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📍 Clissold Park, Hackney, London

📆 14th January 2026

⛅ 2°C, cloudy but sunny, forecasted to rain this arvo

[0:00]

“Okay so this is going to be a voice note for my 2 Years into Strategy Breakdowns article.

I'm walking around Clissold Park in East London. It’s Jan 14th. It's bloody cold, but the suns out.

I feel like… I never know where to start, and I have a habit of putting a bit of pressure on these reflection pieces. So for now I'm just gonna... record myself talking through some stuff that could be interesting to include, and go from there.

[pause]

It's been exactly 2 years since I quit my job to do Strategy Breakdowns full time. Wild!

2.5 since the first article. And about 4 months since I packed up my entire life in Sydney, got rid of all my stuff, and took a one-way flight to the other side of the world.

I've spent the last few months living in Manhattan. Brooklyn. Barcelona. A tiny beach town called Torredembarra about an hour south of Barca. Valencia. Granada. Madrid. New York again. And now here, East London.

2 years ago that was a dream I scribbled in a journal. Now I'm… literally living it.

Still feels totally surreal when I stop and think about it.

[pause]

It’s been a crazy year. So I wanted to record a bunch of things I’ve noticed and learnt.

There's all these… contradictions, that I'm balancing right now. Where I wanna do more of something, but I also wanna do the opposite. I don't think I’ll resolve them necessarily. I think they're just representations of where I’m at.

I think they could be a cool way to structure this article.

So I'm going to walk and talk through 5 of them.

No filter. I just have these 5 ideas in my notes.

Let’s see what comes out.

[12:05]

If there's one thing I know for certain, it's this:

None of it works if people don’t like reading the writing.

Doesn't matter how much effort you put into brand, or automation, or growth hacking, or whatever. If people don't actually enjoy the writing, you just create a vicious cycle. Retention sucks. Sponsorships don't perform. Sponsors leave. No one shares it around. Growth gets too hard because you're filling a leaky bucket.

So the thing I keep learning is: nothing matters more than the product itself. Which is these breakdowns. The actual words on the page.

In software, there's this idea that - today, distribution matters more than product. Since product development is so fast now, the winners will be the folks that are the best at getting their product into the hands of customers, because that creates feedback and revenue, which you use to end up building the best product.

But with writing, the distribution is the product.

When someone reads or even shares an article, they're not just sharing your product, they’re sharing the product marketing too. Which means the product has to be genuinely good, or it won’t… travel. At scale you obviously grow with ads and stuff, but they won’t stick around without an awesome product.

Often I feel like I’m spending way too much of my time writing. Like I should be focussed on ‘the business’. But then I remember it’s kind of the most important thing.

And to be honest, over the past 6 months or so, I’ve realised what it will take to go from ‘pretty good’ to ‘unbelievably good’.

Someone who could focus all their energy on writing the best possible breakdowns would do a way better job than me. It took me a while to admit it (probably some ego getting in the way there) but it’s totally true. Some of my favourite pieces I’ve worked on with other writers.

So I think it’s time to get serious about producing the best strategy writing on the internet…

So then there's the operator side.

This year it really started feeling like an actual business. Not a "hopefully one day it’ll be legit" thing. It’s already way bigger than the audience and revenue goals I had when I started. Wild to say that out loud.

When I first started, to get my initial sponsors, I spent about 6 weeks going hard on outbound sales. Finding companies that had sponsored other newsletters, figuring out who to reach out to, fishing for a ‘test campaign’.

A bunch of those sponsors are still with me now.

But fast-forward to today, every single sponsorship comes from inbound or renewals. I haven’t done any outbound in like 2 years.

To be totally transparent, I genuinely never would have predicted this. I’m still surprised each time I get another DM, and definitely have an irrational fear that each one will be my last.

But I talk to other newsletter folks and this is the #1 thing I get asked about - and I almost don't know what to say. If I had to summarise the playbook that seems to be working, it’d be this:

For inbound - I have the media kit. It's got the demographic data, sponsor testimonials, all the stuff you'd expect. I plug it in the newsletter footer and occasionally on LinkedIn. Great logos definitely help get more great logos, so I lean into that. I think the brand and content needs to pass a quality-filter. And if you choose to write about these types of topics, the audience is naturally amazing, and lots of tech companies are actively seeking out ways to reach those folks through newsletters and podcasts and stuff.

But the truth is, there’s a good amount of luck too. It’d be laughably optimistic to have predicted that doing those things would mean I have a stream of DMs and emails each week asking to sponsor, without me every really actively ‘generating leads’. But somehow I’ve found myself in this crazy position where I say no more than yes, and get to work with just the best sponsors.

And then there's renewals - basically every sponsor ends up renewing. By the book, that means I’m probably not charging enough. But a tangible learning that’s worth sharing is this:

One of my mentors has always pushed me to get creative with going above and beyond for my sponsors. Hyping them up on social, screenshotting and celebrating their wins in Slack, investing time and money beyond the agreed scope to ensure they get epic results, stuff like that. It definitely takes a lot of effort to be the ‘favourite partner’, and it really is a daily thing, but this is unbelievably good advice.

[pause]

And yea - that’s kind of how the sponsorship business works.

[pause]

Maybe I won’t actually include this section. I don’t want this to come across as… I dunno.

But at the same time… the point of this is to reflect on where I’m at.

Build-in-public.

And the sponsorship-side of things is probably where I feel the most satisfied, business-wise.

The reality of what I’m doing day-to-day is like 1/3rd writing, 1/3rd sponsorships, and 1/3rd tinkering with automations and stuff.

So the operator in me is always like… where is the business at, and how do I grow it? What skills do I need to learn? What do I need to do that I’m not currently doing?

Some days I wake up like “I’m a creator who does brand deals and sells a course.”

Limiting self-beliefs, really.

Other days I’m like “I run a media company, it’s just early days. Only year 2. But we get, frankly, unbelievable results for the best sponsors in the world, and we have automations that sell digital products people love on autopilot.”

And when I think like that, I actually start acting like that, and things get built.

Will it always be a media company? Not sure.

But it’ll always be powered by media.

Ok - I don’t even know where I’m going with this one any more.

Next one!

[29:23]

Every month that goes by, I feel more momentum.

Obviously sometimes it’s flat, or things slide backwards a bit. But I’m always more and more optimistic about the opportunity.

So when I look at where things are, there's never been a better time to just... slam on the accelerator. Try to triple the business as fast as possible.

[pause]

But I also know the reasons I set out to do all this: Freedom. Fulfilment. Day-to-day happiness. Choosing my own problems to work on.

And sometimes I need to remind myself that maybe what I need most - especially if I'm overwhelmed by the mental battles of running something like this - is to actually slow down.

Slow down to speed up.

That’s pretty cheesy.

But it’s kinda true. Identify the things that don't matter. Stop doing them. And just spend my time on what matters most.

My happiest days - and my most productive days - are when I spend 2 hours, first thing in the morning, before checking social media, before checking email, before Slack, just 2-3 hours following my energy on the one big thing.

Then maybe 45 minutes of admin to keep the ball moving.

And then I spend the rest of the day exploring. Exercising. Cooking. Swimming. Socialising. Journalling. Daydreaming.

Slowing down, really.

Whenever I make massive progress, it’s never the days when I try to cram 27 things into 9 hours.

But I need to have full conviction in that #1 thing. Full flow state.

[pause]

The #1 thing for me this year was actually outside of work: moving overseas.

My girlfriend and I had been dreaming about something like this for years, but the process of actually moving kinda started when we went to Japan in June. That was so sick. 3 weeks.

We hit the big cities, but we also rented a car and road-tripped around these incredible remote areas. Iya Valley. Onsens up in the mountains. Island hopping around Naoshima and Shodoshima.

That trip was when we actually booked our flights to leave Australia. We finally pulled the trigger at like 2am in this crazy little hotel in the middle of nowhere.

So as soon as we got back to Sydney, we had like 3 months to pull off the move.

Selling furniture. Securing visas. Booking flights. Getting tax advice. Selling the car. My girlfriend’s job hunt. Researching places + accommodation. Coordinating travel plans with friends. Donating clothes. Packing suitcases. Cleaning. Organising goodbyes. Really felt like a never-ending list for a while there.

It was basically a part time job for a full quarter. Definitely spent more time on that than work.

Did I ‘speed up’ as much as I thought I would this year? Not really.

Did ‘slowing down’ actually make things better? More enjoyable and productive.

[46:41]

Every day I face this question:

What do I spend my 2-3 hours of deep work on?

Most of the time, it's writing.

But when it's not writing, I get to choose from a list of options.

It could be improving the website. Adding more resources to StrategyHub. Checking in on my sponsors. Personalising an email sequence. Analysing finances. Helping a friend who's asked for feedback on their SaaS onboarding. Trying to understand if a foreign tax code will apply to me.

Unlimited minor wins available.

Or…

It could be investing in something net new.

A new product. A new channel. A new hire.

[pause]

To be honest, this year wasn’t exactly filled with net new wins. Loads of incremental improvements, I’m happy with my metrics, but by far the biggest concrete win was moving.

I was planning on a massive net change. For about 4 months at the start of the year, I spent most of my not-writing-or-sales time on an initiative that didn’t pan out. An agency-style offering with a good pal - we got a few clients out of it, but I ultimately decided it wasn’t the right direction or model for me to commit to. So I pulled out.

[pause]

One of the companies I admire the most is Every. It's kind of like... my favourite example of a newsletter that's evolved into a product studio. I’ve been subscribed since they were essentially a ‘band of writers’, and now they are fully at the frontier of AI engineering and content, with a bunch of cool SaaS products they incubate. The bootstrapped product studio idea is bit of a pipe dream for me.

Recently, with how good Claude Code and Cursor are getting, it's become possible for someone like me (with very basic technical skills) to actually build software.

So I’ve been tinkering away, building prototypes.

I've always had a software itch. That might be obvious.

I come from a product background. I used to work in tech. I spend all day writing about software companies, product-led growth, product design, stuff like that. I have the ideal audience for it.

Maybe this is the year I scratch that itch.

Hard to know if it’s a distraction, or my ‘2nd Act’.

[pause]

It’s new things that move the needle and take you to the next level.

But you have to choose a lane and commit really hard.

Because compounding + iteration is the only way to make great things.

One of the things I keep realising is: you can do anything, you just can't do it all at once.

I even said that in my 1-year reflection. Clearly takes more than a year for these things to sink in.

It only becomes more true when there’s more opportunity.

[1:04:01]

When I wrote the first edition of Strategy Breakdowns, it was, in a lot of ways, similar to what I publish now.

I mean, a few things have changed - the visual branding is a big one. The voice is more refined now. The research is definitely more thorough.

But the format is basically the same.

The goofy names I came up with: The Chess Move, The Breakdown, The Rabbit Hole.

I definitely didn't expect to still have those. But they just… kinda work.

3-minute read. 3 sections. 3 points in the breakdown. 3 rabbit hole links.

Still the same.

Make it feel ‘productised’

I think people love it.

The format almost compounds because readers know what to expect. And I improve things within constraints, rather than reinventing the wheel every time.

I pretty much owe everything to the weekly newsletter + the daily LinkedIn posts.

The drumbeats that keep nudging things in the right direction.

[pause]

And then even outside of work - consistency can be pretty awesome.

The same routine. The familiar places. The lifelong friendships.

And it was that routine that allowed me to build up the stability, the systems, the audience base, and the self-confidence that only comes from compounding and iteration.

I feel like that more stable era was definitely needed for me to propel myself into this one.

[pause]

But life is really about spontaneity.

Having a random thought, and following that thread through the entire way.

Shipping an easter egg.

Planning a camping trip and setting off the next morning.

These days, the location freedom thing is a forcing function.

Every time you change location, you realise how much more there is to explore.

You have infinite… inspiration, literally at your doorstep.

New places to see. Things to do.

Things to take inspiration from and remix back into your work.

[pause]

Wake up, espresso and a tortilla, walk out the front door with no shoes, no shirt, go for a swim, plug into an audiobook. Come back and write for 4 hours about why some tech companies write books. Clock off at 2. Head out for boquerones, padrón peppers, and sangria. Spend the afternoon exploring the old town, watching the sunset from the docks.

Wake up, head to a reader's office in Madrid. Meet his team. Jamón ibérico and Txuleta for lunch. They all love Strategy Breakdowns and have 100 questions and ideas. I can’t believe it. Spend the afternoon building automations - literally by voice - just dictating things we spoke about and watching Claude Code put it together. Head out for dinner - snails.

Wake up, overground to Shoreditch. Co-working spot. Smash out 3 personalised variations of 7 emails. Onboard 3 new sponsors. Write a strategy memo to myself. Hit the gym. Iconic salt beef bagel shop for a pre-dinner snack. Takeaway chopped herring for tomorrow’s breakfast. Head home, sausage stew and Peep Show for dinner. (The TV show, not the other kind)

I’m probably romanticising a bit.

But not much. It’s honestly been like this.

Variety keeps things interesting.

In life, spontaneity over consistency. For sure.

In business, probably the other way around. But it’s definitely a balance. You have to get creative with it. Have some fun. Otherwise, what’s the point?

[1:21:18]

Maybe the most… frustrating contradiction on the whole list.

Feeling insanely grateful for how things have gone so far.

But at the same time… the ambition to make everything better makes me dissatisfied.

I recently listened to the Lenny pod with one of the Slack co-founders, and he was going on about this feeling of immense dissatisfaction with the product. No matter how many years of work went into making his vision a reality, even with 100s of developers working on the product, he was almost embarrassed by it.

Not because it wasn’t any good. More because he always saw unlimited opportunities for improvement.

I’m obviously not building Slack.

But his… slightly twisted point really stuck with me. I feel it really strongly.

I can think of 1000 improvements I’d like to make to literally anything I’ve built. The website. The welcome sequence for new subscribers. The brand. My socials. Any given breakdown.

It can be a bit destabilising sometimes. Trying to build something you’re super proud of, but always focussing on the flaws and things you could make better.

[pause]

In my first build-in-public reflection 6 months into Strategy Breakdowns, I ended it with a roadmap of my short + medium-term goals.

Back then, the direction was super practical: how can I make a higher-quality version of this? Better for readers and sponsors, and more stable, less risky for me.

2 years was as far out as I could see.

But now, having basically finished the “this is definitely happening” parts of the roadmap, I’m more thinking in 3-5-year horizons.

Incredibly grateful for where things are at. But motivated, and a little impatient, to make it way better.

I bet I’ll be saying the same after year 3. And probably year 13 too.

Ok - I reckon that’s good for now.”

[ 1:38:11]

^{END OF RECORDING}

Recorded with Apple Voice Memos.

Formatted with Claude Cowork.

Edited (minimally, possibly too minimally) by hand, with Yorkshire Tea.

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Thanks for being here ✌️

— Tom