Part 4: Antifragility Principles - Building Entrepreneurial Strength Through Stress and Diversification

Let’s talk about Antifragility.

It’s a very cool concept from Nassim Nicholas Taleb. His ideas are powerful for entrepreneurs but hidden somewhat amongst his dense books.

I recommend his books by the way but do understand they can be HEAVY!

We’ll cover the basics in this Part.

Let’s get started.

Antifragility is a rich concept that is hard to encapsulate in a newsletter.

I’m going to cheat a bit and use this great infographic:

Most people know about fragile and resilient systems. Scaffolding is a great example here.

In the West we tend to use steel scaffolding poles. They are strong, rigid, hard to break.

In the East though, especially in typhoon prone regions like Hong Kong, they use bamboo scaffolding.

If you’ve not seen it before it’s really quite amazing:

The reason for this is that steel scaffolding snaps in a typhoon. It’s strong until it’s not. And when it is overwhelmed it breaks. It’s Fragile. Bamboo scaffolding on the other hand flexes in the wind. It may not be as absolutely strong as steel but it can weather stresses. It ignores the strong winds by moving with the stresses. It rolls with the punches. It’s Resilient. Antifragile on the other hand doesn’t just weather the stress. It gets stronger.

The more stress the stronger it gets.

This is something new. And exciting.

Get swole

Weightlifting is an amazing example here - you build muscle by actively putting it under stress repeatedly.

We need to do this with our entrepreneurial career too.

We don’t want to just be resilient. We want to go beyond and actively stronger the more stressors we experience. We’ve talked about how already. Stressors in entrepreneurship come from failure. Again this is the same in weightlifting. If we lift very light weights again and again and never really push ourselves we don’t get stronger.

We get stronger when we take ourselves to (or close to) failure. Training weights is basically a process of going to failure, backing off, going again, backing off, going again…all with sufficient rest to allow us to return stronger each time.

We do the same with business. We need to seek the hard stuff, the chaos and the volatility. And within that area we create and build.

When we fail, we learn.

And we make sure that we can bounce back from each failure stronger. We learn and apply that learning.

We become antifragile

What about AI?

Artificial intelligence is the ultimate stress test for humanity.

It’s putting skills, jobs, industries and potential the whole of capitalism under stress.

Here is someone much smarter than me discussing this:

https://www.youtube.com/watch?v=2w37ty9gGU8

Around the 2 min mark, Harari says that this is the first time in human history that we have no idea what the world will look like in 20 years.

I agree.

I studied history at Oxford and whilst nowhere near Harari’s level of comprehension (obviously!) I know enough about historiography to know that this time it’s different. This is new.

For those who are antifragile though, change and volatility is a good thing. The antifragile gets stronger amongst chaos.

We are right now looking at immense opportunity. If you are ready to grab it.

OK but HOW?

What about the practicalities of how to become antifragile in business? There are many ways so I’ll just highlight a few here:

• Diversification
• Personal Brand
• Barbell strat (Premium)

Diversification.

Do not rely on one single stream of income. We do not know which income streams will remain relevant. So we need to have a range of income streams live in case one gets destroyed. In my videos I often get great wits saying “ haha lol can’t wait for AI to take your job”. I respond -"fair. But I have many jobs for this exact reason". Right now I have 6-8 revenue streams in action within Prompt Entrepreneur alone.

Because of this I know that if one gets knocked out (and I'm sure they will) I have others up and running. I've been caught out before when a single source of work suddenly dried up. It isn't pleasant.

And AI will make this more of an issue. A new AI tool might drop tomorrow that suddenly wipes out a function. At the time of writing this for example a software engineering AI called Devin just dropped. Just last week I've had conversations with software developers who were singing the " AI isn't good enough to take my job" hymn. Devin seems to have changed their tune - suddenly I'm seeing a lot more software developers calling for regulation and slow down on AI. This tells me that Devin is good…and they are worried. This can (and will) happen at any time. Meaning that relying on one source of income is now extremely fragile. This applies if you have a job. And if you have a business with a single primary revenue source.

Personal Brand

I know I go on about this one a lot but it's important.

You are unique.

Your particular blend of character, background and skills is unique.

Even if one of your ventures fails and you need to move to another you act as a continuity. If people like you and the stuff you do then you are less fragile. In fact your failures become part of your story. People love underdogs!

Building in public or simply talking about your business publicly helps make you antifragile by strengthening your personal brand.

Being known is a super power. And this will be even more the case as bland faceless AI takes hold of most interactions.

Premium Prompt - Barbell Strategy

Barbell strategy The barbell strategy is another idea from Taleb

The idea of deploying a barbell strategy is to avoid the middle.

The middle is where dreams and aspirations go to die.

Instead make the majority of your income/investment is a safe bet.

If you have a 9-5 job keep it. For now!

If you have steady client work that doesn't excite you but pays well, keep it.

If you have these sort of low risk, low upside income streams you have a stable base. This gives you breathing room.

The rest of your work should be wild-ass big bets. Moonshots. Things people will laugh at you for trying.

These will (mostly) fail. And that's fine! We only need one to kick off for us to do wildly well. In my case my digital agency B Street Digital has always dripped in regular income. It pays the mortgage and bills.

Which in turn allowed myself and business partner to make big bets on other projects with high upside. Prompt Entrepreneur is one of these - one that worked. Very well.

It's important that you don't immediately go all in only on the big bet. If you do so without large savings or external funding you've put yourself on a clock. The big bet has to work or else you lose the house. Oopsie. This leads to you making decisions from a place of fear and scarcity. And you'll make bad decisions in this place.

Instead keep your safe bets running to pay the bill and take big swings on the side until one big bet pays off.

Pulling it together

Antifragility is a topic that we could go into a lot more depth on.

This Part has acted as a primer but I recommend you look into it more - perhaps even reading Taleb's book if you want to go deep.

A reminder of what we'll be covering :

• Part 1: The upside of downfalls
• Part 2: Fail fast, fail often
• Part 3: Mental tweaks
• Part 4: Antifragility
• Part 5: It's dangerous to go alone