Before It Clicked 12 Pivots in 5 Years to $130M: Vapi's Origin Story
Nov 5, 2025
01:20:00
Most founder stories jump straight to the win. This one doesn't.
Nikhil Gupta, cofounder and CTO of Vapi, spent 5 years grinding through 12 different pivots before landing on the idea that raised at a $130M valuation. We dig into the false starts, the moments he almost gave up, the pivot that finally clicked, and the tactical decisions that separated failure from hypergrowth.
You'll hear:
- How to know when to pivot vs. when to persist
- How his ideation improved over 12 ideas
- What changed in the pivot that actually worked
- Timeline of the 5-year journey (the real one, not the polished version)
This is the story before the story—no mythmaking, just the messy path to product-market fit.
Chapters:
- (00:00): Cold open — “What is wrong with me?”
(00:19): Intro — show setup & where Vapi is today (400k devs, $130M Series A, 6→45 people)
(02:16): Meeting Jordan at Waterloo, dropping out & deciding to build a company
(06:13): Early ideas: ETF “playlist of stocks” investing app
(07:54): Friend CRM & betterfriend.me — first tarpit consumer idea
(10:33): COVID learning app that got them into YC
(17:46): Getting into YC, moving into a house & pre-batch meltdown
(19:30): Idea framework: frequency, intensity & willingness to pay
(21:06): Discovering the “join my next meeting” button
(25:21): Product Hunt launch, Reddit “YC is funding button companies” & early revenue
(32:29): Two years of experiments: Slack, focus tools & growth hacks that didn’t work
(42:25): Auto meeting notes — listening to the computer & shipping a notes product
(45:27): Realizing most users don’t use notes; doctors & wealth managers do
(47:53): Shutting down a profitable product & moving to SF
(52:13): AI therapist — Dolores Park airdrops & mental-health market worries
(1:00:57): Turning the voice stack into an API & helping Hyperbound
(1:03:37): March launch, virality & why OpenAI’s real-time API didn’t kill Vapi
(1:09:00): Hiring from the community, getting to ~$4M ARR with 6 people & scaling the team
(1:16:30): Nikhil’s closing advice