The Side Hustle Rule Your Boss Breaks Every Single Day episode artwork

EPISODE · Jun 16, 2026 · 6 MIN

The Side Hustle Rule Your Boss Breaks Every Single Day

from The Adrian Tan Show · host Adrian Tan

My former CEO stood in front of the whole team and said: no side hustles. Too distracting. The company needs your full commitment.He had three board directorships, two committee seats, and multiple rental properties.He wasn’t lying to be cruel. He was protecting what he’d built — and hoping you wouldn’t notice the gap between what he said and what he did.I noticed too late. I went all-in on one company for a decade. $5M revenue, 30 staff, everything I had in one place. Then the partners changed, the investors pulled out, and I spent three months not knowing what to do with myself at 9 am on a Monday. Then I drove Grab.This video is what I learned from that — and what your boss already knows that nobody taught you.What is covered:00:00 Side Hustle Hypocrisy00:27 Leaders Diversify Quietly01:41 The Loyalty Deal Died02:18 All In Then Burnout03:04 Uber And Identity Loss03:21 Diversify Without Seniority03:49 Build Assets Under Your Name04:03 Writing Builds Reputation04:30 Fractional Work And Niches05:43 Commitment Versus Concentration06:06 What Equity Are You Building06:42 Do As They Do Get full access to Will That Work? at www.adriantan.com.sg/subscribe

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