IAM2055 – CEO Empowers Travel Organizers by Simplifying Booking Platform

In this episode, we have Darrien Watson, the CEO of Squadtrip, as he delves into his entrepreneurial journey and the creation of his travel tech company.

Darrien shares how Squadtrip was born out of personal frustration with organizing trips for friends, leading to the development of a platform designed to simplify the process for both casual and professional travel organizers.

With 1.5 million in funding and over 7 million in travel sales under his belt, Darrien discusses how Squadtrip supports community building and meaningful connections through travel, offering a robust suite of tools for travel organizers to expand their businesses.

The platform aims to make trip planning accessible to all by providing an easy-to-use interface and dedicated support.

Darrien also emphasizes the importance of being passionate about one's work and adapting to the market's needs to achieve success.

Website: squadtrip.com

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Transcription:

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Darrien Watson Teaser 00:00

The way the platform is built out. It's easy to use and there's a step-by-step trip builder. So if you haven't thought about some of these steps.

Based on how you interact with the platform, we're going to help you and our team beyond the software is there and able and willing to help you out.

Intro 00:20

Are you ready to hear business stories and learn effective ways to build relationships, generate sales, and level up your business from awesome CEOs, entrepreneurs, and founders without listening to a long, long, long interview?

If so, you've come to the right place. Gresh values your time and is ready to share with you the valuable info you're in search of. This is the I Am CEO podcast.

Gresham Harkless 00:48

Hello. Hello. Hello. This is Gresh from the I Am CEO podcast. And I have a very special guest on the show today. I have Darrien Watson. Darrien, excited to have you on the show.

Darrien Watson 00:56

I'm excited to be here.

Gresham Harkless 00:58

Yes, absolutely. And you're doing so many awesome things. So before I jumped in, I want to read a little bit more about Darrien. So you can hear about some of those awesome things.

Darrien, travel tech innovator and the dynamic CEO of Travel Squad Trip has a dedicated mission to foster community and meaningful connections through travel experiences. With a remarkable record, Darrien has successfully secured 1. 5 million in funding generated over 7 million in travel sales and expertly facilitated 6, 000 trips.

And in 2022 funded, he founded Squad Trip, an automated booking platform designed to empower travel organizers by providing a robust site of professional tools, enabling them to expand and flourish within their businesses.

His achievements speak volumes in the travel technology and commerce space. And I congratulate him a little bit earlier on his recent marriage and super excited that he's been able to celebrate and achieve that, but he's a serial entrepreneur. I'm going to call him. And he has a really cool story, I was listening on how and why he started Squadtrip.

Which I'm sure we're going to dive into. But one of the things that he said that really stuck with me in one of the interviews is said, you have to be clear and steadfast with the vision, but flexible with the details.

And I think so many times when we have dreams and aspirations, we get stuck on the how instead of the why. And I love that you're really stuck on that.

So Darrien, excited to have you on the show. Are you ready to speak to the I Am CEO community?

Darrien Watson 02:19

Absolutely.

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Gresham Harkless 02:20

Let's get it started then. So to kick everything off, I know I touched on it a little bit.

I wanted to rewind the clock here a little bit more on how you got started. What I call your CEO story.

Darrien Watson 02:28

Sure. How I got started goes back to quite some years ago. Graduated from college was back in Brooklyn, New York, where I'm from feeling disconnected from all my friends and a little bit burnt out.

And so the first thing that came to mind was that it would be great if I weren't on a group trip with friends, I went to booking.com, tried to basically see if I could plan and execute something for 12 friends of mine wasn't able to do so. So, I basically had to put on my travel agent hat and do the planning, the organizing.

I was tasked with collecting the money, communicating with all my friends and all the vendors and it was a great time, but we had a headache. So started off with. 12 people at first year and then second year balloon to an annual group trip. And now we have 50 people. So as you can imagine what it's like collecting money through cash app, PayPal, Venmo, tracking who's paid what and who owes what it was just a headache.

So now just think for a second, imagine what that's like for a travel agent. Who's not doing it for 12 people. It's 80 people. It's not one time a year. It's hundreds of trips for clients. So I, what I did was ultimately building a solution for myself. That's. Really how Squadtrip it came about.

We're now selling to travel professionals, travel brands. There's even lifestyle brands on the platform, wellness tour operators and even some destination weddings and family reunions on the platform today.

Gresham Harkless 03:58

Nice. I absolutely love that. And just thinking through all of this, I can't even imagine. I'm not really a big trip planner. I'm not that person, that guy.

I love that you created a solution that of course helped out you and the people that were going on the trip, but also help out so many people that are having to navigate and juggle all those different needs, wants, desires, money, all those things, to make it a lot easier to make that happen.

Darrien Watson 04:20

Absolutely.

Gresham Harkless 04:21

Perfect. Perfect. Perfect. So I wanted to drill down a little bit more here, a little bit more about, everything that you all built. Can you take us through exactly like how it works, how you're making that impact and serving the clients you work with?

Darrien Watson 04:32

Sure. Now, if you put yourself in the shoes of a travel organizer, where you're going, you've got your group, but first step is really is getting the information out on paper, right?

You could go to Canva. You could build a WordPress website. Squadtrip makes it easy for you to just fill in the fields and the inputs and in a couple minutes, you'll generate a beautiful trip landing page. It has all the information, all the details frequently asked questions at everybody's fingertips.

So you can just share that with the group, whether it's in a group chat, posting on your Facebook group or page or sending an email blast to all your customers. And once they're ready to actually go through that booking process, you're likely going to have multiple trip options, whether it's like the basic package or the premium or the 4-day versus the 5-day.

Everyone's going to want to choose something different. So we effectively give you those tools to build out those trip packages. So you can manage your inventory, ask any registration questions that are associated with that and allow them to seamlessly check out using. The credit card debit or even Apple Pay.

Gresham Harkless 05:43

Nice. I love that. And I don't know if you Found this. Do you do you find I feel of course, part of the experience is going and traveling being wherever you go at it, whether it's a wedding or your family reunion, all those things that you mentioned that could be happening.

But I feel like part of the experience starts even before you get there. And I think that there's not enough. Kind of information or awareness of that. If you have, if you don't get the payment from the person that ends up being a bad experience that, drip that goes into the trip.

But do you feel like that alleviates a lot of that? So to make sure that the experience is as seamless as possible.

Darrien Watson 06:14

I couldn't agree more. Ultimately that trip experience starts when you book your trip, and you're thinking about where you're going, what are you going to be wearing, taking time off and, for the trip organizer it's best that they keep you engaged information, pictures what you should be wearing.

Maybe if you have to get any sort of shots or visas beforehand. So, there's so many things to think about from trip organizers perspective. And then if they're doing it for public consumption, and they're selling out a trip experience that's open to the public. Now, they need to kick off their marketing efforts.

And if they've got to worry about who's paid, who's up to date, sending out invoices and receipts and reminders, then they won't be able to focus on basically making that experience the best one for when people do arrive.

Gresham Harkless 07:03

Yeah, absolutely. And I think that's where, really technology truly shines.

Do you feel like being able to understand both of those parts, the people that are traveling, the people that are organizing the travel, do you feel like being able to create that solution and simplify that be that matchmaker for lack of a better term? Do you feel like that's part of your secret sauce or the organization secret sauce and what sets you apart and makes you unique?

Darrien Watson 07:24

I think that's a part of it. But I think the real secret sauce is ultimately, just making it really easy for anybody to get started. Now, as I mentioned before, we've got a lot of professionals on the platform. Those who are, making a 6 figure income off of planning and executing travel experiences for groups, but then.

You've got the leisure travelers that just want to bring friends together. That's where we started. So, I think that's ultimately the secret sauce. It's not that hard. The way the platform is built out. It's easy to use and there's a step-by-step trip builder. So if you haven't thought about some of these steps.

Based on how you interact with the platform, we're going to help you and our team beyond the software is there and able and willing to help you out. Because a lot of the planners on our platform they're what I call travel preneurs. They're new to the space they're trying to launch and grow a travel business.

And these the 1st trip that they're planning for their M. B. A. Program members or for their church. Is there for a into travel entrepreneurship and we want to hold their hand, whether it's talking to our team or. And how you engage with the product. And so ultimately, I think that's really the secret sauce.

The rest of them are built for established businesses. They even have checks and approvals that make it harder to even get started. And we remove all that.

Gresham Harkless 09:02

Yeah, I love that simplicity. So I wanted to switch gears a little bit and I wanted to ask you for what I call a CEO hack. So this could be like an Apple book or even a habit that you have, but what's something that makes you more effective and efficient?

Darrien Watson 09:15

I wish I could tell you there was a CEO hack, a book, an app, a habit, Waking up at four in the morning or doing cold showers or reading, thinking, grow rich or headspace using that app or something like that. But I think the truth is that the real hack is ultimately loving what you do and being tied to the mission.

And for me, it's connecting people through travel experiences and seeing travelpreneurs flourish and that keeps me busy and that keeps me going. So there's going to be days where I'm sick. I'm tired. But if you're doing what you love, it just makes it that much easier to continue to persevere, to continue to push through.

Gresham Harkless 10:02

Yeah. I appreciate you so much in talking about that perseverance and a lot of the resilience that a lot of times you need to get through. And so what would you consider to be what I would call a CEO nugget? A little bit more word of wisdom or piece of advice. I like to say it might be something you would tell your favorite client.

If you were to hop into a time machine, one of those travelpreneurs, or you might tell your younger business self.

Darrien Watson 10:23

So I think it's more of a question that I would ask. And when I sit down with. Mentees, they always have a grand vision. Oftentimes they're starting with a solution that they believe that the world needs.

And my question to them is usually, do you want to succeed or do you want to be right? And here's what I mean by that. We have these preconceived notions, a hypothesis and assumption sometimes. You step out into the market and it's a grand slam. But for the most of us, even the biggest founders and CEOs that we know, it wasn't the 1st idea.

It wasn't the 1st product they had to iterate over time. And. So, what's embedded in that question is the fact that you can't be tied to the solution. You can't be tied to doing it a certain way because you might be wrong. Of course, I think the sooner we iterate the sooner we get out of the market. We test does the market want what I'm selling them even if you want it to exist.

The market dynamics have to be in place. It has to be the right time, the right people, the right positioning, the right value proposition. There's so many things that have to be right. And if you can reflect and look at the data. And ask yourself. What the data is telling you and just be honest, sometimes it just might mean that whatever you birth, the initial version of it isn't what the market wants.

And so as long as we're listening to that, the truth and putting our ego aside, then as long as we love what we're doing, we can continue to do it. Even when it's raining, even when you're sick. Even when you get a hundred no's, you'll eventually get it right. And it's just about staying in the game long enough to do so.

Gresham Harkless 12:18

Yeah. I love that nugget. And I appreciate you, sharing that, so much. And I think I was listening to one of the interviews that you did as well too. And that's what made me, really think about, being more attached to the why rather than the how, and you had that experience with, I think we were talking before we hopped on about being in DC and how a lot of times you being in tech stars, being able to get the fun, all those things happened because you were more.

Attached to and tied to that mission that you talked about. Is that a little, what happened for you as well, too?

Darrien Watson 12:45

Absolutely. A, the initial version, this goes back to 2017, 2018, the business model in the initial version, wasn't going to be able to raise money. And for us to affect change, to help as many people as possible, we were going to need to raise money.

And so the name had to go. The position had to go. The offering had to change a bit. And I also had to be willing to move to Tulsa, Oklahoma for that opportunity. And I think that's what guided me and got us here today.

Gresham Harkless 13:24

Yeah, that's huge. And so now I want to ask you my absolute favorite question, which is the definition of what it means to be a CEO. And our goal is to have different quote-unquote CEOs on this show.

So Darrien, what does being a CEO mean to you?

Darrien Watson 13:35

Being a CEO, unlike owner or self-employed founder means that you're in service, you're in service to your customers. You're in service to your employees. You're in service to your investors and you've got to think not just about yourself and what you want.

You've got to think about what's in the best interest of the business. And how doing what's best for the business can serve those stakeholders.

Gresham Harkless 14:10

Yeah, I love that servant leadership and it is right in line with everything you said and being like tied, to that mission. So truly appreciate that definition. And of course I appreciate your time even more. So what I wanted to do now is pass you the mic, so to speak, just to see if there's anything additional that you can let our readers and listeners know.

And of course, how best people can get out of view, find out about all the awesome things you and your team are working on.

Darrien Watson 14:32

Sure. First things first, I want to say thank you, Gresh, to serving the CEO community. It can be lonely. And podcasts like this are helpful. I know I listened to him and it just allows us to get our message out there and connect with other people.

So, I appreciate you for that. And really just having me here and just have this great conversation in terms of anything additional that I want to share. If you are travel planner, know what travel planner, or even you've got events, festivals, conferences, where you're looking to partner with travel planners. reach out to me. You can find us. Our website is squadtrip.com. You can find me on LinkedIn at Darrien Watson, D. A. R. R. I. E. N. And also you can reach out to me on email at darrien@squadtrip.com.

Gresham Harkless 15:28

Awesome. Awesome. Awesome. Thank you so much again, Darrien. In order to make that easier, of course, we're going to have the links and information in the show notes as well, too, so that everybody can follow up and connect and develop all those awesome relationships and connections as well, too.

But truly, thank you so much for the time. It makes it so much easier to be a host and be able to talk with phenomenal people doing phenomenal things. So thank you for doing all the hard work. I just have to. Ask all the questions, which is a lot easier.

But I think one of the things that really stuck with me is again, we get so attached into how we're going to do the things that we're doing and we have to sometimes evolve in the way that we're thinking about our business, our life, our organization in order to see true wins and true success.

So I appreciate you so much again, and sharing the story of my friend and I hope you have a phenomenal rest of the day and thank you so much for reminding us of how important it is to be attached to the why and what we're doing.

Darrien Watson 16:20

Thanks for having me.

Outro 16:20

Thank you for listening to the I Am CEO podcast, powered by CB Nation and Blue 16 Media. Tune in next time and visit us at iamceo.co. I Am CEO is not just a phrase, it's a community.

Check out the latest and greatest apps, books, and habits to level up your business at ceohacks.co. This has been the I Am CEO podcast with Gresham Harless, Jr. Thank you for listening.

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