Too many operators in large companies believe that their latest app idea or AI project will transform their company.
This isn't how it works.
AI transformation requires a clear mission, a well-defined minimum viable problem, a target market, a brand, a go-to-market strategy, a business and pricing model, an end-to-end customer journey, an incredible and disciplined roadmap, and much more.
These elements must align and work together as a system over a sustained period, through multiple iterations, to produce a successful result.
This requires that your entire team is explicitly aware of these key factors and works in alignment to execute them well.
If you're in a large company trying to do something new and disruptive, chances are good that you have the wrong business model, culture, and skills within your existing business. Chances are also good that you have a lot of domain dogma, institutional knowledge, and sacred cows that will hold you back.
If this is true (I'd be surprised if it isn't), it will likely require creating a new business unit (or even an entirely separate spin-off company) with a different set of cultural values, goals, and skills.
If you just ship a new App (AI or otherwise) without aligning the business properly, it will fail.
The clearest example I can think of in recent memory is the Taxi industry. In response to the threat of Uber, many of the Taxi companies released or started more heavily promoting an App. What they failed to understand, however, is that Uber's entire business model was totally different and more efficient than theirs.
Uber featured everyday people acting as drivers rather than employees on fixed shifts (meaning a more elastic fleet that could respond to spikes in demand with more agility), lightweight enablement of drivers via mobile phones (vs. 100k fit-outs of the Taxis with cages, livery, proprietary meters, and other in-car tech, etc), mutual accountability with ratings (vs. unaccountable drivers and riders doing unaccountable things), and yes, massive subsidies powered by a global high-growth, venture capital-based business plan (vs. localized, revenue-based model).
These were the things they were really fighting - not just an app.
These days, legacy companies are fighting against top-down reinvention of entire categories by AI-native businesses.
A much more dramatic and fundamental approach is mandatory if they want to compete.
Product & Startup Builder
Why does Apple win?
A major problem with many products, marketing programs, and everything else is a lack of discipline and long-range thinking that allows for slow, deliberate iteration and optimization over time.
SO why does Apple win?
One of the major reasons is that they create 1 product per category, and they do. not. stop. until. it's. perfect.
Other companies just make stuff up every cycle - seemingly to satisfy the whims of the latest middle manager or product manager.
It seems rooted in the "not invented here" phenomenon.
Focus. Discipline. Iteration. Taste. Judgement. Patience. Time.
Some of the companies I've advised
Every now and then, people ask me what kind of companies I advise.
Here’s a list of just some of the companies I’ve formally and proudly partnered with over the past decade—across Web3, fintech, healthcare, AI, and more. Sharing it here both as a handy link.
🌐 Web3 / Crypto
Immutable – Leading web3 gaming infra with 460 games signed and 4M+ users.
Swyftx – Australia’s largest crypto exchange with 1.2M+ customers.
Coinstash – A$1.3B+ in trading volume and growing retail presence.
💳 Fintech / Payments
Reshop – Raised US$17M, led by Afterpay co-founder, backed by major retailers.
Cake Equity – Manages equity for 20k+ companies globally.
YouPay – Used by 150k+ creators for social commerce payments.
👩🎓 Talent / HR / EdTech
JOB TODAY – 100M+ job matches across 400k businesses.
Hatch.team – 150k+ candidates matched with 120+ employers.
Vygo – Scaling university mentoring at Coventry, Swinburne and others.
Multitudes – Backed by Blackbird to bring AI coaching into engineering teams.
🍽️ Hospitality / Retail Tech
Bopple – Processing orders for 10k+ venues worldwide.
Maropost – Serving 3k+ merchants after consolidating AU retail tech.
Doshii – Standard POS connector across Australia’s hospitality sector.
🤖 DevTools / AI Infra
Agora – Publicly traded, US$33M quarterly revenue, 1.8k enterprise clients.
Salad – Fastest-growing GPU cloud, expanding distributed compute capacity.
Sema – Monitoring codebases across trillion-dollar enterprises.
⚡ EV / Climate
Tritium – One of the world’s largest EV fast-charger makers, expanding in EU/US markets.
🧬 Healthcare / Bio
Microba – ASX-listed, 30% revenue growth and expanding clinical trials.
Cannatrek – Among Australia’s largest cannabis producers, revenue near A$90M.
🎬 Media / Entertainment
Participant Media – 21 Oscars and US$3.3B box office before closing in 2024.
AI has evaluated my brain - here's what it found.
I asked ChatGPT to break down my intelligence across different dimensions based on our chats together.
Here’s what it came back with - objective, clinical, almost brutal in tone. And then, because I’m me, I added my own color commentary.
🧠 IQ: 135–145 (top 1%) - Very high analytical and abstract reasoning ability. Comfortable with complex systems and cross-domain problem solving.
Editor's note: So basically, I can process tax treaties in my head… but can’t decide what to order for lunch without a 5-step decision tree.
💡 Creativity: High - Strong divergent thinking and originality. Excellent at reframing problems in novel ways.
Editor's note: Or in plain English: I can make IKEA instructions feel like a Shakespearean tragedy.
❤️ EQ: High but uneven
Deep empathy and self-awareness. Occasionally impatient with triviality or nonsense.
Editor's note: Which means I can soothe my crying son… but also want to throw my phone when someone asks dumb questions.
🎯 Practical/Strategic Intelligence: Extremely high - Exceptional at structuring chaos, spotting fatal flaws, and thinking several moves ahead.
Editor's note: So, great at global strategy, but I drive my family crazy.
🔄 Metacognition: Exceptional - Consistently reflects on thinking processes. This multiplies other abilities but can lead to overthinking loops.
Editor's note: Yep — I think about how I think, then about thinking about how I think… until I need a nap.
In summary:
The AI thinks I’m in the “gifted” bracket — a ruthless strategist with strong empathy and endless self-reflection.
In other words:
Great for the companies I advise; Terrible for living in the moment and finding contentment.
Startups + Agile is like Peanut butter + Jelly
Startups = Breaking new ground.
Breaking new ground = Uncharted Territory.
Uncharted Territory = Uncertainty.
Uncertainty = Careful iteration (Aka, "figuring it out as you go" or "Agile")
You don't need a business plan, you need an exploration plan.
As an investor and as a leader in a startup, you don't want false precision; you want to trust people with great curiosity, taste, judgment, and hustle.
Viral effects vs. Ad spend
For new well-designed social apps, the ad spend can either be a) mere fractions of the "cost per action" - because each new user invites their friends, or b) irrelevant because people don't use the thing.
Your KPIS might be getting in the way of GSD
For young startups, overly specific growth goals can be a distraction.
Why?!
If you're always solving the NUMBER 1 thing that's stopping you from growing faster, then you'll always be achieving maximum possible growth.
When do they matter?
To set expectations about orders of magnitude (E.g., we want to achieve double-digit growth - not incremental growth)
To align downstream operators who are not sophisticated enough to understand what they should do without KPIs
To measure and reward performance for individuals and the overall company
But don't let the KPIs (and defining them) get in the way of just getting sh*t done.
Being too early is the same as being wrong
Time and timing are among the hardest things for many founders and operators to understand.
Timing for a great idea. You can be too early or too late with your business or startup. This can be catastrophic for even the best ideas executed in the very best way.
Timing for the right target market & persona. They have to be ready to buy what you already have. You can't build everything for everyone at the same time.
Timing for the right feature on the roadmap. Each feature has to address and optimize the use-cases you are trying to solve right now, or you will pancake your product and build something complicated and half-baked.
Timing for when to start or end a discussion. Discussing things far off in the future is often a gigantic waste of energy. This can be a hidden tax on your velocity and quality of execution.
Timing for a particular opportunity or business model. Just because it's AN opportunity, doesn't mean it's the BIGGEST opportunity RIGHT NOW.
You must, must, must understand WHEN to do things - or you will end up trying to do ALL the things and failing to do much of ANYTHING at all.
Some of my beliefs...
Some of my beliefs...
- Improving health is the silver bullet for creating better lives and communities.
- Domain dogma is often outdated - first principles drive innovation.
- Rigor and precision are at the heart of credibility and efficacy. Delivering results is what matters.
- Healthy ecosystems move people and society forward.
- The future is already here, it's just not evenly distributed. Helping innovation cross the chasm takes inspiration, aspiration, and bold leadership.
- Information is power. It drives precious agency and actions. (i.e., there’s no such thing as too much information or transparency).
- Disruption takes bold leadership, rapid learning, and fast, high-quality full-stack execution.
- Great, human-centered design is a fundamental driver of progress, empathy, and change.
Some principles for your company's content strategy
Think of marketing, customer support, and educational content as a holistic superset. Apply the following principles…
- Brand and Content team provide self-serve guides for ALL content types (including customer support content). This ensures consistent tone, voice and vocabulary
- Have a clear and concise review process for brand and risk. Don't allow bottlenecking!
- Bias towards ungated content. Help non-users see how rich your product and support content is
- Ensure there's great consistency with text and image templates for each content type
- Treat customer support tickets as defects - when a ticket comes in, take a moment to update the docs and send the doc (rather than a bespoke answer) and summarize common feedback for the product team
- Disambiguate content types - not all content is the same. Make sure there's clear ownership of content types and clear, lightweight processes for development and sign-off.
- Make sure that support content is intelligently linked from within the product
How do you define speed for your startup?
I define startup speed as…
-- The rate of strategic value delivery to users --
Let's unpack it...
"The rate" - the consistency and interval of events
"Strategic value" - units of value that are aligned with your vision and long-term self-interest (not just doing anything for anyone)
"To users" - not for academics, partners, regulators, internal people, or otherwise
It is NOT busywork, focusing on more than one thing at a time, and/or living in chaos and thrash.
Here's the SECRET 2-step formula for MASSIVE startup success
Here's the SECRET 2-step formula for MASSIVE startup success
Step 1: Build a product that solves a real and urgent problem for people.
Step 2: Let those people know about it in a way that they can understand.
Easy right?
Of course, it's much easier said (or written) than done.
Who are the right people?
What's the right problem?
What's the right solution?
What's the right product?
Where do the right people hang out?
What's the best way of explaining the problem + solution to those people?
Who are the people, processes, and technologies that can help you answer and execute all of the above?
There are countless other decisions and deliverables you need to get right to make this very simple equation work.
But do NOT forget the equation.
Don't lose sight of the goal, and don't make it the execution more complicated than it needs to be.
Because in the end, the goal is actually very, very simple. And the execution is already very, very hard.
On the virtues of saying NO to opportunities
People often struggle with the idea of Focus.
People generally don't intuitively understand why staying disciplined with a "Minimum Viable Problem" and a corresponding Minimum Viable Product is key to their growth and scale.
You'll hear phrases like this...
"Why can't we just support this extra use case?"
"Customers want our product to do X!"
"This is an important opportunity!"
"Isn't it easy to just..."
There isn't an industry, product category, or customer profile in the world where you won't be asked to handle more use cases.
Your customers will ALWAYS want to have more of their needs met across all their use cases.
This ALWAYS appears like a great opportunity. A no-brainer, right?
However, it's not necessarily the right opportunity, or in your startup's best interest, to solve these additional use cases. At least not right away.
Why?
The secret to scale is creating tight alignment from the very tippy top of your funnel all the way to the deepest part of your product so that you achieve real Product Market Fit (PMF) and corresponding rapid growth.
PMF is when a high percentage of users go through the ENTIRE funnel cheaply and easily: Awareness -> Interest -> Education -> Adoption -> Value Creation -> Uh-huh moment -> Retention -> Advocacy
If you carelessly stumble into new use cases, two bad things will happen.
Bad thing 1
1. At first, you will typically just add some features to the product and/or some messaging to your website.
You will typically NOT spend the time and money to create a solid funnel for the use-case from top to bottom (product marketing, product education, product support materials, product features, edge cases etc).
The customer will therefore fail to make it all the way to the bottom of the funnel (retention + advocacy).
This will result in either...
a) Produce high-churn customers who don't make it all the way through the full funnel OR
b) Access to a very shallow pool of customers who are willing to tolerate an incomplete funnel for that use case.
Bad thing 2
You will realize your mistake (hopefully) and work on creating such a funnel. However, this forced and premature effort will pancake the team.
Supporting a new use case is deceptively difficult and costly, cutting across all functions of the team, including marketing, sales, product, engineering, and customer support.
In summary
This is a counterintuitive mistake that diffuses focus too early for startups. A common mistake that many operators often fall into.
You want to nail your first Minimum Viable Product use case.
You want to scale it to everyone who will buy what you have.
You want to avoid stumbling into new use cases and instead make very intentional decisions about when to expand your focus area.
You can typically expand into new use cases only after you have nailed PMF (or decided to pivot) and secured or allocated fresh funding and resources to win in that additional use case.
Head vs. Body
This year's lesson
- Your head: For competence and control
- Your body: For calm and joy
Spend more time in the latter.
Do you deserve any credit?
As a leader, your job is to make your team look good in front of others.
That doesn’t mean lying, obfuscating or dissembling.
It means…
1. helping them to do the very best work
2. Letting them take the lime light and credit when presenting it
3. Clarifying or defending it when others underestimate or misunderstand it
When do you get your flowers?
Hopefully they take the time to give you a shoutout sometimes!
Signs and symptoms of misalignment
💥 Common causes of org dysfunction
Ever found yourself stuck in a dysfunctional part of the business and can’t quite figure out why?
One of the most likely reasons:
Everyone is making things up as they go—and squabbling all the way.
In other words: lack of alignment.
Here are some common (but not exhaustive) reasons why alignment fails 👇
🎯 Refusing to set one clear target
Someone in your chain of command won’t set a single clear focus. They hedge.
This breaks everyone downstream.
Companies need clear (often singular focus).
Without it it’s impossible for everyone to work together to achieve a goal.
🚫 No targets at the top
Leaders above you might WANT to set a target—but never actually do it.
No hard decisions. No documentation. No socialization. No team-wide alignment.
This failure often comes not just from the top (e.g. the CEO) but from a manager somewhere in your chain of command.
Leadership is both top-down and middle-out.
CEOs set high-level targets, but leaders at every layer in the business must define the details, push back where needed, and make sure traders are understood (managing up).
Otherwise, senior leaders are is flying blind.
🔄 Moving targets from the top
Someone in your chain of command sets a clear focus—then regularly changes their mind.
All leaders should be:
✅ Documenting a clear plan
✅ Anticipating and communicating change
✅ Shielding their team from thrash
✅ Defending the plan when leadership gets nervous
🧭 Confusion about what to align to
Focus areas might exist—but leadership hasn’t created or shared a canonical set of principles, assumptions, vision, or roadmap.
Maybe they think everyone “just gets it.”
Maybe they prioritize execution over documentation.
Maybe they keep re-documenting things with different words and diagrams.
Whatever the reason: no shared mental model = no alignment.
🙅♂️ Refusing to get aligned
Even with a clear plan in place, a leader (in your org or another) just… doesn’t align.
They ignore direction, pursue their own thing, and trigger constant re-litigation of previously settled decisions.
Sometimes this is subtle: They say they’re aligned but use vague or contradictory language.
Or they nod along—and then go rogue anyway.
🙃 Failing to say NO to distractions
This is a form of toxic niceness.
Everyone wants to be friendly. Collegial.
But even the most aligned leaders have:
A - Different tactical views day-to-day
B - Random off-strategy ideas
C - A tendency to drift from strategy over time
If your leadership (or YOU) don’t say NO to distractions, even the best-laid plans will crumble.
Plans are worthless unless everyone takes responsibility for sticking to them.
🧠 Complete failure of cognition
Sometimes someone in the chain just has no clue—and no path to figuring it out.
At that point—depending on your role—you have two choices:
Fire them. Or quit.
⸻
💬 Seen any of these firsthand?
Drop your story or advice in the comments 👇
Companies are like human bodies
Companies are like human bodies.
If every organ is working perfectly, except one, the patient will still die if left untreated.
You cannot have a strong product team and a weak marketing team. You cannot have a strong ops team but a weak sales team.
Just like an elite athlete, every organ needs to be operating at peak performance for the body to be able to deliver extraordinary outcomes.
This applies at every level of granularity in your company - from individual people, to functions, to entire squads or departments.
The easiest thing to do is to ignore mediocrity. It’s a form of beta region paradox where the dull pain you’re experiencing is not sufficient to motivate a change - so you end up just tolerating things for too long.
Stop tolerating dull pain.
The truth is the dull pain is -1, whereas your high-performing team should be operating at +10.
For product - “Usage is the highest form of positive feedback”
“Imitation is the highest form of flattery”
We all know that phrase.
There’s an equivalent that can expressed for product.
“Usage is the highest form of positive feedback”
Asking people to validate your ideas is often useful. But until they use it, it’s just lip service.
There are a lot of things
Overheard "Wow, there are a lot of things, aren't there!?"
While working with a designer and a founder to help them think through all the implications of a seemingly simple feature for their product...
Upon hitting about the 10th screen we needed to modify, he exclaimed:
"Wow, there are a lot of things to change, aren't there!?"
I replied:
"Absolutely! This is the difference between product and engineering. Product has to think through all the nuanced and essential details that turn a little checkbox into a delightful feature that delivers on its promise."
Remember:
1. Don't forget to think through all the upstream and downstream effects of your features.
2. When planning your roadmap (or distractions from your roadmap!), never underestimate the cost and complexity of even "simple" features.
Focus. Essential for survival.
I've been thinking about this idea (see attached image) a lot lately.
The power of focus can not be overstated. And when you think you've focused enough, you probably still have more to go.
Want to learn more about how to do this well? Let's talk.
