Brilliant.org pivoted from its original student loan business (Alltuition) not due to failure, but because its success depended on the problem (complex loans) persisting. The founder chose a mission-aligned model over a profitable but misaligned one after an investor's insight.
While most AI products focus on automation, Brilliant.org's AI tutor went viral by positioning itself as a coach that challenges users and enhances their thinking skills. This resonated with an audience wary of intellectual passivity caused by AI.
Brilliant.org chose a direct-to-consumer model to get unfiltered feedback from learners. Selling to schools (B2B) adds layers (districts, teachers) that distance the product team from the end-user, risking the creation of an uninspiring, mandated product.
By benchmarking pricing against the high cost of human tutors ($10k/year), Brilliant.org's $30/month subscription feels like a bargain. This value-based pricing anchors the product as a premium alternative, not just another app, leading customers to ask why it's so cheap.
Brilliant's successful AI tutor integration wasn't a quick pivot. It resulted from a multi-year strategy, started in the GPT-2 era, of building an interactive canvas infrastructure with APIs that LLMs could read and write to, allowing for a constrained and pedagogically sound AI role.
Frontier LLMs are poor tutors because they lack verifiable reward signals for learning. Brilliant's system captures real learning loops, using "did the student actually understand?" as a reward signal. This creates a unique dataset to fine-tune models specifically for tutoring.
Kleiner Perkins' John Doerr attended a pitch meeting directly after a bike accident and ER visit. While he was groggy, his decision to show up despite injury was a powerful signal of his high level of interest and commitment, more so than a typical polite meeting.
A VC canceled a meeting on a founder who had already flown in for it. This single disrespectful act led the founder to tell the story for a decade, actively harming the firm's reputation. It's a stark reminder that in a small ecosystem, every interaction matters.
By ending every pitch asking to repeat the founder's vision, VCs can ensure accurate understanding, give founders a chance to correct details, and signal deep respect. This small process change significantly improves the founder experience and quality of diligence.