🎯 6 months into Strategy Breakdowns

Big news to share with you

Read time: 13 minutes 41 seconds

Hey friends — Tom here

This one’s a big one.

I have some exciting news to share:

I’m going all-in.

I’ve quit my job to go full-time on building Strategy Breakdowns.

For the first time in my career, I have no job and no plan to get one.

Entirely unfamiliar. Humbly fortunate. Slightly frightening. Unbelievably exhilarating.

Today’s edition is a slight interrupt to our usual scheduling.

I’d normally be sitting here, scraping through old company blogs, Twitter advanced search, Hacker News, and the Wayback Machine to synthesise a short strategy playbook from a successful company we can all learn from.

Today, I’m tabbing between Beehiiv, Taplio, Notion, Passionfroot, Gmail, and Google Sheets to write an article on a small and modest company just starting to take shape: Strategy Breakdowns

As a reader of this newsletter, you’re clearly interested in business strategy.
So, here’s mine.

How did we get here? What are the learnings 6 months in? What’s the plan going forward?

Note: I generally won’t be sharing these ‘build-in-public’ pieces here - I want to make Strategy Breakdowns the go-to place for internet businesses to improve their business strategy.

If you want to stay up-to-date with behind-the-scenes updates, stats, and musings on building Strategy Breakdowns, then click here to subscribe to my personal blog.

2 quick thanks before we get into it:

  1. To you, the reader. There’s no way I can say this without sounding cliche, so let’s go with this: None of this would be possible without you reading what I write, so I deeply appreciate you being here.

  2. To our sponsors. They keep this newsletter free. They also add the fuel that is powering the next chapter of Strategy Breakdowns. Show some love to today’s sponsor by checking out what’s on offer below:

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6 months into Strategy Breakdowns

How it all started

In July 2021, I made my first ever post online.

I’d decided to publish 30 LinkedIn posts in 30 days as a sort of reaction project to COVID lockdowns.

Working in consulting at the time, my posts centred around fintech / digital banking / payments, and the Australian startup scene.

Then came crypto, NFTs, the creator economy, productivity tools, and a multitude of other topics.

It took me ~2 years, a new job, and several hundred posts to niche down to a core subject focus.

One that tied a common thread between my writing to date, my career, and a perennial personal interest:

Business strategy for technology companies.

I was magnetised by publications in the space, like Not Boring by Packy McCormick and The Generalist by Mario Gabriele, as well as other flavours of internet-native b2b media brands like Stratechery, growth.design, Visualize Value, Bytes.dev, Demand Curve, Why We Buy, Detailed.com, Lenny’s Newsletter, Product Growth, and Marketing Examples.

Not only the wonderful articles, but the companies themselves.

Built-in-public. Lean. World-class content. Independent. Audience-first.

Possibly most important of all - they looked incredibly fun to run.

Creative. High leverage. Large luck surface area.

I knew this was the type of company I wanted to build.

But, how to differentiate? Not a trivial question.

2 mental models I used to think about this:

  1. Create what you wish existed

There was clearly a proven market for long, detailed, and comprehensive research articles on business strategy.

I worked in the strategy team at Atlassian, putting me squarely within the target audience. But, as much as I loved getting hypnotically deep into a 30-minute read, it was a luxury I couldn’t always afford.

I knew this was on me, not the content itself, since Not Boring and The Generalist were both crushing it with the long-read format. But my hypothesis was that other readers were likely in the same boat as me.

So for my newsletter, I went the other direction: 3 minutes or less - never gets buried in your ‘read it later’ backlog.

  1. Build the product only you can build

Originally a Naval tweet, but I first heard this idea from Harry Dry on the Indie Hackers podcast.

Harry explained “I can do a bit of development, a bit of design, and I really like writing, specifically marketing stuff.”

(Side note: Harry’s website “Marketing Examples” inspired the name “Strategy Breakdowns”. Clear, straightforward, and contains exactly what it says on the tin.)

Now, I’m no investor like Mario Gabriele, and had no capacity for producing exhaustive investment memo-like essays while working full-time.

I’m also no artist like Jack Butcher, and can’t turn business concepts into art that sticks in your mind for months.

But what I could do (and was spending all my working days at Atlassian doing) was break down strategic problems into a specific direction in the shortest, but most convincing way possible.

Plus, I had a large backlog of relevant short-form social media content, performance data on those posts, and an audience of ~25,000 people interested in the subject.

So, I decided that each edition of my newsletter would be a concise, dense article on a single idea.

One playbook, growth hack, or tactical concept, that readers can quickly understand and get immediate practical value from.

And that, friends, is how Strategy Breakdowns came to be.

Now, let’s look at the last 6 months of actually building it.

Business model and learnings

Morning Brew famously had the words “Write, grow, sell” written on the walls of their office.

The breakout success story in the newsletter space was laser-focussed on 3 things only:

  1. Write - the best newsletter possible

  2. Grow - the number of readers, as fast as possible

  3. Sell - as many ads as possible (to fund ‘Write’ and ‘Grow’)

Of course, each newsletter has unique characteristics that impact the goals and approach for each strategic pillar:

  1. Write - how frequently? how many writers? what topics? what format? what voice?

  2. Grow - organic or paid? how aggressively? which channels? which target readers?

  3. Sell - ads? paid content? products? services? events? community? lead generation?

The more time I spend building a newsletter business, the more meaningful this framework becomes.

Here’s the “Write, Grow, Sell” profile for Strategy Breakdowns:


To describe the creative process behind Strategy Breakdowns, I’ll use a slide from a recent creator workshop.

Daily content consumption

I make a point to keep a pulse on tech news, trends, and b2b creators to stay informed and generate ideas. My favourite business content generally comes from HackerNews, Twitter, LinkedIn, and email newsletters.

Save ideas to a database

  • Whenever I come across something that could potentially be a social media post or newsletter article, I will religiously save it to a database.

  • I use a system built in Notion, and am a fan of the Save to Notion chrome extension for 1-click saving content from the browser to my workspace.


  • For social media content, I calculate a weighted average of “Viral Potential” and “Effort” to aid with prioritisation of (hundreds of) content ideas.

  • If this sounds a bit stale and formulaic, I assure you this system is more often than not overridden by “lets just write what Tom wants to write today”. But still, we try.


Just as the slide recommends separating writing the hook (first 3 lines) of a LinkedIn / Twitter post from the rest of the post, I always separate writing the newsletter Subject Line and Preview Text from the email itself.

  • Tip: You can do all the deliverability and open-rate optimisation in the world, but without a compelling Subject Line, people simply won’t open your emails. You owe it to yourself to allocate 80:20 effort here - a slightly better Subject Line will be more impactful to your open-rate than any other change.

Write fast. Break. Edit slow” — I don’t recall where I first learned this idea, but it is now permanently ingrained into my process, and is the most common recommendation I give to new writers. There are 2 ideas here:

Firstly, when I sit down to write, I do everything in my power to just write as much as possible, as fast as possible.

  • Don’t like how a sentence reads? Write it 10 different ways. Then move onto the next sentence. No need to choose your favourite version yet.

  • Don’t like the flow between sentences? Add a horizontal divider, then try splitting, mixing, and matching the ideas in a different order.

  • Whatever you do, don’t stop to edit or delete your work while you are still writing it.

The psychology behind this is well explained as a ‘Creativity Faucet’ by Julian Shapiro.

Secondly, you need to edit your fast-drafted work in a separate work session. Ideally it’s the following day, but a few hours later will do. You’ll spot jarring moments and find better ways to frame things than you would have done in the writing session, simply because you’re no longer too close to the words.


  • The slide shows a screenshot of Taplio, the tool I use for scheduling, analysing, and publishing content on LinkedIn.

  • For the newsletter, I use a simply wonderful creator-first email platform called Beehiiv.

  • If you’re thinking about writing on LinkedIn, or an email newsletter, I couldn’t recommend either tool more highly (and am a proud affiliate of both)!


Engagement for the newsletter is two-fold:

  • Responding to comments on social media posts promoting the newsletter articles.

  • Responding to email replies - if you didn’t know already, you can reply directly to this email and it goes straight to the Strategy Breakdowns inbox! Feedback and general chit-chat is always appreciated - I do my best to respond to every reply, plus your replies help our emails avoid the dreaded ‘Spam’ folder.


  • Data-driven decision-making” is unquestionably a buzzphrase, but is nonetheless fundamental to any successful business today. Perhaps more so for internet businesses, and more again for one built upon email marketing and social media surfaces.

  • The iterative feedback loop plays a pivotal role in shaping Strategy Breakdowns: Change something → Measure the impact (opens, clicks, replies, qualitative feedback etc.) → Learn → Repeat


One reason I adore Beehiiv is it’s best-in-class subscriber and post analytics features. Here’s a summary of our subscriber acquisition sources.


The simple but wildly effective mechanic that has powered 74% of our subscriber growth: Write free content on social media → Recommend people subscribe to the newsletter.

As the newsletter started generating cash flow, I weighed up the options for the most efficient place to redeploy it.

  • ‘Newsletter Twitter’ consistently pointed me towards platforms like SparkLoop, Refind, and Beehiiv Boosts - marketplaces for other newsletters to promote yours in exchange for a commission per engaged subscriber. After all, what better place to find engaged newsletter readers than… in other newsletters?

  • I’m only getting started experimenting with paid growth, but am already bullish on paid referrals. They are simple to configure, provide cost-efficient growth, and are a proven channel for just about every large newsletter.


3.7% of our readers have an acquisition source of “Direct” which broadly means ‘subscribed via the strategybreakdowns.com’ website (as opposed to our join.strategybreakdowns.com social media landing page, or other embeds / APIs).

Similarweb data for strategybreakdowns.com

  • Another interesting data point for digging further into growth channels is strategybreakdowns.com traffic data.

  • Importantly, this is website traffic data, not subscriber acquisition source, so these splits should be considered a proxy for how our “Direct” subscribers landed on strategybreakdowns.com.

  • I’d love to believe a whopping ~52% of all readers subscribed to us via colleagues and friends sharing links to our articles.

  • However, my interpretation is that 52% of the 3.7% of subscribers who are classified as “Direct” landed on our website via these ‘organic word of mouth’ mechanisms. 4.4% of the 3.7% found our website via backlinks from other sites, 17.9% of the 3.7% from search, 17.35% of the 3.7% from LinkedIn, and 8.3% of the 3.7% from links in emails, either our newsletter or others.

Newsletter Swaps

Occasionally we cross-promote other newsletters we like - we recommend them in an email, and they do the same for us. Although free and highly recommended by large newsletter creators, this has not proven to be an effective growth channel so far.

I’ve spent precisely 3 minutes working on SEO, so the ~100 subscribers received from Google Search are a small but welcome bonus.


I’ve only recently committed to growing on Twitter, so I’ve seen negligible subscriber acquisition to-date. To support the cause, each additional follow would really make my day.


My outdated, under-construction, personal website has a humble email subscribe form on the landing page. I don’t link to the site any more, since it needs a refresh, but to anyone who subscribed to Strategy Breakdowns from tomalder.me, I see you and appreciate you!


Monetisation maturity is frankly still nascent. Although we have a healthy ads pipeline, and a surprisingly lucrative paid referrals revenue stream driven by a handful of viral posts, I’d like to see greater compounding of recurring affiliate revenue, and broader diversification overall (more on this later).


The primary revenue stream for the business is advertising. As you would’ve noticed (and hopefully engaged with!), we promote other businesses directly in the newsletter, driving brand impressions and prospective customers directly to their offer.

  • Incredibly fortunately, 100% of our sponsors have been inbound leads, and we’ve passed on more than we have worked with. This has afforded us the luxury of choosing to partner with only the brands who we believe provide high-quality and relevant offers to you, the reader.

  • For the brands we do work with, we aim to be the highest quality media partner on their books. A sponsor recently noted, something we “delivered on better than most newsletter operators [we’ve] sponsored over the past 6 months or so is professionalism and communication. This Google Sheet is a value add as a customer of yours. It makes me feel like you care about my results.”

  • If you’d like to promote your business in Strategy Breakdowns, our next available spots are at the end of March - click here for more info.

Just as we’ve grown Strategy Breakdowns via the SparkLoop and Beehiiv Boosts marketplaces, we also promote other newsletters in exchange for commission. These recommendations appear when people sign up to Strategy Breakdowns, and occasionally in the newsletter articles themselves.

  • This has been a highly variable, but nonetheless fruitful and frictionless revenue stream to date.

  • I expect the absolute monthly revenue to remain consistent, so this revenue stream will decrease as a percentage of overall revenue over time.


As well as fixed-fee ads, we promote affiliate links to products we use and love. These generate a commission for each successful purchase, and often provide recurring revenue (when promoting SaaS tools). A small, but fast-growing and automated revenue stream I am quite excited about.

What’s next?

The last 6 months has been equal parts gripping and fatiguing.

When I launched Strategy Breakdowns in June ‘23, I had no concrete expectations regarding growth or monetisation, but safe to say any guess I could’ve made was exceeded. Scaling a side-project to 34,000 readers and a fully sold-out ad calendar from exclusively inbound leads is genuinely astonishing and humbling.

But, the approach taken was not a sustainable one. Working every weekday plus writing / growing / selling every weeknight and weekend was only viable for a finite period of time. It didn’t take long before the inevitable decision-point emerged:

  • Option 1: Cut back, take a breather, and accept that the future of Strategy Breakdowns is a ‘passion-project’ that will never become what I believe it could be.

  • Option 2: Keep building on the side, risk burning out, and wait indefinitely for the opportune ‘someday’ moment that going all-in seems reasonable.

  • Option 3: Build conviction. Model a few financial scenarios. Commit to a rough plan. Tell my boss I’m leaving.

I chose option 3.

Here is that rough plan.

It’s worth first pointing out that (1) although directionally correct, this plan will certainly change based on what I learn over the next while, (2) strategy is never linear, and (3) timelines are only an estimate.

Also, this will seem more business-centric than creator-brand-building. That’s because this is (part of) the actual plan I made to justify quitting my job and going full-time on a small side-business.

Lots of assumptions. Plenty of de-risking required. Fun times ahead!

Let’s get into it:

Horizon 1 (~3 months)

Focus: Scale our Write/Grow/Sell processes to maximise momentum and cash flow.

Write (Scale newsletter frequency):

  • I currently research → write → edit → publish → promote an article 1x per fortnight.

  • I'll scale this to 1x per week, which will partly be enabled by hiring our first freelance writer (click here for more details).

Grow (Scale top-of-funnel impressions):

  • Social media impressions power follower growth → email list growth → ad revenue. For the last few months I've posted ~1x per week on LinkedIn and Twitter. I'll scale this to 5x per week (each weekday) with the support of my new social media assistant, Paola.

  • I’ll also try my hand at learning and implementing the core growth lever powering every newsletter growing at scale - paid ads.

Sell (Scale ad sales):

  • I'll be moving from 1x "Main Ad" + up to 3x "Secondary Ads" per newsletter, to just 2x "Main Ads". This is a pattern I first noticed some of the world’s best newsletters like Saturday Solopreneur and Why We Buy adopting. Rather than splitting impressions and clicks across 4x sponsors, there will now only be 2x (which according to other adopters consistently generates “the same or better results” for sponsors).

  • This change will be rolled out through Jan - Feb, since a number of ad slots have already been sold in the 2023 format.

  • Along with the increased send frequency, this means 4x as many "Main Ad" sales to optimise for available inventory.

Horizon 2 (~6 months)

Focus: Ship a core offer to create an additional revenue stream and diversify the business model.

Ship a product: 

Ideate → Validate → Build → Launch a digital on-demand b2b product to provide revenue-generating value directly to our readers (diversifying from just ad deals with 3rd parties).

  • My non-negotiable specification is that I can look at the product and proudly say it is best-in-class. The highest-quality, most practical, and most value-focussed product in the market for that subject.

  • I have a few hypotheses for what the product might be, but this will fundamentally be shaped by you, the reader, when the time is right.

  • If you have any early thoughts on the type of offer you’d like to see from Strategy Breakdowns, I’ll be forever grateful if you’d be kind enough to share them in a reply to this email!


Once the product is live, optimise content distribution + digital channels + business operations. Likely focus areas:

  • Conversion Rate Optimisation for landing pages and sales pages

  • Content marketing production and distribution

  • Automations and email sequences

  • Lead magnets and surveys

Horizon 3 (2 years? ish?)

Focus: Live a fulfilling life and create awesome things. Play for style points, not money.

Digital nomad:

I have a pipe dream to get rid of most of my physical possessions, work fully remotely, and explore the world. Realising this dream will be a big focus in the future!


After optimising the advertising and digital product lines of business, I'll eventually expand to something else. With so many unknown unknowns between now and then, I haven't committed to a direction just yet. That said, here are some top-of-mind options:

  • MicroSaaS (powered by free organic marketing)

  • Job Board (a talent network with paid job ads for strategy roles)

  • New channels (Podcast? YouTube)

  • Lead generation for co-owned agencies (new compelling business model increasingly adopted by b2b creators).

  • Additional newsletters (e.g. ecosystem with "Product Breakdowns", "Design Breakdowns" etc)

  • More digital products (upsells, cross-sells etc)

  • Continuity offer (e.g. a subscription-based community)

To see if this speculation becomes reality, I'll be chronically online and highly contactable for the foreseeable future, so please feel free to stay in touch through my personal blog, Twitter [@tomaldertweets], LinkedIn [/in/tom-alder], or by replying to these emails!

Thanks again for being a part of this journey.

Bye for now,



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