Akshay Kulkarni left Microsoft in December 2016, after about 1.5 years there, to build ozz.ai full time. He was 23, had no dependents, and wrote that he was not sure the idea would work. His reasoning appears in a first-person essay published December 23, 2016, on HackerNoon via Medium. It rests on two failed co-founder partnerships, a belief that startups need undivided focus, and a judgment that his circumstances at that age made the move unusually low-risk. This article sets out that reasoning, separates what he reported from what he assumed, and offers a personal-finance checklist for anyone weighing the same step.
What Kulkarni did before he left
The essay is a self-reported timeline. Kulkarni says he had wanted to start a company since his third year of college, and his first attempt was a startup that the essay calls Intigrent. The table below follows the sequence he describes. Every entry is his account, not independently confirmed.
| Stage | What Kulkarni reports | Details he gives |
|---|---|---|
| First attempt: Intigrent | An online course platform he and a co-founder wanted to personalize | The partnership ended in a fight about nine months into the effort |
| After graduation: Microsoft | He joined Microsoft and kept working on the idea on weekends with a new co-founder | They pivoted toward personalized curricula for schoolchildren, built on existing online content |
| Second partnership ends | The partnership ended after a personal falling out | He cites about five months into this second iteration |
| Focus on the day job | He tried to concentrate on his Microsoft work | He says new startup ideas kept pulling his attention |
| Chatbot experiments | He tried chatbot projects and formed the ozz.ai idea, which he described as helping people make smarter chatbots | He decided to leave Microsoft to work on it |
| Departure | His last day at Microsoft was in December 2016 | Tenure of 1.5 years, self-reported |
Two things stand out. Both earlier partnerships ended over interpersonal conflict rather than over a market verdict on the product. And the decision to leave came after he had already tried, and failed, to keep the startup work alongside a job.
The reasons he gave for leaving
Kulkarni describes the decision as personal and situational rather than as a general theory of founding. He points to four reasons:
Do these 3 things before closing this tab:
1Repair Windows errors before they cause bigger problems2Scan for outdated or missing drivers - takes under a minute3Clear out junk files and repair common Windows errors#1 Best Overall
- Two co-founder breakdowns had made him question whether startups were right for him at all.
- He tried to focus on Microsoft, but new startup ideas kept re-energizing him.
- He believed startup work needs sustained, concentrated effort, and that a part-time commitment makes it easier to step back when problems arise.
- He felt the chatbot opportunity was time-sensitive, and that his own circumstances made now the moment to act.
The second and third points carry the most weight in the essay. He is describing a pattern he recognized in himself: enthusiasm for new ideas, followed by a retreat when the work got hard. Leaving his job was, in his telling, a way to remove the option of retreating.
Why he judged his situation suitable
The essay’s case depends on a few personal facts. Each one matters to a finance reader because each changes how much a salary loss would cost.
Rank #2
Dependents and living costs
Kulkarni describes himself as having no family to support and says he could live inexpensively. He does not give a budget, a savings balance, or a monthly expense figure. The claim is therefore a qualitative judgment, and a reader cannot test how many months he could have sustained himself without income.
Career runway
He was 23 and believed he could work for a large company later in his career. That view is a personal judgment about his future employability, not a guarantee that a large employer would hire him back at the same level or on the same terms. The essay treats reemployment as a fallback, and it does not show that the fallback would be easy to reach.
The Tool Desk
Outbyte PC Repair FREEClear out junk files and repair common Windows errorsFree Scan →Outbyte Driver Updater FREEScan for outdated or missing drivers - takes under a minuteDriver Scan →Rank #3
- If you want to build a better future, you must believe in secrets.
- The great secret of our time is that there are still uncharted frontiers to explore and new inventions to create. In Zero to One, legendary entrepreneur and investor Peter Thiel shows how we can find singular ways to create those new things.
Reversibility
Kulkarni’s stated rationale is that leaving was reversible enough to be worth trying. His own words, from the essay, were framed around the question he expected from skeptical readers: “So Why did I Quit?” He also anticipated the objections “Why don’t you work on this in your free time?” and “Why don’t you work on this during weekends?” His answer to both was that part-time effort was the problem he was trying to solve, not the solution.
The question of working on it on the side
Most readers asking why he did not keep the job and build on weekends are asking a fair question, and the essay answers it only in part. Kulkarni had already tried weekend work during his Microsoft years, with a co-founder, and that partnership also ended. His argument is that a part-time founder can always retreat to the salary, which makes the venture easier to abandon when it struggles. That argument describes his psychology. It is not a measured comparison of outcomes between founders who stayed employed and founders who quit, and the essay does not offer one.
Rank #4
What the essay does not establish
- Financial planning. The essay contains no budget, savings figure, or runway estimate, and no independent assessment of his finances.
- Whether full-time founding is better. His preference for full-time work is an opinion drawn from his own experience. It is not evidence that full-time founders outperform part-time founders.
- What happened next. Kulkarni said he was unsure whether ozz.ai would work and that he did not expect to regret trying. That was his expectation at publication. The essay does not report whether ozz.ai or Intigrent succeeded, stayed active, or changed direction, and this article does not claim to know.
- Attributed quotations. The essay attributes an aphorism to Reid Hoffman. Its wording could not be checked against a primary source, so it is not quoted here.
- Market claims. The essay contains no published statistics on startup success or on the chatbot market.
A checklist if you are weighing the same move
The essay is most useful as a list of questions to answer for your own situation. The table pairs each factor in Kulkarni’s account with what you would need to establish before resigning.
| Factor | What the essay states | What to establish for your own case |
|---|---|---|
| Dependents | None, per Kulkarni, at 23 | Who relies on your income, and for how long |
| Monthly essential costs | Says he could live cheaply; no figure given | Your fixed monthly costs, written down, and how many months of savings cover them |
| Health coverage | Not stated | How you would be insured after your employer coverage ends, and at what cost |
| Immigration or work authorization | Not stated | Whether your status depends on your employer, and what a job change would require |
| Employer equity and benefits | Not stated | Unvested equity, bonuses, retirement matching, and the dates each would be forfeited or paid |
| Contracts | Not stated | Invention assignment, confidentiality, and non-solicitation terms in your employment agreement |
| Co-founder agreement | Two earlier partnerships ended in conflict; terms not described | Written equity, roles, decision rights, and exit terms agreed before work begins |
| Idea validation | He said he did not know whether the idea would work | What evidence, such as paying customers or pilot users, would convince you to continue or stop |
| Fallback | He expected a large-company job would be available later | What income you would accept if the venture fails, and how long a job search could take |
Use the table as a worksheet rather than a verdict. Kulkarni’s circumstances at 23 may not match yours at any age, and an answer of “not stated” in his column does not mean the factor is unimportant.
PC Slower Than It Used to Be?
A free scan shows the junk files, broken settings and background clutter dragging Windows down - then fixes them in one click.Free scan · Windows 10 & 11Crashes, No Sound, or Screen Glitches?
Random freezes, missing sound and display glitches usually trace back to one bad driver. Find and replace yours safely.Free scan · under a minuteHow to read the essay today
The essay is almost ten years old. Its value now is as a clear first-person record of how one person framed a risky decision: a history of failed partnerships, a belief about focus, and a bet placed while his obligations were light. Read it as a reasoning sample, not as a model to copy, and check every claim it makes about money, timing and outcomes against your own numbers.
The essay was published December 23, 2016, on HackerNoon via Medium. Any current status of ozz.ai or Intigrent should be checked directly rather than inferred from the essay.
The Bottom Line
Kulkarni’s move was a personal bet placed under specific conditions: no dependents, low expected living costs, a young career, and a history of part-time efforts that had failed. His essay explains his reasoning clearly, but it does not show that leaving a job is the right way to start a company, and it does not report how the venture turned out. Before resigning, you should be able to name your runway in months, your fixed obligations, and the evidence that would tell you to stop.
Quick Recap
Product prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on Amazon at the time of purchase will apply.
