I’ve been a serial entrepreneur most of my adult life. My parents emigrated from Taiwan to the U.S. when I was two years old. Since my father was a petroleum engineer, I grew up in Texas and Oklahoma. This means I’m a suffering Dallas Cowboys fan now living in a Super Bowl-proud Seattle Seahawks town.
Along the way, my career would make any “Tiger Mom” proud. After my senior year in Tulsa, I went to U.C. Berkeley for my undergraduate studies. Yes, I did see the “Naked Guy” lollygag around campus during my time there. What an eye-opening experience for a teenager coming from the buckle of the Bible Belt.
I graduated with distinction and joined the prestigious Strategic Services group of Andersen Consulting for three years. I then went to Wharton for my MBA and with a classmate, Andy Liu, I started NetConversions during my first year. We won a Wharton business plan competition and subsequently raised over $1 million from angel investors and venture capital firms like Guy Kawasaki’s Garage Technology Ventures. We made our share of mistakes, and the company had a near-death experience, coming close to folding. We came out of that scrape okay, and sold NetConversions to aQuantive (AQNT) in 2004.
After serving as executives at aQuantive, Andy and I took a trip together to Peru. It was either the high altitude, voluminous amounts of beers or the guinea pigs we ate that led us to dream up the next company we’d start together. One caveat we agreed upon: we’d never raise money again. So of course, we turned around and raised over $10 million from tier one investors like Madrona Venture Partners and Charles River Ventures to start BuddyTV in 2005.
Even though it was my own baby, I began to feel burnt out at BuddyTV. I couldn’t understand why. BuddyTV operated in a fun and dynamic space combining entertainment with social media. It had a co-founder, board, and team I liked and respected. This conflict completely threw me for a loop: how can someone get burnt out working at his own business?
At the same time, I was also undergoing massive changes in my personal life. I got married and we had our first baby in quick succession. I felt overwhelmed. I decided to break away from my hectic day-to-day schedule and do deep soul searching.
I ended up buying one-way tickets to New Zealand for my wife, baby daughter, and me to travel around the world. I needed to recharge and discover how I could find happiness in my professional and personal life. I called this a careercation (career + vacation). I didn’t want to wait until I was in my 60s to travel, when I’d be collecting Social Security and might be in declining health. I’d rather take elongated career breaks throughout my life to gain perspective, connect with my family, and reinvigorate myself.
During the careercation, our young family had two goals while hopscotching around the world. The first was to create some amazing shared family memories with my wife and ten-month-old daughter. The second was more personal: to interview entrepreneurs about leadership, culture, and managing people. As an entrepreneur, my highest highs and lowest lows originate in those areas. I also decided to interview CEOs who were not in the technology space. I wanted to push myself out of my comfortable Seattle technology ecosystem. With the lessons I would learn, I could diversify and grow.
I wrote this book to share my journey towards entrepreneurial happiness via a careercation. I’m also including over two hundred tips that successful entrepreneurs shared with me. These nuggets of wisdom are good for infusing any company with new energy and ideas, and I use quite a few at my new company.
I hope this inspires others to pursue their own path to happiness.
How to Read this Book
This book is divided into the geographic regions that I visited on my careercation. Each section has an introduction, interviews that I conducted with local entrepreneurs, and my reflections. I recommend reading this book in order; you’ll get a pulse on my beliefs throughout the trip. You can also see how the embers of my current endeavor lit up, and how my thoughts on people and culture evolved.
If you want to read a travelogue, you can just stick to the beginning and end of each section. Or if you want to hone in on best practices for managing people, culture, and leadership, then you can just read the interviews. But in keeping with the spirit of my trip, feel free to roam, and don’t let the structure hinder you from jumping into any part of the book.
Please note that I conducted these interviews in 2012, so when I say “today,” I mean 2012. Some of these companies have grown in size, at least one of them has had to shut their doors, and one of them has been acquired. I also invite you to learn more about each company by checking out their website and following them on Twitter.
Finally, I hope the tips that the business leaders shared inspire you as much as they did me. I left a page for notes after each regional section so you can jot down ideas. Go for it: try some of the suggestions in your own professional and personal journey to find happiness.