How To Start A Startup (2/3) — Founder(s)

Richard Reis
Personal Finance Series by Richard Reis
11 min readDec 5, 2017
By Richard Reis

Ehem… 11min again…

Hello dear,

Last week we talked about startups in general.

Today, we’ll zoom in and look at successful founders. Specifically, what common qualities they share (most of this information comes from Paul Graham’s 150+ essays).

But first, a caveat.

Caveat: Let’s shove aside the elephant in the room (age)

A lot of people think they have to be in their twenties to start a startup (and somehow after they turn 30 they’ve “missed the boat”).

This is bollocks.

Firstly, here are a few successful founders who started after they turned 30:

  • Larry Ellison (started Oracle at age 33)
  • Jeff Bezos (started Amazon at age 30)
  • Elon Musk (started SpaceX at age 31)
  • Jack Dorsey (started Twitter at age 30)
  • Jack Ma (started Alibaba at age 35)

As you can see, no law of physics hinders anyone from starting a startup after their twenties.

The only reason we see so many successful founders in their twenties is because there are more people in that demographic starting startups.

“Why?”

Because of risk.

Startups are insanely risky. And in general the younger you are, the more risk you can take.

But if you can take insane amounts of risk at age 35, you can start a startup.

“So who should start a startup? Someone who is a good hacker, between about 23 and 38, and who wants to solve the money problem in one shot instead of getting paid gradually over a conventional working life.” — Paul Graham

Ok, now that’s out of the way.

Let’s move on to today’s letter: What founders tend to succeed?

Below, you’ll find their top 10 qualities (in no particular order… kinda):

1. Relentlessly Resourceful

One of PG’s favorite metaphors for successful startup founders is be a cockroach.

What he means by this is don’t die (since cockroaches can apparently survive a nuclear war).

This is where the relentless part comes from. Startups are hard, you don’t want to give up too early.

Now you’re thinking “there’s no point in being relentless if what you’re doing is wrong.”

And you’re right! Doing that would be the definition of insanity.

This is where the resourceful part comes from. You have to constantly adapt to new challenges.

Sidenote: If you need a good example of relentless resourcefulness, look no further than this Airbnb story. Those founders are the cockroach kings of the startup world (that’s a compliment).

“We’d noticed a pattern among the most successful startups, and it seemed to hinge on a different quality. We found the startups that did best were the ones with the sort of founders about whom we’d say ‘they can take care of themselves.’” — Paul Graham

2. Obsessed

You’ve probably heard Elon Musk saying startup founders should work 80–100 hour workweeks.

He was not kidding.

Read 2–3 successful founder’s biography and you’ll notice the common thread: They were obsessed.

They had no social life, they’d sleep in their office, and they’d work every day.

No weekends. No holidays.

“Why?”

Because when you start a startup, you’ll have to do things that don’t scale (and if you don’t, your competitors will). That’s a lot of work.

Need a visual reminder to work hard? No problem.

Here’s a RescueTime screenshot fromOpenAI’s co-founder, Greg Brockman (this blew my mind the first time I saw it).

Taken from this @sama tweet

“During this time you’ll do little but work, because when you’re not working, your competitors will be. My only leisure activities were running, which I needed to do to keep working anyway, and about fifteen minutes of reading a night. I had a girlfriend for a total of two months during that three year period. Every couple weeks I would take a few hours off to visit a used bookshop or go to a friend’s house for dinner. I went to visit my family twice. Otherwise I just worked.” — Paul Graham

3. Intelligent

This doesn’t necessarily mean you need a high IQ to succeed as a startup founder (although I’m sure there’s some threshold).

What it does mean is you need domain expertise. You need to know your industry better than anyone else.

Do you need a degree in a field to know a lot about it? No (although of course it doesn’t hurt).

But you definitely need to study it. Doesn’t matter how.

  • I doubt Mark Zuckerberg could have built Facebook if he hadn’t studied psychology.
  • I doubt Elon Musk could have launched SpaceX if he hadn’t studied rocket science.
  • I doubt Larry and Sergei could have built Google if they hadn’t studied the web’s link structure (they even wrote their dissertation on that!).

“ You have to understand a field well before you develop a good nose for what needs fixing. You have to do your homework. But as you become expert in a field, you’ll start to hear little voices saying, What a hack! There must be a better way. Don’t ignore those voices. Cultivate them.” — Paul Graham

4. Cultic

Forget the idea of the lonely genius.

You should avoid starting a startup by yourself (startups are hard enough, don’t make them harder).

However you should also avoid starting with 10 people.

Ideally, you want between 2–4 founders.

How do you pick a good cofounder? This PG test is quite good: Could you describe the person as an animal?

Call the person’s image to mind. Say “so-and-so is an animal.” What happens? (if you laugh, they’re not).

This test should apply to every hire.

“ The low points in a startup are so low that few could bear them alone. When you have multiple founders, esprit de corps binds them together in a way that seems to violate conservation laws. Each thinks ‘I can’t let my friends down.’ This is one of the most powerful forces in human nature, and it’s missing when there’s just one founder.” — Paul Graham

“Hang on, why did you call this section Cultic?”

Because this is how a startup should feel. Like a cult.

I’m not kidding. The most successful startups have all been called cults.

Tesla has been called a cult. Apple has been called a cult. Google has been called a cult.

Your cofounders will become your family. Your startup will be your life’s mission.

To the outside world, this will look weird.

On the bright side, if the outside world refers to your startup as a cult, you’re probably onto something.

“The best startups might be considered slightly less extreme kinds of cults. The biggest difference is that cults tend to be fanatically wrong about something important. People at a successful startup are fanatically right about something those outside it have missed.” — Peter Thiel

5. Resilient

What I mean here is you need to handle stress well.

If you want to start a startup, be prepared to endure more pain/ stress/ worry than you would have with most other jobs.

The bulk of the pressure falls on the founders.

This also makes them unique. It is in the eye of the storm where they thrive (when most would crack, they keep going).

Case in point, David Kirkpatrick describing (in his book “The Facebook Effect”) Mark Zuckerberg’s resilience:

“Though the stresses on him these days were legion, Zuckerberg didn’t seem freaked-out. In fact, he remained peculiarly placid. Even in these most hectic company days, he never lost his temper. (And he shortly reported back to [Robin] Reed that he was actually using her meditation-assistance apparatus, to good effect.)” — David Kirkpatrick

Sidenote: Of course, I recommend meditation. It is no wonder to me why successful founders like Steve Jobs, Ray Dalio, or Marc Benioff swore by it.

If you only remember one thing from this letter, let it be this: Learn how to handle enormous amounts of stress.

This is super important since founder depression has become a thing.

“ If you’re troubled by uncertainty, I can solve that problem for you: if you start a startup, it will probably fail. Seriously, though, this is not a bad way to think about the whole experience. Hope for the best, but expect the worst. In the worst case, it will at least be interesting. In the best case you might get rich.” — Paul Graham

6. Contrarian

PG likes to say great work comes from people who see something and think “I can do better than that.”

Coincidentally (or not), those people tend to have “inappropriate” or “politically incorrect” thoughts. They’re also known as contrarians.

This makes sense. Successful startup founders are by definition betting against what most people believe is true.

This is why Peter Thiel likes asking: What important truth do very few people agree with you on?

One caveat, you need to be contrarian and right. Saying “the moon is made of cheese” does make you a contrarian, but at a terrible cost.

Are there any things you wouldn’t dare say out loud? If so, you’re on the right path.

Sidenote: If you need inspiration for controversial ideas, I highly recommend Sam Harris’ podcast. Of course the man himself is controversial, but so are some of his guests (e.g. Charles Murray, Ayaan Hirsi Ali, Gary Taubes, Scott Adams, etc…). It is a wonderful way to expand your mental horizon.

“To do good work you need a brain that can go anywhere. And you especially need a brain that’s in the habit of going where it’s not supposed to.” — Paul Graham

7. Hacker

A hacker is someone who can make a computer do what he wants — whether the computer wants to or not.

Sidenote: I know I know, some nontechnical people succeed. But if you’re going to start a startup, chances are it’s a technology startup. If so, learning how to code only increases your odds of success.

If Silicon Valley’s history has taught us anything, it’s that companies with hacker-centric cultures tend to succeed in a huge way.

  • Microsoft (back in the day) had a hacker-centric culture.
  • Google has a hacker-centric culture.
  • Facebook has a hacker-centric culture (in fact, Mark Zuckerberg said that in the early days, Facebook made a point of hiring programmers even for jobs that would not ordinarily consist of programming, like HR and marketing).

What good hackers like is other good hackers (hence why you might consider becoming one. If you’re a good hacker, you’ll attract great hackers).

At any given time, there are only about 10–20 places where hackers most want to work. If you’re not one of those places, you’re in trouble.

(image borrowed from this talk by Dustin Moskovitz).

“What you notice in the Forbes 400 are a lot of people with technical backgrounds. Bill Gates, Steve Jobs, Larry Ellison, Michael Dell, Jeff Bezos, Gordon Moore. The rulers of the technology business tend to come from technology, not business.” — Paul Graham

8. Nerd

Did your life suck between the ages of 11 and 17?

If you said yes, chances are you were a nerd in high school!

What’s a nerd? Someone who concentrates on substance. They don’t expend any effort on marketing themselves (you can usually tell this by the way they dress).

“Why is this a good thing for starting a startup?”

I’ll let PG answer this one for me.

“It’s hard to find successful adults now who don’t claim to have been nerds in high school.” — Paul Graham

In high school, nerds were training to get the right answers, while the popular kids were training to please others.

Getting the right answers sucks in school (you get bullied), but it’s incredibly useful in real life!

Another advantage of being a nerd is you don’t care about prestige.

Prestige tends to attract the wrong kind of people (if you’ve watched startup founders constantly promote themselves on social media, you know what I mean).

The best startup founders obsess over their product and their users. Not themselves.

“ If you want to make ambitious people waste their time on errands, the way to do it is to bait the hook with prestige. That’s the recipe for getting people to give talks, write forewords, serve on committees, be department heads, and so on. It might be a good rule simply to avoid any prestigious task.” — Paul Graham

9. Frugal

As you might imagine, this one is near and dear to my heart.

Starting a software startup is insanely cheap. The main cost is people.

If the founders can live really cheaply, they have a huge advantage (I talked about Ramen Profitability last week).

Thankfully, I spent months teaching you how to live as cheaply as (comfortably) possible. Reread those letters if you need.

Oh and then watch this old Jeff Bezos video. When you see a founder worth $10B driving a Honda, keep an eye on them.

“Poverty, might not sound like an advantage, but it is a huge one. Poverty implies you can live cheaply, and this is critically important for startups. Nearly every startup that fails, fails by running out of money.” — Paul Graham

10. Benevolent

Successful startup founders do very much want to get rich. But they’re also very benevolent.

These two things are not incompatible.

Startup founders wouldn’t want to get rich by speculating in stocks, they want to do it by changing the world.

Yes, this sounds naive. But it’s also true.

Think about it. If they were purely driven by money, they’d accept the first acquisition offer that came their way.

Instead, we’ve all heard the stories of successful founders who turn down huge acquisition offers. The reason for this is they’re driven by a (benevolent) sense of mission.

This also helps them attract the best people. Good people want to work with other good people.

Say what you will about Google today, but their “Don’t be evil” motto worked really well for them in the early days.

“If you’re benevolent, people will rally around you: investors, customers, other companies, and potential employees. In the long term the most important may be the potential employees. I think everyone knows now that good hackers are much better than mediocre ones. If you can attract the best hackers to work for you, as Google has, you have a big advantage. And the very best hackers tend to be idealistic. They’re not desperate for a job. They can work wherever they want. So most want to work on things that will make the world better.” — Paul Graham

And that’s it for today!

Today, we learned:

  • Age is just a number.
  • Be relentlessly resourceful.
  • Be obsessed.
  • Be intelligent (or knowledgeable).
  • Be cultic.
  • Be resilient.
  • Be a contrarian.
  • Be a hacker.
  • Be a nerd.
  • Be frugal.
  • Be benevolent.

See you next week (follow the series here to be notified).

Be well.

R

P.S.: Love the PG quotes? Me too. Here’s a final one I think you’ll enjoy.

“When we asked the summer founders what surprised them most about starting a company, one said ‘the most shocking thing is that it worked.’” — Paul Graham

Thanks for reading! 😊If you enjoyed it, test how many times can you hit 👏 in 5 seconds. It’s great cardio for your fingers AND will help other people see the story.You can follow me on Twitter at @richardreeze to find out whenever others just like it come out.📚 Do you like books? If so you might enjoy my latest obsession: 
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Since I write about finance, legal jargon is obligatory (because the guys in suits made me). Before following any of my advice, read this disclaimer.

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Richard Reis
Personal Finance Series by Richard Reis

"I write this not for the many, but for you; each of us is enough of an audience for the other." - Epicurus https://www.richardreis.me/