Why VC-Backed Startups Are So Draining — They Put Pressure on Families (Raj Singh)

In this episode, Raj Singh, multi-time founder and current VP of Product at Mozilla, opens up about the moments that nearly unraveled his career.

From getting called into HR over a side hustle to walking away from a startup after being unexpectedly leveled, Raj shares what it’s like to navigate the highs and lows of building without losing your identity.

He walks us through multiple pivots, including the time he turned down a seven-figure exit and the brutal leadership decision that nearly cost him a co-founder. Raj doesn’t just talk strategy, he gets into the emotional rollercoaster of founding: the resentment, the rejections, and the real mental toll of being the one expected to have all the answers.

In this conversation, you’ll learn:

-Why being a “do-it-all” founder doesn’t scale

-How to manage resentment when you get leveled

-What it really takes to make hard calls when no one agrees with you

Things to listen for:

(00:00) Intro

(01:04) Meet Raj and his startup resume

(02:02) Growing up in the Bay

(04:05) First hustle: installing Ethernet cards

(07:54) Early failures and impostor syndrome

(09:11) Picking product vs. engineering

(10:06) Thanks to our sponsors, Navattic & Appcues

(12:49) HR call over a side project

(16:23) Fear, risk, and side hustles

(24:35) Leaving a startup after a new hire

(29:01) Facing public failure as CEO

(30:06) Rise of IC tracks and redefining success

(34:08) Hardest call of his career

(44:41) Power of incentives

(47:33) His video game theory of growth

(52:06) The real risk: not improving

(56:00) There’s never a perfect time

This episode is presented by:

Navattic: Interactive Product Demo Software - https://navattic.com/value

Appcues: User Engagement for SaaS - https://appcues.com/value

Resources:

Connect with Raj:

LinkedIn: https://www.linkedin.com/in/rajansingh/

Linktree: https://linktr.ee/mobileraj

X: https://x.com/mobileraj

Mozilla: https://www.mozilla.org/en-US/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching