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The Helm

30 Rules of Entrepreneurship I Learned Before Turning 30

Obligatory picture of man on top of mountain giving the thumbs up because why the hell not

I went to school. Studied real hard. Went to college. Got a degree. Got my Masters. Got a job. Hated it. Started a business. Made a little bit of money. Then quit the job to be a full-time entrepreneur.

I’ll be the first to admit, I had no idea what I was doing. And to be completely honest… I still don’t. But over the past six years, I’ve managed to build an incredibly profitable, yet deliberately small business from scratch. Here’s a few things I learned along the way…

1. Nobody thinks you’ll make it.

Before I left my job, there was one line I kept hearing from people. Nothing stung quite as much as: “Well, you can always come back if it doesn’t work out…”

You can’t blame people for thinking this way. There’s a high chance you’ll fail. Even if you’re smart. Even if you know what you’re doing. Even if you come from a long line of entrepreneurs, you’re going to fucking fail. And you’re going to fail hard and fall flat on your face. And all of those people are going to say “HA! I knew it…”

Entrepreneurship means getting back up and fighting another day.



Changing course.


In the beginning, you’ll have haters and doubters. There WILL be a little voice in your head that says “What the actual fuck were you thinking? You’re not an entrepreneur, you’re an idiot…”

But the ones who make it are the ones who keep going.

2. Everything is going to take a lot longer than it should.

Nothing will test your patience like growing your business.

You’re going to have to be OK with this.

You’re going to have to be patient.

And when you think you’ve been patient enough and paid your dues… you’re going to have to be even MORE patient.

Every goal you have will most likely take twice as long as you think. But the time is going to pass anyway.

So put your head down and do the work and good things will start happening when you least expect.

3. You’re not going to make “real money” for a very long time.

My first year in business I made $0 and spent well over $10,000.

The next year I made $7,000. But I spent all of it (and then some) on learning, mentorship, and growth.

It wasn’t until year 3 when I was able to actually “pay myself.” And when I did, it wasn’t much.

I’m actually lucky. I chose a business (advertising & marketing) with high-profit margins. Despite this, it still took me a few years to have enough to reap any profit.

Understand this before going in. You might need to keep a day job. You might need a side hustle. You might need to do contract work while you build.

Get comfortable with this fact, because it’s going to take a lot longer than you think before you start earning like a real business owner.

4. Stay Lean.

It’s going to take a while to profit. It’s going to take even longer if you spend money like an asshole.

Most of us will have to learn this the hard way.

Most of us will chase shiny objects, spend for status and buy things we think we need… but we really don’t.

Forgive yourself for dumb investments. But don’t make it a habit.

The goal is profit, not topline revenue. And you can’t build a profitable business with holes in your bucket.

5. Spend more than your competitors.

Yes, I did just tell you to stay lean. And now I’m telling you to spend more.

Spend on acquisition. Spend on shortcuts. Spend on things that make the boat go faster. Invest in areas of your business that will produce a return.

Advertising is one of the best investments you can ever make. If you can profitably spend more than everyone else, you win.

6. People are going to laugh at you.

You’re going to look like an idiot.

That blog post you wrote. That video you posted. That shitty website you whipped together because you didn’t have enough cash to spend on a professional web developer.

Yeah… people are 100% laughing at you behind your back for the shit you created. I guarantee it.

You know what though?

It doesn’t fucking matter.

If you’re going to let this stop you, go get a job.

My wrestling coaches always use to tell us to get comfortable being uncomfortable. I think that advice applies here.

7. You’ll never be good enough.

Your version 1.0 of anything is going to suck. People might love it. People might buy it. But to you… it will always be flawed.

So, you’ll make a version 2.0.

And that will be better. But it still won’t be as good as you know it can be.

So you’ll make a version 3.0.

And you’ll freak yourself out… because it’s STILL not good enough.

This is business. This is life. This is art.

That is how this works.

The game is not won by achieving perfection. It doesn’t exist and your product can always be better.

The game is won when you dedicate yourself to never-ending improvement.

8. You’ll never be ready.

There has never been an opportune time to quit your job. There has never been a great time to start a business.

If you wait until the stars align, you’ll die.

Just get started and you’ll figure it out as you go.

9. You’re going to miss your job.


Sometimes you’ll wish you could just wake up and walk into an environment where things are figure out already. Where you don’t have to do everything by yourself. Where people get you. Where there’s some camaraderie. Where you’re part of a team.

There are days when I wake up and think “Why do I have to deal with this bullshit. Why can’t someone else just do this?”

As an entrepreneur, you are the leader. Even if you’re a single person business, you are the leader. You have to be.

Leadership starts with leading yourself.

10. People will fuck you over, rip you off and steal from you.

Get used to it.

The first time I got a chargeback for one of my courses, I flew off the handle. I took it as a personal offense. When I found out later on that person pirated my IP and is now profiting off it, I got even madder.

A few days later, my IP got pirated for the second time. Was I mad? Sure.

For about 5 minutes.

I realized this is just par for the course.

Some people are just scumbags. I can’t change them. I can’t control them. But what I can do is continue to build my audience and take care of my people.

Besides, if someone feels comfortable giving their credit card info to a scammer to buy your IP, they are probably a scumbag too. So you really can’t lose.

11. Your business is NOT a top priority for your clients and customers.

I’ve had hundreds of clients and customers. Almost all of them are incredible, awesome people.

I love them.

We have incredibly profitable, productive and happy working relationships.

And the #1 reason I think that is is because at the end of the day… I know they don’t really care about me.

They have their own lives, their own businesses, their own worries and fears and frustrations.

My business is not their top priority. Nor should it be.

We can have great relationships with the people we serve. And we do. But your friends are your friends. And your clients are your clients.

Be friendly, do nice things for each other, care for each other, lend a helping hand, be there for them when they need you, go above and beyond for them and care for their business like it’s your own.

But at the end of the day, just remember that these relationships will end one day.

You’ll die. They’ll die. You’ll go out of business. They’ll go out of business. You’ll sell, they’ll sell. You’ll fire them, they’ll fire you.

This will happen.

Sometimes breaks are clean. Sometimes they’re messy.

Just know what you’re getting into and always have an exit plan.

12. Without a mentor, you’re kinda fucked.

Why hack and slash your way through the jungle of life, when there’s already a well-worn path?

The people who succeed find mentors, learn from them and then put their own spin on the things they learned.

What you’re trying to do has probably already been figured out. Don’t make things harder on yourself.

Take shortcuts. Ride coattails. Pay for time and attention with important people.

This is the quickest way to get ahead.

13. An engaged email list is the greatest asset your business can own.

Every business I’ve worked with that has lasting success has an email list full of engaged customers, subscribers, fans and “brand loyalists.”

When you have an email list, you have all the people who are most likely to buy what you’re selling in one place.

It doesn’t matter if you’re writing an email broadcast to one person or to a million.

It takes the same amount of time, regardless.

It’s the ultimate form of leverage.

It’s the one method of marketing that allows you to consistently turn words into money, literally on command.

Learn email marketing and you’ll never worry about sales or marketing again.

14. Good products sell themselves.

As a direct-response copywriter… I was taught that even good products need incredible marketing to sell well.

Well, I’ve seen a lot of “good marketing” and “bad marketing.”

I’ve seen products with basic pages and mediocre copy sell like crazy.

And I’ve seen shit products with incredibly engineered sales funnels sell garbage products with 40–60% refund rates.

At the end of the day, you have to choose what kind of business you want to build.

I believe the people who find the most success have incredible products that can succeed even with lackluster marketing.

15. Start one-to-one. Then, get leverage.

When I show people how to start building an audience, I teach them to do something called “manual audience building.”

This is the act of building your audience, one person at a time.

You don’t get to 1,000 subscribers without getting subscriber #1. And you don’t get to subscriber #1 until you’ve helped at least one person.

FUBU didn’t appear out of thin air. Daymond John sewed hats by hand and sold them to one person at a time.

That’s how you start.

Now, as soon as you’ve proven the concept in a one-to-one scenario, the goal is to move to a point of higher leverage.

Every question you get can become a piece of content. Ten people ask you the same thing? Time to turn it into a blog post.

From here, you build more and more leverage into your life until your time becomes more in demand and more valuable.

You have to start one-to-one. But once you’ve figured that out, find ways to always move to greater leverage and profits with everything you do.

16. Replace yourself.

I don’t remember where I heard this: “The entrepreneur’s job is to find someone else to do your job.”

It’s brilliant.

That’s the whole game.

You just keep asking yourself: “Who can I find to do ___ for me, so I don’t have to do it anymore.”

Make a list of all the stuff you have to do to make your business run. That’ all the stuff you’re going to replace at some point. Keep that in mind if you want to grow.

17. Stay off social media.

Social media is heroin for your brain.

Every time you log on, you get bombarded with a hyperbolic version of reality.

You only see the best 1% of everyone’s lives. And most things are faked.

Most fitness accounts feature super jacked people “eating” (read: ordering, taking a picture, then throwing out) incredible looking food. Most success accounts are pictures of people with nice cars and houses they don’t own.

Look at this fucking meme I found on Instagram. Just fucking look at this…

You’re going to tell me that some douchebag hired a camera crew, rented a G-wagon, drove it across the median of a bridge, pulled out his laptop, climbed onto the roof of this $150,000 car… had the photographer take a picture… and then photoshopped a random success quote on top…

And this is where you’re going to get inspired?

These are the people you’re considering taking advice from?

Who. The. Fuck. Works. Like. This.

The answer:

No one!

The only thing that would be even sadder would be if this scene was photoshopped… and someone actually thought it’d be a good idea to ‘create’ this picture for inspirational effect.

Social media is the new TV. It’s designed to hijack your amygdala. It’s designed to distract you and mess with your emotions.

These companies have designed ‘infinity pools’ and they will take as much attention as you will offer. You can spend the rest of your life consuming their content and still never run out.

You need to guard your attention.

More importantly, you can’t let these people program your brain with bullshit and dumbfuckery.

We’ll look back on social media a few decades from now and realize it was both the best thing ever for society and the thing that destroyed us all.

So get the fuck off social media, stop consuming and start creating.

18. Be a leader.

Leadership is the most important skill you can learn. And you need to start by leading yourself.

Remember… your job is to remove yourself. The people who you hire to do that will need guidance.

Employees and contractors DO care about pay. But they’ll care more about vision and the fulfillment they’ll get from the work they do.

After the allure of more money wears off, the only thing that keeps people going is the vision that they’re working towards.

I know this because I was an employee and a contractor. The projects I hated most were the ones where the leaders lacked vision.

Don’t fall into the trap of complacency.

19. Consistency leads to compounding gains.

I’ve been creating content for 2.5 years.

For the first 1.5 years, nothing really happened.

Now I have a list, a book, multiple products, I speak on stage and get interviewed regularly on podcasts.

That shit didn’t happen by accident.

It happened because I showed up each week and put a piece of content out into the world and just never stopped.

20. Brands are built through advertising.

Advertising is how brands are built.

You business cannot survive unless it first becomes visible. And once it becomes visible, it must stay visible.

There is always someone out there who’s looking to eat your lunch.

Advertise more, more often, more profitably and you build the biggest brand.

21. Relationship capital is one of your most important assets.

As a copywriter, I realized the power of referrals early on.

Whenever I helped someone solve a problem, they tended to send a client my way every now and again.

I made it a policy to try to help at least one person a day.

Eventually, I had to start turning away clients because I was getting referrals coming out of my ears.

This doesn’t happen over night.

But it does happen as a result of going out of your way to help people, without the expectation of anything in return.

Your business is only as strong as the allies you have.

So focus a lot of energy on being cool and being helpful.

22. Owning your business is a 7-day a week job.

This is something no one tells you.

You pick up a copy of the Four-Hour Work Week, and you think: “This’ll be easy!”

The truth is, every entrepreneur works their ass off for a very long time. Even on the weekends.

When I was building my business, I did it on nights and weekends.

Four years straight of seven day weeks.

That’s what it took.

That’s what it takes.

The lifestyle entrepreneurs you see online pull all-nighters and work 20 hour days sometimes. They work weekends too. They just turn the cameras off.

23. Nobody will care about your business as much as you do.

I learned this from my first mentor, Zach Even - Esh.

It’s 100% true.

The people you hire, the people you work with, the clients, the customers… the might care, but only to a certain extent.

Again… it’s not their job to care about your business.

People will work hard for you. But they’re never going to go “as above and beyond” as you’d like… because at the end of the day, why should they? You’re the one getting rich.

Good leaders find other ways to motivate people to perform at a high level, while hedging for the inevitable discrepancy in maximal effort.

24. This is the most fun you’re ever going to have.

Everything I’ve said in this article kind of sounds gloomy.

You might be not even want to be an entrepreneur after reading this.

I promise you tho… this is the most fun you’ll ever have. Building a business is really about personal development.

The things that happen in your business are an external reflection of your thoughts and your vision.

Build something that’ll allow you to express yourself and have fun and help people.

It will be hard, but you’re going to have an awesome time.

A feeling of accomplishment only arises after prevailing through a struggle. Without the struggle, there’s no joy.

25. Hire people who are good at what you suck at.

I’m not great at doing taxes, so I hired an accountant. She’s incredible… and that’s one less problem I have to worry about.

I’m not great at doing websites. So I hired a web guy named Dave Toomey. (You should hire him.) He’s phenomenal. And he made all of my website problems go away. Again, one less problem I have to worry about.

I hired an integrator team because I’m good at thinking of ideas and bad at doing all the implementation.

Seeing a trend here?

Don’t work on your weaknesses. Find people who ‘play’ at the stuff you suck at and pay them to do what they do best, for you.

26. A business is just a collection of systems.

Abbey Woodcock taught me the importance of systems. She told me:

“If you don’t think there’s a system to what you do, there is. It might be a shitty system and you might not be able to see it… but it’s there.”

If you’re ever going to replace yourself and grow and make more money, you gotta understand the systems that run your business.

Every business delivers a specific result for specific people.

What is the result, who are the people, and how do you do it?

Figure that out and then optimize the shit out of everything you do.

27. You gotta tell your story

I pay very close attention to the discussions have with people on my email list.

I’ve talked to a lot of people who are former teachers… or who are trying to leave their job to become a writer.

It seems like the people who engage with me the most, have a story similar to my own.

This is called resonance.

Whatever story you tell, that will attract a certain kind of person.

When I talk about my transition away from my teaching job on a podcast, a lot of teachers join my list.

When I talk about how I was a Division 1 Wrestler and now I do BJJ, other combat athletes tend to reach out.

Your story is a tool to attract “your people.”

So get very intentional about the story you tell. Brands are built around tribes. Like Seth Godin says: “People like us do things like this.”

28. When in doubt, choose the simplest route.

I’ve been asked to create some pretty complex funnels for clients.

And despite my warnings, people have insisted that they need these extra layers of complexity.

These projects take tons of human resources, capital, and mental bandwidth.

And ya know what?

I don’t really think they out-convert super-simple marketing campaigns.

I’ve met a lot of entrepreneurs who spend months trying to engineer complex funnels… and they ignore my advice of just publishing content and sending emails.

You can choose to make your business as complex or as simple as it needs to be.

But there’s a reason why all the most successful businesses today started off with a one-sentence idea.

29. None of us know what we’re doing.

But that doesn’t mean we shouldn’t try.

Business is the art of figuring things out. Literally.

In order to grow, you gotta solve your current problems. And once you’ve solved those, you’re presented with new problems.

You either understand how to solve the problem. Or you find someone to help you solve the problem. Or you pivot and decide to play a different game.

I’ve worked with hundreds of clients, from pre-revenue start ups to $100,000,000+ a year companies.

Wanna know what they all have in common?

They are really good at certain things.

But by and large, most of us have no idea what we’re doing… and we’re literally figuring out everything as we go along.

Don’t think you have to have it all figured out to get started.

30. The sky is the limit.

If you want to be rich, you gotta be in business.

You’ll always be paid less than what you’re worth at a job.

But with a business, you have the rare opportunity to get paid multiples of the value you create.

If you choose this path, know that it’s going to be hard.

But it is fucking worth it.

Chris Orzechowski is an author, speaker and E-commerce email marketing strategist. Learn more about him at



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Chris Orzechowski

Chris Orzechowski

Author. Speaker. E-commerce Email Marketing Expert. Aspiring Wine Snob