SquadTrip Cofounder and CEO Darrien Watson on Mastering the Art of Selling and Distribution Early On

Sep 24, 2024
Featured

I am the cofounder and CEO of SquadTrip (Techstars 2022). As an avid traveler, builder, and supporter of creators, I am passionate about seeing people succeed and fostering connections through travel. My mission is to empower others to create unforgettable travel experiences and build meaningful relationships.

What does your company do, and why is it important?

SquadTrip streamlines and enhances the travel planning process for group travel organizers and tour operators. We provide tools to create trips, collect payments, manage bookings, and market travel experiences efficiently. This is important because it empowers travel organizers to focus on crafting unique and memorable journeys, reducing administrative burdens and enhancing customer satisfaction.

How is what you are building disrupting your industry?

Before SquadTrip, travel organizers often had to hire a team to manage payments, reservations, and communications. With SquadTrip, a single operator can now save time and money by handling all these tasks through our platform. We enable small businesses to grow and thrive by providing them with the tools to create memorable travel experiences for large groups efficiently and cost-effectively.

What advice would you give aspiring entrepreneurs who are just starting their journey?

Figure out distribution before anything else. Understand how you will sell your product before you even start building it. This means identifying your target market, developing a go-to-market strategy, and validating your idea by pre-selling it. If your solution truly addresses a pain point, people will be willing to prepay for it. Remember, building the product is often easier than selling it. If you can master the art of selling and distribution early on, everything else will fall into place. Focus on securing customers and validating demand first, and the rest will follow naturally.

What has been your proudest moment or biggest triumph in your entrepreneurial journey?

My proudest moment came when the majority of our new customers started coming from word of mouth rather than from cold outreach. This shift was a significant milestone because it showed that we had created real value for our customers. By listening to their needs and continuously improving our product, we were able to help them manage payments and reservations for their group trips effectively. The fact that they were so satisfied with our solution that they felt compelled to recommend it to others, not because they knew me personally, but because of the tangible benefits they experienced, was incredibly rewarding.

Are there any lessons you've learned along the way that you wish someone had shared with you when you started?

A technical cofounder is essential to the success of your business. You can’t outsource your way to launching a new product. Our first startup failed because we lacked the technical expertise to build or lead an outsourced team effectively. It was only after this failure that we realized the importance of having the necessary technical skills to build and lead. We had to become technical cofounders ourselves, learning the skills required to execute our vision. Vision is crucial, but the ability to execute is equally important. If you can’t build or manage the building of your product, it’s much harder to bring your vision to life.

Why did you want to do an accelerator, and why did you choose Techstars?

With a background in product management, I am a builder and a problem solver. However, I realized that to truly scale our business, I needed more than just my technical skills. I needed expertise in go-to-market strategies, raising capital, and building a strong network of backers who believed in my vision. Techstars provided exactly that — capital and access to a community of builders and mentors willing to accelerate our growth.

Techstars is a recognized brand and the most active pre-seed investor in the world. Joining Techstars was the perfect choice to transform our project from a cool idea into a thriving business. The program offered invaluable resources, guidance, and a network that has been instrumental in our success.