Welcome! This is a practical guide for finding, landing, and crushing a job at a startup.When I made the trek to the West Coast five years ago, I considered myself a frustrated "ideas guy" who had lots of startup founder potential but who had realized little of it to date. I wanted to learn from the world's best startups, investors, and founders. There was clearly something they knew that I didn't, and if I could just make it to California, I could learn the secrets of Silicon Valley and become a real entrepreneur.
Of course, it wasn't that simple. My first startup failed gloriously after a year of highs and lows, exuberance and exhaustion, and an incredible amount of hard work. I somehow got a funding offer, but shut the company down rather than accept it: it was hard to admit, but I didn't have enough conviction that my idea would actually succeed. It was a painful experience, but, weirdly, was an unqualified success. I learned how to raise money, recruit a team, and sell to customers, which ultimately led me to a dream role at 50-person, Series A startup with bold ambitions (and a lot to prove).
🛰 Astranis builds small internet satellites to connect the world. I joined about two years ago as a Finance Manager, and as we scaled up as a company (raising $350M, hiring 100+ employees, etc.), I scaled up my personal responsibilities as well. Today, I'm the Chief of Staff to our CEO, which is an incredible position from which to learn — and, hopefully, from which to teach.
Because this guide is written to my former self, it's probably biased towards young, restless businesspeople from the Midwest. But, amazingly, writing for Silicon Valley Outsider has taught me that other subcommunities can also benefit from an explanation of the startup world using normal people words: from military veterans moving to the private sector, to engineers hoping to understand "the business side," to, strangely enough, Canadians. (Oh, so many Canadians!)
<aside> 💡 If you love to explore, learn, and work hard, you're in the right place.
</aside>
Step Zero: Are startups for you?Startup life is hard — really hard.
The odds are stacked against you, so you’ll have more failures than normal. Each failure is objectively worse, as they’re all existential when your company is finding its footing. And, adding insult to injury, everything that goes wrong is your fault and your problem to fix. Even when you do succeed, the highs fade quickly — like the time, pictured below, when I nearly won $1,000,000 in a pitch competiton, only to have my co-founder leave me the very next day.
I wrote about what startups are really like in this post, where I talk about the first and most important startup skill: Drive.
The most important skill in Startup Land: Drive
The same week that I released that post, Paul Graham — the founder of Y Combinator and one of the startup world's best essayists — released a piece on working hard. It's another great glimpse into the kind of person you should be if you want to succeed in startup land.
It's worth noting, however, that "startup" is a word that encompasses many different kinds of companies: everything from the proverbial "two dudes in a garage" to 500-person hypergrowth companies that are adding two new employees every day. It's important to know what stage fits your skills, working style, and tolerance for risk.