that anybody has to say. Of course, we've got to synthesize it. Some of it is bad ideas. Some of it is good.
Darrien | SquadTrip (19:42.591)
But ultimately, the closer you can have your ear to the streets, the better you are as a business. And I think that that's the case regardless of whatever type of business that you run, you just want to be as close to the customer as possible.
So earlier you had mentioned that travel agents and businesses are also primary candidates for being able to find this platform useful. What would you say the difference between working with an individual and a travel agent is? I've never worked with a travel agent before. Something about, so when I first started traveling, if you're new to the show, I leave the country until I was 30. So this was eight years ago.
They, and by they, I mean the homegirls were like, sis, you're doing too much, book it yourself. Cause I initially thought that I had very limiting ideas on what travel looks like. And social media really kind of came into play and opened the world up to me. It was like, oh.
So I don't need a squad to go on a trip. I don't need like home girls or a partner or someone to be with me to travel. And so I ended up embarking on solo travel. But part of what hindered my progress was thinking that I wouldn't be able to do it myself because I didn't know what I didn't know. And I thought that I would need a travel agent to book for me. So at one point,
At one point I thought travel agents were the wave and that I would need that. And then I started booking trip, my trips myself and realized I don't fucking need a travel agent. But I will say now that I've spun the block a few times, I in theory see the benefit of a travel agent, but I'm still not really sold. What would you be able to add that necessarily distinguishes?
the difference between booking something on your own and using a travel agent. Like I hear everybody say the travel agent gets like really good deals or they get promos and stuff like that. But I'm like, there's a million apps and websites and stuff for regular people to go through and get those types of promos and deals. Like, is there a difference? And as someone who works in the platform and in the space that, you know, assists both.
where would you be able to point and say, okay, well, this is a major difference here, and if you don't know, here's information about X, Y, and Z, so maybe you can better make a decision going forward.
Darrien | SquadTrip (22:26.151)
OK. I want to start with what the data shows, first of all. If an individual booking and hosting a group trip for friends or family, birthday, family union, whatever, versus a travel agent that's doing it, the likelihood of success is like five times greater when it comes to travel agents. Because I think individuals, especially when it's solo travel, you get up and go. But the more people, the more complex.
Um, and then, uh, ultimately I think it really comes down to is execution. It's harder to execute and a lot of people, they don't know where to start. Um, they get frustrated. Um, and, uh, when it comes to traveling, that's just what they do. They have all the resources, the connections. You want to go someplace and you name it. Likely they've already been there. You know? Um.
And then so the trip is more likely to happen, first of all, because they just have that knowledge and experience. But if you're motivated, then you can do anything. And I'm sure you'll make it. But again, 10 people, what if it's 50 people? It's really going to be a hassle. And at that point, a lot of people might drop off. Or you may say, you know what? We're not doing the family reunion again, because you don't want to deal with the hassle. You're smiling because you've probably been there before.
Darrien | SquadTrip (23:54.999)
Um, and, but like on an individual basis, if you're trying to decide, if you want to do it yourself versus a travel agent, just know that how bad do you want it? Cause it might fall apart. You might get busy and it may not happen. Um, and funny enough, uh, depending on like the, like the business model, but some travel agents don't charge like an upfront fee. And then, so in that case, they might be able to get you the same price or even a better price.
Darrien | SquadTrip (24:24.295)
Um, and they find they make money off the commissions on the backend anyway. So it's just like, uh, a lot of times, um, you're paying for the convenience. And so you gotta know yourself. Like I could take the bus for two 50 or I could get into Uber, you know, right. Um, it's, it's just one of those things, or you're going someplace new and you don't have GPS, you can get there. I'm old enough. I use map quest. We can get there, but like when somebody knows how to get there, like, and
Darrien | SquadTrip (24:52.619)
Uh, then it's just, at least for me, I know myself, like when I go on vacation, I want to be on vacation. If I got a study to go on vacation, it's not a vacation. That's work for me. And so a lot of people, they say the term, I want to pay my money and go. If you're a pay for convenience type of person, absolutely travel agents are worth it and if it's, if you're solo, okay, like the margin of, I guess, gain is not that high, but
Right. Yeah. It's not gonna fit like a vacation.
Darrien | SquadTrip (25:21.151)
two people, four people, 10, 20, 50. Absolutely, like, it just gets exponentially better to use a travel agent.
Yeah, that's just a lot of people to keep up with. I don't want to answer 50 calls. I don't want to answer 50 emails. I don't want, I don't, my group chats are all muted because I don't want to talk to the group. Like I'll step back in when something's happening, but it's generally like a girl, get in the chat. It's getting crazy. Someone's got to tap on the shoulder.
Darrien | SquadTrip (25:47.487)
Tap you, yeah.
to get me back in there. It's a lot to navigate a lot of different voices and this person wants this, that person wants this, they don't wanna be with this person. One person's talking about something that's 17 steps down the line and we just trying to agree on who are over there.
One thing that came to mind when we were talking about the interface and like who all this is useful for. What about once you're on the trip? Does Squad Trip facilitate anything beyond just booking? Like what type of tech?
is this platform extensively? Is it just for planning or is it also for kind of maintaining and making sure that, like is an itinerary included in that? Can I tap in and say, all right, so Tuesday is the boat day. Did I make sure that I have X, Y, and Z? Like, is there anything else that is included in the platform that helps the trip, trip to its best?
Darrien | SquadTrip (26:43.807)
Yeah, absolutely. So there is an itinerary feature. If you choose to use it, you can basically describe every single day with pictures and then drill down to the hour. So some people I've seen, it's like, OK, welcome day. Starts with welcome cocktails. And then we're meeting at the beach. Please, everybody wear neon colors. So it's like the itinerary. Yep, of course.
Black people love some coordination, baby. We got a color day.
Darrien | SquadTrip (27:14.159)
Yeah, and then a lot of people forget. And I'll be that person too. I'll be the only person with orange swimming trunks at the all-white pool party. Yeah, so for it, no, that's unintentionally. And that's why I like to pay for convenience. Because if I got to study for stuff, it's just going to be too much. I got too much going on. But yeah, you can build out the itinerary and get real granular with it as
There you go. It's always one. Intentionally or intentionally?
Alright. Mm-hmm. I'm gonna go ahead and put this in the fridge.
Darrien | SquadTrip (27:42.859)
granular as granular as you want with all the pictures and descriptions so that people understand like what to wear, what to bring. And then when they get there, they may forget like where we supposed to be. And they can always tap into that. And then we have this text messages in future. So if you've registered your cell phone is still it didn't get turned on, you can the organizer can actually send messages like everybody should be at the bus at this time.
And it just goes to everybody's cell phone. Because a lot of times people don't want to download an app. They're not going to look at the group me. The WhatsApp is muted, just like you said. But that text is going to go through.
Yes. Wow. I didn't even think of that. I didn't even think of that because that's another thing you got to wear so and so because there's, again, there's always whether or not a handful or a couple of, there's always somebody missing when the bus pulls up. It's one of those things. Oh, it's too early or this is too late or where's the, I really did think of everything. That's a really good feature because I flashbacks of
past trips, large trips where you're waiting and waiting, where now we can just, that first person, send that text to everybody. We all know that half the group is here and not wanting to hold on to, you know, that waiting for other people to show up. That's a really good one. Speaking of group dynamics, like getting everybody out of the chat and onto the trip is one thing, but once you're on the trip, like,
Conflict happens. Have you had to navigate, what happens when things go wrong on the trips? Feature for the squad, the platform for one thing, and then just your personal experience in group travels as is. What do you have to throw into the ring on that one? Because some of the reasons why a lot of people don't do group trips is because.
of the likelihood for conflict to arise. It's just a lot of people, a lot of feelings, a lot of emotions, and a lot of times it happens on the road.
Darrien | SquadTrip (29:51.783)
Yep. So on the product side, we've got features that are used in case doomsday occurs, just like the terms and conditions, the waivers and the refund policies. They're all like just memorialized so that it's crystal clear and people have to sign off. So that helps for the organizer if they need to refund you or cancel you or whatever it is.
Darrien | SquadTrip (30:21.207)
And as you understand what the terms and conditions are ahead of time, and that's clearly communicated. Um, and, um, also like, Hey, maybe somebody wants to dispute a payment or something like that, like there are guardrails in place to sort of protect you so that you're not out of money. And if they do dispute, you can automatically download a PDF that says what they agreed to when they agreed to it, their signature, their date, everything, their address.
Darrien | SquadTrip (30:50.991)
And so once people get hit with the facts, it's over. But on a personal note, what it looks like for conflict, you're talking about this family reunion. Family is family. If you got the crazy cousin, I don't know what to tell you. Sometimes you've got to leave people at home. And to that point, you've got a wait list feature.
Yeah, so like you can sort of screen people to say, all right, I don't know if you're a part of the vibe and stuff like that. And I mean, that's the best thing I could say is like, I mean, if it's family, it's family. Um, if you want to invite your, your crazy cousin, it is what it is. But, um, when it comes to like, you know, uh, travel brands, tour groups, travel agents, they can be selective by just adding that level of, um, of, um, I guess filtering.
Look at it here.
Darrien | SquadTrip (31:44.875)
where people have to sign up and you know who they are. You might even ask for their Instagram and more information before you push the button on it. And I think that's also important. You gotta curate the trip. And so even if it's a group of friends, you gotta know who your friends are. And maybe you don't have to put them on the wait list, but if they wanna go on a Caribbean vacation and sit at the beach all day, then maybe you shouldn't bring them to...
Darrien | SquadTrip (32:15.083)
the tour that where they're gonna be on their feet, or they're gonna be at the bus at six in the morning, it's just not for them. And so it really comes down to like knowing yourself, knowing the group, and then just putting the information out there upfront from the beginning. Because sometimes your friend might wanna sign up for the trip, because she wants to hang out with you. But if you fill out the itinerary, she knows, okay, self-select, this isn't for me. Yeah.
This ain't the trip for me. Yeah. I think that also comes in handy when you get to that stage where the trip kind of like rose beyond the initial, hey, let's have a girl's trip. And then Tara ends up inviting.
Courtney and then Courtney ends up inviting her sister and then her sister wants to bring her cousin and it's just like, all right, well, this is my trip and I know Tara, but I don't know Courtney's cousin. I don't know her cousin's sister. I don't know her neighbor and her best friend. And so it's like, now you've got friend groups kind of.
intermingling and while everyone is welcome, not everybody is welcome. So I can see how a waitlist might be like, okay, yeah, we it's cool to tell other people about the trip, but are the other people the people that we want? Are they still our people? You know what I mean? Like that's a really nice feature to be able to kind of open it up.
but then still shut it down when it needs to. It's just like, okay, now that we've got that core click, like the initial friend group can now say, these are our contenders. Like who, I mean, it sounds real snotty, but listen, shit goes left. I've had guests come on and really detail, like, shut out to Keen, the passport abuser. Like group trips can really become trips from hell. And,
Darrien | SquadTrip (33:53.491)
It is what it is.
Yeah, I could see wanting that level of, that little buffer between you and then not really wanting to be the one be like, I don't know her, she's not invited. If that's not you, to be able to directly say that to the rest of the group, then I kinda like that feature. Are there any other little hidden features that you haven't brought up yet? Like, y'all got some really good ones.
Darrien | SquadTrip (34:30.711)
Yeah, I think you're asking the right questions because it's coming up in conversation. We have 100 features. Another one, we actually just dropped two new features this week. One is the refer a friend feature. So once you book, if Courtney books and she wants to invite Tanya, maybe especially sometimes you can make money at volume or you get
the deeper rates, cheaper rates. And so depending on your contract, if it makes sense, you might say, hey, listen, Courtney, if you bring two friends, I'll give you $100 back or 200 bucks back and we can automate that process. So Courtney books, she gets the automated email and then she gets a link. And so now she's like an affiliate. And the other feature was like a V2 version of that where like now like maybe you wanna give if, now this is not gonna work for a family reunion, but like.
Darrien | SquadTrip (35:28.927)
for interest-based trips and it's for profit, you could actually like reach out to influencers or bloggers and give them a link where now they can earn cash for promoting a trip that they're interested in.
Mm-hmm. Okay, okay. So now that we're at money now, what is the payment process for it? Like what is the cost for the platform? Is it a one-time cost? Is it a subscription-based model? How would someone...
Because I guess there are different types of people that would want to use the platform, right? You've got people that want to plan just a family reunion. It's not about profit. I just need a way to keep everybody's information in one spot. Then you have people that it's just like, oh, well, everybody's always asking me when the next strip is. Well, here it is.
Darrien | SquadTrip (36:11.025)
Now I can use this platform to actually build out a trip that I can invite other people to come with. And then you've got your travel agents and your maybe smaller or mid-sized brands that are actually, no, this is what our bread and butter is. This is what we do. And now this platform is just here to facilitate that happening much more easily. Like, do you have different tiers for the different types of people that use the plan? Or like, what is your model in terms of the monies? How does that work?
Darrien | SquadTrip (36:48.511)
Sure, yeah, so the platform is free to use. And all the features except for the text message feature are in the free version. And so how we make money is through transaction fees. So we have a payment processor that we pair up with. And so we basically roll the fee in together. It's a 6% fee on any transaction. So if the trip is $1,000, the traveler is going to pay like $1,060 at checkout.
Darrien | SquadTrip (37:16.415)
The 60 goes to us, the 1,000 goes to you. And there's no other hidden fees outside of that. Now, if you are, I guess, a business owner, you're doing trips for a living, you want to take advantage of some of the power features, like text messaging, custom branding, changing the colors, embedding it onto your website, stuff like that, right? Then you would pay a $69 monthly subscription. You can cancel any time.
Darrien | SquadTrip (37:46.583)
or pay yearly for a discount. And so effectively, again, that's just how we make money. It's either transaction or transaction and subscription.
Like y'all got it all so far. Like what about international? So I know that you can't necessarily, what about flights? Like, so before I get to international in terms of like, if I from the States am leaving from here, I guess I should start with, how does the flight part of it work? Can you help with navigating different flights from different places? Because in my mind, if say I wanna have homie from,
Darrien | SquadTrip (38:01.202)
Barbados and a homie from England and we're all going to Portugal is there a Space that even handles flights or like how do we navigate people from different places? Coming to one space or is that something that like is that part of it? Is that making sense? Like?
Darrien | SquadTrip (38:47.059)
Yeah, so I was going to say, I need you part of my team, because you're mentioning things that we're working on building, in fact. So we don't handle flights and planning, that sort of thing. But you can, if you some people choose to buy flights in bulk. So you can get, I think it starts at a minimum, if you call up JetBlue, American, all that stuff, you can get the flights nine months out.
Gang gang brains man. Okay. Yeah.
Darrien | SquadTrip (39:17.687)
Um, in advance, especially when you're going for some pretty spar, when it's expensive, might want to do that. Um, and then so
Shout out to those of you planning destination weddings. This I is for someone in particular who's no longer doing I.
Darrien | SquadTrip (39:30.139)
Me? I'm actually planning a destination wedding. Ha.
Both, I've got quite a few destination weddings coming up. One of them, thankfully, is no longer a destination wedding because Barbados is wild expensive to get to from the States. Courtney, I love you, but baby. I didn't even know you could do bulk flights, but when JetBlue is charging like two grand just for the flights, it was just like, surprise.
Darrien | SquadTrip (40:00.459)
can't do it.
Yeah, you want people to come to your wedding. You know what I mean? So it's just like, unfortunately, that would have been a beautiful fucking trip and this is a perfect platform to do that. You've got an entire wedding party that's gotta get from the States to Barbados or from wherever.
You know, these other people are coming from, I didn't know you could buy both flights, but now you've got a platform where you can actually have everybody, like you can put your entire wedding party on the platform and figure it out to, y'all really got, y'all got the juice. Okay, I'm sorry, I interrupted you. So you don't do the, yeah.
Darrien | SquadTrip (40:38.207)
So let's say, so you get the bulk flights. And let's say everybody's like, you know what? The wedding is a year away. It's $2,000. We're going to do it anyway for the flights. You can actually, you can add, like, and some people may, I don't know, maybe you live in Barbados, so you don't need to. But you can actually add what we call add-ons. So you could put together a flight add-on. And then now that $2,000 flight is really expensive. But.
Darrien | SquadTrip (41:07.079)
it can get broken down into installments. It's a lot more palatable. What we plan to do in the future though, is sort of bring that search in-house. So what if you could search for group flights, group hotel rates, and do all of that from your cell phone on our website.
Darrien | SquadTrip (41:24.224)
So that's what we're working on.
That was the next question I was gonna ask. Is it a website or an app? Squad trip.
Darrien | SquadTrip (41:28.112)
It's a website.
I like that. Something about apps, I don't dislike, but I like the ease of a website just because I feel like there's one less barrier between, like, I like both, but I also know that some things are just easier on a desktop and apps tend to, and this is for me, I'm not the most tech savvy person, but I'm not a fucking idiot. So it's like, I can manage, but I also just sometimes want to see things much larger as opposed to staring at my phone.
So, y'all got price down. How do you end up doing the, like the installment plans, like the payment plans? Is that something that someone is responsible for paying for everything upfront and then the installment fees go back to them? Or like, or is it through like a Klarna or an after pay? You know what I mean? Like is that, is someone overall responsible for paying for something upfront or y'all have that worked out somehow?
Darrien | SquadTrip (42:21.099)
Darrien | SquadTrip (42:28.527)
Yeah, so the organizers on the platform, what they'll do is they'll pay up front. But the beauty in it, like, if you're getting if it's if it's a hotel block, oftentimes, that 10% deposit isn't due until like 30 or 60 days after you've secured it. And so if you've launched a trip and got deposits, then you can actually use the cash flow from the people making deposits to actually pay that and then hey, if you know,
Darrien | SquadTrip (42:56.755)
30 people said they were going to go, only 25 people end up going, you end up just dropping a couple rooms so you don't have to come out of pocket for them. And then usually the way it's set up is that like, it's using 10% upfront and then 90% right before the trip. And so by month two, month three, you've actually got influx of cash that's sitting in your account and you don't even owe that money into the hotel or to the airline until the end. And I know the airlines definitely...
Darrien | SquadTrip (43:24.547)
some of them make you pay like $50 a deposit per and some of them is just like free. It really just depends on which airline you sign a contract but like if you don't put any money down, like what does it really mean? So yeah, it isn't Karna or anything like that. And that's because we didn't wanna have to like, you know, have the situation where it's like, depending on your credit that allows you to get the payment plan instead, it's just like, we're gonna bill you at this monthly cadence each month this amount.
Darrien | SquadTrip (43:53.467)
It's up to you to make sure that money is in the account. And if it's not, then you'll end up being getting canceled.
Okay, okay. So now I guess in terms of someone not planning and someone who would be going on the trip, right? What type of securities are in place so that someone may be planning a trip doesn't just run off with your bread? Like, is there something that gives, I don't know if there's like a peek into the background or like what kind of securities or I guess,
What's the word I'm looking for? Safety blankets are in place for not just the person planning the trip, but for the person that's actually putting their money up front for a trip. Cause I've heard horror stories of people paying for trips and then fire festival. You know what I mean? Like stuff like that kind of happens. Is there anything in place to protect the user as well?
Darrien | SquadTrip (44:48.639)
Well, I would say just credit card and bank rules are really customer-centric. And that's why, if anything, the protections are on the other end. And so of course, if there's a bad act that they want to take your money and run with it, then you'd have to go to your bank. And then you'd be able to recoup those funds. Our team monitors all the companies that come onto the platform.
Darrien | SquadTrip (45:17.951)
And so ultimately, if there's any suspicious activity, anybody's a bad actor, then we flag their account. And then the payment process that we use also goes through this due diligence process with them as well. Whether it's for your family reunion or for your travel business, either way, you've got to fill out that application. It's quick. But either way, they're still collecting this information. And so because of that, at the end of the day, the organizer.
Darrien | SquadTrip (45:46.595)
is essentially responsible for fulfilling on what it is that they're promising.
Okay. And I guess if you really bout your business, there's some kind of clause or something that you would put into your own terms of service or to, um, what was it that you had mentioned before? The, um,
Darrien | SquadTrip (46:04.939)
terms and conditions, refund those policies. Yeah.
Yes, like all of that information is spelled out in the beginning. So it's one of those things where the same way, if you're, you know, buying something from someone that's not your cousin or someone that's not, you know, a specifically travel based business, then you read those and make your decision based on that. So it's kind of like everybody's got something that is going to have their back at the end of it. You mentioned something about in your account. Do you have to like establish?
a separate or is it like a squad trip bank account where it's just an account that holds the money or is it like linked to someone's personal banking account or credit cards or something like that.
Darrien | SquadTrip (46:48.839)
Yeah, you link it to, so you have to create a Stripe account. And so that's the payment process that we use. So Stripe, similar to like PayPal or something like that. And then you can link it to a personal card or bank account, or you can link it to like a separate account, whatever you choose. And I think a lot of the people who do for personal trips, they'll hold the money in their Stripe account. And then when they're ready, they'll just transfer over the 10, 20, $30,000 into the account.
Darrien | SquadTrip (47:18.839)
of their choosing. But most of the businesses, they already have like their own business bank account set up. So they just link that. And beauty in it is that the like the money gets swept in on a daily basis. So if the money comes in on Monday, it'll be in your account on Tuesday.
Shit. So I mean, you've answered all the questions about the business. Now I'm gonna ask you a personal question. The trip that you said that you were taking with that group of friends, was that the trip that put the nail in the coffin for it or had you had a trip experience with the group? Were there any, what was the writing on the wall? What type of travel experiences have you personally experienced that have actually fed into the different
nuances and the little pieces and pain points of squad trip that, you know, said, okay, now this is absolutely a feature that we need to put in because of X trip or you know what, absolutely making sure this is an option because of blah, blah on that trip. Like what were those trips like for you?
Darrien | SquadTrip (48:25.659)
Um, I would say, uh, this, we got to go way back, uh, to CDE Antigua. Um, and so shout out to my boy, Colin, Colin Williams. Uh, every year or a couple of times a year, he does a trip to, um, his home island of Antigua and, um, and it really got crazy. Um, I think, you know, by 2019 was 500 people. Uh,
Ha! That's wild. Now what is CDE?
Darrien | SquadTrip (48:56.083)
for a four day weekend. So yeah, CDE stands for Colin Devon, like it's literally his name. But it started, yeah, so we came together and to produce the trip. And so we were handling like the software and everything like that. We realized that like,
Okay. Good afternoon, sir. Okay, respect on the name. My bad.
Darrien | SquadTrip (49:24.047)
after one of the trips, it went viral. I'm talking Travel Noir, Shade Room, Time magazine. I can't even remember a bunch of publications. And then influencers were trying to pull up and everything. And at that point, what we had to do is remember the wait list. We did something even more, I say, diabolical. We.
Darrien | SquadTrip (49:53.247)
basically had, because there were so many people that were trying to go. And then we were trying to figure out, okay, do you get this hotel or do we get two hotels next to each other, or do we go with the biggest hotel on the island? Like, like we were just trying to figure out and we didn't know like, you know, what the flow was looking like. So we had a pre-approval process. So like you had to pay upfront and then within 60 days, we'd give you an answer on if you could come or not.
Darrien | SquadTrip (50:23.335)
And then you'd have to mention who told you about it. Because it just got too crazy. Think about it, the island of Antigua, to bring 500 people, that year, it was just all the flights on the, there was one flight on American that day. It was the entire flight. You know, like, you just.
Everybody. You can't have it any other way. Like how many airlines are going to Antigua on a daily basis, period. And you said it was only a four day weekend. So yeah, of course y'all bought the whole plane out.
Darrien | SquadTrip (50:47.911)
Yeah. Yeah, so everybody wanted to come in on Friday, Thursday. And there was like 220 seats. So we had to book the entire plane, book the entire plane out, and then had to get JetBlue, and then book like 70. There was only 75 on that one. And then the other people just had to come on Friday, because it was just like, unless you want to come here on a ferry, you just can't get here. Exactly. There were some people that came on a five jet.
Right, or a private jet. That's wild. Excuse the fuck out of me. Hey y'all, how y'all doing? Call me, yeah? Let's talk. Wow, 500 people at an event. See, I am very crowd-averse. I do not enjoy crowds. That would drive me insane. Now, squad trip wasn't a thing then. How would you say now, in hindsight, how would squad trip have made that trip?
Darrien | SquadTrip (51:18.855)
Run more smoothly.
Darrien | SquadTrip (51:42.731)
So honestly, that software was the precursor to Squad Trip. And so everything we had learned from doing these 500 person trips, we bottled into the Squad Trip solution. And we learned from those experiences. I think the difference is that website was a custom build out. We took three months to build every single button, every single page on the website.
Darrien | SquadTrip (52:11.379)
Um, and then we just got to a point where like I had 40 travel companies, travel brands and tour operators who were like, can you build my website? It's like, if I take, if I take three months for each one of you, it's going to be years before I get all this done. So we ended up building a, um, a software version that like you could actually, it wasn't custom, but it was customizable. So now you can build it, build out your trip page in five minutes instead of five weeks.
Darrien | SquadTrip (52:44.208)
Yeah, we've been in this game for a long time. And I know you said you love solo travel. The funny thing is a lot of people, when they say solo, they don't mean I go by myself. They mean I go with people. I don't go with anyone I know. And so a lot of times they jump on a group trip experience. And even if they're not like, kee keeing with everybody in the lobby, every step of the way, they're skipping some excursions.
Y'all know what the fuck you're doing.
Darrien | SquadTrip (53:10.463)
They got to take advantage of knowing they're with a group that they can access, and then if anything goes wrong, right? And then the other part is they can pay for, I guess, the planning, where they don't have to actually plan their own solo experience. They just tap into the experiences that are planned for the trip, and they were gonna go to the museum. They were gonna go sightseeing anyway.
Darrien | SquadTrip (53:38.947)
and they were going to be on a bus with strangers. It's just that now they just signed up for a group trip.
Right? So I mean solo, like when I say solo, I mean solo. But, but I went on my first group. I mean, okay, so I would travel by myself to go and end up by myself. However, I always book excursions because I'm not spending all this money to get this far from the crib to just live like I'm at home. When I'm home, I'm always in the house. So when I travel, I like to be outside. I'm in the streets. I wanna go places, do things, experience.
Darrien | SquadTrip (53:49.631)
Ha! In the desert all by yourself.
all the shebangs. However, one of the things that I've, and it's wild because I'm from New York. So New Yorkers are kind. I'm from Queens. Southside, we outside.
Darrien | SquadTrip (54:22.667)
Darrien | SquadTrip (54:26.535)
So, we're kind, we're not nice. I, oddly enough, am super friendly when I travel. I will spark a random conversation with a stranger in another country, but sit, mean mug, don't talk to me, you're too close when I'm home. So it's something about traveling that kind of just opens me up to wanting to be more social and to kind of want to be around people, but not crowds.
But I went on my first group trip. Boyfriend's best friend is also doing a destination wedding. Shout out to them. And so we ended up meeting them out in Mexico and the four of us had a great freaking time. So that was like the closest thing to a group trip that I've ever done. Enjoyed it. Also, I went on another group trip with...
Boyfriend's other best friend, we went to Atlantic City, ain't really no planning in that, pull up this Atlantic City, right? But the idea that all of this can be facilitated for you is nuts to me because I, the older I get, the fewer steps I am willing to embark upon to make shit happen. Too many steps.
I am immediately looking at all the plot holes and all the ways for things to go wrong. So this is actively something that I personally am going to look into because like I said, that family reunion, tapping on the shoulder and I don't wanna not do it, but at the same time, I knew that I did not have the capacity to do all of the little things, like the following up.
sending out the mailers, it's a lot y'all. Group trips are a lot and I can actively say that, yeah, I'm a BTAPT in, I'm definitely checking this out. So for the rest of us that will also be checking this out, where can the people find you? Where do we tune in? Where do we tap in? Where do we send you our coins? How do we get more information? Like what do the people need to know?
Darrien | SquadTrip (56:47.787)
Uh, best places to go straight to the website, squad trip.com, or you can head over to Instagram, my squad trip, and you can visit the website, send us a DM, ask us any questions. I'm always accessible. I'll be the one to respond. Um, and if anything, if I can't help you, I can, you know, tag in a teammate or something like that. And, uh, we'll really be happy to have you.
Trying to find it here. Nicole, shout out to Nicole. Is she, I love giving women their props. Is she your PR person? Was she part of the crew? I don't know, because I don't want to say she's just your PR person. Publicist, hi Nicole. I told you in that email, I appreciate you. Thank you.
Darrien | SquadTrip (57:30.907)
Yeah, she's our publicist. Yeah.
Incredible email is so easy to communicate and you know what that's honestly one of the best I don't know how to my brain works in like just ideas and clouds of color I guess one of the precursors maybe an analogy is a better way to put it. It's kind of like when you call a Let's just say you're calling a hotel to book and the person that answers the phone your first
Even better. I got the perfect fucking analogy the hostess at a row at a hotel I don't care how good the food is or how bomb my server is if the hostess is trash I'm not gonna enjoy my meal It's I personally just cannot get past that gatekeeper the first person that you speak to is the tone setter And so I will say that I had an incredible experience with their tone setter
So I am more inclined to believe that the rest of the experience will follow suit. So that I will pers in terms of my own personal addition, I can't tell you how much you're personally want to like it, but I can say that I have had great interactions with the company from jump. And that's not always the case because y'all haven't had me say this in the past, like I don't say that about everybody, but I will say there is an email from.
following promotional, one month free of Squad Trip Premium. So for those of you that are looking to dip your toes into a little bit of brand development or into hosting or facilitating a much larger trip for your audiences, one month free of Squad Trip Premium plus $20 off each month for the first year using code TNS. So holla, holla at that for those of you that are,
swinging your feet into the pond there. I will absolutely have that in the description box as with the website and the social media as well. Obviously description box below, blah, blah. Y'all know where to find it. If not, squadtrip.com. That's easy enough, right? So that is there. Darian, thank you so much. So, so much. Like even as a personal thank you because you may have saved the family reunion.
So did David's family thank you? Absolutely, we invite black people to the cookout. I don't know, Melrose. But yes, so thank you so much for joining me. It was a pleasure to have you here. And I hope that you guys that are listening would love to tap dance. I used to dance. So tap dance is generally my go-to in terms of like this, the movement on the YouTubes. If you're not watching, you're not going to get the reference, but.
Darrien | SquadTrip (01:00:01.2)
Can I get an invite?
If you're gonna try something, I'm gonna say tap dance. So if you're going to tap dance your way to the group trips, fucks with Squad Trip. Give it a shout, give it a try. SquadTrip.com, thanks y'all for joining. And I personally will see y'all next week and y'all can see Darian on the socials or on Squad Trip because he already said he's the one to be answering shit. So holler. All right, y'all, thank you. I'll see y'all next week, bye.
Darrien | SquadTrip (01:00:49.919)
Take care, everybody.