Should you start a startup?
3 min read

Should you start a startup?

There are many resources around how to start a startup. There's not that much that explores whether you should start one. Here are the questions to consider before you dive in.
Should you start a startup?

There are many resources around how to start a startup.

Sam Altman writes wonderfully. Same with Paul Graham.

Tactically, there is a lot of great knowledge out there encouraging people to start a startup. There's not that explores whether you should start one.

I believe everyone should start a business.

And I think most people should try to start a startup.

However, startups have their own unique set of rules that people should know going in. Here are the 4 questions I’d deeply consider before starting a startup.

Are you ok with taking a massive pay cut, and having complete economic uncertainty for the next 5-10 years of your career?

When fired up to start a company, most people answer "hell yeah" when asked this. They’ve saved up some cash, their personal burn rate isn’t that high, and they’re just fed up with the rat race.

Fast forward a month without a salary, and they panic.

I felt this after selling my first business.

Despite almost unlimited personal runway, I felt a lot of anxiety around not having a salary. My burn rate was reasonable, but I had set the goal posts higher.

Coupled with stock market losses and macro-economic uncertainty, I needed to hard reset on what was important to me.

For people without the buffer - it’s 10x harder.

As Nassim Taleb says "the three most harmful addictions are heroin, carbohydrates, and a monthly salary."

Going cold turkey on your monthly paycheck fucks with your head.

Even if you’re ok with it, is your partner? Family pressure can be real. You need to make sure you’re fully aligned on the costs of burning through your savings, and the stress that it causes. That additional fear kills more startups than most.

Not having a steady salary until 5 years into my career was one of the main reasons I stuck it out so long - I didn't know what I was missing.

The best antidote is to start a startup earlier in your career. When I was 20 I didn't have anything to lose, and just needed to make cheap rent.

Set your expectations accordingly.

Can you somewhat enjoy the process?

I originally wrote “can you have fun with it?” here.

I don’t think that’s the right expectation.

Startups are really hard. They’re full of unique highs - getting your first customer, making your first 100/1000/1m dollars in revenue, getting featured in some exciting publication, building something new, making customers happy, meeting amazing people, etc.

For those highs, you’re trading off the fact that EVERY GODDAMN SECOND of your spare time will be spent worrying about something. From a massive existential risk to your business, to some annoying employee issue, to a line of copy on your marketing site that is still bugging you. This underlying anxiety is manageable, but it never fully goes away.

The first vacation I tried to take in years ended up with us getting DDOS'd while my dev-ops engineer was on a 6 hour plane ride. Seeing your net worth evaporate (not really, but it feels like it) every second your site is down is a unique startup experience.

My biggest regret of my last decade of work is not enjoying the ride enough.

Get your mindset right going into it, and you will enjoy it more.

I aspire to Tobi Lutke's view on startups as an infinite game.

The other things to optimize for in terms of enjoying your startup journey are

1) what are you working on?

2) who are you working with?

I messed up both of these, many times over.

Success can't be one of the criteria for enjoyment, because you will NEVER FEEL SUCCESSFUL ENOUGH.

Do you have a group of people that can help you do it?

Starting a startup alone is impossible. Do not attempt.

You can be a solo founder, sure.

But if you think you can sit behind your computer for 12 hours a day and pull a successful startup out of the universe - you are wrong.

Start with a coworking space.

Join one of 1000 accelerators. Get into YC, South Park Commons, Launch Academy.

Find your tribe of people that you can share the real shit with - the actual numbers. The stuff you don’t tell anyone else.

This is the only way to maintain your sanity.

Even if you fail, will you be glad you tried?

All this to say, you should still try it. Give it your best effort.

Understand that failure is likely.

Work on something that is so important to you (and hopefully the world) that even if you fail, it was worth the shot on goal.

If the above is true, you're more likely to succeed.

I'm rooting for you.

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