Hey friends - Tom here 👋

3 years ago I wrote the first edition of this newsletter.

Every 6-12 months, I write a build-in-public reflection.

You can find them all here.

Today’s email is the latest in the series.

Year 3 - the year I launched my first software business.

In my previous reflection (a voice note from an icy walk around Clissold Park, East London), I said this:

Well, I scratched the itch. Exactly 12mo ago.

A hacky vibe-coded screenshot-to-reply tool on my laptop.

Then I got carried away…

Today, I have 2 legendary technical co-founders, a blazingly fast Mac app I open ~45x per day to run my business, 1,850+ people on a waitlist, and 32 paying users (who are, quite literally, building the app with us - more on that later).

It's called 💬 quicker.chat, one inbox for all your DMs: LinkedIn, Slack, WhatsApp, X, iMessage (+ more soon)

I hope reading this article inspires you to check it out!

(Consider this article the only biased Sponsored Breakdown I'll ever write 🤓)

So, this is how Quicker Chat happened. Month-by-month. A 12mo screenshot dump, straight outta the archives.

(Reminder for the builders reading to take more screenshots!)

And at the end, I'll show you some of my favourite things inside the app, which nobody (beside our users) has seen yet.

Enjoy!

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tom@sb: ~/2025/oct $ git log --oneline

My most-opened app of 2025 wasn't Notion, Spotify, or even my browser.

It was a unified inbox app for my DMs.

A tracker told me I opened it 45x a day.

The reason I opened it so much: my business runs on DMs.

And honestly, despite referring probably 20 friends to try the app, I didn't love it.

It barely changed in years, and the occasional updates were always things I’d never use.

At the end of September I was living in Torredembarra, a little beach town about an hour South of Barcelona.

I had an idea for a tiny app, and I was looking for a reason to try out Cursor, which was having its talk-of-the-town moment on X the time.

24 hours later, I had QuickReply:

→ Hit Shift+Cmd+R

→ Drag a box over any conversation, in any app, like a screenshot

→ It reads the screenshot with local OCR, works out who's who, and gives you personalised replies to copy to clipboard in 2 key presses.

Very scrappy. Very fun. Very quick.

I enjoyed taking inspiration from how some of my favourite Mac apps like Granola and Raycast worked.

I enjoyed imagining and then actualising what “Strategy Breakdowns software” would feel like.

I enjoyed making it as fast as possible - fewer and fewer key presses / screens / loading / seconds to get the job done quickly.

Nobody used it except me.

It wasn’t useful for every conversation either.

It helped shortcut to a mostly-there-draft for some more straightforward work chats.

But for things like sponsorship deals requiring strategic replies, or for friends and fam, it wasn’t useful.

So it wasn’t saving me that much time. But it did solve a real problem. It was clear that while it was not a fantastic product, it could be a fantastic feature.

tom@sb: ~/2025/nov $ git log --oneline

November was all StrategyHub.

→ We ran a launch for Websites & Traffic - 3 modules of StrategyHub, sold on their own for 1 week only

→ 8 emails in 6 days: warm-ups, open cart, origin story, social proof, FAQs, last calls

→ ~$12k from the launch. Below target, but I didn’t have to record new course material, and I repurposed the emails + pages into an evergreen sequence doing ~$1k/mo on autopilot, so there’s some long-tail payoff too

Meanwhile, QuickReply sat in my menu bar. I used it a bit, but wasn’t actively improving it. I felt there was a fork in the road with 2 very distinct paths:

→ → → Hacking away for months on the side, having fun, but not building something real

vs

→ → → Finding a technical cofounder, and racing towards hard-launching something awesome and production-grade to my audience

The underwhelming StrategyHub launch taught me a lot about what’s needed to actually get people’s attention AND make people act. It also taught me a lot about what gives me energy vs drains it.

I didn't know it yet, but I'd reuse a lot of these learnings 10 months later.

tom@sb: ~/2025/dec $ git log --oneline

December was quiet.

I sent out 2025 Wrapped: our top 10 pieces of the year, measured 10 different ways.

Then I did a lot of reflecting over the new year.

Spent the month in New York with friends and fam.

Got to kick it with some internet buddies IRL, too!

2026 is the Year of the Horse. In Chinese zodiac that means bold decisions, transition, and new beginnings.

tom@sb: ~/2026/jan $ git log --oneline

January was anything but quiet.

→ I sent out 🎯 2 years into Strategy Breakdowns.

→ I went all-in on duct-taping together sales systems

→ I found my technical co-founders

A week after my "2nd Act" email, I hit up an old pal.

Austin. Originally a high-school mate of some of my uni mates. We ended up playing in a basketball team together ~5 years.

He was a software engineer at a few banks/fintechs. I showed him the QuickReply prototype + pitched the vision. He said he’d think about it. Few weeks later we had a ‘Yes’, and he recruited 2 uni mates, both Atlassian devs, to join the project.

One of them ended up dropping out because he could only commit to a small side-project.

The other, Jeffrey, stuck around.

Both absolute weapons and lovely people and I simply could not build anything like this without them.

At the time of writing, it’s still the 3 of us actively building it, plus my Strategy Breakdowns team (more on this later!) helping out with various testing + content + ops bits.

tom@sb: ~/2026/feb $ git log --oneline

So I was constantly improving our systems for Strategy Breakdowns comms, and in parallel, we were working through the early scoping decisions for the app (LinkedIn-only vs multi-platform? Sales focussed vs speed focused? Waitlist launch vs self-serve launch? etc)

Here’s what I stumbled into.

Every time my DM setup for Strategy Breakdowns got better:

Revenue growth AND time savings.

The dream double. Most apps do neither.

This realisation was a big turning point for me.

I knew solving this problem was valuable. I could feel it viscerally. I personally needed it solved, badly, and every improvement showed up in my revenue and my calendar.

On 18 Feb I built the first version of an internal dashboard to tie it all together.

quicker.chat is that idea, grown up.

Meanwhile, Paola my content assistant, who'd been with me for 2 years, moved on.

I hired James to support on the editorial/ads side, and started looking for an ops hire (that became Karen).

📚 The job ads I posted, in case they’re interesting / useful for anyone’s early-stage hiring!

→ Hiring a Superwriter @ Strategy Breakdowns

→ Hiring a Newsletter Operations Coordinator @ Strategy Breakdowns

Building a team that could run parts of the newsletter without needing me across every single detail is what made the rest of this year possible. I feel incredibly lucky to be surrounded by a group of kind, resourceful, like-minded people to collaborate with every day!

tom@sb: ~/2026/mar $ git log --oneline

On 11 Mar, the team had a proper (virtual) sit-down.

(A+J both in Sydney, me in London)

Company structure, defining what ‘success’ means for each of us, what exactly we're building.

Perhaps most importantly, we left the call with a clear immediate priority:

Race to the first paid subscription. >$0 MRR.

Not because we needed the money. But because it represented the critical path for the project’s survival.

MRR as the quantifiable forcing function for: full conviction in our problem-validation + building something worthy of paid users + launching publicly to the audience.

That same day, I started posting polls:

→ What platforms do your revenue-generating DMs happen on?

→ How many DMs do you send per week on LinkedIn?

→ Do you use DMs more / same / less than email?

We messaged everyone who commented or voted in line with our app’s ICP, and set up calls with anyone willing.

3 objectives for each call:

What we learned a lot from these discovery calls. The biggest takeaway was that there were many people like me who desperately wanted this problem solved.

Creators, agency owners, partnerships people, SaaS founders, etc.

They were DMing loads of people each day, sprawled across platforms, no ability to stay organised / prioritised, no ability to move with speed / intention, with real opportunities attached to those conversations.

tom@sb: ~/2026/apr $ git log --oneline

We had the validation we needed. We had the goal of >$0 MRR ASAP.

So we added structure: a weekly call, async updates, and clear milestones:

The plan at the time was a better LinkedIn messages UI + some AI magic (suggested drafts, categorisation, follow-up reminders).

Launch with that, then decide if we should bring in more platforms, or continue down the LinkedIn path.

tom@sb: ~/2026/may $ git log --oneline

2 big moments:

→ On 26 May, my real LinkedIn messages viewable in our app for the first time.

→ The team got smaller. 1 of the original engineers stepped back, and we carried on as 3.

I started using it daily. Milestone #1 complete ✔️

I wasn’t plugged into the dev workflow yet, so I was logging all my feedback in a doc.

Real messages + a way for us to rapidly iterate = a step-change in momentum

tom@sb: ~/2026/jun $ git log --oneline

→ Jeff did "a gigantic refactor" and rebuilt the whole thing as a proper Mac app.

→ Our first pilot users: my own team first, then friends who run similar businesses. 15 pilot users, and a group to chat with them daily.

→ AI conversation summaries shipped.

We also had a naming problem.

Our working name was Lyrebird (an Australian bird that mimics human voices 🦜). Cute name, beautiful bird, nice analogy.

(Australian’s loved it though - one of our users emailed a story about spending an hour in the bush with one, and that it was a shame we didn’t stick with it)

But problems were:

On the Strategy Breakdowns side, I made our first partnerships hire: Bryan

📚 The job ad I posted, in case they’re interesting / useful for anyone’s early-stage hiring!

→ Hiring a Partnerships Manager @ Strategy Breakdowns

The goal for this hire was to (a) take my time spent on sponsorships from 1-2h/day to <1h/week, and (b) grow our sponsorships to $100k/mo. I could reallocate that time back to making SB and q.c content, plus other initiatives (like launching our new Strategy Breakdowns Media Kit). Bryan also became a valuable test user for Quicker Chat - with LinkedIn, X, Slack, WhatsApp etc all playing a part for our sponsorships.

It quickly became super obvious, watching Bryan + Karen + James all shipping away in harmony with defined domain ownership + freedom to build things autonomously, how much of a bottleneck I had been in my own business.

Every single important metric started going up.

Sponsors were getting better results.

We were landing new sponsors without my input.

Dashboards, automations, agents, all shipping without me even touching them.

Waking up to new stuff every day became the new normal. Easily one of the coolest (+ proudest!) transitions of the last 3 yrs.

(My honest personal growth note-to-self: these things get built not despite my lack of input, but because of my lack of input. The transition is only possible by hiring great people and getting out of the way. If I had to understand/review/feedback/be hands-on with everything we ship, I’d have 100x the things on my plate, and we’d have 100x less things shipped.)

tom@sb: ~/2026/jul $ git log --oneline

On 1 Jul we had a 3hr quicker.chat call to land 1 decision:

LinkedIn-only was ~90% ready to launch.

Should we launch a ‘better LinkedIn inbox’ (soon), or go after ‘unified inbox’ (still soon, but not as soon)?

VERY different solutions. Different ICPs. Different positioning.

Some of our thinking from the call transcript:

LinkedIn-only with 4 more weeks of development, or current features but across 3 platforms? Because those 4 weeks will pass anyway, we just have to decide how we spend it.

…

I literally installed it and opened it 45 times a day, every single day since then. That is rare. Really rare. Think about how valuable that is.

…

The stickiness is massive. The 'holy shit, how did I ever live without this' is way more obvious.

…

You can hear it in 4 words and understand it. All messages, one inbox.

We agreed on a 1 week test to prove it was possible to go from 1 → 3 networks. What happened next:

→ First Slack messages flowing in ~4 hours.

→ 8 July: WhatsApp and X live.

→ 15 Jul: I shipped my first ever change to the codebase, live on the call (shift-select multiple conversations to bulk-archive or bulk-mute). 5 minutes later, I accidentally archived my entire inbox 😅

→ 28 Jul: I replaced my old inbox app completely. I was now in ours 45 times a day.

→ 29 Jul: after dozens of ‘this is the one’ contenders (RIP funner.chat), we finally came up with a name that (a) we loved, and (b) had a free domain. We bought the quicker.chat domain for $100.

tom@sb: ~/2026/aug $ git log --oneline

This is the month I fell in love with building.

It was so fun for me to build, precisely because the app is designed for people like me.

I live in my DMs all day.

So I think of something I want the app to do, and I can build it on the spot.

The shortest feedback loop possible.

When dreaming of software ideas in years gone by, I’d make the fatal mistake of ‘letting the tail wag the dog.’

I’d look at the make-up of my audience, see for example that we have lots of PMs, and think of app ideas for them.

But the problem with that approach is that I’m not a PM.

I’d need to put myself in the shoes of a PM. Interview them endlessly. Get Looms of their workflows. Ship something, ask for feedback, spend time understanding why it’s not useful + what would be more useful + ship my best-attempt at that thing. Then go through the loop over and over again.

It’s not impossible, but the time-to-ship anything valuable blows out by 100x.

Being your own ICP = making months of progress in a day = unfair advantage.

It was also really fun to finally go deep on implementing proper dev workflows, learning from 2 technical funs:

→ Branches, worktrees, commits, PRs, and the difference between pushing code to main vs cutting a release

→ A shared /land skill that rebases, tidies, tests, ships, documents our changes, and checks for tickets / PRs to be updated / closed

→ AWS credentials so I could deploy the bits that touch our AI backend

→ 56 changes in a single day on 10 Aug

→ 402 changes shipped to the codebase in 2.5mo since my first one in July (not too shabby for a creator-co-founder" 🙃)

While A+J owned all network connectivity + APIs + bugs + backend + user-created PRs + Stripe + automations, I had the freedom to build whatever magic moments I wanted.

We decided to wrap Quicker Chat in the Strategy Breakdowns brand.

Early users would mostly come from the audience, so we’d benefit from some small amount of familiarity + resonance, and the app instantly looked more unique.

Plus, it actually saves us a lot of time and cognitive load by removing micro-decisions, since we can align every new landing page + content asset + UI component to existing SB brand guidelines + colour scheme + email templates etc.

I also went to Mauritius.

Then Brazil.

What a month!

tom@sb: ~/2026/sep $ git log --oneline

→ 10 Sep: Spent a whole day writing the landing page, line by line, as a letter

→ 12 Sep: 38.6° fever. False start. Launch delayed 🤒

→ 21 Sep: launch email to the full list. I called 1,000 signups on day 1. We got 1,242 in 24 hours

→ 22 Sep: wiring up waitlist → invite email → checkout → book-onboarding-call → download app → in-app onboarding

→ 24 Sep, 1:47am London: Our first MRR 🎉

(User #1 had the same name as an 80’s NBA legend. We start losing our minds. Confirmed wasn’t him.)

We’d each, in our own ways, been dreaming of that moment for years.

Building a software product, and someone pays for it.

So, why a waitlist?

Fair question. It is a little counterintuitive if you assume growth-at-all-costs is the goal (it's not)

3 honest reasons:

#1 Every person gets onboarded by a human.

Austin (my co-founder) jumps on a 30-minute call with every single new user (what a legend, he’s done 45 as of today) - he makes sure your accounts are set up properly, and you'll learn the best ways to use the app.

To make sure all new users get the best possible experience (dedicated calls, fast feedback loop, bugs fixed quickly, etc) we started with 10 per week and have been scaling over time.

#2 We improve things between waves.

Each additional 10 users inevitably find rough edges, and suggest new ideas for us to build.

We'd rather nail them before the next 10 join, than have 1,000 people sending connection issues, bug fixes, and feature requests on the same day.

Each wave makes the user experience of subsequent waves better.

We're trying to make the best app as fast as possible, not grow revenue as fast as possible. This is the best strategy we could come up with to do that, and we're totally happy sacrificing growth for a wonderful product.

There's a boring #3 too.

It's Mac only for now, it works with LinkedIn, Slack, WhatsApp, X and iMessage, and the tool is designed to solve a specific set of pain points.

If you're on Windows, or you live in Telegram, or you don't use DMs for work - you're still on the list, just further back so we can focus on our ICP first.

By deliberately controlling the flow of new users, we’ve been able to build and scale some genuinely mind-bending systems behind-the-scenes, for example…

→ You tell Austin something on your onboarding call, or hit the feedback button inside the app

→ An agent sweeps call transcripts and feedback submissions each day, matches the request against our backlog, scopes it, writes the damn code, and creates a PR for it

→ One of us can then open the latest version of the app, with the requested feature working, to test it + click around + make any further adjustments if needed + ship it (or bin it, if it’s a bad idea 😂)

→ You get a message telling you your change is live 🫡

219 pull requests closed (ie shipped, not just opened) from these sweeps.

38 code changes came straight from users in the last 7 days, at the time of writing.

Everyone claims to let early users "shape the roadmap."

Ours are actually building the app.

tom@sb: ~/2026/oct $ git log --oneline

One thing we’ve done a poor job of so far is posting in-product screenshots/videos so people (besides our users) can actually see inside the app.

Today that changes! Here’s a few neat things it does, live in the app for our 45 MAU (free + paid):

One inbox for all your DMs.

LinkedIn, Slack, WhatsApp, X, iMessage (+ more soon!). Read, reply, tag, search, mute, archive and set reminders in one place.

Suggested tags

For Strategy Breakdowns, I message Sponsorship Leads on Slack + iMessage + WhatsApp + X + LinkedIn.

Platform of conversation ≠ Type of conversation

So quicker.chat automatically organises your chats thematically. One of the many tiny magic touches that keeps you sane + organised + calm (and you’re not sure how you ever lived without it, once you have it).

Tags are totally customisable too.

You can rename / reorder / reallocate.

You can hide certain tags from the sidebar.

You can hide everything tagged ‘Personal’ from your main Inbox (and conversely - click into ‘Personal’ when you just want to reply to Dad + dinner plans) to keep work + life separate.

Triage

Inspired by Slack’s legendary ‘Catch Up’ feature on mobile (IYKYK), Triage gives you a focused, 1-at-a-time, keyboard-first flow to quickly process the latest things on your plate.

New messages. Unread threads. Suggested tags. Messages requests (LinkedIn InMails, Twitter DMs from non-followers, WhatsApps from non-contacts, etc)

Suggested replies and follow-ups, in your voice.

This part’s cool. Remember those tags from earlier? You probably don’t speak to your childhood bestie in the same way as a client. (Or maybe you do - the feature works either way!)

For each tag, the app learns the key facts, goals, tone, and boundaries that shape how you communicate in those types of conversations.

So the Suggested Drafts for ‘Potential Hires’ match how you communicate with candidates, rather than how you communicate with ‘Investors’.

You choose which tags get Suggested Drafts (e.g. I have it toggled OFF for anything tagged Personal).

You always press send yourself, and can edit from the suggested wording (it’s Suggested Drafts, not automatic replies).

⌘K to go anywhere, and do anything

Global shortcut to jump to any chat/tag/platform, find any message, use any feature.

It also learns where you go most, so if I do [⌘K → “B” → Bryan] a few times, “Bryan” will start appearing above “#beehiiv-x-strategybreakdowns” in the results page.

(Nerdy, but I’m sharing anyway because it was fun to build and I think it’s cool - it uses a ‘Frecency’ algorithm that weighs both frequency AND recency to determine ranking.)

Keyboard-first

This was a non-starter for us. You can use the app 45x per day without ever needing to touch your mouse. It is ‘Quicker’ Chat after all.

Shortcuts have familiar defaults you’re probably used to from Gmail, Slack etc, but they’re all customisable too.

(Couldn’t think of a pic for this one - but its important so it still gets a spot!)

Privacy-conscious

All messages are stored locally on your Mac, and don’t touch our servers.

User choice matters, so you can use the app without AI features if you don’t want messages going to AI model providers.

Your platform sign-in details are encrypted on your device using macOS’s built-in secure credentials storage. They don’t touch our servers.

We do collect data for analytics and operations (performance, reliability, waitlist etc). But we don’t want to harvest any more data than is necessary, even though it would be more profitable to do so, so we just don’t 🙂

tom@sb: ~/2026/oct $ git log --oneline

So I’m pretty damn stoked about all this, as you can probably tell 🤓… but it's not all champagne.

Here’s a few hesitations on my mind:

→ Building vs selling. I wake up every day thinking about how to make the product better, not how to market it. I have to actively stop myself from spending ALL my time on features and UI.

The bottleneck right now is people knowing it exists, not features.

(Hence me spending 30 hours across 5 days creating this article 😅)

→ Writing load. Writing used to be ~15% of my week. With Quicker Chat it's ~60%. Daily social posts, waitlist emails, newsletter intros, email sequences, on top of my regular workload for Strategy Breakdowns articles and sponsor deliverables.

It’s a genuine challenge to stay focused in writing mode for this many hours each day - I'm still adjusting.

→ Onboarding every user by hand. It's the least scalable thing a software company can do. It's also a huge part of why the app is great.

At some point we might have to change it, without losing what makes it work.

→ Running 2 businesses at once. Strategy Breakdowns sponsorships have grown from $15k/mo to $51k/mo over the last 12 months. That compounding is what pays the bills and gives me the freedom to do this in the first place, but it’s also my biggest revenue opportunity as of today.

Every hour I spend on the software business is an hour not spent on the sponsorship business. Tough dichotomy I wrestle with every day.

But here's the thing I keep coming back to.

I’ve always believed in following energy, not dollars. “Fun to run” has been one of my core values for years.

I’m grinning like a child every single day at the moment. I’m pumped to start building as soon as I wake up. We’ve built a genuinely wonderful app, with real, happy, paying users. People DMing us every day about it.

Yes, revenue would be higher + growing faster if I never went down this path. But trading off fun for revenue is a fundamentally lame way to play this game. (And who knows - it might just grow Quicker than expected anyway 🤷‍♂️).

2nd Act.

Strategy Breakdowns started as a newsletter.

As of last month, it's a studio (?) with newsletter and a SaaS product.

House of brands or branded house?

Holding company or incubator?

Does the studio get its own name?

What’ll be next?

No idea tbh. It’s all improv jazz.

For now we run SB, and an app built by SB, for running SB.

If you live in your DMs like I do, come along.

We're letting people in a few at a time, and everyone on the waitlist gets a better price than public launch:

Cheers to year 4!

— Tom

P.S. If you made it this far, I appreciate you. Truly. 5k+ words, and I played with each and every one of them. If you’re keen to give Quicker Chat a go, reply to this email (or email [email protected] if you’re reading online) letting me know and I can bump you up the queue as a thank you for reading.

✌️