EC-1
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Nubank’s first office, on California Street in the Brooklin neighborhood of São Paulo, makes for a great beginning to the company’s story. It wasn’t a Silicon Valley garage, but this tiny, one-bathroom rented house, where 30 people worked insane hours to push out the company’s debut credit card, lends just as well to an image of entrepreneurial spirit and drive.
As Nubank continues to make international waves, more and more VC investors are taking a look at the Brazilian ecosystem and could potentially fund other upstarts in the years to come.
But as Nubank’s story continued, the team eventually had to move out of that early office, and the next several offices, too. Eventually Nubank had to relocate to an eight-story building in São Paulo, which houses a large part of the company’s now 3,000-person team.
The startup reached decacorn status in far less than a decade, and it is growing faster than ever. When I interviewed CEO David Velez back in January to discuss Nubank’s $400 million Series G, he said, “We’ve gone from 12 million customers in 2019 to 34 million solely based on word of mouth.” By September last year, the company was onboarding 41,000 new customers per day.
In the five months since our interview, Nubank has managed to rope in a whopping 6 million customers to reach 40 million. It’s now valued at $30 billion.
Nubank’s present day headquarters in São Paulo, Brazil. Image Credits: NELSON ALMEIDA/AFP / Getty Images
Getting there hasn’t been easy. The company’s three co-founders, Velez, Edward Wible and Cristina Junqueira, had to make key strategic decisions about how to scale themselves to retain the company’s lead in the neobanking market. That lead is getting tougher to sustain every day. Nubank’s proliferating offerings and broader geographical remit has painted a massive target on its back, and a wide number of competitors have cropped up to run on the paths it pioneered.
Like most Disney films, a fairy-tale ending seems in order, but it’ll take a few more rotations of the film wheel to get to the ending.
For the co-founding trio, it became increasingly clear that Nubank’s growing scale demanded critical strategic decisions on how to bring order to the company.
By 2018, the company had thousands of employees, millions of customers, and they still didn’t have a head of HR. Growth until then had been somewhat unstructured. According to Junqueira, waiting so long to hire a head of HR was one of their early mistakes, because it stunted their ability to grow. “[Good] people continue to be our biggest bottleneck,” she says.
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Take a close look at any ambitious startup and you’ll find pugnacity nestled in its core. Stubbornness and a bullheaded belief in the worth of what a company wants to bring to fruition is often the biggest driver of its success, and the people at such companies also tend to share this quality.
So it wouldn’t be too far off the mark to say the people at Expensify are a stubborn lot — to the company’s ultimate benefit. This group of P2P pirates/hackers that set out to build an expense management app stuck to their gut, made their own rules. They asked questions few thought of, like: Why have lots of employees when you can find a way to get work done and reach impressive profitability with a few? Why work from an office in San Francisco when the internet lets you work from anywhere, even a sailboat in the Caribbean?
It makes sense in a way: If you’re a pirate, to hell with the rules, right? And even more so when nobody can explain the rules in the first place.
With that in mind, one could assume Expensify decided to ask itself: Why not build our own totally custom tech stack? Indeed, Expensify has made several tech decisions that were met with disbelief — from having an open-source frontend and cross-platform mobile development to hiring contractors to train its AI and recruiting open-source contributors — but its belief in its own choices has paid off over the years, and the company is ready to IPO any day now.
How much of a tech advantage Expensify enjoys owing to such choices is an open question, but one thing is clear: These choices are key to understanding Expensify and its roadmap. Let’s take a look.
I think another question Expensify also decided to ask in its early days was something like: Why not have our database on top of a technology that’s built for small-scale application software?
It may sound incredible, but Expensify actually runs on a custom database built on top of SQLite. This is surprising, because despite being one of the most widely deployed database engines, SQLite is known for running on small, embedded systems like smartphones and web browsers, not powering enterprise-scale databases.
It may sound incredible, but Expensify actually runs on a custom database built on top of SQLite.
This custom database is called Bedrock, and its architecture is as unique as they come. Expensify explains it as an “RDBMS optimized for self-healing replication across relatively slow, relatively unreliable WAN (internet) connections, enabling extremely high availability/high performance multi-datacenter deployments without any single point of failure.” RDBMS means relational database management system, describing SQLite and other row-based databases where entries are interconnected with each other.
But why would Expensify build this instead of going for any number of widely available enterprise database solutions?
To answer that question, we need to go back to the early days of the company, which was originally a side project for its founder and CEO, David Barrett. His initial idea was to develop a prepaid card for the homeless, but this required putting a server on the Visa network, which brought several strict requirements and challenges. “I would say one of the most difficult [parts] was that I needed the ability to automatically replicate and failover,” Barrett told TechCrunch when we interviewed him a couple of months ago.
This was no easy feat in 2007, but Barrett was up for the challenge. “I just hit a moment where the technology available off the shelf just wasn’t that good. And I happened to be a peer-to-peer software developer who had tons of spare time and really wanted to build this thing to put on the Visa backend,” he said. The P2P aspect was important, as Barrett had the skills to make it work. His first hires for Expensify, P2P engineers he had worked with at Red Swoosh and Akamai, were also unusually suited for the job.
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Expensify may be the most ambitious software company ever to mostly abandon the Bay Area as the center of its operations.
Expensify may be the most ambitious software company ever to mostly abandon the Bay Area as the center of its operations.
The startup’s history is tied to places representative of San Francisco: The founding team worked out of Peet’s Coffee on Mission Street for a few months, then crashed at a penthouse lounge near the 4th and King Caltrain station, followed by a tiny office and then a slightly bigger one in the Flatiron building near Market Street.
Thirteen years later, Expensify still has an office a few blocks away on Kearny Street, but it’s no longer a San Francisco company or even a Silicon Valley firm. The company is truly global with employees across the world — and it did that before COVID-19 made remote working cool.
“Things got so much better when we stopped viewing ourselves as a Silicon Valley company. We basically said, no, we’re just a global company,” CEO David Barrett told TechCrunch. That globalism led to it opening a major office in — of all places —a small town in rural Michigan. That Ironwood expansion would eventually lead to a cultural makeover that would see the company broadly abandon its focus on the Bay Area, expanding from a headquarters in Portland to offices around the globe.
It makes sense that a company founded by internet pirates would let its workforce live anywhere they please and however they want to. Yet, how does it manage to make it all work well enough to reach $100 million in annual revenue with just a tad more than 100 employees?
As I described in Part 2 of this EC-1, that staffing efficiency is partly due to its culture and who it hires. It’s also because it has attracted top talent from across the world by giving them benefits like the option to work remotely all year as well as paying SF-level salaries even to those not based in the tech hub. It’s also got annual fully paid month-long “workcations” for every employee, their partner and kids.
Yet the real story is how a company can become untethered from its original geography, willing to adapt to new places and new cultures, and ultimately, give up the past while building the future.
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The influence of a founder on their company’s culture cannot be overstated. Everything from their views on the product and business to how they think about people affects how their company’s employees will behave, and since behavior in turn informs culture, the consequences of a founder’s early decisions can be far-reaching.
So it’s not very surprising that Expensify has its own take on almost everything it does when you consider what its founder and CEO David Barrett learned early in his life: “Basically everyone is wrong about basically everything.” As we saw in part 1 of this EC-1, this led him to the revelation that it’s easier to figure things out for yourself than finding advice that applies to you. Eventually, these insights — and the adventurous P2P hacker attitude he nurtured alongside his colleagues and Travis Kalanick at Red Swoosh — would inform how he would go about shaping Expensify.
Expensify’s culture can’t be separated from its hiring and growth processes — by joining the company, employees self-select into a group that isn’t likely to get hung up about trade-offs.
It’s striking how Expensify has managed to maintain this character 13 years later, even on the threshold of an IPO. How did this happen? During a series of interviews in February and early March, we found the answer is tied to the level of thought and effort this expense management business puts into its culture.
You see, the people at Expensify are prepared to invent their own playbook, develop it and, if needed, rewrite it completely. Its HR policies and strategy are tailored to find people who would have fun building an expense management product. It has a unique growth and recognition scheme to offset the drawbacks of a flat organizational structure. It’s even got a “Senate” that vets all major decisions. No kidding.
All this, and more, has ultimately helped Expensify reach more than 10 million users and achieve $100 million in annual revenue with just 130 employees. Let’s take a closer look at how Expensify makes it happen.
It’s clear Expensify’s unusually high employee-to-revenue ratio is intentional: “We want the fewest people necessary to get the job done,” Barrett says. But how do you actually achieve it? How do you hire and keep people who can deliver such results? Barrett had to learn how the hard way.
Expensify’s first team was based in San Francisco and comprised Barrett’s old Red Swoosh and Akamai colleagues, who joined a few months after Akamai fired him. A small team was enough to get started, but it was much more difficult to hire additional people. Barrett is eager to clarify the Valley is not really the best place to recruit talent: “Sure, Silicon Valley has a ton of really awesome people, but all of them have jobs!,” he says.
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Let’s make it clear from the outset that this story is about an expense management SaaS business called Expensify. As you’d expect, yes, this is about the expense management market and how Expensify has grown, its technology and all of that. Normally, that would make us change the channel. But this is also a story about pirates; peer-to-peer hackers who asked, “Why not work from Thailand and dozens of countries across the globe?” and actually did it using P2P hacker culture as a model for consensus-driven decision-making — all with pre-Uber Travis Kalanick in a guest-starring role.
Most interestingly, this is a story about just not giving a damn about what anyone goddamn thinks, an approach to life and business that led to more than $100 million in annual revenue, and an IPO incoming on what looks to be a very quick timetable. Prodigious revenues, 10 million users and only 130 employees running the whole shebang — that’s a hell of an achievement in only 13 years.
If you’re going a bit “WTF,” well, we’d concur. Expensify is as contradictory as they come in the enterprise world. It’s managed to take what might well be the most boring part of the corporate business stack and turn it into something special. It doesn’t borrow its culture from other startups, it built its own tech stack from the ground up, and even hires in a completely radical way. Oh, and no one really has job titles either, because why the hell bother with hierarchy anyway? They’re pirates after all.
If expense management is about avoiding corporate plunder, then letting the pirates and hackers run the ship is probably the best approach. And now, Expensify is plundering the corporate spend world one travel ticket and business meal at a time just as the world is rebuilding in the wake of COVID-19.
TechCrunch’s writer and analyst for this EC-1 is Anna Heim. Heim is a tech journalist and former startup founder who has written for different tech publications since 2011. She recently joined Extra Crunch as a daily reporter, where she will be sharing insights on startups, particularly in SaaS. The lead editor of this package was Ram Iyer, the series editor was Danny Crichton, the copy editor was Richard Dal Porto, and original illustrations were created by Nigel Sussman with art direction from Bryce Durbin.
Expensify had no say in the content of this analysis and did not get advance access to it. Heim has no financial ties to Expensify or other conflicts of interest to disclose.
The Expensify EC-1 will be a serialized sequence of five articles published over the course of the coming weeks. We interviewed the company in February and March, well before the company announced a confidential filing of its S-1 to the SEC. Let’s take a look:
We’re always iterating on the EC-1 format. If you have questions, comments or ideas, please send an email to TechCrunch Managing Editor Danny Crichton at danny@techcrunch.com.
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Individuality often has no place in the enterprise software space. In a market where a single contract can easily run into the millions, homogeneity is the herald of reliability and serves to reassure buyers of the worth of their potential purchase.
So it’s natural to think a company in the expense report management business would keep it simple and play it by the book. But one look at Expensify is enough to tell you that this is a company that never even looked for the book.
Expensify’s origin story is one of a scrappy group of developers who turned travel into a catalyst for ideas and stuck together through highs and lows, ending up building one of the most unexpectedly original companies in enterprise software today.
Right from its famous “workcations,” to its management structure and its decision-making policies, Expensify has it in its DNA to eschew so-called best practices for its own ideas — a philosophy rooted in its founder and early team’s P2P hacker background and do-it-yourself attitude. As a result, Expensify is atypical of startups in many ways, inside and out.
Founder and CEO David Barrett made it clear his company was different in our first call itself: “We hire in a super different way. We have a very unusual internal management structure. Our business model itself is very unusual. We don’t have any salespeople, for example. We’re an incredibly small company. We focus on the employees over the bosses. Our technology stack is completely different. Our approach toward product design is very different.”
That description would make some people call Expensify weird even by startup standards, but this essential difference has set it apart in a space dominated by giants such as SAP Concur and Coupa. And that’s ultimately been to its benefit: Expensify reached $100 million in annual recurring revenue in 2020, with hefty 25% EBITDA margins to boot. There were also rumors of the company planning to go public during our interviews for this EC-1, but they stopped speaking to us in March, and now we know why: Expensify confidentially filed to go public on May 3.
Expensify’s origin story is one of a scrappy group of developers who turned travel into a catalyst for ideas and stuck together through highs and lows, ending up building one of the most unexpectedly original companies in enterprise software today.
To truly understand Expensify, you first need to take a close look at a unique, short-lived, P2P file-sharing company called Red Swoosh, which was Travis Kalanick’s startup before he founded Uber. Framed by Kalanick as his “revenge business” after his previous P2P startup Scour was sued into oblivion for copyright infringement, Red Swoosh would be the precursor for Expensify’s future culture and ethos. In fact, many of Expensify’s initial team actually met at Red Swoosh, which was eventually acquired by Akamai Technologies in 2007 for $18.7 million.
Barrett, a self-proclaimed alpha geek and lifelong software engineer, was actually Red Swoosh’s last engineering manager, hired after the failure of his first project, iGlance.com, a P2P push-to-talk program that couldn’t compete against Skype. “While I was licking my wounds from that experience, I was approached by Travis Kalanick who was running a startup called Red Swoosh,” he recalled in an interview.
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Education may well be the most important activity we conduct as a society — and it may also be the hardest space to build a startup in. Selling to school districts and universities is notoriously difficult, but enticing consumers is even harder. Learning takes focus, patience, tenacity and resources, and most consumers would prefer to watch some lip-sync videos on TikTok than stare at math equations (not to mention that such entertainment is free). Engagement and education feel aggressively at odds, which limits the way that startups can scale and succeed.
Yet, the revulsion VCs have traditionally had for the space has slowly dissipated over the past 10 years. Consumer and enterprise startups in edtech are increasingly attracting funding, and there is a growing crop of edtech-focused investors who are betting big on the future here. What’s changed isn’t the market or its potential, but rather the perception that ambitious and sustainable companies can truly be built in education.
One of the companies that has led the charge in transforming those perceptions is Pittsburgh-based Duolingo. It’s a language-learning app that has caught fire. From humble origins a decade ago as a translation platform for news agencies, it’s now used by 500 million people across the world to learn Spanish, English, French and more, all while generating bookings of $190 million in 2020. It’s a smashing success, but a success that was hard earned after a years-long effort of product and revenue experimentation to find its current niche.
TechCrunch’s writer and analyst for this EC-1 is Natasha Mascarenhas. Mascarenhas has been covering edtech from the very first day she joined TechCrunch as a venture capital and startups writer, and she has built up a reputation as a fearless chronicler of this increasingly vital ecosystem. The lead editor of this package was Danny Crichton, the copy editor was Richard Dal Porto, and illustrations were created by Nigel Sussman.
Duolingo had no say in the content of this analysis and did not get advance access to it. Mascarenhas has no financial ties to Duolingo or other conflicts of interest to disclose.
The Duolingo EC-1 comprises four main articles numbering 12,200 words and a reading time of 48 minutes. Here’s what’s in store:
And finally, note that Duolingo CEO and co-founder Luis von Ahn is coming to Disrupt, so make sure to grab your tickets because the conversation will continue there.
We’re always iterating on the EC-1 format. If you have questions, comments or ideas, please send an email to TechCrunch Managing Editor Danny Crichton at danny@techcrunch.com.
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Luis von Ahn, an entrepreneur who has dedicated his career to scaling free education, has probably annoyed you more than once. In fact, you’ve likely been annoyed by his work dozens and maybe hundreds of times over the years.
A decade before he co-founded the whimsical and language-learning app Duolingo, one of the most popular education apps in the world with over 500 million downloads and 40 million active users, he was building the technology that would become CAPTCHA, those human-annoying but bot-preventing little tests that pop up when registering or logging in to popular internet services like email.
It may seem like a radical pivot, but in fact, the lessons of how to create useful security tests at scale for consumers would one day offer the core DNA for building one of the most successful edtech companies in the world. The immigrant entrepreneur would soon learn himself that crowdsourcing, language and a willingness to adapt and ignore critics could change the face of an industry forever.
Von Ahn grew up in Guatemala City, where he saw firsthand the wretched state of public schools in impoverished countries. His mother spent most of her income sending him to “fancy private school” as he puts it, and he estimates she spent over $1 million on his education over his lifetime. The price tag weighed on him, and he knew he wanted to broaden access to education in the future.
After attending Duke as an undergrad, von Ahn was an enterprising first-year computer science Ph.D. student at top-ranked Carnegie Mellon University when he attended a talk by Yahoo’s chief scientist about 10 of Yahoo’s biggest headaches. One issue stood out: hackers were creating bots that register thousands of email addresses to send spam.
Inspired and full of immigrant grit, von Ahn and a team led by his then-adviser Manuel Blum created a nifty little test that could distinguish between bots and humans. The test, called a CAPTCHA, presented squiggly, ink-blotted words whenever a user tried to log in. Computer vision at the time couldn’t read the obscured text, but humans easily could — creating a useful signal. The deceptively simple test worked, so von Ahn, then a 20-something student, gave it to Yahoo for free, not understanding the value it would one day have.
Luis von Ahn, the inventor of CAPTCHA and reCAPTCHA, and co-founder of Duolingo. Image Credits: Duolingo
A fire was lit. With Yahoo as a distribution channel, CAPTCHA tests exploded in popularity, becoming an almost universally recognizable security checkpoint feature. At their peak, people spent 500,000 hours a day typing up to 200 million CAPTCHAs around the world. About 10% of the world’s population had recognized at least one word, von Ahn estimates.
For all the technology’s success, though, there was a downside. “During those 10 seconds while you’re typing in a CAPTCHA, your brain is doing something that computers can’t do, which is amazing,” von Ahn said. But the tests were annoying and pointless, so he wondered, “Could we get those 500,000 hours a day to do something useful for humanity?”
So in 2005, he launched reCAPTCHA. These new tests would have the same goal of CAPTCHA, but with a twist: the prompts would all be scans of books. Users would complete the security test while also helping to digitize books for the Internet Archive.
The early design of reCAPTCHA. Image Credits: Duolingo
This time, von Ahn knew his nifty idea was worth something. In 2009, he sold reCAPTCHA to Google, a transaction conducted just a year after the internet giant had purchased a license to one of his other research projects, a game focused on image labeling.
Luis von Ahn presenting about reCAPTCHA and CAPTCHA, two of his iconic inventions. Image Credits: Duolingo
The acquisition offered not just a monetary award (exact terms of the deal were not disclosed), but also suddenly garnered von Ahn serious clout in the industry just a few years after acquiring his Ph.D. Yet, instead of taking up tenure at the tech company, he stayed local in Pittsburgh and became a computer science professor at his alma mater.
Entering the world of education as a professor felt like an answer to his original dream of expanding access to education. What von Ahn didn’t know, though, was that his iconic work was simply foreshadowing. Carnegie Mellon, crowdsourced translation and even Google would all play a role in his next project as well, albeit in wildly different ways: incubation, failure and investment. For him, the success of two tools that used language as a barrier was the beginning of a long journey into discovering if, and how, language could instead be a bridge. It was an insight that would grow into a startup valued at $2.4 billion with the goal of making language learning fun: Duolingo.
In 2011, edtech startups such as Coursera and Codecademy were popping up — companies that today are valued as multibillion-dollar businesses. The rise of iPads and tablets in classrooms gave permission to founders who believed the future of education was on the internet. Enthusiasm was boiling, and virtual instruction felt like a nascent, but ambitious, place to bet on.
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Duolingo CEO and co-founder Luis von Ahn was tired of the gray and dreary design aesthetic edtech companies used to emulate universities. Instead, he and the company’s early team sought inspiration from games like Angry Birds and Clash Royale, looking to build a class that screamed more cartoon anarchy than lecture hall. From that frenetic creativity came the company’s distinctive mascot: a childish and rebellious evergreen-colored owl named Duo.
Duolingo didn’t just throw out the old colors though — it wanted to completely rethink language learning from the bottom up for mobile. So it replaced top-down curriculums with analytics-driven growth strategies, becoming consumed by an ethos that has more recently been dubbed product-led growth.
Used by companies such as Calendly, Slack and Dropbox, product-led growth is a strategy in which a company iterates its product to create loyal fans-turned-customers who popularize the product with others, creating a viral growth loop. It’s an attractive route because it vastly lowers the cost of acquiring users while also increasing engagement and thus retention. Duolingo, for example, has taken this model and found ways to embed engagement hooks, pockets of joy and addictive education features within its core app.
With early venture capital in its pocket, Duolingo could afford to focus on product over profits.
In part one of this EC-1, we explored how von Ahn’s previous products around CAPTCHA led to Duolingo’s launch, the rise and fall of crowdsourced translation as a way to disrupt language learning, and the accidental iteration of a top education app by a pair of interns. The startups’ early signs of success gave it energy to focus on growth to accomplish two things: know what they’re doing works, and garner a lot of user data so it continued iterating the product into something that was ever more addicting to use.
Now, we’ll analyze how Duolingo used product-led growth as a lever to expand its consumer base, and how a company built on gamification tries to balance its whimsy with education outcomes.
Duo, Duolingo’s mascot, flying around. Image Credits: Duolingo
Tyler Murphy, having graduated from his intern position at Duolingo launching the company’s iOS app, noticed that the gaming world was rapidly innovating around him in the mid-2010s. Angry Birds was no longer the only popular game on mobile, and video games generally were getting more engaging, with in-app currencies, progress bars and an experience that felt creatively addictive. He suddenly saw connections between the entertainment that games provided and the patient learning required for languages.
“Wouldn’t it be cool if the skill got harder and harder, kind of like how a character in a game gets more powerful and powerful?” he remembers asking. Duolingo had taken early inspiration from Angry Birds as well as Clash Royale later, following that game’s launch in 2016. “Half the people at Duolingo were playing Clash Royale, at some point,” he said. “And I think that shaped our product roadmap a lot and our design language a lot.”
Games solved a problem that was acutely personal for Murphy. The employee, who would go on to become chief designer at Duolingo, had gone to college to teach Spanish to students, but ultimately left the field after struggling to inspire kids in a classroom setting. The realization that Duolingo could borrow from gaming instead of monotonous edtech companies gave an adrenaline rush — and permission — to the team to experiment with new approaches to learning.
Every game needs some form of experience points and leveling up, and for Duolingo learners, that progress comes in the form of skill trees.
These trees, which were conceived by a design agency during the company’s early development, are Duolingo’s core experience, a visual representation of language skills that are interconnected and get progressively more difficult and refined over time. Each skill is a prerequisite for another. Sometimes it’s just logic: in order to be able to speak about restaurants, you probably should be able to introduce yourself first. Sometimes, however, it’s a necessary building block: in order to speak about your routine, you should be able to speak about basic everyday activities.
In Duolingo, each unit has its own suite of skills, each of which is broken down into five lessons. Once you complete all five lessons, you can move to the next skill. Complete all skills and you can move to the next unit. Depending on the language, a user might encounter an average of 60 skills across nine different units within a course.
Duolingo Skill Tree UX in 2012. Image Credits: Duolingo
Duolingo Skill Tree UX in 2021. Image Credits: Duolingo
Duolingo had its “leveling up” model figured out, but now it had to integrate gamification into every nook and cranny of its app. One of its first challenges was rebuilding the sort of teacher-student emotional bond that can help students stay motivated to learn. No one likes to fail, and Duolingo stumbled upon a scalable approach through its cartoon owl mascot Duo — also thought of by the design agency behind the skill trees.
Whenever users succeed or fail at their lessons today, they are likely to be encouraged or admonished by Duo’s presence. Designers sprinkled Duo throughout the product, looking at Super Mario Brothers as an example of how to use iconic art to create a friendly gaming experience. In early iterations of the app, Duo was present but static, more of an icon than a personality. That changed as the company increasingly pushed harder on engagement.
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As its meandering route to monetization will demonstrate, Duolingo isn’t mission-oriented, it’s mission-obsessed.
Co-founders Luis von Ahn and Severin Hacker never wanted to charge consumers for access to Duolingo content, a purpose imbued throughout the company’s culture. For years in order to work at Duolingo, you had to be comfortable with joining a company in Pittsburgh that was in no rush to make money. The startup, filled with education enthusiasts and mission-driven employees, became “very college pizza vibes,” Gina Gotthilf, former VP of Marketing at Duolingo, described. Everyone was against making money and having structure — some employees even threatened to quit if Duolingo ever charged a cent to users.
“One thing that recruited me was this brilliance that we can kill two birds with one stone,” she said, referring to Duolingo’s original translation-service business model we talked about in part one of this EC-1. “It was obviously tied to Luis’ thinking and reCAPTCHA and it was magical and brilliant.”
Free may not have paid the bills, but it did come with a valuable upside: growth. By 2017, Duolingo would boast having 200 million users, which was double von Ahn’s goal when he first launched to the public on the TechCrunch Disrupt stage.
Duolingo launched saying it would never do advertisements, subscriptions or in-app purchases — approaches that now all exist on the platform. Today, Duolingo has a simple freemium business model that is remarkably unconventional. It has a free version with all of its learning content, and it charges a subscription of $6.99 per month for paywalled features such as unlimited hearts, no advertisements and progress tracking. It also has a number of other revenue streams it’s developing, such as language proficiency tests.
As we’ll explore, Duolingo’s route from anti-business rebel to conventional consumer subscription is complex, full of twists and turns. While Duolingo never wanted to look like other edtech companies, as we saw with its product strategy in part two, it turns out that evolving from college pizza vibes meant that it would have to take a page from its peers.
Duocon, Duolingo’s new conference to celebrate education and language. Image Credits: Duolingo
“They had users and in Silicon Valley, there was this notion that if you have users, you can turn anything into money,” said Bing Gordon, the Kleiner Perkins Caufield & Byers (KPCB) partner who led Duolingo’s $20 million Series C in 2014.
“This was not very controversial back then, at least with investors,” von Ahn said. “This became controversial for us once we raised a ton of money, and we still weren’t making more money.”
While the company’s investors were relatively lenient in the early years, patience was starting to run thin. In June 2015, Duolingo raised a $45 million Series D round led by Laela Sturdy of Google Capital (later rebranded CapitalG), valuing the company at $470 million. She invested because of Duolingo’s growth and engagement numbers, but confronted von Ahn with some direct advice.
“She said to me, ‘Look, it worked for you to continue getting bigger and bigger checks from venture capital,’” von Ahn said. “‘But this is the last time it works for you … if you’re trying to con people, you cannot con anybody bigger than us [at Google].’” Duolingo’s valuation wouldn’t just be at stake next time it went fundraising on Sand Hill Road — its very survival would be as well.
Looking back, Sturdy said that she always “had confidence that they would come up with a revenue model” because of Duolingo’s passionate and organic users.
When a startup chooses to raise venture capital, it sets itself on a heavily-prescribed course. Suddenly, success isn’t defined merely as cash-flow breakeven with a long-term sustainable business. It has to be an exit of some sorts, and a big one at that. While Duolingo used venture as a lifeline to fund its product development, venture also came with pressure to become a billion-dollar company, or more. And that meant making revenue, not just growing engagement.
Von Ahn says his conversation with Sturdy is what really changed his mindset about money. After the Google check hit Duolingo’s bank account, he and Hacker began thinking about ways to make Duolingo as much a monetary success as it had been an educational one.
Duolingo’s Pittsburgh HQ. Image Credits: Duolingo
“It was clear that Luis didn’t have commercial instincts, he had cultural instincts and a deep focus on learning,” said Gordon. “[When we invested] Duolingo predicted it was on the verge of revenue growth, and it turned out it was not on the verge of revenue growth.”
What Gordon is alluding to was a litany of monetization attempts in Duolingo’s past. Translation, which helped von Ahn’s previous two startups, didn’t work when applied to language-learning services, and the company only secured two customers before ending the service. Business partnerships, such as a relationship with Uber to certify and train drivers in Brazil to speak English, didn’t catch fire.
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