When It's Time to Leave Your Safe Job and Build a Business with Chieh Huang

Leaving a safe career to build a business sounds exciting, until you're the one making the decision. In this episode, serial entrepreneur Chieh Huang shares what it's really like to leave a prestigious law career, build multiple startups, experience successful exits, take a company public, go through bankruptcy, and start all over again.

He explains why entrepreneurship is never a straight line, why there is never a perfect time to start, and what separates founders who keep going from those who quit.

Chieh Huang is a serial entrepreneur and the co-founder of AstroApe, Boxed, and Pelago. His first startup was acquired by Zynga, he later helped build Boxed into a public company, and his TED Talk, Confessions of a Recovering Micromanager, has been viewed millions of times. Today, he's building Pelago, a platform helping companies improve the employee offboarding experience.

He discussed:

-Why there is never a perfect time to leave your safe job and start a business

-The mindset that tells you it's finally time to become an entrepreneur

-Why every startup eventually breaks—and why that's completely normal

-How Boxed grew from a garage startup into a public company with over 1,000 employees

-The biggest leadership mistake founders make as their company grows

-What bankruptcy, being fired from your own company, and starting over taught him about success

Timestamps

00:01:20 What Makes an Entrepreneur Truly Great?

00:04:36 Why He Walked Away From a Dream Career

00:10:23 What the First 6 Months of a Startup Really Look Like

00:12:15 Why You'll Never Feel Ready to Start a Business

00:13:34 The One Sign It's Time to Go All In

00:14:43 Why Starting a Business Isn't as Risky as You Think

00:17:17 Why He Left Zynga to Build Something Bigger

00:18:03 How Boxed Went From a Garage to a $900M Company

00:20:04 The Truth Every Founder Learns the Hard Way

00:22:42 Why They Turned Down Acquisition Offers

00:26:04 The Collapse That Changed Everything

00:32:53 The Leadership Mistake That Nearly Cost Him Everything

00:39:44 Getting Fired From the Company He Built

00:44:19 Will AI Create More Entrepreneurs or Kill Jobs?

00:46:04 How Success Changed After Building Multiple Companies

Connect with - Chieh Huang:

LinkedIn - linkedin.com/in/chiehhuang

Website: Pelgo.com

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