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Last week, I sent a newsletter explaining what I had spent on two investments, but didn’t include the total amount:

• $35,372 with a book publisher
• $30,000 with a YouTube agency

I explained that betting on yourself is the best way to come alive.

A lot of people wished me luck, and a few asked about my favourite resources to help think bigger.

So today, I’ll give you a concept that completely changed my relationship with risk.

The best bets are not as reckless as you think

The book and the YouTube agency are minimal downside, high upside moves.

Aside from the financial risk, there is no real danger.

It’s the monkey mind that f**ks us up.

You have something you want to achieve, but then doubt creeps in. What if you fail? What if you lose what you have? What will people think?

These thoughts become so pressing that they can consume you.

But it is just monkey-mind chatter.

You and I are running around with an outdated operating system. Fear exists to keep us alive, but we no longer live in a world where everything wants to kill us.

We are safe: the body just doesn’t know it.

If you can look at risk with rationality, you open up a world of opportunity.

Consider my bets…

The worst-case scenario is that I end up with a good book and more media. The best case is I catapult my brand to new heights.

—This is called an asymmetric bet.

And I have been obsessed with this idea since reading Nassim Taleb’s fantastic book, Antifragile.

Kieran Drew @ItsKieranDrew Just finished reading Antifragile. Was a fantastic book. So many interesting concepts, changing the way I think about risk. Two ideas I loved: the world needs more risk-takers (with skin in the game). And the barbell strategy. Many use cases in life. Would recommend. Next up 3:30 PM • Aug 22, 2026 31 Retweets 310 Likes Read 26 replies

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In the book, he explains the concept of Black Swans.

A Black Swan is a rare event with outsized results. He explains you have negative Black Swans as a result of stupid judgement, like the financial crisis on a societal level, or getting cancer through smoking despite knowing the risks.

But he also explains you have positive Black Swans.

And that you should be taking on as much INTELLIGENT risk as you can for the latter.

One example is writing online.

You might spend years sharing your thoughts for little reward. But then something pops off, and a huge influx of opportunity emerges as a result. For example, I only quit dentistry because I went viral after 13 months of writing with zero results.

It was the catalyst for a new future.

Starting a business is another example.

Nothing is going to happen when you make your first sales pitch.

But when you've put yourself out there a thousand times, there is a high chance you've changed your life. Especially because you learn the skills and mindset that set you up for decades of success.

With regard to my book:

The potential upside of a book is an outlier result. If this ends up being one of the most popular books for people who want to build their business through writing online, I become a trusted advisor in this space.

But if it’s a smaller lift, that’s cool too.

Because even if a few hundred people read it, that’s a small town's worth of readers who have spent 5-6 hours with my best ideas.

Plus, there are more benefits to taking risks than just the external reward. Writing a book was hard and took a lot of time. But it has made me a much better writer, and if I’m honest, a better person.

Because doing hard things shapes your character.

The problem is the monkey-mind cannot comprehend future potential. It is only focused on staying alive, so it creates elaborate mental constructs to keep you thinking small.

So long as you are ‘safe’, you are OK.

But staying safe is just another way of slowly dying.

So let me tell you how I approach making bets.

Everything is an experiment

When it comes to risk, you have two choices: you can freeze like a deer in the headlights and overthink until opportunity slips you by…

Or you step up into the arena and see how things go.

Which is why I treat everything as an experiment. This helps remove the pressure of an outcome. You cannot win or lose an experiment. You're just gathering data for what to do next.

Writing a book and working with an agency are two ‘bigger’ experiments.

But to get here, I have run hundreds more.

Starting a blog was an experiment.

Posting on social media was an experiment.

Starting YouTube was an experiment (I wrote earlier that I would just post 10 videos to see how things go, with zero expectation. I’ve posted 55 now. That’s a signal that it’s worth pursuing).

Every experiment pushes the boundary of what you think is possible.

Compare:

Person A does nothing, waiting for the ‘one big shot’ that never arrives (if you wait for the perfect timing, you will miss it).

Person B is constantly testing new things and finds the path as a result.

So here's my request to you, Reader.

Think about the goals you want to pursue in both your personal and professional life.

Then for each, ask yourself:

What is one experiment I could run this month?

You don’t need to know how things will end.

You just need to decide to start.

Have the courage to go for it,

Kieran

P.S.

Starting next week, I will release a 14-day email course sharing my favourite lessons around building a business through writing online.

You don’t need to do anything to receive it. I’ll spread the emails across November.

But if you’d like an entire blueprint…

You’d love my upcoming book, Magnetic Writing.

I’m aiming to launch early 2027.

But if you join 1,600+ people on the waitlist at the link below, you get early access to some of the material (there’s a free chapter already, and another coming soon).

​>>> Join the waitlist here.​

Appreciate your attention 🥂