Two weeks ago, I wrote about my dirty weekend away with Claude Code.

I expected the honeymoon to end by Monday. Or that I'd burn out by Wednesday. Unexpectedly, we're now going steady.

Between coaching calls, burning off Easter calories, finishing song two and life, I shipped three projects this week. Two with real world utility, one for fun:

• bigfeet aggregates mens shoe deals in Australia in size 14 - 17

• Free Cloudflare Podcast Hosting replaces an annoying podcast hosting bill I was not getting any value from

• daily movie bot drops dialogue from one of my all time favourite films, Heat, into a private telegram channel 3x a day

bigfeet

• Pain point - I wear a US 15 / 16 and finding shoes was depressing

• Solution - source, aggregate, dedupe and present them

• Outcome - saved ~$250 so far

Free Cloudflare Podcast Hosting

• Pain point - I was paying a podcast host $20/mo for hosting

• Solution - tell Claude my pain, see if I could build it free on Cloudflare

• Outcome - saving ~$20/mo

daily movie bot

• Pain point - nil. I love film and came up with this idea over a beer

• Outcome - 3 lols a day

Learnings

• An audience of one is a great place to start. I am selfishly solving my own problems. If someone else benefits, great. It's not my definition of success - instead, I measure success against: did I learn something new and did I complete the project. The reward is the process itself, rather than an outcome, like admiration or users.

• It's easy to hyperoptimize workflow. I could tune token budgets, use Openrouter to get the right model for the job and run a precision workflow. There's thousands of suggestions on how to do this on LinkedIn. At this stage, I don't care (and maybe you shouldn't either). I bought a Claude Max plan and it usually lasts 4.5 hours out of a five hour session. NB: if you're on Pro, spend the extra ~$130 on Max and just. freaking. build.

• It's fun to hyperoptimize speed. I use Wisprflow to dictate (thanks Eva!), I run concurrent windows and when I build something on the web, I optimize it to be as fast as it can be. Demoing a product and having someone say "holy shit that's so fast" opens up a conversation for me to say "yes, I can show you how to do that." Speed creates momentum and is addictive.

• Batch processing helps throughput. My bookmarks are overflowing with interesting stuff to listen to and to learn from, but unfortunately, I can't ingest information AND build at the same time - I end up doing both poorly. So, I save bookmarks in a to-do folder and come back to them when I need a break. On that note - token burn, Github commits and other numbers are fun to show off, but aren't really representative of output or progress (for me) because...

• I'm not writing BRDs, PRDs or product decks, yet. I'm consciously fumbling through projects, allowing them to emerge, take shape and following the thread. This means I'm going to be way less efficient and burning way more tokens. As a former Business Analyst, Group Product Lead and Director of Product, I learned Bigco "product management" was about 2% product and 98% management and/or regurgitating a leader's product vision back to them. That administrative constraint doesn't exist for an army of one and I'm loving it.

If you're building something cool or want to, but don't know where to start, comment or DM me.

I'm happy to help.

In early 2025, I fervently launched myself into vibe coding, subscribing to Cursor, Replit and Windsurf with hopes as high as their valuations.

Unfortunately, they all hallucinated my feature requests into a black hole of recursion.

Between randomly spawning dark mode toggles and marooning me in Google Cloud config, my experience was ho-hum.

On the Easter long weekend, I decided to give Claude Code a go. I'd heard great reviews from technical folks and across LinkedIn.

TLDR - Claude Code is awesome, I had fun and built some cool shit which I'll share at the end of this post.

Here are some lessons learned along the way:

You might develop a kink for config

I used to proudly identify as a 'non-technical' person. I'd delegate anything that seemed technical to an engineer or someone who worked for me. I was convinced that I found technical stuff boring. This belief originated from the acute case of Java-textbook-induced narcolepsy I developed as an undergrad IT student.

Claude shattered this belief.

It crawls with me at my slow technical pace. Because of this, I found myself enjoying (!?) how the sausage is made. I learn, reflect and think through implementation, rather than just coin toss for the fastest/easiest/cheapest option or revered "build it perfectly, no mistakes" yolo prompting.

Doing delivers a drip feed of dopamine

I find flow in writing, intense exercise and open water swimming. It's an elusive feeling of being entirely focused and present, with zero distraction. It's my favourite creative zone to operate from. I can now add coding with Claude to that short list.

I found my only two constraints to flow were token consumption...

Just me and my boy Nacho, apparently...

...and my circadian rhythm.

There were a few nights I was awake til 2AM, pushing and pulling. I'd wake up the next day and keep tinkering away, coffee in hand.

The future is bright... unless you're a publicly traded SaaS

I asked Claude for the most technically impressive thing we accomplished on the project.

It (he/she/they?) responded:

Technically, Claude built it... so I'll take half the credit.

If you're an email service provider (ESP), part of your value prop just got chiseled by a (still) 30-something caffeinated ex-founder with limited (but late-blooming) technical chops.

Now, be a Founder of an ESP. Not only do you have to compete in a very mature market, but you also need to fend off an army of vibe coders, open sourcing every one of your hard-won features to Github. 24/7. Eesh.

Let's look at the share price performance of Atlassian and Figma on the public markets to see how this "feature-flattening" and other existential AI threats have been priced in:

Figgy pudding, now 70% off

Ay carumba

Some SaaS companies have zigged as features have zagged to zero. Tyler Denk (CEO of Beehiiv) now ships an equivalent number of features in one release that once was a meaningful chunk of a Y Combinator cohort:

• AI website builder (built on TypeDream)

• Podcast hosting

• Digital product sales (0% commission)

• Link-in-bio

• Real-time website analytics

• more here

I digress.

My point is - if software truly has become fungible, what's the final frontier? Data? Distribution? Content?

Time melts when you're having fun

Speaking of content, I found 80 video clips from five years of live music events. I'm not giving AI access to my photos... just yet.

I organized, taxonomized and enriched their descriptions. I uploaded the clips and earned a sneaky 10,000 YouTube views.

I mashed up my Letterboxd movie reviews, Goodreads reviews, beehiiv newsletter RSS feed, my self-hosted articles and an inspiring quote ( Bukowski, not that Jay Shetty nonsense) to deliver via the weekly dispatch from my brand-spanking-new site here.

Here's what it took:

Here's how it looks:

If you're building anything cool, reply and let me know.

You can find the other stuff I'm working on over at www.claff.co

Onward.

Business

I retained my existing coaching clients, but didn't add any new ones. I didn't do any marketing, because, frankly... I've felt hamstrung by AI. It's almost free, very useful and available 24/7. That's become a mental block for me. The good news is that personal patterns, predispositions and blind spots aren't something AI has nailed... yet.

What does Q2 hold? TBD. Something will change here.

Health

I lost ~9kg (or 20lbs) in Q1. Woo!

In 2025, a knee injury got the better of me and I started to eat my feelings. After Christmas, I turned the corner and spooled up hybrid training, weightlifting and thoughtful nutrition. Metrics like sleep, HRV and resting heart rate have rapidly improved.

Q2 goal? Lose ~10kg.

Creativity

This has been a landmark quarter for creativity:

I co-wrote a feature length film script. I stepped away from the project on the penultimate page, with no hard feelings and plenty of lessons learned. I felt as locked-in as the first year of my startup.

I'm two weeks away from completing my second song and very excited to bring it to life. Here's a 43 second teaser. I recorded vocals with a professional musician/friend and work on the track weekly with a brilliant mentor.

I tinkered on a few side projects in photography and vibe-coding. I was inspired by a Twitter thread about an autogenerated morning summary to pair with my morning coffee. Behold v1 with demo data of the Daily Dossier.

Goals for Q2? Complete script #2, song #3 and refine the Doss.

Lessons (re)learned

• Creating is far more rewarding and energizing than pontificating

• Hiring experts for coaching and mentoring is a force multiplier

• "Balance" looks wildly different for people, so choose your own

Quarterly favourites

• Film: Incendies

• Podcast: The Rewatchables

• Song: oskar med k - spellbound

• Live music: Deborah De Luca at Field Day

• Person: Hudson Walker, he did a 900 on a skateboard at age 10 🤯

Pics from Q1 2026

Here's to Q2.

During a Sunday stroll through the Botanic Gardens with a close friend and founder, I was hit by a mule.

I asked a standard coaching-flavoured question to learn how they were going with their soon to be venture-backed startup:

"What's the most important thing for you to work on right now?"

I admit - it was a leading question. I believe TALKING TO CUSTOMERS must be a top three priority, by default, always.

We did plenty of customer research at my long ago exited startup - long live WP Curve!

We codified and scaled it post-acquisition at GoDaddy, which was catalyzed by the CEO baptism of a marketing exec who gave a non-answer about why customers were canceling.

Years later, I implemented User Research in Canva China. The spiritual home of the 996 lauds pumping out features instead of listening to customers and figuring out what they need, so I had to advocate and step on some toes to get it across the line and the Great Firewall.

Even with my trio of anecdotes, I had no way of supporting my sentimental attachment to customer research, apart from the fact that it's served me extremely well. And while I've read and recommend the Creative Act, I couldn't justify my position through Rubin-esque vibes.

I knew the work was useful, but for most, especially my bob-the-builder friend, building is OH SO MUCH more fun, rewarding and frankly, energizing, than digging deep into customer need. It's also incredibly accessible thanks to vibe coding tools.

I presented the MULE.

As a founder, I charge you to prioritize the Most Useful and Least Exciting tasks to the top of your to-do list. Think of it as eating your veggies before digging into dessert.

The MULE incentivizes you to do the needful. The necessary. The not-so-sexy but oh-so-useful.

Here's a standard founder to-do list:

1. Prepare content plan

2. Read cringe LinkedIn posts (hopefully not this one)

5. Have a difficult conversation with co-founder

5. File and pay overdue taxes

5. Talk to customers

(all the 5's will slip until your hair is on fire)

Here's what a MULE prioritized list looks like:

1. Have a difficult conversation with co-founder

2. File and pay overdue taxes

3. Talk to customers

(planning is code for procrastination and LinkedIn kinda sucks)

I guarantee that you will make more meaningful progress towards your goals. And before you ask, isn't this just "Eat The Frog"?

...ish.

But who really likes the taste of Cuisses de grenouille?

If you're considering the leap into Founder life and are set on the idea of achieving, feeling like or even becoming a success, I can tell you from firsthand and countless secondhand experiences, that a restful state of success for a Founder is a mirage. An illusion. Or as Matthew McConaughey, circa 2013 in Wolf of Wall Street puts it:

Googlio defines success as "the accomplishment of an aim or purpose."

Yes, you will accomplish things, but like it's elusive bedfellow happiness, success is not a restful state or place you can hang your hat.

Blame the hedonic treadmill.

Blame it on the realization that even if you had an asshole boss who was made of Teflon™, you'll probably be 10-20x less forgiving than they were.

Blame the fact that founding, building, almost killing and resurrecting your startup will put all of your weaknesses, worries and warts under an industrial grade microscope.

Plus, being a Founder will age you in dog years. Woof.

Yes, you will catch momentary glimpses of success.

Think Northern Lights instead of say, gravity.

But, the goalposts will move.

There will be no back pats, no kudos and certainly no mailing it in.

Your startup also won't resolve any personal or emotional voids that you have from family, friendship or other life issues that have haunted you. It can momentarily distract you from them, though. In some cases, these issues might even help fuel you. Note: it's probably not the most sustainable, cleanest or renewable fuel source.

To all of this I say:

* DO IT ANYWAY

Find out who you are and what you are made of. If you have the opportunity to get after it, go ahead and:

• Prove yourself

• Change the world

• Generate an above median return on your time invested

• Fail spectacularly

• Dust yourself off and do it all over again

Send this post to a friend or colleague who yearns for the Founder life.

I'm more than happy to talk them into or out of it.

HNY!

Below, I’ll share a list of questions to help you make your 2026 goals wildly achievable.

As a bonus, I’ll put a goal I achieved in 2025 under the same microscope. It was the most meaningful goal I have achieved since selling my company in 2016.

We’ll use the trusty SMART framework with two small modifications:

• Achievable/Attainable is replaced with Actionable

• We will add Y for 'You' at the end - SMARTY!

Grab your goal and let's get started:

Specific

• Is my goal a dollar amount or an abstract number when I’m not really motivated by money or a random milestone? Could I use a different metric that I’m more excited about, and as a bonus, anchors to an emotion? > Coach Claff - instead of $xxxx, could it be “pay my rent from my side hustle” or instead of losing xx kg, could it be “weigh xx kg… so that I feel proud of my appearance.”

Measurable

• How will I know if I’m on or off track? What system will be in place to track my progress?

• What would a stretch version of the goal look like? Can I commit to that?

Actionable

• Do I understand the specific actions to achieve the goal? Can I plot them out on a timeline?

• What guardrails do I have in place when inevitable delays and roadblocks arise?

• What is my backup plan if it’s waaay more difficult than I first expected? What “break in case of emergency” activities will I complete to get back on track?

Relevant

• Do I really care about what achieving the goal gets me? > Coach Claff - it’s truly remarkable how often goals are committed to out of duty or expectation, rather than linking to a purpose or an emotional anchor.

• Is this goal a copy-paste from 2025? What, in concrete detail, is going to be different this time around? 

• What is the cost of not achieving my goal? How painful would it be for me not to achieve it? How can I make non-completion even more high-stakes?

Time-bound

• Am I sandbagging? Could I compress the timeline by half? What would need to change?

• Do I have time carved out every day/week in my calendar to achieve the goal?

• What am I willing to give up in service of achieving the goal? Social events? Family time? Scrolling on IG or Tiktok?

You

• How will I celebrate achieving my goal?

• Who will I tell about my goal?

• Am I surrounded by people who will support me, like positive friends or a community of like-minded people?

• Have I hired someone who has achieved this goal? This might be a mentor, coach, advisor or expert. If not, why not?

Try the questions on for size and see how you go.

Ideally, by the end of the exercise you will have clearer definition and more connection to your goals.

Now, for the bonus.

During COVID, I fell in love with a song called Silence by Kidnap.

It captured the emotion of an ‘uncertain time’ while also being cathartic and inspiring. I listened to it on repeat for hours.

After leaving Canva in 2022, I decided to create my own “Silence”. I enrolled in and completed an intensive music training program at Liveschool over four months. 

I looked this stressed for 4 months… ha!

I attained beginner-level expertise in the Ableton Live Digital Audio Workstation (DAW). I kept chipping away, watching tutorials and listening to as much music as I could. My musician friend William Derederenalagi challenged me to follow through and finish what I started.

After three years (!?) of Will nudging me, there was a shift.

I got so frustrated with being out of integrity - I was talking the talk, but choosing not to walk the walk.

As soon as I felt the shift, synchronistically, Steven Weston, a Grammy-winning producer posted a story on Instagram. He was offering mentoring. I booked the next available call, fanboyed out for about five minutes and then told him my goals.

We constructed a plan and got to work.

Six gruelling weeks later, I achieved my goal.

I published my first song. 

Let’s run my goal through the SMARTY framework:

Specific

• Is my goal a random dollar amount / an abstract number when I’m not even really motivated by money or a random milestone? Could I use a different metric that I’m more excited about, and as a bonus, anchors to an emotion? The goal was very clearly defined: “I will have a full-length melodic house song mixed, mastered, and uploaded to Spotify before the end of the year.”

Measurable

• How will I know if I’m on or off track? What system will be in place to track my progress? I had a specific breakdown of what stage we would be at the end of every week, which I asked Steven to put together for me. It’s natural to let a creative project take as long as it takes, but I needed structure and a deadline, as my perfectionism was thinly veiled procrastination.

• What would a stretch version of the goal look like? Can I commit to that? The stretch version of my goal was to launch with a music video accompanying the song, which I am super proud of. I commissioned Jason from Drone Shark to film a one-shot from Bondi to Bronte, which was the original inspiration of the open water concept.

Actionable

• Do I understand the specific actions to achieve the goal? Can I plot them out on a timeline? 100% clear.

• What guardrails do I have in place when inevitable delays and roadblocks arise? The ultimate unlock was having a hands-on weekly session with a Grammy-winning mentor who could help me work through anything I got stuck on. The backup was having my mate Will in my corner.

• What is my backup plan if it’s waaay more difficult than I first expected? What “break in case of emergency” activities will I complete to get back on track? I cleared my calendar to do things the “hard way”, which meant I spent hours upon hours editing and tinkering with tiny and nuanced details that frankly, no-one is likely to hear.

Relevant

• Do I really care about what achieving the goal gets me? Yes - this goal has haunted me since 2022, so I put just about everything else on hold to achieve it. I needed to rebuild my self-trust and see it all the way through, no matter what.

• Is this goal a copy-paste from 2025? What, in concrete detail, is going to be different this time around? Not applicable.

• What is the cost of not achieving my goal? I felt out of integrity and I wanted that feeling to go away. I'm sure Will was tired of asking me about it, too.

• How painful would it be for me not to achieve it? Extremely painful - the haunting would continue.

• How can I make non-completion even more high-stakes? I told every one of my friends that I would publish a song before the New Year so that they would ask me about it. I hired one of my favourite musicians to mentor me, which meant I needed to play half-baked ideas to my musical hero (cringe!) I shared early versions with friends, even though it was nowhere near ready.

Time-bound

• Am I sandbagging? Could I compress the timeline by half? What would need to change? No, six weeks was as aggressive as I could be.

• Do I have time carved out every day/week in my calendar to achieve the goal? Yes.

• What am I willing to give up in service of achieving the goal? Social events? Family time? Scrolling on IG or Tiktok? I put everything else behind this, including my health. It was a conscious trade-off and Uber Eats became a daily ritual.

You

• How will I celebrate achieving my goal? Sharing and listening to the song with family and friends. The first listening party was with my #1 fan and sister, Kate. Then on Christmas, Will played it to a small group of friends.

• Who will I tell about my goal? I told anyone who would listen. I also blogged every 4-5 or five days about my experience at roo.fm - reading back on these posts, I was a bit delirious at times.

• Am I surrounded by people who will support me, like positive friends or a community of like-minded people? Yes - special shout-outs to my sister Kate, my guy Will, Nacho Miranda for being a constant source of positivity and Eva Sheluhina for vocals.

• Have I hired someone who has achieved this goal? This might be a mentor, coach, advisor or expert. If not, why not? Yes - I hired the best person I possibly could to help me get across the line.

So, before you burn a couple of weeks in 2026 with an ambiguous goal, try the above questions on for size.

If you need help achieving your business goals in 2026, reply!

I'd be honoured to help.

PS - My second song 'chasing presence' will be ready on March 31st.

I'm writing this to you from the land of sugar cane and bird spiders:

Far North Queensland.

Over the past week, I've taken a week away to enjoy a reset.

I've prioritised:

• catching up with family and friends

• swimming, hiking and wandering around the tropics

• unplugging devices and leaving my headphones at home

• breaking rhythms, habits and patterns to jumpstart a reboot

I got a DM yesterday about a potential client relationship and the best reply I could muster was:

"...my brain is scrambled from the sunshine but I'll reply on Friday"

It took me about five minutes to formulate that sentence.

Why am I sharing this?

I didn't reset anywhere near enough when I was a founder.

I would get sick or have a few extra beers to take the edge off.

My half-assed version of downtime was to walk to the local cafe with my laptop on Saturday morning, gulp down an extra-strong coffee and mash my keyboard for three hours.

The point?

As a founder, your company's problems take up a remarkable amount of rent-free space in your head.

In time, you manage to mute the ever-present background hum of things to do, but in the interim, here's your permission slip to take a breather.

Find a space to reset.

Put it on your calendar.

I recommend this Friday afternoon.

Unplug and see what flows through.

I got a late night call from a friend last week.

He had been offered the opportunity to co-found a startup.

His prospective cofounder has a great track record, having grown his last business to 100+ venues and replacing himself with a management team.

My friend has complementary skills for the opportunity and has also built a great business of his own. He is seeking variety for intellectual stimulation and would feel more financial security if he had a secondary, non-correlated revenue stream.

We walked through the details of the offer, which I’ll keep anonymous here.

The opportunity ticked a few boxes, but there were a few red flags too.

One immediate call out he made was:

“…he’s a great business guy, but he really likes the sound of his own voice...”

Hmm…

So, I posed a few questions to him. 

The questions were not anchored to the opportunity, but his goals as a founder. I like to work founder-out, not opportunity in. The assumption is that the founder is capable enough to make any given opportunity succeed.

This framing helps the founder get clear on what they might learn, rather than compare opportunities side by side. 

This is important because the tail can wag the dog, where the opportunity drives the founder, rather than the founder pursuing an exciting opportunity.

I learned the pitfalls of this with my first company. I should have been more excited about the category overall, as I was easily distracted and started multiple other projects while the original startup was doing just fine.

Here’s a sample of the questions we dove into:

• Could you see yourself working with this person for 50-60 hours a week for the next few years? If yes, how do you feel about that?

• Would you be happy to put your friendship at risk if you took this opportunity on?

• How do you think this opportunity will help you grow?

• Would this be the highest and best use of your time, given the other known opportunities you could pursue at this point in time?

• What held you back from an immediate, emphatic yes?

These are great questions to consider as you’re starting out. 

If there are any questions you wish you had been asked, pre-startup, please reply and let me know.

“The world is full of people suffering from the effects of their own unlived life.

They become bitter, critical, or rigid, not because the world is cruel to them, but because they have betrayed their own inner possibilities.

The artist who never makes art becomes cynical about those who do.

The lover who never risks loving mocks romance.

The thinker who never commits to a philosophy sneers at belief itself.

And yet, all of them suffer, because deep down they know: the life they mock is the life they were meant to live.” - Carl Jung.

I’d like to add:

The founder who never starts a company and settles for a comfortable, but soul-crushing corporate existence.

Does that hit?

Here are some examples from both sides of the fence.

I know a bloke who is excellent at everything. I’m envious of his brilliance. He’s a critical thinker, a community builder and a creative. He was once walking his passion path in film. He gradually slid into corporate and now holds a role with my least favourite tech company of all time.

I have zero judgment - I do not intimately understand his motivations or goals, but I am certain the world would be a brighter place if he threw his shoulder into his full potential.

I met a younger, curlier-haired version of this fellow when I studied music production (which I was terrible at, but thoroughly enjoyed). He’s wonderfully talented and has the stage presence of a young Michael Hutchence.

I firmly believe he could take it all the way, whatever that means for him. He was considering a similar slippery slide. He asked me what to do. My advice to him is the same to anyone who might lack the courage, self-belief or see the tactical steps to take the leap:

“Please, please, please go FULL SEND on the thing you really want to bring into the world. If you fail, you’ll get to know yourself in a way few get the opportunity to. I cannot guarantee you any success. I can guarantee the path will be way more difficult and far more harrowing than corporate. You might even hate it once you’re in it. But, it will enrich your life in a way that no one can take away from you and few will fully understand. You can make this happen and I will help you get there in any practical way I can.”

I do not preach this advice to everyone - but you're still reading, so thanks for the permission.

I do not judge people who choose a more comfortable path. They might have constraints to work within, whether they are health, financial or familial.

My argument is: there is a risk-managed path for you to create what you want. Here’s a list of people who have backed themselves and are getting after it with all their might:

Kirk Reynoldson & Kate Morgan - they have been grinding for six years to bring Eggy to life. Their courage and tenacity to build tech that makes people’s lives easier is inspiring to me.

Chanel Clark - a future LinkedIn Top Voice, marketing dynamo and community builder who calls a spade a spade. She lays it all out there and her transparency is refreshing.

Craig Reid - the GOAT of process, a reliable bloke and the founder of a brilliant scaled service. His attention to detail helped him to stitch together a service and solve a series of complex problems that most would shy away from.

Jess Ruyter - a thoughtful designer I briefly met during my Canva days. He’s documenting his path of leaving Google and following his passion (link in comments). He is the inspiration for this post - thank you JR.

I’ve got a loooot more folks who fit this profile.

BTW - you don’t have to fully cast off the corporate shackles to get started on your thing.

Sacha Dixon and Alec Stobie are building Nook and holding down full-time gigs, as well. They have what it takes to go all the way.

Now, I don’t think any of these founders will tell you what they’re doing is easy. And they probably wouldn’t even say that most of the time, it’s not really that fun.

But, this act of pursuit creates a personal freedom that few get to experience.

In closing,

The world needs less alignment meetings, 100+ page slide decks and Game of Thrones-esque corporate shenanigans.

The world needs more of you, doing what you are called to (even if you fail) and living your unlived life.

Greetings,

I’ve spoken to some very talented service business founders who have seen their revenue collapse by 90% in a matter of months. The worst market I’ve seen so far is copywriting - it’s a bloodbath.

The success stories I’ve seen are founders who have:

1. A profitable and scalable model: most are running a “productized service”, which is the business model that allowed me to exit my first startup. It’s a people-driven service delivery model that gets more, not less, efficient with scale

2. A clear understanding of their business value:
   - the service replaces 50% to 100%+ of a Full Time Employee’s contribution for a fraction of their fully burdened cost and/or
   - generates sales pipeline or revenue, aka is very close to the money and/or

   - warrants an annual contact value of $20k - $100k+, well clear of the dreaded danger zone for subscription services (lower than $10k per annum). “Nice-to-have” services have zero moat

3. A killer offer: their service is built around a complex process, specialised staff training, a custom system, or some other combination of hard to copy ingredients

4. Working acquisition channels: Two concurrent marketing channels are running like clockwork (typically paid and cold outbound). The founder has also adapted their SEO strategy to capitalize on ranking in LLM responses

If your business sounds more like a one person consulting shop with steady churn and referrals as the only working channel, what should you do?

1. Exhale. Everything is figureoutable

2. Score your business 1-3 (1 bad, 2 good, 3 great) against the scoreboard of:
   - profitable & scalable model
   - creating true business value
   - delivering a killer offer
   - two acquisition channels
   If your score is less than 12, go back to the drawing board, get creative and reimagine your service. Reimagine your category. Dream up a new one. A score less than 12/12 probably won’t survive

3. Reply to me with the before and after - I’m happy to take a look

This might seem bleak and you also might be wondering - is there any upside for service businesses during this epochal AI shift?

Success leaves clues.

Scale and Surge, two AI unicorns, are heavily dependent on humans to label data. Large chunks of their businesses fit into the productized service / tech-enabled service model. Surge has reported a remarkable $1B ARR of bootstrapped revenue.

A quote to ponder:

“Energy cannot be created or destroyed, it can only be transformed from one form to another” - Albert Einstein.

Could the same be true for service businesses?

Have you ever been silently frustrated at someone because their behaviour does not match your expectations?

Have you worked in earnest, without feeling like you’re where you need to be, but also don’t know specifically what winning looks like?

Do you compare yourself to a competitor who appears to be crushing it, unsure of whether you can ever catch up to their ever-widening lead?

This pattern is something I like to call…

invisible expectations

It's SUPER common among founders and is one of the driving forces behind burnout.

Here are some examples:

• you made $10k last month, but you won’t be “legit” until you make $83k/mo (aka the invisible $1m arr threshold of legitimacy)

• your peers tell you that you’re crushing it, but you have a creeping sense of dissatisfaction even though you attained your targets for last quarter

• you grind yourself to the bone to get through a difficult project, but you don’t take a second for a breather or to celebrate how far you’ve come (the invisible sisyphean work loop)

• you don’t even know how to spell balance - your health is waning, your relationship is stretched and you feel lethargy holding you down (the invisible flattening battery)

So, what can you do if you’re in this loop?

First, if this post resonates, don’t shove it away. read it twice and let it sink in.

Then, dig into one of these invisible / below the line zones. It can take some doing and if you get stuck, AI can help.

An example prompt to put through your favourite LLM could be:

I'm feeling a sense of dissatisfaction with how my business is progressing. Here is what the last few months have looked like [insert summary here]. Can you help me triangulate what invisible expectations I might have that are draining my energy and making me feel like I'm not where I need to be?

Next, give yourself five minutes to create an arbitrary goal for an area where you have invisible expectations.

This might be your current growth rate, your product development velocity or your team engagement.

Invisible expectations hide in corners where things can be difficult to measure and are more felt/vibey than quantified.

A good indicator is that you’re not happy with where something is at, but you also don’t have a metric to know whether you’re tracking on target for it.

Then, brainstorm a bunch of actions that can help you move the needle towards your newfound goal.

There's a possibility that one of these actions might be to accept that you cannot influence a certain area, but you decide to fully take that on board and move on.

Create a dedicated window, ideally when you’re at most productive, to tackle this fuzzy area. The actions should be clear enough that you can verb noun them, see:

• chase accountant for xyz

• meet w/ designer to understand gap

Pop those in your calendar and you’ve got some to-dos.

Finally, create a placeholder calendar invite for when you achieve the goal that was once invisible, ambiguous or fuzzy. Push this out n = 3 weeks from today.

It only needs to be 30 minutes long. and frankly, you’re probably not going to take yourself out to dinner because you “did what you should have already done.”

This practice creates a new pathway in your brain and leaves you with a process to lean on when things are wonky, but you don’t know the way out.

If you have a sticking point like this in your biz and can’t figure out how to find it or fix it, reply to this email. I can help.

Each founder has a unique definition of success.

My personal definition is "applying myself with 100% effort in service of a goal."

If I can hand on heart say I've given it my all, I've succeeded. I work my ass off towards the goal and trust/hope the score will take care of itself.

With that preamble, I present to you, the inimitable Brigitte Lyons.

When we first worked together, Brigitte's definition of success was to build a business that allowed her to be location independent, live van life, hike through America's beautiful national parks and work twenty hours a week.

Her path was an absolute rollercoaster and her story reminded me that as a founder, you are forced to face yourself all the damn time. Your business becomes an extension of you: your strengths, your shortcomings and your blind spots.

We dove deep into her story, which is refreshingly unconventional. Brigitte:

• proactively offered customers the ability to cancel contracts during the pandemic

• ran her company without Slack, but got a ton of leverage out of regular 1:1s

• listed her business for sale through a LInkedIn post

• shut down her company, then sold it post closure (!?)

• and lots, lots more

This has been my favourite interview so far (with Jake coming in a close second place), please give it a watch.

Cheers,
Claff

I’m restarting my founder coaching service from scratch. Here are some of my marketing metrics to date:

LinkedIn has been fickle. Painstakingly edited posts have performed poorly, while a few throwaway posts have gone semi-viral. Impressions ≠ enquiries, so there’s lots to learn here.

YouTube has been fun. I’ve interviewed four former clients and a colleague/friend/ROI baron. I’ve clipped dozens of daily shorts and a few have performed well. Instagram and TikTok reels are simply reposts of YouTube shorts.

As I pored over these numbers one Sunday night, my inner coach whispered:

“Vanity metrics are distracting you”

Oops.

The single leading metric that matters RIGHT NOW is the number of free coaching sessions I complete. Upstream metrics like impressions, subscribers, likes and comments are weak progress indicators.

In reality, the prospect’s journey for coaching looks something like this, give or take a year:

That’s a long ass sales cycle, which needs a bit of elbow grease to jump start.

So, let’s break down how to accelerate.

By the way, please ask these questions for yourself and reply to me with your answers, if you'd like.

What’s your leading metric that matters?

It might be sales call completed, demos completed, active trials or proposals sent. Use the last measurable step before a prospect makes a buying decision.

For me, it is number of free coaching sessions with qualified prospects.

What percentage of your time are you investing in driving that metric?

My total time investment to improve this metric is maximum ~10% of my week.

What would change if you doubled your time invested?

I’d likely double the number of proposals sent and all things being equal, accelerate my progress towards my goal by 2x.

What’s your ideal state?

When I achieve my goal of 15 concurrent clients by year-end, I’ll be able to spend way more time creating content, which is very fulfilling and stimulating for me.

I’ve got hundreds of hours of coaching call transcripts that might make a nice book… WHOA! There’s my carrot and reason to do things I don’t love, like outreach.

How will you get there, specifically?

• Connect with ten founders who fit my profile each day from LinkedIn on my phone, before I get out of bed, or I’ll find a way to push it down my to-do list

• Then, introduce myself in a non-salesy way (Coach Mitch helped me here)

• After a few days, do some thoughtful research and send them something useful

• If they respond, ask if there’s anything else I can help with and offer a call

• Plus, let everyone in my network know I’d love a referral and will reward them handsomely for a successful intro OR make a donation to a charity of their choice

• Ask for specific intros to prospects I believe I can help

So, you can probably guess what I’m going to say now.

I’m aiming for five free coaching sessions a week which doubles the current 2.4 per week - my leading metric that matters most.

If you need to get unstuck, reply to this email and I’ll send you my calendar booking link.

To doubling and beyond,
Claff

Circa 2018, I would get out of bed, mainline a coffee, sit down at my computer and rip into a mountain of work.

About three minutes after sitting down, I would stop dead in my tracks.

Instead of doing the "very difficult thing" I had prioritized as my must do, #1, do-or-die task the night before, I'd start chipping away on easier tasks.

I could quickly tick them off and build momentum to the main thing, right?

Wrong.

My #1 priority task would find a way to rot through the week, earning the prestigious "#1 but never done" title on my otherwise well-pruned to-do list.

These blocking tasks would fall into one of three buckets:

• sales: doing cold outreach (rejection... eek!)

• admin: a must-do, but a huge waste of time

• conflict: having a difficult conversation

No amount of humming 'eat that frog' could get me going.

My brain was doing its job - thanks, brain! It was leading me away from pain towards pleasure.

I needed to circumvent my brain and my procrastination.

After much experimentation (cue montage of a guy experimenting with weird processes in a lab), I stumbled across a solution.

What was it?

I set a calendar invite with a link to a deeply private Google doc. The doc was called "Win Wall". It was overflowing with kind notes, screenshots of client testimonials and photos of key memories that made me feel great.

I would bomb my brain with so much goodness that I didn't look for dopamine to-do list ticks.

I had enough juice in the tank to wrangle that gnarly task, straight out of the gate.

Give it a go.

It feels weird the first few times, but it freaking works.

PS - please reply if there’s anything I can help with. My calendar is starting to fill up with more calls, but I have set time aside for a few free calls with my loyal subscribers. That’s you!

When I was to-ing and fro-ing between trying to get another job (shudder) and pitching myself for some fractional consulting, I needed help to improve my LinkedIn profile.

I reaaallly didn’t want to participate in LinkedIn.

It was awash with embellished accomplishments and humblebrags.

I chose to sit it out, selling myself short with zero information about what I’d achieved.

It wasn’t working for me.


When I’m stuck in a loop, I use a hack: invest a non-trivial amount of cash to move forward.

It creates a financial stake, which helps my brain switch from being passive to active.

I found Mitch, paid for a session and in the first two minutes he said four magic words that earned my trust for life:

“Your LinkedIn is sh*thouse.”

He was 100% correct.

It’s hard to find people who will be this stone-cold honest with you.

• Family members will generally be supportive and hype you up

• Friends will try to be helpful, but might not have relevant expertise

• Some service providers fight misaligned incentives; they might be trying to maximize your lifetime contract value or maximize the investment they’ve made in your company

That’s why uninvested honesty is so powerful.

When there’s a good baseline of trust - uninvested honesty cuts through nonsense, puts your ego aside and stabs you right in the cause, rather than tiptoeing in the fluffy stuff.

It’s a very powerful tool, if you choose to take action on it.

A week or so ago, I felt my writing was going off the rails and I needed a quick steer.

I paid for another session with Mitch and after an hour, walked away with 15 action items.

As we were wrapping up, I started egging Mitch on to productize his expertise.

Mitch had already been cooking up a product called “How to sell on LinkedIn without hating yourself”

With a friendly nudge, he decided to send it!

Here’s his launch post.

BTW - Mitch has no idea I’m shouting him out - frankly, it might make him feel awkward.

I’m just returning the favour - he gave me uninvested honesty and I’m sending it right back to him.

He’s great at what he does and I fully endorse him.

Cheers,
Claff

PS - my free coaching calls will continue.

I had a great yarn with Patrick a few weeks ago. He just quit his job to kick off his biz. After an hour, he walked away with a by the numbers plan of his goals and the actions he’ll need to accomplish, month by month. Kinda cool, given there are a million and one distractions when you’re starting out.

Hit reply if you want to grab some time for some uninvested honesty.

I coached Justin, founder of the done-for-you video editing service Video Husky in 2018.

He sprinted hard towards $1MM in ARR (and made it) but got sideswiped by COVID.

One of Justin’s best traits is that he makes decisions that suit his personal goals, regardless of what conventional wisdom says. Here’s a list from our interview:

• over-invested early - spending $60k (!) on a website to boost conversions

• onboarded both good and bad fit customers to recoup marketing expense

• had his staff vote in a 20% pay cut, rather than more layoffs during COVID

• hired a General Manager and stepped back from the business in 2021

• moonlighted in coaching, but didn’t love it so helped his uncle instead

• is now learning to code and gearing up for an AI opportunity

He collects profit from his business and has time freedom. It’s not the path for all, but he’s made it work and I’m very proud that I got to help him set the foundation in the early days.

Check out the full interview below.

I’ve added chapters in the YouTube description so it’s easy to bounce around topics.

Chat soon,
Claff

PS - I’ve had so much fun offering free coaching calls that I am going to keep offering to do them as time permits. If you want to talk through your business related challenges, hit reply and I’ll send you a calendar link.

There’s no sales pitch.

Greetings and salutations.

When’s the last time you thought about managing risk?

If you’re like most founders, you probably had to squint to really think about it.

Don’t worry - I got you. I took a verrry boring topic, made it accessible and then added some actions you can take to manage risk. It wrote itself, which always feels good.

Here’s the first of seven bullet points, then head to LinkedIn to read the rest.

1. You get sued by an ex-employee for unfair dismissal

In Australia, you can expect a meaningful financial impact (~$80k for a max penalty - this is not legal advice), moderate operational disruption (delayed projects due to time loss), and significant reputational risk (employee distrust, negative Glassdoor reviews and maybe you'll end up in the AFR).

If you settle out of court, you're looking at $50,000-$100,000, plus legal fees of $10,000-$20,000. Let's not forget the hundreds of hours lost to legal meetings, stress, and reputational damage among current employees.

For startups, there is a moderate probability of, say, 20% given lax HR processes, hiring 'ninjas' and CEOs who are spread thin.

The risk begins in hiring but then weaves through management practices, poor documentation of employee issues, and unclear termination processes.

Your next steps: you might still get taken to Fair Work or an equivalent US body like NLRB, DOL or EEOC, although the "at-will" nature of many US employment contracts can help reduce this risk. The risk management practices I'd suggest are:

• Implement a formal performance management system with clear KPIs and regular reviews (e.g., quarterly check-ins)

• Establish a defined warning process: verbal warning, written warning, performance improvement plan (PIP), and termination protocol

• Train managers on dismissal practices to comply with Fair Work Australia 

• Use lawyer-reviewed employment contracts with clear termination clauses

BTW - a handful of y’all set up a free call with me last week, so thanks for taking up the offer. I’ll keep it open for one more week and then I am locked in.

Reply to this email if you want to grab sixty minutes w/ me, for free!

Cheers,
Claff

Hey {{first_name}} - it's me, Claff!

I’m back! And I’m coaching founders again.

I have an invitation for you, because you’re one of my OG readers circa 2019.

Reply to this email and I’ll send you my calendar link.

I’ll give you sixty minutes of my time to help unblock whatever is in your way.

Zero obligation and zero cost to you.

I also wrote this post, which I hope is useful to you:

What they don’t tell you about selling your startup

It’s all the non-obvious things I experienced during the acquisitions I’ve been involved in, as a seller and an advisor to other founders.

Thanks for your attention and I look forward to (hopefully) catching up with you soon.

Until next week,
Claff