became dean or something. So maybe it has to do with inflexibility or something.
X: What’s the one message you want people to get if they’re coming to you and your book for the first time?
TH: I would say, be true to yourself and follow your passions. The other stuff will naturally fall into place if you actively pursue that. That’s happened for me from an entrepreneurial background. Another way to say it is, don’t let inertia win.
X: What is your philosophy about blending one’s personal life with business?
TH: Well, I think they should be the same. That’s the great thing—if you just start doing stuff you’re actually passionate about, then it’ll somehow magically blend together. Especially in today’s world where anyone can start their own website or whatever.
X: That’s all well and good, but what about the entrepreneur who is struggling to raise money and make ends meet?
TH: I think there’s a lot of assumptions built into that question. Like that you need money. Maybe it was true 10 or 15 years ago. At LinkExchange in ‘96, we were spending probably $50,000 a month for servers and high speed internet and all that. You get better connectivity and computing power today for $50 a month. So definitely [bootstrap if you can]. It’s never a question of not having enough resources, it’s a question of not having enough resourcefulness. It’s like blending creativity with optimism with bootstrapping, and you just figure things out as you go. Not everything’s going to work out, but also part of being an entrepreneur is recognizing that when you fail at something, that’s just part of the learning process—and it’s a necessary step. There’s very few entrepreneurs where the first thing they tried was a major success.
X: Your two biggest companies were acquired by Microsoft and Amazon. How did those two negotiations and partnerships compare?
TH: Complete night and day. The reason for selling my previous company, LinkExchange, was to get out. We sold it and I left the company shortly thereafter. Whereas for Amazon, it was so that we could fulfill our vision at Zappos even faster. As a precondition, we told them we wanted to remain independent, continue to grow our culture and our brand, and our way of doing business. From our point of view,
