The Single Best Way to Build a Career in Startups
One strategy, two hacks, and a long con
🚀 The single best way to build a career in startups is to find a rocketship, and hold on for dear life.
At a rocketship, you will be assigned jobs that any normal company would hand to a team of people headed by a tenured expert. The jobs assigned to you will change fundamentally every 3-6 months. As your startup grows, you solve the easier problems and are left with progressively harder ones; and just as problems are getting harder, the stakes riding on the success of your problem-solving skills will increase.
Living through hypergrowth with your job intact is evidence that both you and your startup were able to scale. Achieve that, and you’re set. You can start a company of your own and double down; you can take a leadership position at your current company as it continues to grow ever-larger; you can take a role at a bigger company and settle down.
No matter what you choose, however, you’ll have the narratively-important street cred of being a “successful operator,” and the actually-important street smarts that you built while crushing a challenging job.
But finding a rocketship startup is far, far easier said than done.
Your goal is to find a company that is right on the verge of hyperscaling: one that is just about to raise, or very recently raised, a major funding round.
As a directionally correct benchmark, this probably means that you’re looking for a company that:
Has 10-30 employees
Has raised a seed round, and is about to raise a Series A (or, equivalently, that has raised single-digit millions of dollars and is about to raise double-digit millions)
Has a working product
Has found success in at least one core market
Has their most important metrics growing quickly in that market
There isn’t much written on what companies like this look like to potential employees, but there is plenty written about what a Series A company should look like to an investor. Imagine that you’re a founder who is trying to raise a Series A. What metrics should you hit? There are plenty of resources out there — and these metrics can help you on your job hunt.
Of course, there’s no single set of criteria that captures what it means to be a hyperscale startup, because there’s no correct way to navigate the startup idea maze. For instance, Astranis started hyperscaling after our $250 million Series C fundraise, which came about a year after our Series B; Webflow raised a seed round in 2014, then spent five entire years building its core product and a profitable business before stepping on the gas with a $72 million Series A in 2019, a $140 million Series B in 2021, and a $120 million Series C in 2022.
While sitting on the outside, it’s hard to know exactly when a company is about to go pedal-to-the-metal.
Here are four tips that might help: one strategy, two hacks, and one long con.
First, the strategy: don’t overoptimize for role.
I know people who have turned jobs at rocketship startups because another company offered them a sexier title. I also know people who have joined bigger companies over rocketship startups because they wanted to start off with a higher base salary at the bigger company.
Both of those decisions were, for those individuals, mistakes. Of course, you should try to get the best title and pay that you can — but it’s wrong to evaluate a startup role by its current job description without thinking about what the role could be in a few months or a year.
Your job at a rocketship startup changes fundamentally every 3-6 months, so trajectory is more important that current state. When I joined Astranis, I was promoted twice in my first year, and despite having “finance” in my title, I helped out with recruiting, legal and regulatory work, and far more.
If your startup is growing, and you’re executing your job well, you’ll be asked to help out with more and more important projects, so your responsibilities will grow quickly over time.
The counterpoint to this is that job hunting is more about signaling than actual skills, which is sadly true — but even then, you should optimize for the name of your company more than the name of your role. Hiring Managers are smart enough to see through inflated titles, so being an Operations Manager at a rocketship that you scaled from 100 to 300 people is more impressive than being an Executive Vice President at a failed, 10-person company.
In short: optimize for the rocketship, not the seat. You can figure out the latter over time.
Hack #1: Browse the lists.
The Breakout List is great. So is Y Combinator’s Top Companies list. Ali Rohde has a great newsletter for business jobs at startups.
If you want to dig deep, you can periodically troll through HackerNews, become a TechCrunch junkie, or browse through AngelList Jobs.
Hack #2: Find an investor you respect, and track their deals.
Finding amazing startups is hard. If you could do it consistently, you’d be the greatest venture investor that ever existed. But — of course — you are not. So my second hack is to crib notes from the people who are: find a great investor (which you can do via Twitter, the Midas List, or back-searching through the investor lists of startups you admire), and follow their new, Series A / Seed deals.
This strategy led me to Astranis when I was recruiting — I connected with an Andreessen Horowitz partner on Twitter when he posted about his cool project to provide connectivity to Native Nations.
When it was time to kick off my job search, I looked into every company in his portfolio, and noticed that one was a crazy space company at about the stage I was looking for. To be clear, I didn’t pester him to ask for an intro or anything — he didn’t actually know me — but because I knew him and respected him, I considered Astranis to be a vetted, known entity worthy of my recruiting effort. (I did DM him on Twitter telling him I was interviewing, on the off chance that he would mention that to Astranis — but I’m pretty sure that didn’t actually work.)
One important caveat: this strategy works when you focus on individual venture partners, but not when you focus on firms. Andreessen Horowitz, for instance, is a huge firm with many partners that invest in very different kinds of technology. The real strategy is to start with a company you know and like, find the individual partner who did the deal, then trace back to see what other, perhaps more obscure companies they’ve invested in. The “individual” piece is key: tracing Martin Casado’s deals will help you find great enterprise software companies; tracing Andrew Chen’s deal will help you find great consumer companies. Tracing Andreessen Horowitz deals broadly won’t help you narrow things down.
And, finally, the right answer: make friends with ambitious, technically-savvy people.
Since I joined Astranis, three of our alums have founded companies that got funded by Y Combinator: UTVATE, Buoyant, and Gridware. A few of my business school classmates founded Kyte, twentyeight, Oxygen, and Vested. And many, many more of the folks that I’ve met throughout my five years in San Francisco (even with a pandemic thrown in the middle!) are founders and operators at great, young companies.
The best way to find a rocketship startup is a long con: befriend people who are inspiring, smart, and technical. And perhaps, if you wait long enough, one of them will need your help to scale up a company.
My journey to Astranis was incredibly improbable. I applied on their website, cold; I got rejected; then I re-applied and got in the door. Contrast that to the way that my original boss at Astranis found the company: she knew our founder, introduced him to an engineer who would eventually become one of the first five employees, then got recruited by the founder and that same engineer to join Astranis when it was about ten people. I was lucky; she was smart.
Of course, it’s hard to follow this advice. It might be hard to find such people, depending on where you live and how technical you are. But if your goal is to have a successful career in the startup world, figuring out how to become part of such a community is absolutely critical — so you’d better get started!
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