This guide is for people who might want to join an early-stage technology startup, when it has between 1 and 100 team members. 

It includes commentary from the first employees at multi-billion dollar startup successes including:

• Anthony Chen (employee #1, Flexport)
• Micah Bennett (employee #1, Zapier)

Here’s an overview of this 3-part series:

• Should I join a startup? 
• PROs and CONs of joining a startup 
• Why people join startups 
• Should I join a startup or start a startup? 
• How do you pick which startup to join? 
• How to evaluate founders
• How to evaluate markets
  
• How to join a startup
• How to nail a startup interview 
• Negotiating startup compensation
• How to succeed in a startup you’ve just joined 
• Creating a 30/60/90 plan
• Communication best practices
• Prioritizing problems to solve
• Cheat sheet

Should I join a startup?

Not if you’re optimizing for work-life balance, top levels of base salary, or social status.

Plus, critics say that joining a startup is risky and foolish. Most startups fail, and you could make more money at an established company like Google.

So, why do people join startups? 

Here's what the critics are missing: not all startups are created equal. 

The startup world is the Olympics of business. The best of the best go there to compete because it’s the hardest challenge. 

All Olympians make serious sacrifices. Most never break through. But the outliers make millions, build a reputation, and become world class.

Similarly, at startups—founding team members make serious sacrifices. It's a grind to build a company from nothing. Most startups fail. It makes people feel like they've wasted years, while being under-compensated. 

The key is to join the right startup. 

Because, in the case that the startup you join early does succeed, it can:

• Make you millions (or billions) of dollars 
• Accelerate your rate of career growth
• Give you a deeper sense of fulfillment in your work

And, many founding team members of successful startups found even more success later:

• Brian Armstrong (cofounder CEO of Coinbase) was on the founding team at AirBNB
• Marissa Mayer (formerly CEO of Yahoo) was on the founding team at Google
• David Sacks (managing partner, Craft) was the founding COO at PayPal

Startup teams are so small that everyone learns how to do multiple jobs. You get trained in getting stuff done, being resourceful, and ruthlessly prioritizing problems.

You learn quickly that you have to let some fires burn, so you can focus on those that could kill the company.

So, what makes the right startup great? 

Top startups have a higher chance of success and a greater opportunity, even from the early days. They don’t just get lucky. Luck plays a role, but the best startups have a different and better foundation.

When they succeed, they don’t just create generational wealth  for the founders and investors. Their founding employees make tons of money, too:

Lasting early employees (#1 to #100) at Google, Stripe, and Facebook made $10,000,000+ each, and some much more than that.

Which startup should I join?

Don’t start with the startups that happen to have open roles matching your skill set.

Instead, pick which startup inspires your confidence using the process below. Then reach out to them. 

The best startups are always hiring excellent people who are passionate about the mission. The content of their "Careers" pages is secondary.

‍How do you evaluate startups? ‍Think like an investor. 

Except you aren't investing money. You are investing your most valuable resource—time—to make that company succeed.

Unlike an investor, you can earn equity in only one company at a time.

How to Think Like An Investor

The best investors tend to make investing decisions based on two things:

• Founding team (world-class startups are built by world-class teams)
• Market (world class startups are either built in massive or rapidly growing markets)

Start With The Team

‍“Startups become the team they build, not the plan they make.” - Vinod Khosla (Founder, Khosla Ventures – investor in Square, DoorDash, and Stripe)

Founders are only as good as the team they can attract. It’s important to start here. 

• What is the quality of the existing team? 
• Are they intimidatingly great at certain things? 
• Are they even better than you in some ways? 

Then, look for certain founder traits. The #1 early-stage startup investor of all time (YC) uses the following criteria:

• Is this founder relentlessly determined to succeed at this startup? 
• Does this founder seem super smart? (top 1% intelligence)
• Is this founder among the most resourceful and imaginative people I’ve ever spoken to?

Kyle Norton, the first sales leader at League and Owner, shares his wisdom:

“It’s worth emphasizing just HOW great a founder needs to be. There are tons of smart people starting companies (especially in this bull market) but the big winners are going to be with founders that are the best of the BEST. People (particularly early career folks) are too easily impressed because they don’t fully understand just how high the bar is.”

You can evaluate a person’s determination by learning more about their life story.

Some questions that I'd ask founders:

• Can you tell me more about how you got to where you are today? 
• What were you up to before building this company? 
• How did you meet your cofounder and recruit your leadership team?

While they answer, I’m thinking and taking notes on:

• When faced with obstacles in the past, what happened? 
• Did they become demoralized and let the obstacles stop them? Or did they find a way to persevere and grow stronger?
• Do they have a track record of extraordinary achievement? (aside from fundraising)

As you’re listening, it’s also important to listen for strong communicators. 

Sam Altman was formerly president at Y Combinator and is a legendary startup investor. He has found that strong communication skill is one of the most predictive founder traits.

As the founder is speaking:

• Do you feel compelled and impressed by their communication abilities? 
• Are you becoming more enthusiastic about the startup the more you chat with them? 
• If so, it’s a great sign. Keep going. If not, it’s a red flag, and should make you reevaluate.

Finally, in evaluating founding teams, it’s important to pay attention to the dynamic on the leadership team. Cofounder alignment is critical. Infighting between cofounders is one of the leading causes of death for startups. You may be able to predict that from the outside. 

Solo founders can work (e.g. Jeff Bezos). But it’s almost always better to have two or three strong cofounders with complementary skill sets. 

Then, study their relationships:

• Ask about the other cofounder(s). 
• How do they describe each other? 
• How in sync do they seem about the company when they answer your questions? 

There’s one other team-related factor: alumni network.

Naval Ravikant said: 

“For someone who's early in their career—and maybe even later—that the single most important thing about a company is the alumni network you're going to build. Who are you going to work with, and what are those people going to go on to do?”

When you join a startup, you establish a network of people. You can keep working with them throughout your career. People who joined the right teams, like the early team at PayPal, continued to work together on subsequent projects. And they all got rich as a result.

After PayPal, that team went on to start and fund over 20 multi-billion dollar companies together:

It’s also important that you feel that you fit in with the company. Peter Thiel, one of the heads of the PayPal mafia, has described the company culture at PayPal as one of extreme hard work and dedication. The PayPal Mafia was a band of Silicon Valley outsiders who were determined to prove themselves. Most were entrepreneurs at heart, even if they didn’t have the title of cofounder. Their alignment in values, plus cult-like dedication, built the company.

People aside, there’s one more important thing to consider in joining a startup.

How To Evaluate A Market 

The founder is important, and the team is important. But the market is equally important. You want to join a startup in a market with a chance of major success.

Andy Rachleff, cofounder of Wealthfront and Benchmark, says:

“When a great team meets a lousy market, market wins. When a lousy team meets a great market, market wins. When a great team meets a great market, something special happens.”

What makes a great market? 

One of two things needs to be true.

Either:

1) The market is already large ($10B+ in annual revenue) and ripe for disruption.

Or:

2) The market is currently small, but will be huge in the future.

Let's look at the first type of market.

1) Big $10B+ market ripe for disruption

The easiest markets to take are the ones that are already large, but where no existing company has over 50% market share. Those markets haven't yet seen the winner-take-all effect of software companies. (That effect later blocks competitors from entering).

Flexport is in this category:

• When it started in 2013, freight forwarding was $186b just in the USA. Largest freight forwarder (DHL) had <20% market share.
• 9 years later, Flexport is generating over $3b in revenue and still growing fast.
• Flexport was recently valued at $8 billion, and is climbing in market share.‍

Now let's look at the second type of market.

2) Small market that will get huge

Is this market small right now, but growing exponentially with massive potential? 

Google is in this category:

• When it started in 1998, all of search engine advertising worldwide was less than $1 billion worldwide. Its business model in that market looked laughably small.
• Today, less than 25 years later, the market which it took is worth over $200 billion worldwide. 
• The early market leaders had incredible word of mouth from being first movers (becoming the industry default).

In some cases, a market is and will always be small – but a product that can be built for it can grow to consume other adjacent markets. 

PayPal is in this category:

• When PayPal found product/market fit, it was the leading payment platform for eBay transactions. That’s it.
• Today, eBay’s entire market cap is $25 billion. PayPal’s is $110 billion.
• When a market is small but inspires products with broad use-cases—startups can benefit from creating a monopoly in that market. Then the monopoly perks—like organic growth and passionate users—help them reach adjacent markets.

Sometimes, you can even foresee a network effect in the future. A network effect is a characteristic of the product. It means each additional user increases the value for other users.

Facebook is in this category. Each person who joins Facebook makes it more valuable for others by producing content and engaging.

Network effects contribute to growth and defensibility. Some markets make it easier to secure bigger, more powerful network effects. Those are the markets in which startups become rocketships.

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So, once you've decided you want to join a startup and have an idea of the type of startup you want to join, how do you get your dream job there?

That's the topic of the next part of this guide: How To Join and Succeed at a Startup. This guide is for people who might want to join an early stage technology startup, when it has between 1 and 100 team members.