Jeremy Liew has made his career by following great people.

“That works for people like me who don’t know what they want to be when they grow up,” he says. “You learn a lot from them, and great people tend to move upwards quickly and they tend to pull other people around them in their slipstream. But you can’t control the direction of their moving, so that’s why it only works when you don’t know what you want to be.”

He’s followed former bosses to various companies all around the world. When his boss at McKinsey moved to California to help start Citysearch, Jeremy moved from South Africa with him. Citysearch got bought by IAC, so after two years at the Stanford Graduate School of Business, Jeremy went to work at IAC as VP of Strategic Planning. He then followed the President of IAC when he became CEO of AOL, and Jeremy became SVP of Corporate Development at AOL.

“I think it would’ve been different if I’d had an overwhelming passion, but I was quite happy to be carried by the wings of serendipity,” he says. “I think that’s not an unreasonable way to allow your career to move in the early part. At some point you then decide what you want to do and then you have to move toward it.”

In 2006 Jeremy got a call from a business school classmate who, at the time, was at Lightspeed Venture Partners, and they were looking for an Internet partner. That call led him to move back to California and become a venture capitalist.

The irony of this is that he never imagined he was going to be an “Internet guy.” “I used Usenet when I was in school, then didn’t use it when I worked for banking clients and oil and gas clients,” he says. “What I found interesting was business models and business problems.” 

Being a venture capitalist and working with entrepreneurs suits him better than working at large corporations, though. “When you work at a big company, you focus on what can go wrong, what can threaten you from hitting your numbers—so you become a pessimist,” he says. “When you work with startups, you’re looking to the sky thinking about best-case scenario, how this becomes a billion dollar company—so you become an optimist. And I prefer to be an optimist.”

He started blogging shortly after joining Lightspeed to broadcast what he was interested in, since he didn’t have a portfolio of past investments yet. “Blogging is a terrific avenue to differentiate yourself from a whole set of other VCs who can be somewhat indistinguishable; as an entrepreneur, you may not know who’s interested in e-commerce vs. social media vs. gaming,” he says. “By writing about what you’re interested in, demonstrating some level of understanding of those topics, it helps the right sort of entrepreneurs in contacting you.”

Jeremy is a thesis-driven investor, who takes a view of what he thinks will be interesting and then looks for companies that fit. “Some people think by talking and I think by writing—it helps me identify inconsistencies or holes in my thinking,” he says. “Pushing it to the blog is a trivial step from there.”

He takes in information about world news, macroeconomic trends, new companies, and fixates on one or two theses to explore. “There are probably 100 different theses someone could emerge with, but you don’t have to do every good deal, you just have to do enough,” he says.

For example: “In 2008 I made the fairly trite observation that it’s a really shitty time to sell ads. So if it’s a bad time to sell ads, then it’s a good time to buy ads, so who’s going to benefit from cheap customer acquisition costs?” he explains. “That led me to thinking about e-commerce companies, and gaming companies, and that led me to an investment in Playdom, Living Social, Shoedazzle, Bonobos, and a whole set of these companies.”

His favorite kind of post to write, which is generally well-received, is applying elementary analytics to a problem to derive insights—like his popular post a few years ago estimating Zynga revenue from publicly available information (he ended up very close to the real number, when Zynga filed its S-1.)

His emphasis on the greatness of individuals, as evidenced by his early career path, doesn’t quite extend to entrepreneurs, due to his thesis-driven approach. But, he says, he’s learned to pay more attention to the greatness of entrepreneurs over time. “I have in the past mistaken great progress for great entrepreneurs—they are not the same thing,” he says.

 “They say training a venture capitalist is like training a jet fighter pilot—it takes about 10 years and you crash $50 million into the ground first,” he says. “I’m probably halfway through my training period.”