Gratitude, Humility and Simplicity

I can’t imagine anyone enjoying today’s newsletter.

In fact, it’s going to be a bit grim.

Stuff that’s liable to keep you up at night.

Not that it’s my goal to depress you, mind…

It’s just that, sometimes, the only thing to do is to call it like it is.


If you pay close attention, you will also find things to inspire you.

Lift you up and give you hope… like a miracle bra for the soul.

See, this is stuff that’s been on my mind recently.

I’m struggling to shake it off.


And that’s usually a sign I need to write about it.

So, I really don’t know how this will go down…

But you can take comfort in the fact that, by writing this, at least I’m doing something useful for myself.

I Want Nice Stuff, Dammit!

Recently, the legendary Frank Kern told a story on his podcast, which I think is worth paying attention to.

It was a story about success.

Or rather, about the pursuit of success.

He was talking about how, earlier in his career, he started desiring a lot of material things.

Here’s what he thought:

“If I’m going to work hard to get things, I may as well buy the stuff now and then work hard to pay for it. That way I get to enjoy it now!”

So, he went off and bought a bunch of fancy lifestyle s***, presumably on credit…

I’m guessing cars, houses, that kind of stuff.

But years later, he had a change of heart:

“Eventually, I figured out that all that stuff doesn’t matter anyway.”

Then the kicker:

“So it’s better to just live your life… and not care about any of the stuff.”

Why do I tell this story?

Because so many entrepreneurs I meet feel inadequate for not being more successful.

They feel like they should be mega rich, and have stuff.

Like the guys on social media with their Rolexes and tales of millions.

They feel that the whole world is ahead of them.

But the truth of the matter is…

While some entrepreneurs have become obscenely successful and rich…

The vast, vast, vaaast majority are not.

If you knew the truth about what most entrepreneurs go through…

You’d feel a lot better about yourself, frankly. And have a totally different perspective on life.

Next, I’m going to offer some cautionary tales that demonstrate why this is true.

Then, I’ll tell you what I think this means for the likes of you and me, so we can live a happy and balanced entrepreneurial life.

Is EVERYONE Driving A Bugatti?

I know a lot of entrepreneurs.

Probably more than most.

I’m a big networker, own multiple companies, have an audience of 15,000 business owners…

I see a lot of stuff.

And here are some recent experiences I’d like to share, that represent the TRUTH about what entrepreneurs actually go through.

(When they’re not bragging on Instagram.)

1. Post-exit founders

I know many people who have sold their business for 10s or 100s of millions.

Most of them are confused and unhappy.

Usually, they’re divorced/separated.

Such is the chaos of post-exit life, they all immediately start searching for the next business in order to feel “normal” again.

If selling a business for 100s millions is actually good for you… I have yet to see the evidence.

2. Business collapse

A friend of mine recently told me how he lost 90% of his organic search traffic overnight.

His business is on its knees.

I’m sure he’ll recover, but after 15+ years in business, this is a terrible blow.

3. Family trouble

A close friend’s marriage is on the rocks.

He feels he has no choice but to split with his wife and leave the house and their two kids.

4. Lost empire

Yet another friend borrowed millions to buy dozens of online businesses.

He wanted to roll them up and create a larger company.

It was all fine until costs got out of hand, he started to default on loans and he had to start selling assets to avoid bankruptcy.


Another friend split up with his girlfriend.

No big deal, you might think.

Except his girlfriend ran the backend of his whole business.

He’s spent the last 3 months drowning in admin and racing to replace essential tasks.

6. Business shutdown

One entrepreneur friend recently had his YouTube account shut down.

Taken away, like a lollypop from a baby.

The channel was hacked, so YouTube decided to just shut the whole thing down.

$25k/mth in revenue… gone.

And you can’t even get anyone on the phone.

7. Angry customers

I recently heard a podcast episode with Ryan Pineda interviewing my old mentor Russell Brunson.

He described how they screwed up Clickfunnels (his famous software) a few years back, and had 2-3 years of development hell with people cancelling their accounts and the reputation of the software left in tatters.


I could go on.

But you get the idea.

Oh, guess what –

Nobody posted about any of this stuff on Twitter.

Funny, that.

This, my friend, is the reality you never hear about.

And these are just some of the people I know! Imagine what else is going on!

You know how there’s nothing like a funeral to make you take a long, hard look at how you’re living your life?


After hearing endless stories like these recently, from people I care about…

It’s made me reflect very deeply on my own entrepreneurial life.

Think long and hard about what I actually value.

Here are the lessons I’ve drawn…

How To Avoid Losing Your Shirt

In no particular order…

1. Downside risk

You know how everyone is “All in, bro!”?

F*** that.

Protect your downside.

Make money, yes.

But then take something off the table.

When the day comes that you’re staring into the abyss, you’ll be grateful you did.

2. Large numbers

Stop dreaming of large numbers.

Nobody cares.

It’s just your ego talking.

You don’t need a huge exit to live an incredible life.

More than likely, it’ll mess you up.

Instead, build self-sustaining cashflowing assets:

  • Digital products
  • An audience that buys everything you make
  • Rental properties
  • Index fund investments

My friend Rob asks: “How many different ways can I make £10k a month?”

Now that’s a question.

(I might make a workshop on that. Would that be interesting?)

3. Keep costs low

Keep costs low and margins healthy.

High costs usually mean lack of discipline.

And lack of discipline is like a sleeping bear – it’ll kill you eventually.

Maybe not today.

But sooner or later. And when you least expect it.

4. Be the best

Here’s the easiest way to make a LOT of money, while avoiding the trap of “more”, and keeping costs low:

Become the best at one thing

Like I taught in One Person Empire, when you understand your point of maximum personal leverage, you can create a simple, highly-profitable and very stable business that you can live from forever.

5. Timeless assets

Being the best at one thing means creating timeless assets.

Timeless assets will pay your way for years to come – people remember them, value them, share them.

So if you’re wondering whether to write that book…

You probably should.

(I’ve published over 100.)

I wrote a 118-page case study for that reason.

And you know that YouTube video you spend a whole month working on?

It was time well spent.

6. Avoid shiny objects

From #5, it follows that you should avoid getting distracted by shiny objects.

They don’t work out 99% of the time.

They distract you and slow you down.

They also increase risk and complexity, which can be a death sentence when things don’t go to plan.

7. Cascade expertise

While you shouldn’t chase shiny objects…

You should learn to cascade your expertise into related opportunities.

For example, my main business is StoryLearning. That’s where I learnt my trade.

But I’ve used that expertise to become part-owner of multiple other language learning businesses:

…which allows me to use my expertise to grow enterprise value in the exact same vertical, with very little of my time needed.

This creates more stable, diversified income, and makes you harder to shake.

8. Presence

Chasing “more” anchors you in the future.

You can’t be happy when you’re stuck in the future.

Instead, learn to be present.

That doesn’t mean you can’t be ambitious.

It means avoiding attachment to future outcomes, which causes anxiety.

As far as I’m concerned, presence is the key to the Good Life.

But that sounds rather grandiose.

So I’ll just say: “It’s a big deal!”

Read Michael Singer.

Or any Mindset posts on my blog.

Figuring this out will help you stay grounded when you do get tested.

9. First principles

I’ve worked hard over the years to adopt a “first principles” approach to life.

It means figuring out the parameters you want to live by – and sticking to them.

Doing this simply helps you to be:

  • More happy
  • More of the time


In recent moths, I’ve been shocked by the ups and downs that I’ve observed entrepreneurs go through… first hand.

It’s great to be ambitious.

But, increasingly, I also think it’s important to grow responsibly, and protect your downside.

If you’re ever faced with getting it all…

Or losing it all…

I’d wager that you’d give your right arm to avoid the fate of the latter.

And so it pays to ignore the bullsh*t hype of “All in!” entrepreneurs on social media, and intentionally build resilience into your business.

Even if that means going slower.

Even if that means fewer bragging rights.

When all is said and done…

You’re only accountable to yourself

I’ve taken these lessons to heart in my own businesses, and the key lessons for me are:

  • protect your downside
  • keep costs low
  • become the best at one thing
  • create timeless assets
  • avoid shiny objects
  • learn to be present

In the end, it all comes down to figuring out the parameters you want to live by and sticking to them.

This “first principles” approach to life can help you be more happy, more of the time.


That’s yer lot.

Probably not what you were expecting at 5pm on a Friday.

I hope I haven’t put you off your sushi.

Next week, I promise to lift the mood, like Viagra in a retirement home punch.

Just you wait and see…



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