In this episode, Gururaj Pandurangi, three-time founder and CEO of ThriveStack, opens up about the near-death moments, pivots, and internal reckonings that shaped his entrepreneurial journey. From growing up in Mumbai with dreams of becoming a scientist to leading multi-million dollar product bets at startups backed by Microsoft and Deloitte, Guru shares what it really takes to build when the vision keeps shifting and the runway keeps shrinking.
He walks us through two moments when his companies nearly ran out of money and the uncomfortable decisions that pulled them back from the edge. From flipping into consulting just to survive to gambling everything on a risky conference booth, Guru doesn’t just talk strategy. He talks about fear, team trust, and the mental load of being the one who has to believe before anyone else can.
In this conversation, you’ll learn:
- Why being a “product purist” almost killed the company and what saved it
- The mental spiral founders face when bets aren’t paying off
- How to keep a team motivated when the vision keeps changing
Things to listen for:
(00:00) Intro
(01:13) Meet Guru: a story of resilience
(02:30) Growing up in Mumbai and early inspiration
(04:45) Hustling during a solar eclipse
(08:16) Engineer to reluctant founder
(10:10) 14 years at Microsoft and why he left
(10:47) Thanks to our sponsor, ThriveStack
(15:20) Taking VC money (and the fear that comes with it)
(23:03) Pivoting to consulting to survive
(28:05) Spending nearly $1M on the wrong product
(30:25) A pivotal meeting with Microsoft
(34:45) Battling imposter syndrome
(39:37) The pivots behind ThriveStack
(44:19) Redefining the product for real customer needs
(47:08) Losing team members as the vision shifts
(51:18) Why founders should share failures
(54:04) Guru’s biggest mindset shift
(55:41) A real take on VC funding
A huge thanks to this episode’s sponsor:
ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/
Resources:
Connect with Gururaj:
LinkedIn: https://www.linkedin.com/in/gururajp/
ThriveStack: https://www.thrivestack.ai/
Connect with Andrew:
LinkedIn: https://www.linkedin.com/in/andrewcapland/
Substack: https://media.deliveringvalue.co
Hire Andrew as your coach: https://deliveringvalue.co/coaching
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