The Death of Vanity
The first idea of a founder is often their most beloved. It is an extension of their ego, a "vanity product" built not for a market, but for their own sense of what is cool, innovative, or disruptive. The first, and perhaps most difficult, test an entrepreneur encounters is their willingness to kill this beloved idea when the market inevitably rejects it. This act of intellectual unsentimentality, of sacrificing the "cool" idea for a useful one, often marks the beginning of a viable business.
Ashish Chaturvedi's journey flourished the moment his ego died. His first ventures were the products of what he calls a “young man's ambition”: a voice-based social network, then a location-based messaging app. They seemed clever, technically brilliant, and they "bombed." Ashish’s turning point was a mundane moment of parental frustration at his son's bus stop over a missed note about a chart paper. This seemingly trivial, real-world problem led Ashish to pivot, abandoning his "cool" ideas to design a practical, painpoint-solving communication tool. It became the first idea the market was willing to pay for and raises the question: what is the essential mark of a founder: the genius of their idea, or the clarity required to abandon it for one that works?
"Every entrepreneur does that, right? The first product everybody builds is for their vanity, something they thought would work, something not for the market."
Waiting for the Punchline
At the turn of the millennium, ambition had a clear and narrow definition in India. The cultural mindset, shaped by a generation that valued stability above all else, steered its children toward the perceived safety of a corporate job at a respected firm. Entrepreneurship was not yet the celebrated, "sexy" path it would later become. It was an outlier's game, an unnecessary risk in an ecosystem built for predictable careers. Within this context, Ashish Chaturvedi and a friend found a different use for starting a company. For them, rather than a business plan, it was social currency. As young men wanting to "look cool, look different," they turned the concept of entrepreneurship into a recurring joke, a piece of lighthearted defiance aimed at their job-chasing peers. Their claim that one day they would create a company and hire their friends was not meant to be taken seriously at that time. It was a performance of an alternate ambition, a way to stand apart from the crowd. The joke was, in its own way, the first vanity product they built.
Repeated over the years, this performance began to work on its creators in a way they never intended. Ashish’s intention was not to fake a persona to become real. It was an accidental demonstration of a deeper psychological principle he would only later find articulated in an ancient Hindu scripture, the Upanishads. The scripture posits a direct, causal chain: “You are what your deep driving desire is. As your desire is, so is your will. As your will is, so is your deed. And as your deed is, so is your destiny”. Through sheer repetition, the joke burrowed into his subconscious and became his driving desire. The external performance designed to project a particular image to the world slowly rewired his internal belief system. The desire to appear ambitious became ambition. In action, the distinction between the joke and the goal dissolved. What started as a superficial act to manage his social identity became the foundational logic for his future.
The transformation from a casual joke to a core belief created an "internal romance" with the idea of building something on his own. This newfound conviction soon collided with the formidable reality of familial and cultural expectations. His parents discouraged the entrepreneurial path, advocating for the security of a stable job and a life free from the struggle they knew business ownership entailed. The pressure was to settle down and follow the established map to a comfortable life. The joke had now become a point of friction. The identity he had casually constructed for sport had solidified into a genuine conviction. This belief, born from the vanity of youth, was now the only force capable of resisting the pragmatic logic of his embedded reality. He was left with a choice: abandon the joke and accept the safety of a conventional career, or commit to the prophecy he had unconsciously triggered and then written for himself.
"From a joke that was used to look cool... we both ended up starting our own companies. It looks like the phrase has worked for us."
The Wisdom in Insanity
After completing his MBA, Ashish was presented with the prize his culture valued most: a lucrative, stable job offer. The rational path forward was one logical conclusion to years of work. He chose to reject it. This decision was born from internal reflection, an act that his first investor would later describe as fundamentally "insane". Ashish agreed with the assessment. To give up a secure career for an unproven idea is not a move that can be justified on a spreadsheet. It is a decision that operates outside the bounds of conventional risk analysis. It requires a different logic and a willingness to make a leap based on a conviction that cannot be quantified. The choice to abandon the calculated path was his first entrepreneurial move. It forced him to act on the internal belief he had cultivated, sacrificing the tangible security of a job for the intangible "romance" of his idea.
This act of insanity was a direct rejection of the very mindset his business education had worked to instill in him. Ashish argues that, from an entrepreneurial perspective, an MBA is the "worst degree to have". A business school's primary function is to teach a person how to deconstruct, evaluate, and mitigate risk. It trains the mind to be "calculative," to see all the potential points of failure before taking a step. This heightened awareness of what can go wrong becomes a liability for a founder. It creates hesitation where boldness is required. An entrepreneur, he believes, cannot operate with the cautious logic of a financial analyst. They must be willing to "jump from the top of a 5-story building, assuming there is a mattress downstairs". The MBA provides the tools to prove the mattress is not guaranteed to be there. The founder must possess the irrational faith to jump anyway.
His leap was not, however, an act of blind faith. It was an engineered act of self-deception. Ashish admits that he first needed to prove he could succeed before rejecting the corporate world. He sat for the job interview to confirm he was "good enough" to command a high salary. Succeeding became the raw material confirmation for a psychological safety net. He "fooled himself" with the narrative that if his venture failed within a few years, his credentials and proven abilities would allow him to re-enter the corporate world without issue. He used this logic to convince his worried mother and, more importantly, himself. It was a strategic maneuver, a way of using one form of vanity, the need to feel validated by the system, as a tool to justify defying that same system. He designed the confidence he needed to do something he knew was fundamentally irrational.
"If you are very calculative, you cannot be an entrepreneur. You have to jump from the top of a 5-story building, assuming there is a mattress downstairs."
Bombed
An entrepreneur’s first brainchild is often the one they are most attached to. It is the purest expression of their initial vision. For Ashish, this came in the form of two technically clever but commercially unviable ideas: a voice-based social network, followed by a location-based messaging application. He describes this early work as "the idea I was in love with," a product born from his own fascination with what technology could do, not from what a customer needed done. These ventures were the quintessential vanity products. They were interesting, innovative, and in his words, “they bombed". The market’s indifference to cleverness was the first hard lesson in his founder's education. It proved that a product, no matter how intellectually appealing to its creator, is worthless if it does not solve a problem someone is willing to fix. His love was not enough to make it viable.
The breakthrough did not originate in a flash of strategic insight. It was discovered in the accumulation of mundane, everyday friction. The first data point came from a moment of parental frustration at his son's bus stop over a missed note about a chart paper, a failure of a simple, analog communication system. The second data point came from his wife, a preschool teacher who needed a professional way to contact parents without sacrificing her privacy by sharing a personal number. Neither of these problems was innovative or disruptive. They were persistent, aggravating, and unglamorous. They represented a clear pain point, an unmet need not for something new, but for something that worked. A genuine business case that the market finally recognized emerged in this intersection of low-tech failures.
Ashish already possessed the tool. The communication engine he had built for his location-based app was a solution in search of a problem. The pivot required an act of intellectual unsentimentality: he had to abandon the "cool" application he was in love with and apply his technology to a practical but sober pain he had observed. He took the existing platform to his wife's preschool. The market's verdict was clear. After months of use, the school wrote him a check. As an entrepreneur, this was the only validation that mattered. It was the moment he stopped building what he wanted and started building what the customer desired. Abandoning the beloved idea for the useful one marked the death of his vanity and the birth of a viable company.
"Every entrepreneur's first product is for their own vanity. They build something they want to, not what the market wants... they pivot and arrive at that product which somebody wants to pay for."
Enough
After an entrepreneur kills their vanity, they are left with the question: What is the new motive for building? What purpose remains if the goal is no longer to create the most disruptive technology or to chase the validation of a massive scale? For Ashish, the answer is a doctrine of 'enough'. This philosophy is a direct counter-narrative to the prevailing startup culture of infinite growth and unsustainable ambition. It requires a founder to consciously define their own metric for success, independent of external comparison or market hype. It is a shift from an external, ego-driven goal to an internal, deliberate act of redefining success on terms that bring personal satisfaction.
This philosophy was not developed in a vacuum. It was forged in the unforgiving reality of the Indian market, which Ashish describes as a "brutal" ecosystem that "levels your ego". He calls the B2B EdTech space a "bigger graveyard," a market where customers demand incremental value for decremental cost. In such an environment, the Western model of venture-funded, hyper-growth ambition is a near-certain path to failure. The market itself acts as a corrective force, stripping vanity from vision. It humbles founders and punishes unrealistic goals. Survival requires a patient, persistent, and pragmatic mindset. Therefore, the doctrine of 'enough' is no personal preference but a feasible survival strategy in a market designed to crush undisciplined ambition.
The outcome of killing one's vanity is clarity. By defining what is "enough," a founder can escape the destructive comparison cycle that plagues ventures. The goal ceases to be about becoming the biggest. It becomes about building something of sustained value. Ashish’s initial joke was about creating jobs, and in the end, that has become his framework. He is no longer chasing the victory of looking cool or the practically useless goal of a billion-dollar valuation. The doctrine of 'enough' provides freedom. It is the freedom that comes from no longer needing to prove anything to the world, or to oneself. The death of vanity does not end the founder's journey. It allows the founder to emerge and eventually begin.
"As a company or individual, everybody should define what their enough is. Somebody's enough may be very different from the other people."
What I learned from Ashish Chaturvedi
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The First Pivot is Psychological. The most critical move a founder makes is not strategic but psychological: the willingness to kill their beloved "vanity product" for a useful one that the market will actually pay for.
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Belief Can Be Engineered. A goal, even one that starts as a joke, can become a reality through persistent repetition. This is not "faking it," but a form of internal programming that rewires desire and destiny.
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Calculation is a Liability. True entrepreneurial leaps require a degree of "insanity" that defies rational risk analysis. A formal business education that teaches you to identify every potential failure can paralyze the irrational faith needed to begin.
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Define Your 'Enough'. The most durable motivation is not the endless pursuit of scale but the conscious definition of "enough." This provides freedom from the destructive cycle of comparison and clarifies the true purpose of the work.
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Listen to Mundane Problems. Breakthrough ideas are rarely born from strategic genius. They are often discovered in the unglamorous, everyday friction of real life. The most valuable problems are frequently the ones no one considers necessary to solve.
Comprehension Challenge: Ashish Chaturvedi
Philosophy
Ashish Chaturvedi’s philosophy is a testament to intellectual unsentimentality. He argues that a founder's most significant test is the willingness to kill their "vanity product" (the cool, beloved idea born from ego) in favor of a practical solution the market will pay for. This requires rejecting calculated, risk-averse thinking and embracing the "insane" leap to pivot. This challenge tests a leader's ability to sacrifice a brilliant vision for a viable business.
The Scenario
Imagine 'Riya,' a gifted coder who has spent two years creating a beautiful, technically brilliant music discovery app called 'Aura'. The app uses her proprietary algorithm to create perfect playlists, and she considers it her life's work. Despite its elegance, Aura fails to gain traction in a saturated B2C market, and her funds are nearly depleted.
Option A (The "Vanity" Path): Pursue a final round of seed funding to finance a massive marketing push for Aura. This path is a high-risk bet on her original vision. It preserves the "cool" product she is in love with and keeps the dream of a B2C unicorn alive, but it ignores the clear market feedback.
Option B (The "Unsentimental Pivot" Path): Accept an immediate and profitable offer from a large B2B company that provides background audio for hotel chains and retail stores. They want to license her core algorithm to create in-store playlists. This path guarantees revenue and survival but requires her to kill Aura, abandon the consumer market, and apply her brilliant technology to a "boring," unglamorous industry.
The Task
Drawing on Ashish Chaturvedi's philosophy, what is Riya's imperative? Should she cling to her beloved "brainchild" (Option A), or should she execute the unsentimental pivot to the boring but profitable B2B model (Option B)?
Develop the argument Riya must make to her small, equally passionate team to justify killing Aura. How does she reframe the "death" of her vanity product not as a failure, but as the first necessary step toward building a real, sustainable company?