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Craig Bailey

Business Strategy by Day, Life Strategy by Night

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Substack

I ve been posting every month or so on Substack. My longer, more thoughtful pieces. (Where as this blog is much more ad-hoc, short and long) I quite like Substack, and have found that I spend a reasonable amount of time there each day, reading through articles. It feels like it is the only place I [ ]

inflAItion

Two typical ways companies charge for AI: The first is fine. The second is the rort. The pattern: The issue: consumption pricing gives you control. Subscription inflation doesn t. You can opt out of agents. You can t opt out of a price hike.

Temu HubSpot

Most of the vibe coded CRM ‘products’ I see breathlessly announced on social (mainly X, but I see them as screenshots on Threads funnily enough) seem to be just Temu HubSpot. There’s a market for these vibe coded CRMs, just like there’s a big market for Temu shit no doubt, but even Temu doesn’t pretend [ ]

Consolidation

Part of streamlining life and business is the action of consolidation. It can start with simple things, just to get the ball rolling. Here s a few simple examples I ve actioned in my personal life this year: Consolidating extends into business as well. At XEN, we ve been consolidating: Our Tech Stack Thought it might be interesting [ ]

Overwhelm

People are completely overwhelmed. In their personal lives. In their professional lives. From the simple basics of everyday life (which toothpaste to buy) through to the news they consume, the advertising they are blasted with, the advice they are subjected to on social, the streaming services they watch, the inboxes they avoid, people are struggling [ ]

Complexify

The process of adding new features, tools and AI garnish to a software platform, with the effect of overwhelming and alienating the original customer base who loved it for its intuitiveness and ease of use. Usually followed by a series of paper cut pricing increases to reflect the added value of the enhancements . Enterprisification The [ ]

Health Profit

As a business owner it can be easy to fall into a reductionist mindset and assume everything is a business problem to be solved. Sometimes that’s useful, other times not. Here’s an example (which I probably saw on social somewhere*), which you may find useful (I did), maybe not. It’s about your health. Treat your [ ]

Strategic Grind

Doing what you Hate so you can do what you Love I’ve been chatting about strategic grind with the team lately. Every business owner and team member has things in their day they don’t like doing. It’s part of work. In this column, we’re going to discuss the kinds of work you don’t like doing [ ]

Two Levels of Stupid

It seems there are (at least) two levels of stupid. Level 1 stupidity is being totally uninformed. On big topics. Fuel prices, vaccines, One Nation, ICE, Iran, Trump, raw milk, etc. That’s the first level of stupid. But the second level of stupid is when people who actually understand the issues for example, experts [ ]

Conference Panels

Panels at Events (conferences, trade shows) are essentially the seafood extender of the event. They are the blunt instrument of lazy organisers who have access to high-powered guests but don’t know what to do with them. So they organise a panel and then insert an unprepared moderator to shotgun questions at intelligent panel members, but [ ]

Streamline

This year my theme is: Streamline Across everything: life, business, health, wealth, relationships I’ve even streamlined my work office, moving to a smaller, simpler office, removing a ton of stuff accumulated over the years. For XEN, we’re making streamline our guiding theme. We’re applying this principle to our internal processes, our tech stack, our product and service offerings, [ ]

Patience

One of the side effects of being on social too much is that our patience reduces drastically to the point where even being on social we get frustrated We’re scrolling through our social feed and a post catches our eye. But it requires us to click in to thread to see the rest of [ ]

Nuance

Often the difference between good and great is due to nuance. Nuance is hard to capture via emails and written communication. Often, nuance only comes out as part of a conversation chatting through, discussing, highlighting taste.​​​​​​​​​​​​​​​​

Best Lives

Look around. So many people just wanting to live their best lives. People from all walks of life. Young, old, ugly, beautiful, smart, dumb, rich, poor, short, tall Should it be a crime if you deliberately get in the way of someone trying to live their best life? Perhaps. First step:

Inverse Mission Law

The Inverse Mission Law states: In a conversation, the time taken to state your company mission is inversely proportional to the dishonesty of that mission. Put another way: the quicker a company executive rushes to tell you their company mission, the more likely it is bullshit. I was at an AI conference a few weeks [ ]

How to be an AI first Company

When I read this note from Dare, it really hit home: The skill of being an effective AI worker is having enough competency to catch errors. Anyone and everyone can use AI tools but an ever diminishing number of people know how to review and catch the errors. These people will be the biggest beneficiaries [ ]

Anchors

Interesting to consider how low our standards of quality have dropped in light of the inconsistent experiences we have with AI tools. The race between vendors driving constant, often buggy, sometimes dangerous, releases. Think back to when Dropbox was launched there was a product that was as close to perfect on release as anything [ ]

Loop Marketing

HubSpot launched their new marketing playbook Loop Marketing a few weeks back at their INBOUND conference. It s worth chatting about: to get a sense of what is useful, versus what s noise. I ll cover a few cynical notes first, then highlight the good stuff. For a more detailed discussion about the topic, see also [ ]

Relative Happiness

Steve Wozniak recently commented about wealth and success. His point was simple: “I gave all my Apple wealth away because wealth and power are not what I live for. I have a lot of fun and happiness… Life to me was never about accomplishment, but about Happiness, which is Smiles minus Frowns.” It’s an attitude [ ]

HubSpot Updates that Matter

Drowning in HubSpot Updates? You’re Not Alone. If you’ve been inside HubSpot lately, you’ve probably noticed the flood of new updates, betas, and product changes rolling in. It can feel like every time you check the Product Updates page, there are dozens of new features — many of them marked New to you — and [ ]

HubSpot Ads Tool Deep dive

When we first chat with new clients about their HubSpot portals, an early topic is about connecting their advertising platforms into HubSpot. I don’t have hard data, but I’d estimate that only 50% of clients portals we review have any of their ad platforms (Meta, LinkedIn, Google) connected. [1] HubSpot Ads Tool benefits For those [ ]

Using Claude, Manus and Perplexity to analyse a HubSpot Service Offering idea

(Disclaimer: AI wrote this blog post based on my YouTube video here.) Using AI to Test Product Ideas We’re seeing more clients using AI to test product ideas. It’s fast, cheap, and offers instant feedback. But just like with most things AI-related, there’s a catch. Below is a real example of a simple service idea [ ]

The Rebirth of Authentic Online Communities

The topic of communities, a concept that has existed for decades, is currently undergoing a significant transformation. While many individuals are already part of numerous groups and communities, there is a clear indication that a strong move back to very specific, niche communities is occurring. This shift is primarily driven by emerging pain points within [ ]

Forced Value

Most people I chat with don t use all the AI features being forced on them in Google Workspace. I m the same, always closing the sidebar pop-out, dismissing the annoying notifications across the top, sending the announcement emails to spam, etc. At least when they started rolling out the AI features, they were an optional paid [ ]

HubSpot GROW Sydney 2025 Review

Last week I attended HubSpot s GROW event in Sydney. (Spoiler: it was really good) I prepared an update deck that I went through with the XEN team, covering the key insights, plus the good, the bad and the hype. You can access the slide deck from here. I ve also added a lesson in our HubShots Skool [ ]

Chief Entropy Fighter

I was leaving the office late the other night, and chatted with the cleaners. They are always here late, doing an excellent (but I suspect, largely unknown) job. I asked them what time they usually finished. Around 11:30pm. Is this your second job? Yes, they turn up at the office block around 6:30pm most nights, [ ]

Networking Event thoughts

If you know me, you know I m not the networking type instead I m the hide in the corner type. But, tough as it is, I ve been trying to attend a few in-person events lately and network with people. A quick note: Our head designer created two simple images for me: In case they are [ ]

Inefficiency

Went with my wife to a medical specialist appointment yesterday (she s fine, all routine). It was at a Health Hub (healthcare in Australia is wonderful), very modern and new. You know the kind, where you get confused using touch panels to call the elevator. Went up to the floor, walked the beautiful corridors, and entered [ ]

Annual Strategy Review

I thought I d share a few thoughts about what I m doing this month. It s not related to HubSpot directly, but is indirectly, because it goes a step higher and thinks about business strategy. Every year, usually in May, I take four weeks off to clear my head, read, learn, and think about the business [ ]

Should You Build Your Website on HubSpot? A Comprehensive Guide

An In-Depth Look at Scenarios, Pricing, Features, and Considerations for Choosing Your Web Platform Introduction: Setting the Stage The Age-Old Question Welcome to this comprehensive guide based on the insightful discussion from HubShots episode 312, Should You Build Your Website on HubSpot? . In this guide, we aim to answer a question that frequently arises [ ]