Atypical Startup Career Advice Learned from 4 Billion-Dollar Exits

Four of the companies I’ve worked for during my career have been acquired for over $1 billion dollars. Make no mistake, my contributions to these successes, particularly early in my career, were relatively minor, and I’ve had my share of failures, too. But I’ve been fortunate to learn important lessons from each experience. Here is the most important career strategy lesson I have learned:

Don’t focus your career search on companies. Instead, build a target list of people.

Many job searchers target companies that seem “hot”. But the best jobs – the ones with the most upside – are the jobs that are available in companies before most people are aware that they exist. Whether you’re an engineer building initial product from the ground up, or on a firm’s revenue side securing early customers, startups offer outsized opportunities to contribute and grow professionally. Unfortunately, finding the best startups is difficult because most companies look similarly compelling from the outside, and qualifying whether any given company is a place you’ll want to work requires a lot of networking. It’s a very inefficient process. So the best way to find the best companies is by finding the people with whom you want to work – people that you will like, trust, respect, and learn from. Maximizing your upside requires information asymmetry – you have to know something that the rest of the world hasn’t yet figured out. Trusted relationships offer the best kind of information asymmetry: focus on finding the best people and they will lead you to the best jobs – the life-changing ones with companies that are on the brink of greatness.

Ask your best people for introductions to their best people

A people-focused job search starts with your personal network (especially your weaker connections) and moves one degree past them for leads. Invest 95% of your time here. The remaining 5% can be allocated to recruiters and job boards, but the investment you make in your personal network will be amplified and produce far superior results.

Call high – and invent your own role

Seek trusted referrals to senior leaders – people with hiring authority – and talk them into creating a custom role just for you. A firm’s hiring plan will describe commodity roles for commodity candidates. Ignore it. Never think of yourself as a commodity. Your uniqueness makes you a scarce resource. Scarcity increases demand. Conveying the confidence derived from this mindset is more than half the battle in selling yourself into a position where none previously existed.

Over-invest in each person you meet

For more senior positions, each meeting is a big swing at bat. Don’t use a shotgun approach. Be prepared. It’s worth it. Emphasize quality over quantity. Think of each meeting as an investment in what will become a lifelong, enduring relationship. Invest a day (or more) creating a custom-tailored pitch on how you will solve an important problem for the person you are meeting in a way that is linked to your unique talents. If necessary, consider offering your services for free to begin addressing the problem and proving your value (never work for free unless it’s part of an agreed-upon path to securing your ideal job). And for the right person, don’t be afraid to take a role that seems “beneath” you. As Eric Schmidt famously advised Sheryl Sandberg when she hesitated to accept Google’s job offer (back in 2001, before Google’s remarkable success), “If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.”

Focus on working with great people and everything else that matters will follow

Career strategy is important. You want both an affiliation with success and attribution for your contributions to it. Focusing on people is what will get you there. Here’s why:

Affiliation: Great people create growth. Growth is the best measure of business success. Following great people leads to an affiliation with success.

Pro tip: lots of people settle for this affiliation. But you want more than mere affiliation – you want attribution. Here’s why following great people leads to that, too:

Attribution: Because of the information asymmetry I mentioned earlier, you’re more likely to get a foot in the door with a company that’s on the brink of greatness (like Google in 2001). And because you’ve avoided “commoditized” roles and brokered your own path, you are more likely to maximize your contributions by working in a role that is aligned with your talents.

So, avoid the stock job openings and focus instead on finding and working with great people. In the end, the rocket ship that propels your career won’t actually be a particular company or series of companies – it will be the people with whom you work.

P.S. I’m hiring – come join our team!

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