Choosing to Join a Startup

Welcome back to Launchpad, a newsletter about the hiring process from finding a job to just figuring out what the heck you want to do for a living.

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A case study of one of the best new startups out there

I always have trouble actually starting these, because it’s hard to actually decide what to highlight; I don’t like reading boring articles with ‘checklists’ or LinkedIn-style Very Important Points, so I’m always hyper-sensitive to starting my writing with clichΓ©s.

Today, I want to make the case for why (or why not) you should consider working at a startup, and I want to do it by talking about an app I absolutely love: Notion.

If you haven’t heard of it, Notion is a really fantastic app with a grand vision for how people should use technology to be productive. In fact, I’m using Notion to draft this right now.

But Notion’s much more than a productivity app. You can write things with Notion, yes. But you can also craft Airtable-style databases, build your own personal CRM, manage your calendar, and collaborate with your team. All in one app.

It’s beautiful software (so, as a product designer, Notion makes me really happy).

But, here’s what’s even more cool:

This incredibly polished, beautiful, useful app you see above was crafted by only a handful of people. Today, the Notion team is <20. That’s incredible.

When Notion’s founders started the company, they did so out of a belief that despite the omnipresence of technology, managing the different services we all use in our lives has just gotten really hard.

There’s so many apps, tools, things you have to manage. So, work sucks. We all have to dig through Slack chats and emails and google docs and UGH just to find what we’re looking for.

What I find coolest about Notion is that the founders, some of the most brilliant product people in the Valley, decided to act on their frustrations with typical productivity apps and actually meaningfully reinvent computing.

They had a belief about what the experience of using productivity tools should be, and for the past three years, they’ve just been executing on it amazingly well.

That’s why, despite their small size, they’ve also solicited investment from some of the best investors in the Valley.

“Chances are you are already using the products they helped to create.”

I love that line so much.

So, why am I bringing up Notion? Are they paying me or something? (For the record: the answer is no.)

I’m bringing up Notion because they’re the perfect example of a startup you should work for, even if you’re early in your career.

Yeah, they’re <20 employees and work out of a small office in San Francisco’s Mission District.

But damn, their team is amazing. They think through everything they do. They don’t come to work to do “busy work”. They come to work to change the world.

They have a clear product vision, have found product-market fit (just look at all the praise for them on Twitter!), and are backed by solid investors with lots of experience actually building things.

How to decide whether or not to work at a startup

Notion isn’t just an example of a great company to work for because I like them, although make no mistake – I do really, really like them. (Their Tools & Craft podcast, featuring the original inventor of the Macintosh and designer of the computer mouse, is absolutely fascinating as well.)

In my view, they’re a great company to work for because they fit three key criteria:

1. Clarity of vision

The Notion founders have a super clear vision of where they want to take the company; rather than being at the exploratory phase, they’ve already determined they’ve found product-market fit, which basically means they’ve already heard from their market (their users) that the product they’re building is useful enough that people are willing to pay for it. (I am one of those people.)

This is super important because especially as a junior hire, your goal is to learn as much as you can as quickly as you can. Through working with amazing people, you want to come out of the summer having gotten really, really good at something – and while it’s possible to learn from chaos, if the company keeps pivoting to a new idea every two weeks, you won’t be able to devote the focus you’ll need to be successful in that endeavor.

2. Experienced + well-known founders and investors

This might sound weird to say given that in the last issue I specifically said not to care about working for prestigious companies, but when we’re talking about startups, it really matters who you’ve raised from.

This shouldn’t be your concern now (unless you’re fundraising yourself!), but who you’ve raised from before is actually highly indicative of the quality of investors you’ll raise from in the future, and cash-strapped startups with vulture investors breathing down their backs don’t tend to make good decisions.

Basically: if the company you’re working for has $25 million in the bank and awesome investors, it’s more capable of taking risks and working on shipping a quality product; if the company has $500k and investors who want to see returns – NOW! – your experience working there will suffer as a result.

You need to have an experience that enables you to hone your craft, and being worried where your next paycheck will come from won’t accomplish that goal.

There’s another reason this matters though: if the company gets acquired, being close to the founders is a massive professional + personal bonus.

For example – recently, former Y Combinator Partner Daniel Gross and AngelList engineer/Dorm Room Fund partner Rishi Narang co-founded Pioneer, a global competition to find the most amazing creative talent around the world.

Daniel and Rishi initially met, though, while Rishi was interning at Daniel’s first company, an app called Cue that he later sold to Apple for $40 million. Several years later, the two are now working together as cofounders.

3. Whether or not you’re a specialist or a generalist

At large companies like Google or Apple, your job at the lower rungs of the company is largely to be a specialist – essentially, you’re to do one thing, and do it really well.

It makes sense why this would be: after all, when you have to manage tens of thousands of people, everyone needs to have a specific function. You can’t just have people floating around!

Startups, though, turn this on its head. At a small company, you might have to take lots of responsibilities (“putting out fires”, as I would put it to our interns); at a larger growing one, you might have to refactor old processes or parts of the codebase to be less hacky and more ready for scale.

While interviewing, you should ask lots of questions about which of those two scenarios the company is actually going through, and where you could add most value. Company leadership should be blunt and honest in their responses about what they’d find most helpful from you (and if they’re not, run – it won’t be a fun experience working for them).

Another way you can figure out which scenario best describes the company you’re looking at is to look at the company’s funding stage.

  • Pre-seed companies have typically only a few team members and not all that much money. These types of companies are typically far more volatile; if you’re interested in gaining startup experience and taking on tough challenges, these companies are good, but know that this is a more generalist role for sure. Pre-seed companies typically fundraise from smaller investors, friends & family, and accelerators.
  • Seed stage companies are a bit larger, between 10-20 employees, and have clearer product direction (investors had to give them money on two separate occasions, so at least someone thinks their product has value). This is an awesome time to join a company, because things are still exciting, and your role will still likely be a generalist role, but there will likely be more direction from management on what to do.
  • Series A companies are much larger and a lot better financed (they’ve raised a round of at least $1 million in funding typically). They have a more firm hierarchy and structure, and will likely require you to be more of a specialist, but you’ll be able to have far more impact on the company than at larger ones. A friend of mine was an intern at a rideshare app (can’t say which) while they were still in their earlier stages; as a result, he got to design part of the interface y’all use every day. His contributions are still there.
  • Series B and beyond companies act much more like larger companies, and you should evaluate them accordingly.


If you’re thinking of working at a startup, seriously consider it – it can be insanely rewarding, and you’ll learn so much!

That said, be aware of what you’re getting into. Also, check out the links section below for help getting started on your search.

Good luck!


πŸ“š Stuff you should check out

Y Combinator Startup List

  • Y Combinator is the gold standard among startup accelerators, and it consistently churns out really awesome companies – including products you use every day, like Dropbox, Reddit, Twitch, Quora, and Airbnb. (They even invested in Lever, that website where you’ve probably applied to a job before.)
  • YC also maintains a list of the companies that graduate from their accelerator, ordered by recency and coupled with a one-sentence description of what they do.
  • I’d recommend reviewing the list to find new companies to apply to, or even just founders to reach out to for advice and feedback.

Breakout List’s “New Grads Take Note” tag

  • Some more companies that would be awesome to work for as a new grad. Some of these names you might know (Cloudflare, Gitlab, InVision, Instacart, Reddit) but there’s a bunch you might not recognize that are actually really awesome places to work.
  • If you get a sweet Google or Facebook offer that’s awesome, but it’s important to remember that it’s not at all necessary to work at a name brand company to succeed in Silicon Valley.
  • An example of this is Flexport, a company that’s super well-known here (and known to have an excellent engineering team) but might not be on your radar. Among the hiring managers I chat with out here, Flexport staff are highly coveted, and working there’s a strong signal that you’re a strong engineer.
  • But, remember: choose companies FIRSTLY based on their mission and the types of problems they are solving, THEN think about prestige. While it’s not particularly intuitive, sometimes you just have to trust that if you work hard at a place you enjoy, you’ll get recognized for your talents.

AngelList’s Job Search

  • AngelList is a professional network for startups, and it’s a great place to search for available internships and jobs (much better than searching LinkedIn or job board sites). You can enter lots of tags for what you’re looking for, and it’ll spit back what’s available and allow you to directly apply.

Thanks, y’all πŸš€

Thanks for reading this week’s issue! If you liked it, have an idea for how it could be better, or have a question for me, please don’t hesitate to email me directly at [email protected].