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

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 Connect to Entrepreneurial-Excellence Podcast: LinkedIn - ⁠https://www.linkedin.com/company/entrepreneurial-excellence-podcast⁠ Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod TikTok - ⁠https://www.tiktok.com/@eepodcast24⁠Facebook - https://www.facebook.com/profile.php?id=61570329516959 Website - https://www.hirechore.com/resources/podcast