The Self-Made Man: Tony Hsieh

At first glance, Tony Hsieh is a factory-issue CEO ? he graduated from an Ivy League school, started an investment firm (a frustratingly vague term in and of itself) that threw money at different companies until one stuck, joined that company, ran it for a while before selling it to an even larger corporation for a ridiculous sum of money, rinse, repeat. Hsieh has done this twice, once with LinkExchange, an online advertising network that he later sold to Microsoft, and more recently with online shoe retailer Zappos, which he sold to Amazon.

Take some lessons from Tony

Of course, he wouldn’t be this week’s Self Made Man if his story was that simple.

Hsieh is something of a quandary, because he’s a youngish bajillionaire (as of this writing, he’s 38) who doesn’t see corporate culture as an absolute. His professional career started off at Oracle, where he only lasted five months before quitting to start LinkExchange. Any fresh college graduate who gives up a secure, well-paying office gig to work 16-hour days on an Internet start-up of their own devising probably had some issues with management.

It’s not hard to see why ? typical corporate culture has a lot of problems. It’s overly bureaucratic, petty, insular, hostile to new or unorthodox ideas, and ultimately run by the kind of people who saw Wall Street and identified with Gordon Gecko. Hsieh has been pretty outspoken about not following that blueprint,?and told Retire@21 that ?if you get the culture right, then most of the other stuff…will happen naturally on its own.?

Hsieh is not often pressed on what his ideal version of company culture (which he calls ?the science of happiness?) actually is, but I’ve gathered from interviews that he prefers it when companies keep moving forward and innovating, don’t become obsessed with maximizing profits above all else, and don’t grind to a screeching halt every time they make a mistake. His reasoning seems to be that if people actually like their jobs and feel rewarded by them, it stands to reason that they’ll be more productive. But again, interviewers don’t prod him for specifics too often.

His redefinition of corporate culture is symbolic of a common paradox among his generation of businessperson ? how does one make big heaping truckloads of money without violating every principle they have? It’s hard to listen to the very important and intelligent things Hsieh says about running a company whose work atmosphere isn’t completely toxic without thinking that he’s going through the same build-a-company-up-and-sell-it dance recital as all the corporate headhunters he’s trying not to emulate. Maybe he’s more forthcoming in his book.

In any case, Tony Hsieh took a risk and created a company he wanted to work in, instead of toughing it out in a company that wasn’t the right fit for his personality. What he did seems crazy, now more than ever, but it paid off handsomely for him and, one can only assume, his employees. Here’s an interview where he talks more about his career path, with emphasis on the getting rich parts.