Exclusive Interview: Cluely Founder Roy Lee on Building a $5.3M AI ‘Cheating’ Tool After Columbia Suspension

March 2025 marked a turning point that nobody saw coming. A simple X post from 21-year-old Columbia student Chungin “Roy” Lee would spiral into one of the year’s most divisive tech stories. His message was straightforward: he’d been kicked out of university for building an AI tool that helped students “cheat” and ace technical interviews. The aftermath? Anything but straightforward.

DesignWhine reached out to Roy Lee, the controversial founder behind Cluely, to discuss his journey from academic suspension to Silicon Valley success.

Read on to know his side of the story and what he thinks about Cluely and the future of AI-assisted exams.

Introducing Cluely: The Controversial AI Assistant

For readers unfamiliar with the platform, Cluely is an AI-powered desktop assistant that provides real-time, undetectable support during virtual interactions such as job interviews, sales calls, exams, and meetings. The software operates by displaying helpful content and AI-generated responses in a hidden interface that remains invisible to the other party during video calls or online assessments. Users pay $20 per month or $100 annually for unlimited access to this controversial tool that the company openly markets as helping people “cheat on everything.”

The technology has evolved from its original focus on coding interviews to encompass a broad range of high-stakes virtual interactions where users seek a competitive advantage.

The post exploded across social media. Within days, venture capitalists were reaching out. Less than a month later, Lee had secured $5.3 million in seed funding for Cluely, a startup that brazenly promotes itself as helping users “cheat on everything.”

Cluely’s manifesto boldly embraces the label of “cheating,” positioning their AI assistant as the natural evolution of tools like calculators, spellcheck, and Google, all once considered cheating but now standard practice.

The company argues that AI represents a fundamental shift where success will be determined not by memorizing facts or manual effort, but by leveraging AI to ask the right questions and access information instantly. They contend that the future will reward those who embrace this technological advantage, predicting that when AI assistance becomes universal, the concept of “cheating” will become obsolete.

What began as a college disciplinary action had morphed into Silicon Valley’s most polarizing success story of the year.

Yet behind the headline-grabbing marketing and heated debates lies a nuanced story about shifting generational values, AI democratization, and pressing questions about fairness in our machine-learning era.

This is how one student’s academic troubles became a multimillion-dollar venture and what it tells us about the evolving landscape of human evaluation in our AI-saturated world.

When Academic Rules Met Silicon Valley Innovation

Cluely’s roots stretch back to a sophisticated engineering project that Lee and co-founder Neel Shanmugam built during their Columbia years. Their original creation, “Interview Coder,” was engineered to deliver real-time support during technical interviews, those make-or-break coding challenges that determine whether computer science students snag prestigious internships at companies like Meta and Amazon.

The technology operated through a concealed browser window, invisible to interviewers, enabling students to receive AI-powered guidance while appearing to work independently. Columbia discovered the system after a demonstration video surfaced, showing how their AI tool could help students secure internship offers from major tech companies.

The university’s reaction was immediate and uncompromising. Lee faced suspension by the end of March, with co-founder Neel Shanmugam (now Cluely’s COO) also caught up in the disciplinary proceedings. Both ultimately left the institution.

DesignWhine: Looking back, was getting suspended from Columbia the best thing that happened to your entrepreneurial journey?

Roy Lee: Looking back, being suspended from Columbia for creating Interview Coder was a pivotal moment. While it was challenging at the time, it forced me to step outside the traditional path and burned all other bridges except entrepreneurship, which was both necessary and helpful for me. I would not be where I am now without that turning point of a moment; it helped clarify my priorities by limiting my options.

This wasn’t mere startup rhetoric. It also demonstrated recognition that sometimes the most valuable opportunities emerge from apparent disasters.

The Social Media Catalyst

Lee’s transformation from suspended student to startup founder began with his choice to share his story publicly. The company emerged after Lee published a viral X thread detailing his Columbia suspension following the development of a tool designed to help software engineers cheat on job interviews. The post resonated powerfully, accumulating millions of views and igniting passionate discussions about AI’s place in education and hiring.

The timing couldn’t have been better. Early 2025 saw AI tools reaching unprecedented sophistication and accessibility, making Lee’s narrative particularly compelling to a generation that viewed artificial intelligence as a natural tool rather than an alien concept. His story of an innovative youth punished by outdated institution perfectly matched Silicon Valley’s disruptive philosophy.

Co-founder and CEO Roy Lee, 21, revealed the funding news on LinkedIn recently, transforming what might have been a career-ending scandal into a fundraising victory. The company’s controversial positioning proved advantageous while most startups carefully craft messaging around productivity and improvement, Cluely embraced the provocative “cheating” label with almost rebellious enthusiasm.

Understanding the Generational Shift: A DesignWhine Deep Dive

Cluely’s rise reveals fascinating insights about generational perspectives on AI assistance. Lee’s audience leans heavily younger, primarily consisting of individuals who perceive AI not as a crutch but as standard equipment similar to how previous generations viewed calculators or spell-checkers.

When DesignWhine explored this demographic pattern and questioned whether we’re witnessing fundamental changes in how younger generations perceive “cheating,” Lee’s response highlighted the philosophical underpinnings of Cluely’s methodology.

DesignWhine: Your user base seems to skew younger – people who’ve grown up with AI as a native tool rather than a foreign concept. Are we witnessing a generational shift where older notions of “cheating” simply don’t apply anymore?

Roy Lee: Our user base does skew younger, and I believe that’s reflective of a broader cultural shift. For Gen Z, AI-usage is universal, and everyone understands that people use AI in their classroom assignments. The concept of “cheating” is evolving as access to information becomes more democratized. Rather than seeing AI assistance as cutting corners, many in my generation see it as the new normal, and soon, the rest of the world will as well.

This generational outlook forms Cluely’s philosophical foundation. The company has released a manifesto drawing parallels to historically controversial innovations once deemed cheating calculators, spellcheck, and even Google search. The argument holds merit: numerous tools now considered indispensable were initially met with skepticism by educational and professional institutions.

Critics counter that this comparison ignores critical distinctions. This philosophy has generated both praise and criticism, with detractors warning that Cluely could damage trust in educational and hiring systems. Unlike calculators or spell-checkers, which operate transparently, Cluely functions covertly, specifically designed to remain undetectable to other parties.

The Engineering Behind the Ethical Debate

Cluely functions as an AI-powered desktop assistant engineered to deliver real-time, undetectable support during virtual interactions including sales calls, job interviews, and meetings. The technology has advanced significantly since its Interview Coder origins. Now operating under the San Francisco-based startup Cluely, their AI platform has expanded well beyond coding interviews.

The system works through what the company calls “undetectable” assistance, offering users real-time information, suggestions, and responses during live interactions. The company charges $20 monthly or $100 annually for unlimited access, making it available to a wide range of students and professionals.

However, the technology’s sophistication has generated substantial ethical concerns. The primary ethical challenge with Cluely stems from its marketing as an “undetectable” solution. This directly contradicts privacy regulations and its own policies requiring user consent for audio/screen capture. The company’s strategy places users in legal and ethical ambiguity, potentially exposing them to consequences extending far beyond academic or professional contexts.

The Backlash and the Dystopian Moment

Cluely’s vision of AI-assisted everything hasn’t achieved universal acceptance. A viral launch video depicting Lee using Cluely on a date triggered backlash, with critics comparing it to a Black Mirror episode. The video, which has accumulated over 10 million views, shows Lee receiving AI assistance during a personal conversation which many viewers found deeply disturbing.

The video portrays a young man using AI to misrepresent himself during a date. It’s uncomfortable. It’s deliberately controversial. The response was immediate and largely negative, with critics arguing that the company was encouraging dishonesty and undermining genuine human connection.

While some perceive the tool as innovative progress, others worry it could promote widespread dishonesty and erode trust in crucial selection processes. The criticism extends beyond individual ethics to systemic concerns about the future of human assessment and evaluation.

Cluely’s ability to secure $5.3 million in seed funding while explicitly marketing itself as a cheating tool reveals a concerning shift where financial support overshadows ethical considerations. Critics argue that the company’s success represents a troubling prioritization of profit over integrity, potentially normalizing deception in professional and personal environments.

Reimagining Assessment in the AI Era

DesignWhine: What do you believe is fundamentally broken about current hiring practices in tech, and how might AI change the future of professional assessments?

Roy Lee: From my perspective, current hiring practices in tech often overemphasize rote memorization and artificial scenarios that don’t reflect on-the-job realities. AI has the potential to shift the focus toward skills like adaptability, critical thinking, and collaboration. In the future, I think we’ll see more personalized, real-world assessments that better evaluate a candidate’s potential and ability to learn, rather than just their ability to memorize riddles.

This assessment evolution vision forms the core of Cluely’s philosophical defense. The company contends that traditional evaluation methods are fundamentally flawed, depending on outdated metrics that fail to capture real-world capabilities. In their perspective, AI assistance doesn’t represent cheating but rather a more accurate reflection of how work actually occurs in the modern world.

However, this viewpoint raises profound questions about the nature of individual capability and achievement. If AI can provide real-time assistance during assessments, what exactly are we measuring? Are we evaluating a person’s ability to collaborate with AI, or are we simply observing AI performance with human oversight?

The Democratization Defense: Battling Digital Inequality

One of Cluely’s most persuasive arguments centers on democratization and inequality. Lee frames the company’s mission not as promoting cheating but as preventing a world divided between AI haves and have-nots.

DesignWhine: You’ve dismissed anti-cheating tools as “pointless.” What are your thoughts on ethical boundaries, and where do you draw the line?

Roy Lee: I have compared anti-cheat tools to failed video game anti-cheat systems because both tend to focus on enforcement rather than understanding user motivation. At Cluely, our goal is the opposite of what you might think. If there isn’t a tool that widely democratizes the use of AI, half the population will continue to moralize against AI while the other half benefits from it. In order to avoid this world of massive inequality, I think it is important to A) lessen the impact of the concept of cheating with AI, and B) to spread the tool to as many people as we can.

This argument reframes Cluely’s mission as fundamentally egalitarian ensuring that AI advantages are accessible to everyone rather than limited to those with technical expertise or expensive tools. It’s a compelling narrative that positions the company as a champion of equality rather than a promoter of deception.

Yet critics argue that this democratization comes at the expense of authenticity and trust. As awareness of ethical AI (and ethical product design) grows, users may increasingly reject tools perceived as deceptive, potentially limiting the company’s long-term viability.

Silicon Valley’s Diplomatic Approach: Managing Contradictory Messages

The tension between Cluely’s provocative public messaging and its institutional backing became evident when Andreessen Horowitz, the prestigious venture capital firm, described the company quite differently than its own marketing suggests. The firm positioned Cluely as “an AI-powered desktop assistant that delivers real-time support during everyday moments” which is a notably gentler framing than the company’s own “cheat on everything” branding.

This discrepancy raised questions about whether Cluely’s aggressive marketing contradicted its institutional backing.

DesignWhine: Andreessen Horowitz describes Cluely as an “AI-powered desktop assistant that delivers real-time support during everyday moments”, a much softer positioning than your “cheat on everything” branding. What’s your take on that?

Roy Lee: I appreciate the feedback from Andreessen Horowitz. At Cluely, we’re intentionally taking really bold steps with our marketing, and I appreciate that our investors are able to support our approach without unnecessarily adding fuel to the fire.

The careful phrasing of Lee’s response (acknowledging his investors’ “feedback” while maintaining his commitment to “bold steps”) suggests a delicate balance between entrepreneurial independence and investor relations.

The Lingering Questions

As Cluely expands beyond interviews to exams, sales calls, and potentially other high-stakes interactions, fundamental questions about ethics and boundaries remain unresolved. When asked about ethical limits, Lee’s response was notably focused on broader societal impact rather than specific restrictions.

Legal grey areas, broken trust, and the potential for backlash all make it a high-risk option. Especially in a world increasingly wary of AI fakery, using a tool like this might not just harm your reputation but also hurt others’ chances too.

The company’s rapid growth and substantial funding suggest that many people are willing to embrace AI assistance despite these concerns. But as the technology becomes more sophisticated and widespread, society will need to grapple with fundamental questions about authenticity, fairness, and the nature of human achievement in an AI-augmented world.

At DesignWhine we believe that Cluely’s greatest contribution may not be its technology but its role in forcing society to confront these questions now, while we still have the opportunity to shape the answers.

The revolution may indeed be undetectable, but its implications are becoming increasingly clear.

What’s your take on this shift? Share your thoughts in the comments below.