Somya Gupta didn't come to New York to build a startup ecosystem. He came to go to class, pass his exams, and live a comfortable life. Two and a half years later, he's thrown 75+ founder events, shut down his own company in the most painful way possible, and somehow walked away calling it the best thing that ever happened to him.

In this episode, Somya and I unpack the full arc — from co-founding an AI-powered edtech platform at NYU, growing it to 3,500 users, pivoting to B2B, landing university pilots, striking what looked like a game-changing partnership… and watching it all collapse in a single phone call. We also get into what it actually feels like when your company becomes your identity — and then disappears overnight.

But this episode isn't really about failure. It's about what you do with the version of yourself that comes out the other side.

In this episode:

• Why Somya says "delusion" is a competitive advantage
• The Washington Square Park customer interview mistake (don't do it)
• Why VCs hate EdTech — and why he gets it
• The Georgian restaurant conversation that ended Context
• What's next: IRL experiences, hackathons, and making NYC #1

Timestamps

• 00:00 — Intro & small talk (pickleball, NYC spots)
• 07:09 — Welcome + who is Somya Gupta?
• 08:52 — From India to NYU: the mindset shift
• 14:16 — How Context was born
• 17:53 — The problem they were solving (and why it was personal)
• 21:53 — B2C to B2B pivot: the hard conversation
• 25:53 — 3,500 users, zero revenue — now what?
• 31:24 — The moment it felt like it might fall apart
• 38:29 — Fundraising, EdTech's VC problem, and $15K from NYU
• 42:08 — University pilots and the California partnership
• 45:24 — The phone call that ended everything
• 48:17 — Identity crisis on the Brooklyn Promenade
• 50:14 — What came next
• 54:47 — Building NYC's founder ecosystem

Find Somya:LinkedIn: https://www.linkedin.com/in/somya-gupta-sg/

Instagram: Coming soon 👀