Revealed: My Covert Strategy For Building This Newsletter

So you’ve read my $10m case study…

You’ve read a few of my emails…

Perhaps you’re one of the hundreds of people who have emailed in, telling me your own businesses. (Fascinating. Tear-jerking. Humbling. Inspiring.)

But did you ever wonder…

What the hell is Olly up to?

A few comments I’ve received over recent weeks…

  • “I’m curious what the end game is.”
  • “I admire your strategy of sponsoring others’ newsletters.”
  • “You must be INSANE giving away your case study for free.”

So I was thinking…

How’s about I tell you what I’m up to?

Today, you’re getting the behind-the-scenes:

  • Why I’m building this newsletter
  • Why I’m not selling anything
  • How I’m financing it
  • My growth strategy
  • Takeaways for you on strategic thinking 

Go on, admit it…

You’re just a tiny bit curious.

I’m curious too…

I have no idea what I’m going to write yet!


Why Build A Newsletter In The First Place? 

So, in case you’re new here (Hey!), here’s a quick summary of the situation:

  • I own a $10m business in the online education space
  • This newsletter is my way of documenting and teaching what I’ve learnt
  • I know it’s useful to others, but it’s also highly therapeutic for me to get ideas out of my head
  • I have nothing to sell (I’m fortunate not to need to)

So the question is…

(As someone commented recently on a Facebook ad...)

“If you have a $10m business, why do you need to do this?”

The answer?

I don’t need to do this.

But, the thing that non-entrepreneurs can never understand is that:

The game never stops.

Before you have money, you tend to think that money solves everything.

Once you have money, you realize it does nothing of the sort.

To be an entrepreneur is to feel obligated to create value in the world. You don’t stop creating value, hang up your boots, and sip piña coladas by the pool just because the number on your bank statements changes.

I’m thrilled with the success of StoryLearning.

But all that that success makes me want to do is…

Do more!

And “do more”, in my case means: Teach it!

I simply can’t help it.

I’m a teacher at heart. Perhaps with a splash of entrepreneur thrown in.

Can you relate?

So, why a newsletter? Well, in any new endeavour, I always ask: 

What is the unfair advantage I have that could make this a success?

If I don’t have an unfair advantage in some way, I likely won’t touch it.

For example, in my other business Creator Empires, we work with leading influencers to build original educational assets.

My unfair advantage in that business is that:

  • I know the influencer world really well (i.e. I’m one of them)
  • I’ve built tones of education businesses myself (i.e. rock solid proof & credibility)
  • My business partner is a world-class executer (i.e. we can do a seriously good job)

When it comes to this business newsletter, here are my unfair advantages:

  • I know my s*** (10+ years)
  • I have legit credibility (from my main business)
  • I’ve mentored many entrepreneurs (I understand my audience)
  • I’m good at writing (and can keep it up for long enough to succeed)
  • I have cash to spend to accelerate growth

As such, when I was thinking about starting to teach other educators to grow their businesses, and thought about all these elements…

I looked at the idea of creating a newsletter for online education entrepreneurs in the cold hard light of day, and thought, with all humility: “It’s virtually impossible for me to fail at this.”

And, as a fellow-entrepreneur, I know you’ll understand when I say, it’s basically impossible to let go of an idea like this once it takes hold.

And so here we are.

You and I.

Sharing this moment.

Isn’t it cozy?

What Do You Believe?

business building beliefs

In the opening, I told you a bit about my personal reasons for starting this newsletter.

Here are some of the more “macro” strategic beliefs I have that led to me pulling the trigger:

  1. Audience - My fundamental belief is that audience is the single most valuable asset you can own. When you have audience, you always have options. (It’s how I grew from the ground up.)
  2.  Value of audience - The cost of acquiring audience (e.g. Facebook ads) has grown exponentially over the last 15 years, and will continue to accelerate. I believe this makes the future value of my audience even greater. 
  3.  Online education - Online education is only just getting started. I believe the next 10 years will see ever-more people teaching their expertise online, and needing help to do so.
  4. Skillset & credibility - I believe I have the skillset and credibility needed to make this work.

Beliefs are a funny thing.

When I first got started with my blog back in 2013, I didn’t have any beliefs.

I just had the idea and got on with it.

But the more time you spend around higher-level entrepreneurs, the more you see people operating based on beliefs, and having complete faith in those beliefs.

Richard Branson gave an interview recently where he said something to the effect of:

“When I move into a new industry, I don’t really have a plan. I just believe that if I take an existing business model… and make it 10% better… it will succeed.”

The great thing about this is that…

When you have strong conviction in your beliefs, it’s a lot easier to stop sweating the details.

It’s another way of saying…

Get the big calls right and the small decisions take care of themselves.

We’ll circle back to this at the end of the newsletter, when I’ll give you some takeaways to apply to your own thinking.


All this talk of beliefs is pretty important to understanding the next section - how I’m paying for it all!

    How I’m Funding The Newsletter?

    Having spent 10 years growing, one of the things I know about getting a new project off the ground is…

    Building audience takes time!

    And since building audience takes time, consistency is king.

    (If you read my case study, this should be crystal clear!)

    So, when it came to finances, I wanted to make sure I put my money mindset in full alignment with my plans.

    This meant I wanted to have a clear idea of the budget I was going to put into this project, and over what period of time.

    I needed to avoid slipping into “bank balance management” on this project, whereby the amount I spend depends on whatever is in the bank account on any given day. (= reactive spending)


    None of that.

    I’ve done too much of that in the past to know that it’s a recipe for disaster – too much deliberation, vulnerability to emotions, and inevitable under-spending.

    (Read this edition on money mindset if you want to know more.)

    Instead, I wanted to make sure that the flow of cash into the project was fixed, regular, and ongoing.

    Here’s what I did:

    • I allocated an overall seed budget of $200,000 (this is “get it off the ground” money)
    • I loaned this entire sum to a third party at 20% interest, repayable over 20 months
    • This created a monthly inflow of $12,000 for 20 months straight

    This way, I could entirely remove the question of “How much should I spend this month?” from the equation.

    My job is now simple…

    All I have to do is spend the money that’s coming in each month!


    I’m not saying this is the right way to do things.

    Or that you should do this yourself.

    It’s just that – knowing myself, and my own tendencies around money – this is what was going to work best for me.

    It creates the kind of abundance mindset that tends to make creativity in work easier.

    Perhaps you see now why the earlier discussion on beliefs was so central to this? The only reason I can commit to something like this is that I have complete conviction in the outcome.

    Newsletter Growth Strategy

    So far, I’ve told you about the “why” of the newsletter, and how I decided to finance it.

    There’s just one thing left…

    The small matter of creating the newsletter!

    (A.K.A. “Doing the work”)

    As I was thinking about the framework for the newsletter, I knew it was vital to keep things simple.

    For something to grow and gain traction, it doesn’t need to be complicated.

    You just need to get the key ingredients right.

    For me, here’s the formula for the newsletter:


    (Apply this formula to any media property, by the way. You can’t fail.)

    Let’s take this one-by-one.

    First, the laser-targeted audience.

    Here’s my audience:

    I write this newsletter for online education entrepreneurs who want to scale to 7-figures.

    Obviously the newsletter can be relevant for people who don’t precisely fit this criteria.

    But I’m writing it strictly for that avatar, because that’s the audience I want to cultivate.

    That’s the audience who will start salivating at the lips when they read the content, because it feels oh-so-perfect for them.

    Next, the world-class content.

    For all the reasons given earlier, I believe I’m one of the few people in the world who can write such a newsletter to this level.

    The tricky thing is to actually do it.

    To be clear…

    There are many people out there with my level of expertise (and far beyond) in online education business.

    But are they actually going to sit down and write a newsletter about it, day after day, year after year?

    If they are, I haven’t seen it.

    Many people get all excited and start something. But...

    As soon as life gets busy and the novelty wears off, they’re gone faster than the babysitter’s boyfriend when the car pulls up.

    But me?

    When that car pulls up I stick around and face the music.

    And if that means taking a smack in the face when the front door opens… so be it.

    Getting roughed up is all part of the process!

    When I start something, I stick around… even long beyond the point of reason.

    It’s what I’m good at.

    Shortly before I started the newsletter, I re-read The War of Art by Steven Pressfield… and boy am I glad I did.

    I decided to surrender to the work.

    The routine.

    The rhythm.

    The art of creation.

    And so now, every day, I sit down a 9am and write for 3 hours.

    That’s it.

    I’m doing it right now, at 09:42 on a Thursday morning.

    Come what may, that’s what you’ll find me doing, Monday to Friday. At current pace, I can churn out 2.5 newsletters a week in that time. This gets me 1.5 newsletters ahead every week, which is what ultimately creates freedom.

    (Discipline in the small things creates freedom in the big things.)

    A lot of the time, I’m writing from my favourite café, looking over the beach.

    And no…

    I’m not telling you where it is… don’t even think about asking!

    So, to repeat… the world-class content is something I can - and will - do.

    Lastly, Amplification.

    Here’s a lesson that’s been learnt in the school of hard knocks over the years…

    You’ve got to learn to market what you do.

    Take your pride, lock it in a box, and throw away the key.

    Derek Halpern used to say that your time should be 20% content creation, 80% promotion of that content. And while your mileage may vary on the percentages, the point is well-taken.

    If you’re writing truly world-class content, then you’ll get the success you deserve in the end.

    But in order to reach escape velocity, and to get that content out into the consciousness of your target audience, you’ve got to:

    Hack your way up the mountain, step-by-step, with bloodied hands, climbing over the dead bodies of would-be content creators who thought marketing was beneath them and couldn’t stay the course.

    Amplifying content means using the levers of the internet to get more eyeballs in front of the content.

    • Social media
    • Paid advertising  
    • Email marketing 
    • List swaps
    •  Etc

    Marketing tactics are ten-a-penny, but in my case, I decided to do two things:

    • LinkedIn and Twitter - “Repurpose” the raw content I put so much energy into each week and use it to build a following on the two platforms that make most sense for my niche.
    • Newsletter Sponsorship - The principle here is to get directly in front of my target audience, which I do by sponsoring relevant newsletters.

    (I’m also running Facebook and Instagram ads for the newsletter, but I’m not clear if I’ll keep that up, as response and quality is poor.)

    And so that’s Amplification.


    To take it back to the “unfair advantage” discussion, remember that I have the following in my favour when it comes to executing on this:

    1. I have the time to devote to creating great content  
    2. I have the resources to put towards amplification  
    3. I don’t have to sell anything to fund it

    If that sounds like a lot to you, remember that this can all be done using time rather than money.

    It’s just that, if you have the resources available, it allows you to do more, and faster.

    So why not?

    (By the way, right now, I’m trying to get my Twitter off the ground. If you’ve enjoyed this so far, could I ask a favor? Follow me on Twitter here and leave a comment on one of my posts. Things are still small enough that I can check and reply to every comment!)

    4 Mindset Questions To Help Grow Your Business

    For me, the thing to take away here isn’t the “tactics” of what I’m doing wit the newsletter…

    But rather the mindset around growing something new.

    Here are some questions to ask, if you want to challenge yourself around strategy:

    1. What are the core beliefs that are underpinning your work? (Internal - about yourself. External - about your industry and the wider world.) 
    2.  Are you working to an explicit timeframe? Have you squared that timeframe with the time and resources you’re willing to devote to the project?
    3. What are you willing to invest in? If you won’t put your money where your mouth is - why not? Do you truly have convictions behind your beliefs?
    4.  Have you structure your finances to create an abundance mentality? Could you structure cash-flow in such a way that empowers you, rather than being a source of anxiety?

    So there we have it.

    In this newsletter I’ve told you about why I’m building this newsletter, and how I’m paying for it.

    Then I covered what the work itself looks like, and the formula that I believe will grow it.

    Lastly, I left you with some questions to reflect, for your own project.

    If you know someone who’s trying to grow a content business, I’d love it you hit “forward” and send them this email.

    Got a question?

    Head over to Twitter and ask away!

    And if you're not subscribed to the newsletter, then, by Jeeves, go ahead...

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