in Life Optimization

Andrew Chen on Job Searching Like a Founder

I recently had the good fortune to chat with Andrew Chen, he of viral startup marketing fame. We took a power walk through downtown SF while talking career advice, with me struggling to keep up. The man walks as fast as he talks, (very fast!) which should be no surprise given his prodigious body of writing.

He cut to the heart of my job search by asking “Where are you trying to be in 20 years?” I admitted that the logical conclusion of my startup love was to start one myself someday, even if now was not the time. Thus, the rest of Andrew’s advice was geared towards building a career that facilitated that goal. After listening raptly, I rushed to take notes, know it would make a perfect “How to Find Your Next Job Like a Founder” blog post, and so here we go:

Think Like an Investor

Taking a job is like investing in yourself in a company. Beyond the simple paycheck – it also determines things like future job experience, professional network, and career trajectory. You can’t compare this investment to finance, where you invest money and reap dividends off of a single metric. And you can only work one full-time job at a time, so it’s not like a stock portfolio where you can diversify your holdings among multiple options. Investing yourself in something is far more difficult, and important than investing your money. You need to choose wisely.

You Can’t Pick Companies Well

Continuing the stock investment analogy, you’re not going to hire a novice portfolio manager to take care of your finances. You look for someone who knows the landscape, has seen a few cycles come and go, and is able to make an informed decision concerning who is the best choice, backed up with reasons why.

A job search is just as fraught with deceptive promises and a tumultuous landscape, and you can’t hire someone to do it for you. Recruiters, family members, and everyone else have their own vested interests in where you end up – only you know exactly what you’re looking for. And you are an uninformed picker. You’re not an informed chooser – all you’ve got to work off of is what you’ve heard from the public, what the company website claims, and (hopefully) input from friendly employees.

One needs to do some serious research into options while soliciting advice from varied sources because they can make a confident choice as to what is really the next best step for them. Andrew noted that if I had come to him with a ranked list of the top 20 companies with current hockey stick growth and reasons why they’re A) appealing to me and B) growing sustainably, then he could trust my decision. But as it is, I’m working off of a few weeks of online guessworks and executive opinion.

The Best Teams are Obvious

I brought up some companies I was excited about, citing personal beliefs in their product and smart teams ripe for learning. Andrew shot back, asking “How do you know they’re smart? They’re not one of the hockey stick growth companies that everyone is talking about right now (Uber, Airbnb, etc), which is where all the best talent is heading. There’s a reason why their startup isn’t the talk of the town.”  Look at objective company results, not at your subjective opinions of the team.

(I’m unsure if I’m completely swayed by this particular argument, since market expectations can falsely pump up companies, and just because a good idea isn’t one of the top 5 doesn’t mean it’s not a good idea. But it is important to distinguish between objective and subjective.)

Establish Credibility First

Andrew pointed out that neither of us are Stanford CS majors. That’s who venture capitalists are looking for. It’s a checkmark on their resume that says they’re one of the least riskiest options for investment. Since we lack that qualification, we need to to look for other ways to establish personal credibility in order to get a foot in the proverbial door (here, it’s a literal ‘close the round of funding’).

The best way to do that as a new grad is to join one of the aforementioned hockey stick growth companies. Andrew mentioned a friend of his who was something like the 100th employee at Facebook and spoke at a small conference. His Powerpoint sub header (chosen by the conference) was ‘early hire at Facebook’. Ten years later, that header remains his primary indication of expertise. It may not be the best indication of expertise, but this is the way the world works, and there’s no doubt all the early hires at a company like that learned a ton.

Establishing credibility is critical if you’re trying to raise money, but it’s good to have no matter what you end up doing. Andrew noted that if I was trying to be a venture capitalist, his advice would be different, though credibility still would factor into it. (He cold called Mohr Davidow every week for four months after college in order to win a year long unpaid internship, finally culminating in a actual job there) Credibility gives you optionality – regardless of whether you end up taking those options.

I brought up the Clinkle founder as a counter example to this (a VC’s wet dream whose company isn’t doing well) and he stood firm, noting that Lucas Duplan and any Clinkle alum are bulletproof, because they somehow retain that credibility, bolstered now by the lessons of failure.

Optimize For the Long Run

This is bitter medicine to take for a rosy-eyed young startup romantic like myself, but it’s hard to argue with the long term results. Just look at his sister Ada Chen, whose Linkedin profile reads like a textbook execution of this strategy. There’s no guarantee here, but this method minimizes risks while maximizing probable reward. Taking any other course may be the right path for you, but it’s not the objectively strongest option.

Andrew brought up the story of his friend who got dumped by a long term girlfriend and spent a few weeks despairing. Then he got into online dating, and realized that his old girlfriend was at best an average partner for his needs. We’re so used to optimizing locally, based off of what is available, instead of the absolute best option, which may not be immediately visible. Zoom out, and look at things from a birds-eye long-term perspective as an informed observer. Only then are you qualified to make the best possible choice.

Big thanks to Andrew for taking the time to sit down with this young grasshopper, and to Tom Bedecarre for connecting us.