Kat Chan on Duolingo’s Marketing Strategy: Taste, Trust, and the Power of Being Unhinged

Everyone wants Duolingo’s marketing strategy.

Far fewer companies would actually be comfortable executing it.

That tension gets to the heart of what makes Duolingo different. The language-learning company has turned its green owl mascot, Duo, into something closer to an internet celebrity than a corporate spokesperson. Duo participates in fandoms, jumps on cultural moments, makes dark jokes, collaborates with entertainment properties, and occasionally threatens learners who have neglected their lessons.

But behind the chaos is a surprisingly disciplined philosophy about creativity.

In an interview on Office Drama, Kat Chan, Senior Director of Brand Marketing at Duolingo, unpacked the thinking behind one of the internet’s most recognizable brands—and her lessons extend far beyond social media.

For entrepreneurs trying to build brands people remember, Chan’s playbook offers a powerful reminder: differentiation isn't created by copying someone else's tactics. It comes from developing taste, trusting creative people, moving quickly, and having the courage to actually behave differently.

Before Duolingo, Kat Chan Learned What Success Didn’t Look Like

Chan’s career has taken her through Live Nation and Ticketmaster, Red Bull, Tesla, Facebook, and eventually Duolingo.

Those experiences gave her an unusually close look at ambitious organizations and powerful leaders. But they also forced her to reconsider what she actually wanted from work.

At Tesla and Facebook, Chan described environments filled with intensely ambitious people. Her time at Tesla was particularly demanding. At one point, while working on Model 3 deliveries, she found herself managing a problem nobody had really solved before.

She felt completely out of her depth.

A trusted leader gave her a perspective that stayed with her: nobody knew exactly what they were doing because nobody had done this before. Continuing to put one foot in front of the other was itself progress.

That lesson is especially relevant for early-stage entrepreneurs.

Founders often interpret uncertainty as evidence that they're unqualified. But when you're genuinely building something new, uncertainty is part of the job.

Chan eventually learned another lesson: prestige and proximity to powerful people weren't necessarily her definition of success.

“I was so trapped in the idea of what success should be in a corporate environment,” she explained.

After burning out, she stepped away, reset, and became much more intentional about her next chapter. When Duolingo came along, she looked not only at the role but at the system she would be entering: its culture, mission, values, and the way people treated one another.

For entrepreneurs, that distinction matters. Don't only ask whether an opportunity looks successful. Ask what kind of person its environment will require you to become.

Duolingo Didn’t Invent Its Unhinged Brand. It Listened to Its Users.

One of the easiest mistakes entrepreneurs can make is studying a successful company's tactics without understanding why those tactics worked.

Duolingo is a perfect example.

Other brands see a mascot behaving outrageously online and conclude that the formula is:

Mascot + unhinged content = viral growth.

Chan argues that they're missing the foundation.

Duo had already existed inside the product for years. Meanwhile, Duolingo's persistent lesson reminders had inspired users to joke that the owl would come after them if they skipped their language practice.

Instead of manufacturing a new personality, Duolingo amplified what its community was already saying.

“We were reacting to the culture, not trying to create our own thing,” Chan explained.

That's an important distinction.

Your customers are constantly telling you what they find memorable about your company. They create jokes. They complain about things. They describe your product differently than your marketing team does.

Great brand builders pay attention.

Before inventing a personality for your company, ask: What personality has the market already given us?

The Best Creative Guardrails Are a Floor, Not a Ceiling

Duolingo's social presence may look spontaneous, but the team isn't operating without boundaries.

Chan described having detailed dos and don'ts around potentially sensitive subjects. But she thinks about those guardrails differently from many corporate organizations.

They're a floor—not a ceiling.

Once creators understand the boundaries and quality bar, they need room to experiment.

That autonomy is essential because social media moves faster than a traditional approval chain.

Chan believes in taking the “shortest path from idea to post.” That means hiring people who can move between ideation, editing, copywriting, and publishing—and eventually allowing them to ship day-to-day content without senior leaders approving every post.

That's uncomfortable.

It's also the point.

You cannot demand internet speed while requiring committee-level certainty.

For a founder, the lesson extends beyond marketing. If every meaningful decision eventually travels back to you, you've built a bottleneck rather than a team.

Creative Teams Need Trust More Than Pressure

Chan offered an especially useful paradox for leaders.

Businesses want creative work to produce measurable results. But obsessing over those results can make the creative work worse.

“The team that cooks are very creative, and creativity does not flow in a fear-based environment,” Chan said. “It flows in a trust-based environment.”

That doesn't mean ignoring performance. Duolingo's team knows its numbers.

The distinction is between measuring the work and making people afraid of the measurement.

When experiments fail, Duolingo looks for patterns rather than immediately punishing individual misses. And because social content often fails simply by disappearing unnoticed, creators have room to try things.

That creates an important entrepreneurial principle:

Accountability and psychological safety are not opposites.

You can maintain a high bar while giving talented people permission to miss it occasionally.

Taste Isn't About Knowing What's Cool

Chan's definition of taste may be her most valuable lesson for entrepreneurs.

Taste, in her view, isn't simply the ability to judge something as good or bad.

It's curiosity.

Someone with taste wants to understand why something works—even when the thing itself seems strange, lowbrow, or completely outside their personal preferences.

That means examining the word choice. The camera angle. The tone. The audience. The tiny creative decisions that produce an emotional response.

“Taste is about the ability to articulate the why behind a judgment call on something that is subjective,” Chan explained.

That's a trainable entrepreneurial skill.

Study products you wouldn't buy. Ads you don't personally like. Communities you don't belong to. Entertainment outside your normal algorithm.

Chan's advice for developing taste is simple: consume voraciously outside of social media.

Read books. Visit museums. Watch anime. Explore nature. Study mediums far removed from your own.

Original ideas often come from connecting dots that weren't sitting next to each other.

AI Can Give You the Average. Your Job Is to Escape It.

That philosophy becomes even more important in the age of generative AI.

Chan sees AI as useful for getting unstuck or creating a jumping-off point. But she is skeptical of treating its output as the final creative idea.

Her explanation is straightforward: AI tends toward the average.

“And good ideas are all about being not in the average.”

That's a crucial distinction for entrepreneurs.

AI can increasingly make competent execution cheaper and faster. But when everyone has access to the same tools, competence itself becomes less differentiating.

Taste matters more.

Judgment matters more.

Knowing what not to make matters more.

The entrepreneur's job isn't simply to produce more content, ideas, products, or campaigns. It's to recognize which ideas deserve to exist.

If You Want to Stand Out, You Need Skin in the Game

At one point in the interview, Chan was presented with a hypothetical employee who enthusiastically pitches a massive idea—and then announces they'll disappear for two months while everyone else executes it.

Her response captured another principle founders should remember:

“If you believe in it, you got to put your skin in the game.”

Ideas are cheap when someone else bears the execution cost.

Strong creative cultures don't just celebrate ideation. They connect ideas with ownership.

And perhaps that's the deeper lesson behind Duolingo's success.

Companies frequently say they want bold marketing, entrepreneurial employees, experimentation, speed, creativity, and cultural relevance.

Then they build systems designed to remove every ounce of risk.

Duolingo made a different trade.

Its advantage isn't simply that its mascot is funny.

It's that the organization created enough trust for talented people to make choices other organizations would be too afraid to make.

For entrepreneurs building something from scratch, that's the real opportunity.

Don't copy the owl.

Build a company brave enough to discover its own version of weird.