AI Entrepreneurial Journey

Summary

Roy, founder of Cluely, detailed his journey from creating Interview Coder—a controversial AI interview tool that led to his expulsion from Columbia—to building Cluely, a desktop AI app positioned as the future of human-computer interaction.
Cluely recently launched and is nearing $5 million in ARR, having closed a $5.3 million seed round led by Abstract Ventures and Susa Ventures.
Roy discussed viral marketing strategies, product vision, and the broader impact of AI on productivity and society.
The discussion also covered risk-taking, personal motivations, and perspectives on success and entrepreneurship.

(No specific action items were assigned or mentioned in this transcript.)

Roy created Interview Coder to challenge the inefficiency of technical interviews, particularly the use of LeetCode-style questions, which he believes waste candidates’ time and don’t measure real skills.
The tool gained notoriety after Roy publicly demonstrated its use to secure a job at Amazon, resulting in viral attention and institutional backlash, including expulsion from Columbia University.
Roy pivoted quickly from Interview Coder to establish Cluely, capitalizing on viral momentum to raise funds and build a more expansive and sustainable AI product.

Initial growth was slow despite controversial publicity, with significant virality occurring after persistent online promotion and engagement.
Roy shared insights on leveraging Twitter’s preference for controversial, polarizing content to drive engagement and awareness for Cluely.
He emphasized that online controversy, even when negative, has driven positive outcomes—greater attention translates to more downloads and users for Cluely.
Roy distinguishes between online persona (intentionally provocative for viral marketing) and his real-life relationships, focusing personal trust within a small group.

Cluely’s core innovation is a seamless, multimodal AI that overlays transparently on the user’s screen, aiming to create the new standard for interacting with AI beyond chatbots.
Key technical challenges include reducing latency, increasing accuracy, and fine-tuning personalized user experiences.
The company is developing custom evaluations and analytics-driven improvements, with ambitions to host its own AI models for further optimization and latency reduction.
Roy’s long-term vision is to make Cluely the default tool for everyday productivity, changing workplace and societal behaviors by normalizing ubiquitous AI assistance.

Roy argues that as AI becomes prevalent, traditional job interviews and skills assessments will be rendered obsolete, replaced by holistic, data-driven matching of candidates to roles.
He envisions widespread AI adoption exponentially increasing productivity, revolutionizing industries, and accelerating societal advancements.
Cluely aspires to lead this transformation by getting users comfortable with AI integration into every aspect of daily work and life.

Roy credits his success to a combination of competitiveness, willingness to take risks, and supportive family background.
He encourages aspiring entrepreneurs to take bigger risks, emphasizing that the downsides are usually less significant than imagined while the upsides can be transformative.
He highlights the accessibility of AI as a field—suggesting even newcomers can quickly become impactful contributors and company builders.

Pivot from Interview Coder to Cluely and aggressive fundraising — Rationale: Interview Coder was inherently unsustainable as companies would adapt; a broader, more defensible product (Cluely) was needed to capitalize on viral attention and create long-term value.

What are the next specific product milestones or launches for Cluely?
How will Cluely continue to differentiate itself as larger tech companies enter the space?
What additional features or use cases does Cluely plan to address as AI capabilities advance?