It's been a really long ride at
I've been through the highest highs, and the lowest lows.
But now, looking back on it all, with $9.99 coming into my bank account every month
just like clockwork, I can definitively say:
It's all been worth it.
Here is the story of how I managed to turn 7 years of my life into cold, hard cash.
And not just any amount of cash.
$9.99 so far.
You can't succeed without starting
7 years ago, I was just another incredibly privileged highly-skilled software developer whose parents can support him indefinitely meaning he doesn't have to get a proper job and can risk it all on starting a business, even though his Uncle Les offered him a good, stable living as a junior accountant at his firm, as his mum never goddamn stops reminding him.
Today, I am the CEO of a successful startup.
How did I get there?
One day, I woke up and navigated to
You might not have heard of it if you aren't a software developer.
It's a place you go to buy startup websites.
It's really that simple. You think of a name, and then you go there and type it in.
seconds, you'll have results showing you whether your name is available.
For me, it took a few tries to get it right. I started off trying
business.com because I wanted my business to have a name that made it clear that it was a business.
But it was already taken.
So I moved onto
company.com. That was taken too.
Eventually I landed on https://cloak.ist.
The journey had started.
The long hard slog
But boy, it was one hell of a journey.
This is where another key startup concept comes in:
I wasn't always banking hot, fresh Benjamins from selling custom domains as a service, like I do now.
I went through 365 different products
a year before I settled on custom domains.
You might be thinking 'Huh, strange – that's the exact number of days in a year'.
You've hit the nail on the head. Cloakist started off by offering NCaaS.
They say you should start with a problem that you see in real life.
Well, in my mum's neighborhood, I saw hundreds of problems.
And there were people willing to pay for
all of them!
There was Mr Baxter, whose toilet got blocked by his cat. That was a particularly hard pivot to make.
There were many, many clients in the plus-age category who needed ambulatory assistance with regards to pedestrian activity.
In other words, they needed help crossing the road.
And there was teaching coding to the kids at the local primary school, until the bullying became too much for me to handle.
But here's why none of those NCaaS offerings could ever have worked:
I wasn't getting recurring revenue.
None of my customers came back for a second time.
It wasn't anything to do with me. I know this because my mum told me so. It was that the products I was offering weren't sticky enough.
I wanted – I
craved – my Stripe account filling up with money every month without me even having to do anything! Sometimes your customer is right under your nose
I still remember how it happened.
I had spent another night cranking on code in my mum's basement.
I came up to get some orange juice from the fridge.
A shoe came hurtling through the air at my computer, which fell and smashed on the ground. I lost all my code, because for 7 whole years I'd never figured out a way to back it up.
"You lazy, no-good piece of crap!"
My mum was angry.
seen her this angry.
I knew something had to change. And I got this twinkle in my eye.
"Mum, do you need a custom domain for one of your public sites like Notion, Trello, Airtable, or anything else?"
I'd found my first customer.
But boy, did she fight me on it.
I started off asking for $100 a month, to try and recoup some of the costs of working for nothing for 7 years.
My mum wasn't having it. She didn't understand what a custom domain was, and she didn't understand what a public site was.
That severely limited the amount she was willing to pay for my solution.
I offered $50/m. She said no.
I offered $20/m. She went to take out the trash. And when she came back, she still said no.
Finally, I offered $10/m. And...
She said $9.99.
And I said...
We both started crying.
Me, out of joy.
Her, I think out of sadness for what I am and what I've become.
But still – it was raw, unfettered emotion.
The MRR had started to pour in.
And who cares if it's tied to other conditions, like me moving out and promising to think again about Uncle Les's accounting firm.
MRR is MRR. It's as simple as that.
It doesn't stop there
The crazy thing about where I've got to now is how much momentum I'm feeling.
Next month, if all goes well, it's looking like I'll have $19.98 in my bank account.
The month after that, $29.97.
Because that's how momentum works.
Once you get it started, it just keeps going on its own.
Here's to the next 7 years!
Thank you so much for reading.
Give yourself a congratulations: you've just completed Startup Lesson 101: How To Succeed.
If you'd like to enrol in further classes, feel free to .
And if you'd like to read a true, but much more boring story about getting MRR, go