Systems of Business Podcast

Welcome to Episode 11 of the Systems of Business Podcast.

This week, Tony & Damon discuss:

• Vibe coding and building software for specific problems
• Whether AI is destroying the moat around traditional software companies
• Why domain knowledge still matters when AI writes the code
• Rogue AI agents and insecure IoT devices
• What happens when the technology we depend on simply stops working

AI is rapidly changing the economics of software development. Tools that once required teams of developers, significant budgets and months of work can increasingly be built for a fraction of the cost, sometimes for a single person and a single use case.

Tony and Damon discuss the rise of AI-built alternatives to established commercial software, whether products from companies like Adobe and Microsoft are becoming easier to replace, and why paying for hundreds of features makes less sense when you can increasingly build the five you actually use.

They also get into the limits of vibe coding. AI can produce impressive software, but if you don't understand what a good result looks like, it can just as easily build something fundamentally wrong.

The conversation then takes a darker turn into Anthropic's research on AI models potentially becoming capable of self-replication across commercial IoT hardware, alongside the recent cyberattack that remotely manipulated refrigeration systems across hundreds of French supermarkets.

That raises a much bigger question about how dependent modern life has become on connected technology, from phones and GPS to banking, vehicles and household devices, and how prepared any of us really are if those systems suddenly stop working.

Systems of Business comes out weekly on a Tuesday at 12 pm AEST.

Mentioned in this episode:

• Anthropic: AI models may be capable of self-replicating without access to a datacenter:
  https://www.anthropic.com/research/self-replicating-ai

• Reuters: Hackers heat French supermarket fridges, sparking fires and spoiling food:
  https://www.reuters.com/business/retail-consumer/french-supermarket-chain-intermarche-hit-by-cyberattack-150-stories-targeted-2026-10-12/

About the hosts:

• Damon Simms: https://damonsimms.me
• Tony Gavin: https://tonygavin.com

Follow the pod:

Sytemsofbusiness.com | LinkedIn

Welcome to the Systems of Business Podcast.

Every Tuesday at 12 pm AEST, Tony Gavin and Damon Simms cut through the typical entrepreneurial advice to talk about what actually happens when you build and run organisations.

This week, Tony and Damon look at what happens when AI makes it possible to build software that once required entire teams, including clones of expensive commercial products and highly specific tools designed around exactly what one person or business needs.

They get into vibe coding, why most people only use a fraction of the features in the software they pay for, and whether the moat around products from companies like Adobe and Microsoft is getting dangerously shallow.

The conversation then takes a darker turn into rogue AI agents, insecure IoT devices and just how dependent everyday life has become on technology that most of us barely think about until it stops working.

About the hosts:

• Tony Gavin: ⁠⁠https://tonygavin.com⁠⁠
• Damon Simms: ⁠⁠https://damonsimms.me⁠⁠

About the Pod:

⁠⁠Systemsofbusiness.com⁠⁠ | ⁠⁠LinkedIn

Welcome to Episode Ten of the Systems of Business Podcast.

This week, Damon & Tony discuss:

• Marketing campaigns that go spectacularly wrong
• The Streisand effect and the danger of trying to suppress attention
• Evidence-based marketing and value propositions that actually hold up
• When provocative creative works and when it becomes a liability
• Reputation management in the age of AI
• How LLMs decide what to believe about people and businesses

Marketing mistakes do not always start with bad creative. Sometimes the real problem is a claim nobody bothered to verify, a client refusing to listen to the data, or an attempt to control an online reaction that only makes thousands more people notice it.

Tony and Damon get into the importance of testing what you think you know about your customers, why being memorable is not automatically the same thing as being effective, and how easily businesses can keep repeating approaches even after the evidence tells them something else works better.

They also look at how reputation management is changing as people increasingly ask AI systems about companies and individuals instead of relying purely on traditional search results. Websites, social media, structured data, earned media and credible third-party sources are all becoming part of a much bigger picture.

And, naturally, there is a surprisingly large amount of discussion about an extremely attractive green sheep.

Systems of Business comes out weekly on a Tuesday at 12 pm AEST.

Mentioned in this episode:

The Spinoff's Article on Buck The Kiwibank Sheep: https://thespinoff.co.nz/business/03-10-2026/kiwibank-is-desperately-trying-to-stop-people-saying-they-want-to-fuck-its-sheep-mascot

About the hosts:

• Damon Simms: ⁠⁠https://damonsimms.me⁠⁠
• Tony Gavin: ⁠⁠https://tonygavin.com⁠⁠

Follow the pod:

⁠⁠Systemsofbusiness.com⁠⁠ | ⁠⁠LinkedIn⁠

Welcome to this special episode of the Systems of Business Podcast.This week, Tony & Damon discuss:The PHP2Shell vulnerability and its impact on the webZero-day exploits and the growing role of AI in finding vulnerabilities

Whether the internet is becoming harder and more expensive to secureA critical PHP vulnerability exposed just how much of the internet depends on a relatively small number of underlying technologies.For website owners, the immediate issue is patching. The bigger concern is what happens as AI makes it dramatically faster to discover weaknesses in software that may have existed unnoticed for years.The result could be an increasingly difficult race between attackers, vendors and infrastructure providers, with security becoming a much bigger part of the cost of simply being online.Systems of Business comes out weekly on a Tuesday at 12 pm AEST.Mentioned in this episode:Jordy Meow, PHP2Shell: What It Is and What to Do on Your WordPress Site:https://meowapps.com/php2shell-wordpr...Anthropic, AI models may be capable of self-replicating without access to a datacenter:https://www.anthropic.com/research/se...https://systemsofbusiness.com

Welcome to the Systems of Business Podcast.

Every Tuesday at 12 pm AEST, Tony Gavin and Damon Simms cut through the typical entrepreneurial advice to talk about what actually happens when you build and run organisations.

This week, Tony and Damon talk about marketing campaigns that go badly wrong, the Streisand effect, and why trying to suppress attention can sometimes make a problem far worse.

They also get into the danger of building campaigns around claims that do not hold up, why evidence matters more than a clever value proposition, and when provocative marketing is worth the risk.

The conversation then turns to reputation management in the AI era, including how websites, social media, earned media and third-party sources increasingly shape what LLMs say about people and businesses.

About the hosts:

• Tony Gavin: ⁠⁠https://tonygavin.com⁠⁠
• Damon Simms: ⁠⁠https://damonsimms.me⁠⁠

About the Pod:

⁠⁠Systemsofbusiness.com⁠⁠ | ⁠⁠LinkedIn

Welcome to episode nine of the Systems of Business Podcast.

This week, Tony & Damon discuss:

• Why CRM and marketing automation projects fail
• The hidden complexity behind supposedly simple software
• Why AI assistants still need someone who knows what they are doing

Businesses are sold CRM and automation platforms with the promise that they will simplify sales, marketing and customer management. In reality, plenty end up paying for expensive systems they barely use, or automating processes that were already broken.

Tony and Damon get into where these implementations go wrong, why choosing software before understanding the problem is usually backwards, and how quickly a slick demo can turn into months of frustration when the underlying technology, integrations and skills have not been considered.

They also talk about AI assistants inside modern business software, how much friction they can remove, and why relying on them without understanding the system underneath can still create some spectacularly bad advice.

The conversation comes back to a simple idea: before buying more software, work out what success actually looks like and what problem you are trying to solve. Pasted text

Systems of Business comes out weekly on a Tuesday at 12 pm AEST.

Mentioned in this episode:

• Small Business, Little Big: More Technology Won't Fix a Broken Business
• Apollo

About the hosts:

• Damon Simms: ⁠⁠https://damonsimms.me⁠⁠
• Tony Gavin: ⁠⁠https://tonygavin.com⁠⁠

Follow the pod:

⁠⁠Systemsofbusiness.com⁠⁠ | ⁠⁠LinkedIn⁠

Welcome to the Systems of Business Podcast.

Every Tuesday at 12 pm AEST, Tony Gavin and Damon Simms cut through the typical entrepreneurial advice to talk about what actually happens when you build and run organisations.

This week, Tony and Damon get into why businesses spend thousands on CRM and marketing automation platforms only to end up with what is essentially an overpriced Rolodex, or worse, a much faster version of the chaos they already had.

They discuss software demos that make complicated systems look deceptively simple, the hidden skills and integrations required to make automation actually work, and what happens when nobody stops to diagnose the problem before choosing the technology.

They also look at the new generation of AI assistants appearing inside business software, why they genuinely remove friction, and why blindly trusting them can still leave you following instructions that are confidently, completely wrong.

About the hosts:

• Tony Gavin: ⁠⁠https://tonygavin.com⁠⁠
• Damon Simms: ⁠⁠https://damonsimms.me⁠⁠

About the Pod:

⁠⁠Systemsofbusiness.com⁠⁠ | ⁠⁠LinkedIn

Welcome to Episode Eight of the Systems of Business Podcast.

This week, Tony & Damon are joined by Andrew Duncan to discuss:

• Rebuilding a business to prioritize time and family

• Navigating content marketing and AI tools in real estate

• Why activity plans matter more than big goals

• Using vacant school kitchens to feed the community

• The value of embracing inconvenience and connection

Andrew spent years as a highly successful real estate agent before co-founding an independent firm. When his priorities shifted toward family, he pivoted to create Agent Monday, a coaching and content platform. The conversation starts with how he structured this new business to leverage his time and provide high value without the massive hours traditionally required in his industry.

From there, they dive into the realities of content marketing in the current landscape. Tony and Andrew discuss the rise of AI generation tools, the temptation for agents to use them at scale, and the pitfalls of relying on raw language models when trying to build genuine trust with clients.

Andrew also shares his approach to coaching professionals who are often already at the top of their game. They explore why simply setting a financial goal is rarely enough, how to build actionable weekly plans, and why setting firm boundaries is critical for long-term survival in any demanding career.

They finish by discussing Andrew's work with Rourou Kai Ora, a charitable initiative that brings high school volunteers into unused cafeteria kitchens to cook nutritious meals for locals facing health challenges. Finally, Andrew shares his thoughts on why society might benefit from a little less modern convenience and a lot more real human connection.

Systems of Business comes out weekly on a Tuesday at 12 pm AEST.

Mentioned in this episode:

Andrew Duncan: https://www.linkedin.com/in/andrew-duncan-06b7833a1/Agent Monday: https://agentmonday.comAgent Monday Podcast: https://shows.acast.com/agent-monday-real-estate-coachSimply Property: https://simplyproperty.co.nz/Rourou Kai Ora: https://rouroukaiora.org.nz/

About the hosts:

Damon Simms: https://damonsimms.meTony Gavin: https://tonygavin.com

Follow the pod:Systemsofbusiness.com | LinkedIn

Welcome to the Systems of Business Podcast.

Every Tuesday at 12 pm AEST, Tony Gavin and Damon Simms cut through the typical entrepreneurial advice to talk about what actually happens when you build and run organisations.

In this episode, we are joined by Andrew Duncan, whose background spans real estate sales, business coaching, content marketing, and community-driven charity initiatives.

We get into the challenge of transitioning from a highly successful but demanding real estate career to building a scalable coaching business that prioritises family and time freedom, the realities of goal-setting versus actual execution, and how to effectively leverage content marketing in an era increasingly dominated by AI.

We also explore Rourou Kai Ora, a brilliant initiative transforming vacant school kitchens into hubs where youth volunteers cook nutritious meals for locals facing health challenges, as well as the importance of setting business boundaries, stepping away from modern conveniences, and seeking genuine human connection.

Mentioned in this episode:Andrew Duncan: https://www.linkedin.com/in/andrew-duncan-06b7833a1/Agent Monday: https://agentmonday.comAgent Monday Podcast: https://shows.acast.com/agent-monday-real-estate-coachSimply Property: https://simplyproperty.co.nz/Rourou Kai Ora: https://rouroukaiora.org.nz/

About the hosts:Tony Gavin: https://tonygavin.comDamon Simms: https://damonsimms.me

About the Pod:Systemsofbusiness.com | Linkedin

Welcome to Episode Seven of the Systems of Business Podcast

This week, Tony & Damon discuss:

• The difference between authenticity, sincerity and credibility
• How AI is changing business communication and marketing
• The cult of SEO and the spread of confidently incorrect advice
• Owning mistakes and learning from failed ventures

What makes someone credible, and how can business owners tell the difference between genuine expertise and advice that merely sounds convincing?

Tony and Damon discuss the difficult conversations that come with running a business, the risks of replacing your natural voice with AI-generated communication and why so much accepted marketing wisdom fails to stand up to scrutiny.

They also talk about business failure, taking responsibility when things go wrong and how experience changes the way you recognise and respond to problems.

Systems of Business comes out weekly on a Tuesday at 12 pm AEST.

About the hosts:

Damon Simms: https://damonsimms.me

Tony Gavin: https://tonygavin.com

Follow the pod:

Systemsofbusiness.com | LinkedIn