Shaina Shiwarski & Stephanie Daniel: Unlocking the Power of Personalized Travel

Shaina Shiwarski and Stephanie Daniel, the co-founders of travel tech company Legends, are on a mission to reshape the travel industry. Their innovative platform leverages data-driven insights and AI to deliver personalized, authentic travel experiences for both travelers and brands. In a recent interview with Machinelab, the co-founders shared their personal stories, discussed the challenges they faced, and outlined their vision for Legends…

A Journey Shaped by Personal Experiences

Shaina, born into a Ukrainian-Italian family in Pittsburgh, PA, was inspired by her mother, who broke barriers as a software engineer in the healthcare tech sector. Her early love for travel and problem-solving led her to a career in tech consulting and later the tech-startup world.

“In 2019, I embraced the digital nomad lifestyle, uncovering first-hand the challenges related to the current tech ecosystem in travel, which led us to the problem we’re solving today with Legends,” states Shaina.

Stephanie, on the other hand, grew up in a small village near London, England, where her father's travel stories sparked her own passion for exploration. With an academic background in economics and a belief in the power of data-driven insights, Stephanie embarked on a successful 15-year career in global strategic roles before taking the entrepreneurial leap.

“My dad in particular had to travel a lot with his job and always returned with amazing stories of places and people,” she says, “As I began to travel myself I realized its power in helping us understand ourselves, each other and the world, and the ability to drive individual and collective growth.”

Unveiling the Idea: A Legend is Born

Legends was born out of the co-founders’ shared frustration with the lack of personalization and authentic connections in the travel industry. They recognized that the current tech ecosystem failed to capture and utilize travelers' preferences effectively.

“The travel industry felt too commodified with a 'one size fits all' approach and no understanding by travel providers of who we really are,” says Stephanie, “Shaina and I bonded immediately over these shared pain points when we first met over 8 years ago and a belief that there had to be a better way. Over time we realized our complimentary skill-sets made us a great team to try to solve it!”

By leveraging unstructured data from travelers' phones and photo metadata, Legends creates real-time preference profiles called Travel DNA. This privacy-controlled data empowers travelers and allows them to share insights with trusted brands, fostering a new era of personalization.

“Our mission is to empower travelers to form more authentic connections with themselves, each other, and the world,” she states.

Additionally, Legends employs a proprietary process to gather and analyze phone and photo metadata, transforming it into detailed preference profiles and insights. These profiles encompass various areas, such as aesthetics, activities, lodging, seasonality, sentiment, and predictive trends. With a single authorization from the traveler, Legends creates dynamic real-time profiles, giving travelers control over which brands they choose to share this information with. The technology ensures user privacy and the ability to revoke brand access to data at any time.

Revolutionizing the Travel Industry Through Personalization

Legends aims to revolutionize the travel industry by addressing the critical challenge of personalization. By fostering better connections between brands and travelers, the platform matches the right travelers with the right brands at the right time. This shift toward data-driven, personalized travel experiences benefits both travelers and brands, reducing costs and reshapingtheir interactions. Legends' vision is to make travel more personal, tailored, and rewarding, transforming the generic travel booking experience into one that aligns with individual preferences.

At the core of Legends' AI strategy is the Legends Travel DNA, a proprietary process that instantly transforms data into actionable insights. These insights power tailored recommendations, smart itinerary planning, predictive trend identification, seasonal preferences, and lifestyle and value-based matching. By using large language and predictive models, Legends can deliver unique, personalized experiences for both individual travelers and the brands serving them.

“Imagine checking into a hotel that asks you to share your Travel DNA by scanning a QR code. With that single action, the hotel's CRM and PMS systems would instantly know where you just arrived from, your preference for morning yoga, and your love for fresh seafood at dinner. Or alternatively, while using the hotel’s app, you could opt in with one click to map your Travel DNA, instantly populating an enhanced profile with insights like your typical 10-day trip duration, your consistent January travels, and tailored suggestions for activities in Costa Rica based on your Travel DNA,” Shaina states.

Overcoming Challenges and Lessons Learned

The entrepreneurs faced various challenges during the development of Legends. Hiring the right talent, balancing resource efficiency, and prioritizing execution were key lessons they learned. Additionally, they highlighted the importance of being open to feedback, iterating quickly, and building a community of supportive partners and advisors.

“We have learned that building a company is definitely a journey that constantly includes challenges and wins! But in a way that’s what makes it one of the most rewarding journeys you can take on in life and helps us evolve as people and as a company,” says Stephanie.

“Fundamentally, as a startup, you obviously have to be incredibly resource-efficient and balance many demands - we should be proud of what we have been able to deliver and I think we have a great foundation to continue that ethos as we move into our next phases.”

Differentiation in a Crowded Market

Legends differentiates itself by its DNA data foundation, which unlocks untapped data sources and transforms them into actionable insights. By prioritizing the needs and motivations of travelers, Legends focuses on solving core industry problems, rather than addressing surface-level issues. Their solution offers unique features such as deep data insights, clear consent and permissioning, real-time dynamic updating, and seamless integration with existing systems, setting them apart in the market.

Looking ahead, Legends aims to become the essential tool and application for the travel and hospitality industry. Their immediate focus is on refining their SDK and API, building strong partnerships with key brands, and bringing their first B2B application to market.

“Over the next 2 years, we see our product evolving to incorporate additional SDKs and APIs, tailored to specific use cases and solutions for line of business owners, developers, marketers and data scientists for data enrichment around segmentation, loyalty, personalization algorithms and business resource planning. We also envision an analytics and insights platform that can provide real-time intent and behavioral data across all travelers,”Shaina reveals.

“Ultimately we are the tool to power a new data driven ecosystem that puts the human first, powering personalization for a better customer experience while unlocking revenue and loyalty opportunities,”Stephanie adds. “We’re at a really exciting inflection point for the company as we enter this next phase. Our current focus is on working closely with development partners on the B2B product for metrics driven case studies, and then building upon this as we expand.”

Advice for Female Entrepreneurs

Both Shaina and Stephanie offer valuable advice to aspiring female entrepreneurs. They emphasized the importance of being true to oneself, as authenticity drives success. They also stressed the significance of building relationships and actively engaging with the startup community. By fostering connections and supporting one another, female entrepreneurs can create a vibrant and inclusive ecosystem.

“Be yourself,” quips Stephanie. “You hear a lot of things about needing to be a certain way for the startup or in particular, the VC ecosystem. A key reason to be an entrepreneur is freedom to work on your passions and for me it’s important to do that in a way that is authentic to who I am, and to empower the rest of the team to do so as well. That’s how I believe we will deliver the best value for all our stakeholders. I’ve found that by doing this the right long-term fit of partners, investors, team and advisors have happened. Secondly, relationship-build! I say that deliberately, versus ‘networking.’ I have loved engaging with others in the startup community - founders, investors across stages, as well as others in the industry. The ability to learn from and support each other is key and as you expand your network, you expand your potential for warm intros. Join relevant groups, events, speak at conferences. It takes a big time commitment to do this especially if you are moving from another industry, but it’s all worth it and the earlier you start the better.”

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Photos courtesy of: Legends