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  • Writer's pictureKimberly Dinehart


Did you set a New Year’s Resolution to learn a new language? Or keep up with your high school Spanish? If you’re like most Americans, your resolution is starting to look a bit less resolute by now. Toucan is here to help you keep the momentum going. By teaching you a new language as you go about your day online, Toucan takes away the hardest part of learning a new language - finding the time and making it a habit. The team behind Toucan exemplifies lifelong learning, and it has paid off. The company raised a $3.5M seed round in September from GSV Ventures, Amplifyher Ventures, Wonder Ventures, Golden Ventures, Halogen Ventures, Vitalize Ventures, and others.

The free Toucan Chrome extension replaces English words within the text of any webpage using natural language processing (NLP) with words in Spanish, French, Italian, Portuguese, or German; users can use context clues to learn the word, or hover over the word to see the original English word revealed if they are stumped. Toucan can also read the word out loud so you can know how the word is pronounced. Once you feel confident with a word, you can mark it as learned and Toucan won’t show it again. When you open a new tab or click play when hovering over a word, Toucan creates a short game to ensure that you are retaining the words that you see. Toucan users see an average of over 2,000 of these “micromoments” of learning each day without ever having to open up a separate app.

Toucan also offers a premium tier ($4.99/month for an annual subscription or $8.99/month for a monthly subscription) with additional vocabulary and functionality. In the premium tier, you can highlight text and have Toucan translate any word on any webpage. You can also install specific vocabulary packs to prepare you for a job interview, a date, a sporting event, and more. There are unlimited games you can play right in your browser to test your knowledge or just have fun. And, for aspiring polyglots, you can learn more than one language at the same time.

Toucan has partnerships to support its free tier and the continued development of its NLP engine. One of their monetization features is “Own the Word,” where an individual or an organization can have their name listed alongside a word on the site either for free for seven days or indefinitely for a small weekly fee; every time a user hovers over a word to learn the definition, the user can click on the owner and be directed to another site.

About the Founders

Toucan co-founder and CEO Taylor Nieman is an LA native who, after a few Ithaca, NY winters, decided to move back to LA after graduating with a degree in business and communications from Cornell, where she captained the D1 volleyball team. Always knowing she wanted to be a founder, Taylor taught herself how to code while at Cornell using YouTube videos and creating prototypes in her dorm. When she moved back to LA, she didn’t yet have a product idea of her own, so she went to work at some of LA’s most exciting startups. From Headspace (employee #20) to Fair, Taylor specialized in business development and strategic partnerships, specifically distribution without paid acquisition, helping these now iconic companies gain some of their first customers and partnerships organically.

After a few years in the startup world, Taylor decided it was time to take the leap and found her own company. While that startup did not succeed, Taylor learned several key lessons that she has brought with her to Toucan. First, your team is everything; founders need co-founders who compliment their skillset because, especially for early stage companies, your competitive advantage is your team. Second, “be dangerous enough” with your technical skills; while Taylor does not have an engineering degree, she knew enough coding to be able to create prototypes that would get engineers excited about working on her product with her. Lastly, Taylor learned to be comfortable with rejection. Launching a startup is full of highs and lows and rejection is common, especially when fundraising; it is important to be able to keep moving forward without losing enthusiasm.

Throughout this experience Taylor was getting to know other founders in the LA startup community as well as top tech talent in the city. Rich Pierson, co-founder of Headspace, was an important mentor to Taylor as she went on her startup journey. So was Honey’s Ryan Hudson, who provided a lot of advice and feedback early on as she developed the idea for Toucan. She also met her future co-founders. Brandon Dietz, co-founder and CPO (UCLA ‘09), was a co-worker at Headspace and the two stayed friends after they both left to pursue other opportunities. Taylor met Shaun Merritt, co-founder and CTO, at Science Incubator, where they were each working at different portfolio companies. In their spare time, she would pitch him ideas, he would give her feedback, she would take his feedback and code up a mock website, and he would dig into the code with her. They then both joined Fair together before leaving to found Toucan.

Taylor, Brandon, and Shaun always wanted to learn new skills, but found it difficult to carve time out of their day to make it a habit. Taylor knew from her background in distribution and customer acquisition just how hard it is to create new customer habits, and sought to solve this problem at Toucan. The team at Toucan wasn’t originally planning on creating a browser extension, instead seeing the platform as an interesting and free channel to send traffic to an app. However, as Brandon and Shaun looked into it more, they found that they could build all the functionality that they wanted in an app into the Chrome extension itself. This discovery changed the trajectory of their company. By meeting people where they are--on Chrome, browsing the internet--Toucan has eliminated a huge barrier to entry facing apps, which require people to consistently set aside time in their day to access them. Based on the strength of Toucan’s founding team as well as their hypothesis about user acquisition via browser extension, Wonder Ventures wrote Toucan their first check to build the beta version.

The Toucan team was heads-down, building and iterating their product to ensure they had the right engagement and retention metrics before a big launch. Toucan originally sought to be a broad knowledge platform, enabling people to study not only languages but also other subjects such as history or science. During this initial building and testing phase, the team discovered that users were overwhelmingly interested in the language learning application over any other use case. At that point, Toucan pivoted to focus exclusively on language learning. Language translation provides a unique engineering challenge - you can’t just directly translate words, as grammar is different in each language and context can change a word’s meaning. Toucan’s natural language processing is top-notch thanks to the tremendous efforts of Shaun, Brandon, and their nimble six-person tech team as well as a group of translation advisors and language teachers throughout the LA-area.

COVID-19 has made the already challenging proposition of starting a business even harder, but Taylor is no stranger to the risks a founder takes on when they bet on their idea. To her, the uncertainty of this past year has been an opportunity for herself and others to develop new habits, making it a perfect time to launch. Since Toucan was featured in the Chrome store in July 2020, Toucan has acquired over 30,000 users who are learning languages on the platform daily. Toucan is excited to work with some of the top names in EdTech, from GSV Ventures to advisors like Google’s Chief Education Officer Jaime Casap, to make their product integral to the daily lives of its users.

What's Next

The team at Toucan is continuously looking to make their product as useful as possible to as many people as possible. Their first goal is to prove their value proposition on desktop before eventually adding mobile functionality. To that end, Toucan is looking at extensions for Firefox and Safari to truly be the foremost browser extension on the web today. Additionally they are working on building internal tools to create content, allowing users to create “single player” or “multiplayer” modes to curate curriculum as well as to enable partners to better make use of Toucan’s platform. Toucan is launching over 30 language vectors this year, including Korean later this month, Japanese in February, and English for speakers of a number of other languages.

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