#149 – Chris Williamson Live & The Future of SaaS

Good morning everyone,

Hope you’re having a great week!

Here are 5 things I found interesting over the past few days.

Let’s jump in.

read online on my website

read time 3 minutes

#149 – The Rundown:

• Quote: The enabling characteristic.

• Podcast: Mark Bouris x Craig Laundy.

• Article: Why AI won’t nuke SaaS.

• Event: Chris Williamson Live.

• Tweet: Is Germany in trouble?

Quote:

Podcast:

Straight Talk with Mark Bouris #231: Craig Laundy

Craig Laundy is a former Australian Liberal Party politician and now leader of the award-winning family hospitality group, Laundy Hotels.

What I found most intriguing in the conversation was the way Craig unpacked his thesis behind Laundy’s recently-announced $56m acquisition of Nine Radio.

A great pod more broadly around rugby league, politics, the economy, and productivity.

Listen on Spotify, Apple Podcasts, or YouTube.

[Duration: 1 hour 3 minutes]

(P.S. I made a Spotify playlist with every podcast I’ve ever recommended. Hope they bring you as much value as they’ve brought me.)

Article:

Why AI Won’t Nuke SaaS

While the internet seems to be flooded with a bleak outlook for employment when it comes to AI – certainly not all of which is unwarranted – it can create somewhat of an echo chamber whereby people seemingly at the forefront of innovation can, as I wrote last week, misconstrue technological capability with widespread adoption.

With that in mind, I have found it quite refreshing to read perspectives by those who take an opposing view, such as Craig Tindale in his recent piece, ‘AI Won’t Nuke SaaS: Why the White-Collar Apocalypse Is Just Tech Bros' Dreaming Nonsense.’

These were my key takeaways:

1) AI is creating lazy thinkers and readers alike. This extends to meaningful analysis of the impact AI could/will have on employment, industries, and economies.

2) “They assume that because coding costs have been compressed, all SaaS will be replaced by in-house-developed bespoke AI code, with their SaaS subscriptions replaced almost immediately. Enterprises will stop what they’ve been doing for the last 50 years and jump on board a simplistic bus to the future; if they don’t, it’s off to the gravel pit for the enterprise. WTF?”

3) AI operating expenses are not zero and the products for highly regulated, hardware-integrated, bespoke business solutions are not simply waiting in the wings.

4) Companies do not optimise for the lowest software spend in isolation. They optimise for continuity, risk containment, compliance, internal political stability, and predictable execution. Software typically accounts for a small fraction of total operating costs.

5) The rigorous elasticity question of AI migration is therefore not whether SaaS prices fall. It is whether AI alters the labour structure enough, under stressed economic conditions, to justify workflow re-architecture despite migration risk. Absent that combination, inertia dominates, and disruption remains incremental rather than systemic.

As always, very curious to hear everyone’s thoughts on this. Hit reply.

You can also check out the full article here.

Event:

Chris Williamson Live in Sydney

The other week, I had the privilege of attending Chris Williamson’s Live Tour at the ICC Darling Harbour Theatre here in Sydney.

Unlike Chris’ ‘Self-Discovery’ show which I attended back in 2024 and comprised of an album of his most powerful insights from his podcast, Modern Wisdom, the ‘Mostly Wise’ tour I attended the other night was a little different…

It was comparatively unique both in content and in format.

In content:

For the 2024 show, it felt like the focus was on how to get from ‘zero to one.’ In whatever it is that you’re doing, how do you overcome the initial hurdles? Powerful, absolutely loved it.

Whereas his new show was more about how to effectively manage the landmines that may crop up as you go from 1 to 3 to 5 to 10. All for it.

In format:

Both the 2024 and 2026 shows were hilariously opened for 15-20 minutes by James Smith, but Chris’ segments were a little different…

The first tour consisted of 45 minutes of speaking, followed by a 10-minute intermission, another 45 minutes of speaking, and then 20 minutes of microphone-led/moderated Q&A.

Whereas the new show had no intermission and was instead 4 x 25-minute speaking segments from Chris broken up by 15 minute portions of the crowd basically shouting out questions/prompts/statements akin to the stand-up comedy format but skewed towards self-development.

I personally much preferred the 2024 format as it felt like there was more of an opportunity for Chris to really hone in on certain points rather than hover over them (which it felt like he did in the new show).

And the ‘crowd shouting stuff out’ aspect, while I’m sure Chris loved the challenge of needing to think on his feet, I don’t think was conducive to thoughtful and meaningful questions from the audience that matched the tempo of the night.

TLDR: not as good as the first time, but still worth going.

These were my biggest takeaways:

• When you succeed, do you feel satisfaction or relief?

• Choose your regrets.

• What would you do to make your 85-year-old self miserable? Do the opposite.

• Worrying will not improve your performance.

• The key to telling any narrative is having tension in the story.

• You were born to live. Not to prepare to live.

I think it’s so important to support those creators who dedicate their entire lives to their craft.

Awesome night.

P.S. Chris’ Australian vlog and BTS of the Sydney/Melbourne shows is very cool.

Tweet:

Is Germany in trouble?

Wow.

And Germany is the largest European economy…

Thanks for reading! Grateful for your support.

Stay hungry, stay humble, stay curious. ⚡

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See you in the next one,

Dimi

(P.S. the best ways to get in touch with me are via email or LinkedIn).