Cover of Ex-Microsoft Engineer Failed 8 Startups in 4 Months, Then Raised $250K

Ex-Microsoft Engineer Failed 8 Startups in 4 Months, Then Raised $250K

Ex-Microsoft Engineer Failed 8 Startups in 4 Months, Then Raised $250K

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Nishant Chahar left Microsoft, built his first startup to 10,000+ students, sold it within a year, then failed at 8 different ideas in 4 months before raising $250,000 to build Miles, a live AI app with thousands of users today.


In this episode: what actually happened between the exit and the raise, how Entrepreneurs First's selection process really works, the real product mechanics behind Miles, and why he thinks coding syntax is becoming worthless while problem-solving becomes everything.


What we cover:

- Why Nishant actually left Microsoft

- Building AlgoPrep to 10,000+ students and selling it in a year

- How Entrepreneurs First actually works

- 8 failed startup ideas in 4 months, explained one by one

- How Miles was born from a failed WhatsApp assistant

- The real tech behind Miles: knowledge graphs and AI retrieval

- Choosing between Claude Sonnet, Haiku, Fable, and Mythos

- Raising $250K after repeated rejection

- Why personal brand is now a founder's biggest edge

- Defending the claim that CS grads face higher unemployment than arts majors

- Whether the software engineer of 2027 is just a manager of AI agents


Find Nishant:

Miles: trymiles.ai

LinkedIn: linkedin.com/in/chaharnishant11

Instagram: instagram.com/nishantchahar.ai

X: x.com/nishantchahar11


Apply to Entrepreneurs First: apply.joinef.com


Deployed is hosted by Farhan Rakhangi from Dubai. Real builders, real AI, no theory.


Follow Farhan: instagram.com/farhannrakhangi | linkedin.com/in/farhanrakhangi

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