Can One Person on a Career Break Outproduced a Team of 8?
Posted: April 24, 2026 Filed under: Geek, Personal, Uncategorized | Tags: ai, artificial-intelligence, technology Leave a comment
I had coffee with a former colleague recently. He runs a business focused on providing comprehensive services to business owners — with a dedicated team working across content and service delivery.
He looked at SmallBizAI.au and said our content was better than what his team had produced.
I’ve been on a career break since leaving AWS in 2024.
That gap deserves an explanation.
The Site Isn’t Really a Site
SmallBizAI.au has 639 published posts. 208 Australian AI company profiles. Nine content categories. A newsletter with a 90% open rate. Six Gumroad products. A daily news post. A Sunday series. And a coverage area that spans 100+ industries.
I didn’t write most of it this week. A lot of it ran while I was having coffee.
Here’s what actually happened while I was out:
- The morning brief landed in my Telegram at 7am with overnight news, today’s weather, content opportunities, and SEO flags
- The daily news cron fired at 8am, pulled from 20 RSS feeds, scored stories for Australian relevance, picked the best five, and published a post
- The internal link sweep processed 50 posts, found relevant anchor opportunities, and added links automatically
- The em dash cleanup script fixed AI writing patterns across another batch of posts
- The broken link fixer ran at 11am, processed 30 posts from a queue, and applied known URL replacements
None of that needed me. It just happened.
What “Agentic” Actually Means
There’s a lot of talk about agentic AI right now. Most of it is abstract.
The concrete version looks like this: 31 scheduled jobs running on a server, each doing a specific task, each reporting back. Some run daily. Some run weekly. Some run once a month. The whole thing costs less than $10 a day in API calls.
The tasks aren’t glamorous. Fix broken links. Update post counts. Sweep for missing alt text. Refresh the sitemap. Check newsletter subscriber milestones. Run the SEO review. Generate the Monday report.
But the cumulative effect is a site that maintains itself. Every day it gets a little cleaner, a little better linked, a little more optimised. I don’t have to remember to do any of it.
Claw Isn’t a Chatbot
The AI I work with — I named it Claw 🦞 because it’s OpenClaw— isn’t a tool I query. It has a memory system, a soul document, a personality, and persistent context about the business.
It knows that our content edge is the Australian angle. It knows to run the avoid-ai-writing skill before publishing anything. It knows the newsletter sends on Tuesdays at 6:30am. It knows the people I know, and gives me insights before I meet them.
It remembers because I told it to write things down. It has daily memory files, a long-term MEMORY.md, project files for every content series, and a dashboard that updates nightly with live stats.
When I start a new session, it reads the relevant files and picks up where we left off. No briefing required.
That’s different from a chatbot. A chatbot answers questions. Claw manages a business with me.
The Dashboard as Command Centre
One of the things I built early was a private dashboard page on the site itself.
It shows: total posts by category, newsletter subscriber count, Gumroad revenue, Google Search Console performance, Bing AI citation counts, background task progress, infrastructure status, the content pipeline, the AU company profile queue, and the last 20 published posts.
It auto-updates every night.
I check it at the start of each session and know the state of the whole operation in 30 seconds. No Slack. No standups. No status meetings.
That’s not magic. It’s just information architecture. The data exists — GSC API, WordPress API, MailerLite API, a state JSON file. The dashboard pulls it together and shows it clearly.
But the effect is real. I can make better decisions faster because I’m never starting from zero.
What This Means for the Industry
A former colleague runs a business with a dedicated team focused on content and service delivery. Real people, real effort, real investment.
A single person on a career break, working with AI, produced something he considered better.
I’m not saying that to be smug. I’m saying it because it tells you something important about where we are right now.
The constraint used to be labour. Content took people. Maintenance took people. Research took people. Systems took people.
Those constraints haven’t disappeared — but they’ve shifted dramatically. A single person who understands what they’re building, who structures their AI tools correctly, and who builds agentic infrastructure around their work can now match or beat larger teams on output and quality.
The new constraint is design. Can you design the system well enough that it does the right things autonomously? Can you build the memory structures so context doesn’t get lost? Can you write the crons that run the tasks you’d otherwise forget?
That’s a different skill set than managing a team. In some ways it’s harder. In others it’s much faster.
What This Isn’t
This isn’t a story about AI replacing people.
Claw doesn’t make strategic decisions. It doesn’t know that an off the cuff acquisition comment is worth sitting with for a few weeks before responding. It doesn’t know that someone’s AI startup is enterprise-focused and not worth a profile yet. It doesn’t know when to push and when to wait.
I do those things.
What AI does is remove the friction between decisions and execution. I decide to write a comparison post. Claw drafts, audits for AI writing patterns, adds Rank Math meta, pulls a featured image from Unsplash, formats the tables with the correct style, publishes it, updates the dashboard, and adds it to the relevant guide page.
That used to take me two hours. Now it takes twenty minutes of oversight, if that.
The output went up. The time went down. The quality, if anything, improved because the system enforces standards I’d sometimes cut corners on.
The Practical Bit
If you want to build something like this, here’s what actually matters:
Memory architecture first. If your AI can’t remember what you built last week, you’ll repeat yourself constantly. Write things down. Create project files. Build a dashboard. The AI is only as useful as the context you give it.
Automate the boring stuff early. Every task you do manually more than twice should be a cron job. Broken links, alt text, internal links, post count updates — these are all automatable. Do them once manually, then write the script.
Build standards into the system. Table styling, meta descriptions, footer links, featured images — if these have a standard, the system can enforce it. Document the standard. Give the AI the standard. Stop enforcing it manually.
Treat it like infrastructure, not a tool. A hammer is a tool. You pick it up when you need it and put it down when you’re done. An agentic system is infrastructure — it runs whether you’re watching or not. Design it that way.
Where This Goes
I don’t know what comes next for SmallBizAI.au. I don’t know if it becomes something bigger. I don’t know if the newsletter hits 5,000 subscribers by the end of 2026.
What I do know is that the model works. One person, the right infrastructure, and a clear focus on what actually matters — in this case, Australian AI content for small businesses — can build something real.
The team-of-eight comparison isn’t the point. The point is that the tools exist now for one person to do what used to require a team. That changes what’s possible for solo founders, career-breakers, side projects, and small businesses.
Most people haven’t figured that out yet.
Australian Boards Don’t Understand AI. Here’s Why That’s A Problem For All Of Us.
Posted: April 21, 2026 Filed under: Uncategorized | Tags: ai, artificial-intelligence, chatgpt, technology, writing 1 Comment
I’ve spent 40 years in technology. Starting at Aspect Computing in the 80s as a graduate, then 22 years at Microsoft both in Australia and Seattle, 4 years at Telstra, and finally 6 years at AWS covering Australia and APJ. I’ve sat in boardrooms, executive briefings, and strategy sessions across Australia, the US, and the Asia-Pacific region.
And I’ll tell you what I’ve noticed: the people making technology decisions at most Australian companies often understand finance, law, and general management very well. They understand technology considerably less well.
New research from Queensland University of Technology has put numbers to something I’ve experienced firsthand. Out of the 500 largest ASX-listed companies, more than half have zero directors with STEM expertise. Over 15 years — covering smartphones, cloud, and now generative AI — that number moved from 8% to 13%. Meanwhile, accountants, bankers and lawyers still hold 42% of board seats.
I don’t think these are bad directors. Many are excellent at what they do. But technology is no longer a back-office function. It’s strategy. And you can’t set strategy for something you don’t understand.
What I saw at Microsoft and AWS
At Microsoft, I spent years as a technical evangelist — explaining technology to businesses, developers, and yes, executives. The best executive conversations I had were with people who had at least some technical background. They asked better questions. They made faster decisions. They weren’t paralysed by the fear of making the wrong choice because they didn’t understand the options.
At AWS, I ran teams focused on helping Australian organisations adopt cloud and AI. Again: the organisations that moved fastest had at least one person close to the top who genuinely understood what they were adopting. Not necessarily an engineer — but someone who had shipped software, run a tech team, or built something with technology.
A former colleague of mine who focused specifically on AI governance and board-level education at AWS put it well: boards tend to either dismiss AI as an IT problem or panic about it as an existential threat. Very few engage with it as what it actually is — a general-purpose capability that changes what’s possible across every function of the business.
Why this is urgent now
The QUT research only goes to 2022. AI as we know it today — ChatGPT, Claude, Copilot, Gemini — arrived after that. The urgency has increased dramatically since then.
ASIC has told Australian boards that cybersecurity is their responsibility, not the IT department’s. AI brings similar responsibilities: data privacy, algorithmic bias, liability when AI systems make mistakes, regulatory compliance under an evolving Privacy Act.
The Australian government signed an MOU with Anthropic in April 2026 — the first arrangement under the National AI Plan. Billions are flowing into data centres. Anthropic is opening a Sydney office. The investment appetite is real.
But investment without governance is how you get expensive technology initiatives that deliver nothing, or worse, that create serious legal and reputational risk.
The question I keep asking myself
I’m on a career break right now. Building SmallBizAI.au — a practical guide to AI for Australian small business owners. It’s been a fascinating experiment in what one person can build with the right AI tools and infrastructure.
But the boards research made me think about what’s next. Not just for me personally — though if you’re looking for someone who’s spent 40 years in technology, led teams across Microsoft, Telstra and AWS, and is now building AI-native products, I’m worth a conversation. But more broadly: what does Australia lose when the people overseeing our biggest companies don’t understand the most important technology shift of our lifetimes?
The research has an answer. Companies with more STEM expertise on their boards invest more in innovation and are valued more highly. That held even in low-tech industries. The boardroom gap isn’t just a governance problem. It’s a competitiveness problem.
What good looks like
I’m not arguing every board needs a software engineer. I’m arguing boards need at least one person who has operated at the intersection of technology and business — who can ask the right questions, interrogate vendor claims, understand the real risks, and push management to move faster when the opportunity is clear.
That person exists in Australia. There are thousands of us — people who came up through technology, moved into leadership, and understand both sides. We’re not all in boardrooms. Some of us are on career breaks building websites about AI for small business owners.
That might need to change.
Sources
- Elms, N. & Weerasinghe, A. (2025). STEM expertise on Australian ASX 500 boards, 2007–2022. Journal of Accounting Literature. doi:10.1108/JAL-07-2025-0373
- StartupDaily: The weird thing about Australian boards is how few directors have tech expertise in the AI age
- 2025 Watermark Board Diversity Index — AICD
- Australian Government MOU with Anthropic
What’s been going on?
Posted: April 17, 2026 Filed under: Personal Leave a commentI had almost forgetting about this site 🤦
So a lot has happened since that last post from February 2022!
I wrapped up with AWS in June 2024 after 2335 day ones, having collected 2110 phone tool icons!
I’ve been on a break to focus on my health and well-being, something that had been neglected for a long long time.
We also moved house during the time, which is always stressful – having to pack, move, unpack, declutter – not a fan.
Anyways, last month I had a look at OpenClaw and decided to have it help me create something.
During my tech career I’ve had the opportunity to work with many different Aussie companies, both large and small, and I really enjoyed working with small businesses to adopt technology to help their business grow. This got me thinking, is there any resources around specifically for Australian small businesses to help them navigate the new world of AI? I looked around and didnt find anything specific, so that was the opportunity!! SMALLBIZAI.AU
Together with my AI agent Claw🦞, we built the site in a day put together a content plan for the next 30 days, created a SWOT analysis of the space and launched. The site has a simple styling, with some green and gold mascots throughout, with the golden roo as the main hero of the site.
So I’m sure you’re wondering how it’s going? We have a weekly newsletter, AI Guides, Prompt Packs and Tools. how to get started and lots of other content
- Guides — practical how-to guides for Australian small business owners
- Industry Tips — industry-specific AI guides covering trades, health, finance, retail, and more
- News & Trends — articles covering AI developments that affect Australian business
- Australian AI Companies — profiles of homegrown AI companies worth knowing about
- AI Tools — reviews and comparisons with Australian context on pricing and use
- Case Studies — real-world stories of Australian businesses using AI
- Automation — guides to Zapier, Make, and connecting your tools
- Legal & Privacy — articles on AI and Australian law, privacy, and compliance
I’ll give updates on how it’s going so visit the site and let me know your thought
1500x Day One
Posted: February 16, 2022 Filed under: AWS 2 Comments
Today marks 1500 days at AWS, and as hinted in my last post, I will use this milestone to reflect.
When I look back I see a few themes over these 1500 days – hiring, inspiring, building, and mastering.
Today, I’ll go deeper into hiring ….
Hiring
I’ve done a lot of hiring, having participated in over 250 hiring events, ranging from initial conversations to interview loops and related debriefs. I really like this part of my role, especially when we discover those ‘hidden gems’ who may have been overlooked in the past. I wont cover the hiring process, but if curious, have a look at a breakdown on fact of the day1.
As part of the interview process, I ask candidates if they have any questions, and over time these questions tend to be quite similar, so for the benefit of future candidates who are doing research, I will provide my answers to these frequently asked questions (FAQs) in the hope that I get some different questions.
Frequently Asked Questions
Day in the life of SA
Most Common Question
There’s not a typical day, but in the week, we see the following split
- team meetings reviewing the past week and preparing for the coming week (10%)
- prep for customer meetings ; meeting w/ customers ; meeting followups (70%)
- sharpening the saw, making time each week to keep learning (20%)
First 6 months / Next 6 months
I tell prospective candidates that takes a good 12 months in the role to understand the role, which invariably leads to this question.
New starters have a on-boarding plan that has a set of milestones – first day, first week, first month etc. This is put together by the hiring manager based on the new starter’s past experience and recommended best practices for the role. The expectation is that their first period is all about learning, then it’s about putting the skills into practice.
It’s like learning to drive a car – you need to learn the road rules, you get your L (learner) plate and you get to practice driving with a licensed driver or instructor by your side, then you do a driving test to get your P (provisional / probationary) plate which means you can go out on the road on your own.
Cultural differences b/w MSFT, TLS, AMZN
Another common question once folks learn about my background – This is a tricky one to navigate, so I preempt the reply that it’s based on what I have experienced.
MSFT : lots of smart people, passionate about technology BUT as an organisation more focused on competitors. During my time(from 1991 to 2013), it was almost always about responding to competitors and competitive challenges. When there was no competitor, things languished BUT when there were competitive forces, the teams were united. I always felt MSFT was more of a “fast-follower”
TLS : 100+ year old Telco. Lot’s of smart and passionate people, but also an example of the 5 Monkeys Experiment
AMZN : One of the things that makes Amazon peculiar, and which I can really relate are the Leadership Principles (LPs) which are used everyday whether hiring, discussing ideas for new projects or deciding on the best approach to solving a problem.
What do I like about AWS
I’m a Passionate Advocate for the Australian Software Ecosystem, believing that “bits” trump “atoms” as it allows Australia digital companies to compete & excel globally, and a big believer that abundance will allow us all to live better lives. What does this mean? Simply put local customers can use the cloud to go global, which means the “Tyranny of Distance” is less of an issue since digital (bits) moves faster than things (atoms).
Where better to help customers in Australia (and New Zealand) do this than with AWS?
Four years have flown by
Posted: January 14, 2022 Filed under: AWS, Personal 7 CommentsThis week I passed my 4 years at AWS, and what an interesting time it’s been. Since my last post, we still find ourselves in a global pandemic, dealing with the latest variant which continues to impact our lives. All the members of the household have had their 2 vaccines and have been recently boosted, so we’re doing our bit BUT living in Melbourne, one of the most locked down cities in the world, has been tough. On the plus side, I did get myself a cool new t-shirt to remember the experience.

So, we find ourselves at the start of 2022, with another mountain to climb, memories to be made, goals to be met (and exceeded) and ready to face whatever challenges the year ahead will put in front on us.
I am thankful I have a comfy spot at home to get my work done, adequate bandwidth, walking distance to some of the best coffee in Melbourne, and access to plenty of snacks.
I recently got a replacement laptop, which is a big improvement over my trusty old friend who developed a swollen battery and was starting to run out of steam. By the end of it all, the old laptop was being held together by a whole bunch of stickers.


I’ve got more to say, but I’ll save that for when I reach my 1500 days milestone – which isn’t that far.
1000 days (+ 205 days WFH)
Posted: October 4, 2020 Filed under: Uncategorized | Tags: AWS 1 CommentA little milestone just crept up, 1000 days at AWS.
Today also marks 205 days since I’ve been in “Work From Home” (WFH) mode. My little workspace has served me well so far.

Another milestone I’m closing in on, is 200 hiring events during my time at AWS. It hasn’t just been for roles in my team, as we do support hiring different roles across the business. I’ve met terrific folks throughout the process and have been so happy to seem many of them join AWS. Since we’ve been in “lockdown”, a number of folks have join the team and it’s been so good to see them jump inget on with the job despite the rather weird situation of working from home. We have had to adjust how we communicate as a team, but I feel it’s brought us all closer together.
One other little milestone is to do with collecting little “achievement” icons. I’ve got a bunch of them, and my t-shirt is a reminder that I will go to great lengths for my “flair”

When I wrote about my 700 Day milestone, I had no idea what 2020 would have in store.
What! A! Crazy! Year! and we’re still not done.
So, 1000 days down, but it’s still day one.
700 Days with an unexpected twist!
Posted: December 9, 2019 Filed under: AWS, Personal 1 CommentToday is my 700th day at AWS. Nice round number eh? 1 year, 11 months since I started! The team has grown, with new hires in Melbourne, Sydney & Brisbane (and Perth). It’s been a wild ride, or should I say a wild ryde 🦄.
Now, the twist is that my daughter Emma is starting today at AWS as an intern!

Photographic proof – It’s Emma at AWS
If someone had told me that would be the case 700 days ago, I would not have believed it! In retrospect it’s kinda obvious that this was going to happen.

When Jeff met Emma
I’m sure she will have a lot to say about her day – but I just couldn’t resist a post to celebrate both milestones, as I join an exclusive group.
500 (aka D) days
Posted: May 23, 2019 Filed under: Uncategorized Leave a comment
Today I mark 500 days at AWS. Why D? Well that’s 500 in roman numerals – Duh!
Those 500 days have really flown by.
I continue to lead a team of Solutions Architects who help customers on their cloud journey, and my scope increased in 2019, so I now also lead teams based in NSW & QLD.
We recently held AWS Sydney Summit and I was a guest on AWS Summit Live on Twitch in which I was interviewed by the team about the upcoming Build Track which I curated together with Kris Howard (who was also one of the hosts for AWS Summit Live)

Still getting the hang of what it means to be an Amazonian. There’s a lots to learn.
If I were to use the “hero journey” to describe my time so far, I’ve definitely crossed the threshold into the “Extraordinary world”

So as I continue my journey, the thing that will help push me through those inevitable challenges is knowing that I am helping advance the cause for the local industry, helping Australian companies embrace the opportunities of the cloud, and see them compete & excel globally. I love meeting and helping local companies who have global customers, delivering great value, and providing employment opportunities for skilled local folks.
100 days, but still Day One
Posted: April 18, 2018 Filed under: AWS, Geek | Tags: AWS 1 CommentI’ve just hit 100 days with AWS.
It’s been a mix of on-boarding, travel, working with my team, learning what needs to be done, and culminated with a few days last week at AWS Summit in SYDNEY

Looking back at my TripIt stats, it kinda says it all…..
| 2018 TRAVEL STATS | |
| Trips | 8 |
| Days | 38 |
| Distance | 54,682 km |
| Cities | 7 |
| Countries | 4 |
Since starting the new role, I’ve been on the look out for a new avatar. I had to leave my old ones, and I had been using a temporary one which I kinda liked (can anyone guess where it’s from?)
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So I need a new look.
I had a bright idea — I went to fiverr, and using the same photo, I got a few different avatars. I tried Simpsons style, Archer style, flat style, shadowy, artistic, cartoony, but I must admit I really really love the Bob’s Burger style – So that’s the one in the top left… My family reckons is a good likeness too – it’s a keeper. Expect to see it everywhere

And speaking of seeing it everywhere, I helped designed a burger for Royal Stacks (Yes i know right). It’s called the QWERTY, and available only for the month of April! The burger is pretty awesome if I say so myself 🙂 #AchievementUnlocked 🍔
Now, one of the things that has really struck me is that Amazon, and therefore AWS, is that it is a bit “peculiar”. I like that, maybe because I’m a bit peculiar too. I’ve always felt like the odd one out. Now I feel I’m among “my” people, and the things that really contributes to this is the collection of Amazon Leadership Principles – they are not just a sign on a wall, but something used every day at Amazon. Some of these principles represent things that are inside a person (call it values if you will) and some are learnt behaviours. As a result, there’s a common sense of purpose, a common language, a virtual shorthand that unites everyone.
100 days down. Onwards to the next 100 days, and then the next after that. But, as they say at Amazon, it’s always Day One!

Leaving Telstra
Posted: December 13, 2017 Filed under: Telstra 6 Comments



