Growth strategy update – Optimising for Intimacy (Vol 2)

Yesterday, I went for a long lunch with my friend, author and top podcaster Rob Dix.

We talked content strategy, personal brands, and alignment.

Rob and I are going through similar evolutions in our businesses. This makes our conversations incredibly productive.

Spending 2-3 hours with Rob is a bit like realizing you’ve been wearing the wrong prescription glasses for months.


You slip on the right pair, and the world suddenly comes into sharp focus.

So anyway…

Lunch ended up being a big ol’ strategy review for both of us.

And I’m going to tell you about my conclusions from that conversation today.

Most of my newsletters are giving advice in some form...

By being open about how I’m thinking about strategy for my own business, you’ll get to see how my ideas get applied in a real context.

State of My Newsletter


Here’s the state of the newsletter since my last update 6 months ago:

  • As of September 2023, the newsletter is 8 months old and this is issue #32 (Phew!)
  • There are c.10,000 people on the newsletter 
  • Average open rates are at 52%

I’ve begun monetizing far sooner than expected, in two ways:

  1. A 5-day marketing workshop that I delivered live last week (recordings here)
  2. Mentoring a number of entrepreneurs 1-to-1 to scale their businesses. (This isn’t something I’m offering publicly, it just came from direct requests for help.)

Why monetise?

After all, as I mentioned in the March update, my intention was simply to build audience for a few years, and decide what to do with it later.

Here’s what happened:

Over the last few months, I’ve now figured out how to reliably reach my ideal audience:

  • Newsletter sponsorships
  • Twitter ads
  • Twitter / LinkedIn organic
  • Podcast appearances
  • Referrals (esp. from the Case Study)

However, this stuff is expensive, and I’ve spent well over $75,000 on sponsorships, ads, managing organic social, podcast booking services etc, plus hundreds of hours of my own time on writing.

Now, that’s all good…

It’s what I was expecting…

But, if you’re using those kind of resources, sooner or later you need a sense check on whether you’re deploying those resources effectively.

My question was simply: Am I reaching the right audience?

(6-7 figure online education business owners.)

Just a bit of indicative data.

After all, without data of any kind, the risk is waking up in 2-3 years with an audience of non-buyers, and a $250k black hole where my bank account used to be.

No bueno.

So I stuck a wet finger in the air and pointed it at the wind.

The result that came back:

I generated 2X in revenue what I spent on growth this year.

In other words…

For every $1 that I spend, I’m making $2 back. (Or 200% ROAS in hustle-bro terms.)

Now, I don’t plan to talk much more about revenue, because I’m not a fan of building in public. But it’s important for the strategy conversation, because this means:

The newsletter has reached self-sustaining growth.

Which is to say…

Everything I spend on growth pays for itself. (A few times over.)

And what does any self-respecting entrepreneur do in this situation?

That’s right, Jack…

You pour as much money as humanly possible into said growth!

So, to summarise:

  1. I tested monetisation in order to get indicative data on audience value
  2. Having established the audience value, I’ll continue to generate revenue in order to plough it right back into growth

Finding Alignment

In March, I wrote about a “slump” that I was feeling:

  • My growth strategy was plateauing
  • Unfinished things were bugging me
  • I’d started comparing myself to others
  • My “business” model was out of alignment

This stuff has been mostly resolved now.

The comparison thing was a strange one. In retrospect, I think that was just because, at the time, the only available metric I had to pay attention to was “audience size” – social followers and newsletter subscribers.

And judging yourself on vanity metrics like that is a losing proposition from the start – there’s always someone with bigger numbers than you.

I found that the arrival of revenue pretty much completely did away with that, because it validated the fact that even a tiny list was going to be extremely valuable.

So, all in all, I feel in a good place.

So this brings me to my lunch with Rob.

He asked me a phenomenal question:

What would you do differently if you had 250,000 followers today?

I thought for a moment.

The answer didn’t take long:

Absolutely nothing. I’d still be here having lunch with you.

Reality checks like this are incredibly valuable.

  • You’re chasing something
  • Once you get it, nothing will change
  • So why are you chasing it?

You could just chill out and enjoy the ride instead.

It exactly what I wrote about in Non-Attachment and Business Success.

I need these reminders on a regular basis just to stop fixating on the future, and to be present in the here-and-now, because attachment is the root of all suffering.

(Why do you think I write about this s*** so much? I need to remind myself all the time.)

Optimising for Intimacy

With that said…

That doesn’t mean I’ll just sit on my backside and do nothing.

Rather than go meditate in a cave, the question is more:

Given what I know, what’s the optimal way to spend my time and resources?

And the truth is, I have more revenue coming in than I can spend right now:

  • There’s a hard limit on the newsletters I can sponsor with my ideal audience
  • I don’t want to over-index on Twitter ads
  • Growth on organic social is more a question of “time” than money

So then, I ask:

Of all the content I produce, what element is missing?



I know my content is highly relevant for my target audience. And by doing newsletters, podcasts and social, I’m getting distribution.

But intimacy is missing from that, and the work I plan to do with entrepreneurs requires intimacy in order to build trust.

The way to generate real intimacy is with either podcasts or video.

I don’t want to start a podcast, because growth isn’t there…

Which leaves video.

Therefore, my best use of resources right now is to do long-form video.

I talked this through with Rob, and we discussed the Ferriss-eque question:

What would this look like if it were easy and fun?

And we had some ideas…

Boy, did we have some good ideas…

But rather than tell you what those ideas are, I’ll wrap it up here and send you over to my new-look YouTube channel when it’s ready to go.


So, that’s it for today.

I’ll leave you with a photo from this week – the first in a series of dinners I’m holding for UK-based online entrepreneurs:

Entrepreneur Dinner

We’re rubbish at building community here in the UK…

Everyone ends up shlepping across the pond to attend events in the US!

That’s in spite of the fact that we have such INCREDIBLE entrepreneurs over here!

I’m determined to put a stop to that.

If you’re in the UK, expect to receive an invite from me at some point – it would be great to meet IRL!



CASE STUDY: Blueprint Of A $10m Online Education Business:

  • Business model blueprint
  • Product ecosystem
  • Team structure
  • Evergreen sales strategy
  • And much more

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