Entrepreneurial Resilience PART 1


This week is about failure.

And how it is essential to success.

The road to entrepreneurship requires failure.

It’s part and parcel of the process.

Yet it causes so many of you to bounce off and not achieve your goals.

Because of this we’re going to tackle the issue head on.

We’ll cover:

  • Part 1: I get knocked down, but I get up again
  • Part 2: Fail fast, fail often
  • Part 3: Mental tweaks
  • Part 4: Antifragility
  • Part 5: It’s dangerous to go alone

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Let’s get started:

I get knocked down, but I get up again

This took me a while. And was pretty painful!

But here’s a roll-call of my businesses.

  • bulk buying sweets and selling at school (pocket money)
  • selling pirated games (first cease and desist)
  • chipping Playstations (bricked a console, had to buy a replacement)
  • event promotion (rubbish at it)
  • film production (failed)
  • property data product (failed)
  • dropshipping (failed)
  • real estate investing ebook (failed)
  • Chinese language learning posts (failed, pivoted)
  • Chinese language learning digital posters (succeeded, automatic, low cash but something)
  • FBA business (failed)
  • niche blog like How to get Taller .com (lol)
  • language learning T-shirts (failed)
  • language learning reference cards (failed)
  • habit tracking app where trees grew over time with habits (built, failed)
  • 30 Days of Doing (failed)
  • Building Businesses Online (failed)
  • International Sourcing Platform (failed)
  • Out of the Box Business websites (failed)
  • Happy Knit Club (knitting kits, failed)
  • Email Sponsorship .com (revenue but shutted)
  • purchased an estate agency (failed)
  • Crushed Content newsletter (pivoted to Prompt Entrepreneur)
  • B Street Digital (digital agency, run for years, paid bills, shut down client work early 2023 to pivot to Prompt Entrepreneur)
  • Prompt Entrepreneur (ongoing)

Honestly there are more – but I got tired of going through old website domain lists!

I also, as anyone who knows me will attest to, have a terrible chronological memory!

You get the idea though.

Lots and lots. And lots. Of failures.

And a tiny handful of successes.

This is the norm. It’s just most entrepreneurs don’t talk about it out loud.

Here’s my favourite @levelsio tweet:


Talk to any entrepreneur and they’ll have a similar list.

The problem is that what most aspiring entrepreneurs see are the successes.

Basically survivorship bias – the only people you see left standing (and who have a big enough platform to be heard) are those who made it.

Just remember that their “overnight success” is generally years and years of complete disasters.

What about you?

Here’s a question – how many businesses have you tried to launch?

Zero? One? Two? Three? Four?

If so – it’s not enough.

You need volume.

Most (nay, all?) early businesses will flop.

And why wouldn’t they? You’ve not done it before!

Learning to do a backflip. Do you expect to land it first time? No.

Learning Spanish. Expect that first time ordering empenadas to go smoothly? No

But with business we for some reason have the expectation that the first idea, the first implementation, the first time is going to work. Nonsense.

Instead we, as entrepreneurs, need to keep stepping up to bat. It’s about gaining the skill of building a business as well as building the business.

Does that mean to learn, learn, learn first? Nope. Knowledge without action doesn’t build skill.

It means we need to build our first businesses as learning projects. We can hope but don’t expect them to hit immediately.

And we make sure that if they fail the failure doesn’t end our entrepreneurial dreams. We make sure that the failure is fast, small, cheap and doesn’t mentally hurt us. This will be what we’re covering this week.

If you are starting your first business (or simply a new idea to add to an ongoing concern) let’s use this prompt with your idea:

Act as a business strategist

My business idea is [provide details, as much information as possible]

Assume I have limited time, zero capital/assets. Use the lean methodology

Give me the first 5 steps of deploying this idea, each building upon the last and only being deployed once the previous has shown the business idea to be valid. 
For each step provide a description and precise, actionable definition of success/failure 

I’ll run this prompt with “selling custom jewellery”. It gives me 5 steps.

The first for example is :

Notice that this step requires no cash and very little time.

And there’s a distinct success/failure metric.

This allows us to test our business idea without going all in, spending money, building a team, designing a logo and all the other silly things people do when starting a business.

It’s this sort of focus on the trappings of a business (logo, business cards, business plan, fundraising, renting an office etc.) that makes business failure catastrophic.

Instead if we build step by step, testing and validating as we go we can keep each “failure” small and controllable.

We’ll get into more details about this in the next Part.

For now run the prompt with your business idea to get a set of sensible deployment steps.

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