How to find a business role at a startup

Step One: Do as I say, not as I did

Welcome to Silicon Valley Outsider, a newsletter for aspiring startup founders and investors who live outside the SF Bay Area.

🍎 Quick Bite of the Week: SpaceX launched and landed a rocket that will be capable of launching 100 metric tonnes to orbit. And, per SpaceX’s own copy, “As if the flight test was not exciting enough, SN10 experienced a rapid unscheduled disassembly shortly after landing.” Must-watch.


I was incredibly lucky to find Astranis.

I’m not being faux-humble, I truly mean it.

My startup job search was like buying an actual lottery ticket: a negative expected value bet that no rational human should take.

I started with an ill-defined goal: “find a business role at a startup.” I was vaguely aware that startups were hiring Product Managers, so I applied to roles with that title; I knew that I wanted to “get in early”; and I knew that I wanted to work at a well-known company. That was about it.

After getting rejection letters from a few of my top choices — including Astranis — I freaked out and applied to every Silicon Valley company I’d ever heard of. Nearly all of them either said no without meeting me in person, or just totally ghosted me. Eventually, I found my interviewing rhythm and got invited to some on-site interviews, but still couldn’t catch a break — one company brought me on site four times, and then said no over Zoom. Months later, I finally got an offer, but wasn’t I particularly pumped about the industry or my prospective role.

I was ready to accept it anyways. Recruiting was painful and humbling, and I was ready to be done. But in an insane moment of courage, and cashing in a lifetime of luck, I was able to parlay my existing offer into an expedited hiring process at Astranis. They brought me on site and overlooked my terrible answer to a brain teaser about how moon phases work, giving me an offer to join as one of the first businesspeople at the company. I told you — I actually got lucky.

Luckily for you, I’ve now been around Silicon Valley long enough to have a much better idea of how businesspeople can find great roles at startups.

Here are a few tips.


1) Take the time to understand which startup stage is best for you.

As a native Midwesterner, I naively assumed that there was a category of companies that lived in Silicon Valley called “startups,” and that they were all roughly the same. Wrong.

As I wrote earlier this year, there’s no such thing as a “startup.” Each stage is unique, and startups at different stages will require different skillsets from its employees, have a different feel around the office, offer different level of risk and reward, and so on. You need to find the stage that best fits what you’re looking for — and understand what that means you’re giving up.

Want the “couple of folks in a garage” experience? Join a seed or pre-seed company with fewer than ten employees. You’ll get the high highs and low lows of entrepreneurial life, you’ll own a (relatively) significant fraction of the company, and you’ll get to help the company find product-market fit. But you won’t get glitzy perks like they have at Google, you likely won’t have (m)any in-company mentors to teach you how things work, and you’ll probably work around the clock.

Want the “blitzscaling” experience? Join a Series C company with 100-250 employees. You won’t get the same comradery that you’ve read about among small, close-knit startups, and you won’t own as much of the company, but you’ll get help double the team in 12 months and rapidly expand into new geographies, facilities, and product lines.

If you don’t know what you want, consider the following criteria:

  • How hard do you want to work? (Earlier = harder.)

  • How much risk in your compensation are you comfortable taking on? (Earlier = riskier, but higher potential reward.)

  • Are you more of a generalist or a specialist? (Earlier = better for generalists.)

✨ One you’ve decided which stage is best for you, finding the stage of a particular startup is easy: just google “[Company Name] fundraising,” and look for Crunchbase data or a recent press release from the company.

(NB: One common pro-tip given to folks trying to break into Silicon Valley is to pay close attention to funding announcements, because new funding means new hiring. That’s certainly the case — but what you really want to do is find a startup that’s succeeding and about to raise a new round. The company won’t yet be buried in resumes, and your stock options will be worth more.)


2) Look for great companies, not great roles. (And don’t try to become the world’s greatest investor.)

The secret to having a successful career in Silicon Valley is to find and join the most successful startup you can. That may sound obvious, but it’s important to realize what it leaves out: your role. As immortalized in the words of Facebook’s COO, Sheryl Sandberg:

(FWIW, roles don’t matter because great startups are chronically understaffed. Once you’re in the door, they’ll use every skill you’ve got. At Astranis, I was hired into a finance role, but also designed the website, recruited engineers, and drafted international regulatory filings in my first six months.)

The literal million-dollar question is how to identify rocketship startups, and the secret to doing so is simple, but unsatisfying: there is no secret.

If anyone knew how to consistently identify billion-dollar startups, they would be the richest human on planet Earth. So, unless you’re talking to Elon Musk, you should be skeptical of anyone who claims to have uncovered a secret way to find amazing, early-stage startups. (Even if that person is me.)

There is a middle ground between applying indiscriminately and becoming the smartest, richest human on the planet: outsourcing your judgment of what makes a great startup.

First, check out the Breakout List. It’s a good place to start — I have heard of most of the companies on this list after being in Silicon Valley for a few years, but I expect that many of them have not broken through to the general public consciousness. (Meaning, I wouldn’t have known about them when I lived in Minnesota.)

Second, find a few venture capitalists that you respect (or that have invested in companies that you respect), and check out their portfolios. This strategy led me to Astranis in the first place — I connected with an Andreessen Horowitz partner on Twitter when he posted about a really cool project he was working on 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.

One important caveat: this strategy works best when you focus on individual venture partners, not 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.

✨ To find what specific investor led a deal, check out their VC profile page or LinkedIn. Most VCs add themselves as “employees” of the startups they’ve invested in.


3) Join a community before starting your job hunt.

Some of the best roles in Silicon Valley never get posted publicly — they’re exclusively shared through existing, insider-y networks, and get filled before they ever see the light of day.

The challenge, of course, is finding communities while you’re still on the Outside. I’ll do my best in this newsletter to share great groups and resources with you when I hear about them — e.g., by sharing Ali Rohde’s new jobs-focused newsletter — but I can only do so much! I’d recommend diving into industry- or role-specific communities to help find great jobs.

One such group is Renaissance Collective: a high-quality community for self-identified “smart generalists.” (Ali Rohde and I are both members!) The membership is mostly, but not entirely, Silicon Valley tech folks, so it’s perfect for people all around the world who are business-minded and want to find a role in tech. (It’s also free to join, as long as you pass through their rigorous application process.) The “#jobs” channel on Slack is absolute fire:

Some other communities I’m aware of are:

  • YC’s Startup School: A free course for prospective startup founders. (They also have a new Future Founders program for those who aren’t yet running a company!)

  • South Park Commons: A free-ish community for prospective founders in the Bay Area.

  • Skillful: A paid ($) community for folks interested in recruiting for Strategy and Operations roles at startups.

  • On Deck: A paid ($$) community for tech networking.

  • Business School at Stanford or Berkeley: Paid ($$$$$$$$) communities for the risk-averse among us. (NB: I went to business school at Berkeley to ease my transition into the world of Silicon Valley.)

There are many more such communities available in person in Silicon Valley and the SF Bay Area, but most are (understandably) on hold until the end of the Coronatimes.

🔌 Shameless Plug

If you’re a talented businessperson looking to break into Silicon Valley, my team at Astranis is hiring! We’re a Series B startup building next-generation satellites to bring the world online.

We are actively hiring for an FP&A Manager, but I’m always interested in meeting talented folks. Click my name below to reach out via Twitter DM, or add me on LinkedIn.