David Chang. Founder & Angel, Ex-PayPal & Goldman Sachs, Early Stage Maven, Startup Boston Guru, Ep. 15

Still in his forties, David Chang seems to have a lifetime of achievement behind him. Six startup exits, stints with TripAdvisor, PayPal and Goldman Sachs as well as close connections in the world of VCs give David a most informed perspective on startups. In this candid and instructive interview, David highlights the dos and don’ts of tech startups in clear and engaging prose. He provides a wealth of suggestions on how to approach markets and technologies.

He immigrated to America from Taiwan as a child and grew up on Long Island. David Chang distinguished himself in computer science as an undergrad at Cornell. Later on he attended Harvard Business School after seven years on Wall Street.

Topics covered in this interview include:

• David Chang Bio
• Came to US from Taiwan with His Family at Age 3 – Grew Up on Long Island
• Job Market Tight in 1992 – 38 Rejection Letters – 2 Job Offers – Wall Street vs. Silicon Valley
• Applied to Harvard Business School Thrice - Third Time Lucky – Stays in Boston Working at a Small Startup
• Dumb Luck Had Brought Him to a Phenomenal Company - edocs
• Co-founds Mobicious – Just in Time for Financial Crisis
• Quits Fulltime Stable Job – Decides to Start Company – Daughter Is Born – All in One Weekend!
• Mobicious Sells for Pennies on the Dollar – Thought Would Never Work in Tech Again – Lands in Where, a Company into Location Awareness – David Beisel of NextView Ventures
• Decision to Sell Where to PayPal
• Genesis of Where Angel Fund
• David Chang’s Biggest Failure as a Startup Operator – Lacked Focus on First Startup – Guardrail to Guardrail
• The Role of Thrift in Startups
• How David Chang Came to Make His First Angel Investment
• Great Startups David Chang Passed On
• Why Is David Chang Not a Full-time VC?
• David Chang’s Advice to Startups Raising Money
• Be Clear About What’s Your Basecamp and What’s Your Summit
• What David Chang Looks for In a Founding Team
• David Chang’s Favorite Pivot – TripAdvisor Stumbles upon the Idea of Doing Reviews
• Startups David Chang Is Excited About
• Nightmare Mistakes Founders Make
• How Do Founders Decide to Raise Another Round or Shut Down? The Value of Knowing Your Place in the Market You Serve