What Olivia Rodrigo and Robert Smith can teach us about enterprise software today.

I listened to an awful lot of The Cure when I was school and university. I managed to like both The Cure and The Thompson Twins. The Cure has remained a mainstay of my listening for the best part of 40 years, and I really enjoyed the new The Cure album, Songs of a Lost World, that came out 18 months or so ago. Robert Smith spoke to middle-ageness for those that found solace in The Cure in the 80s and 90s brilliantly.

Olivia Rodrigo wasn’t really on my listening radar until this month, even though she is a massively successful singer-songwriter. Turns out she is a big The Cure fan too. Robert and Olivia sang together at Glastonbury. Her latest album has many references to The Cure, and Olivia and Robert sing a duet on the album.

I have it playing on repeat. It brings a big smile to my face, and I’m not really a smile-a-lot sort of person. The whole album is brilliant.

And I suspect the combination has introduced a whole bunch of younger folks to The Cure back catalogue. This is goodness.

Now to Enterprise Software: The vendors that have been around for 50 years with a strong back catalogue can gently reduce R&D, forgo genuine innovation, and stick with what they they know. Repackage their hits onto coloured vinyl, trade on their past, profitably playing to a slowly dwindling audience, but becoming irrelevant for many more. I suspect many will ease into this decline, it will take a decade or two. They won’t disintegrate1 immediately.

Or they can take risks, embrace new ideas, new techniques, new partners, rethink their ecosystems and appeal to new audiences beyond their traditional fans. They must stop assuming one needs decades of experience to do enterprise. Figuring out what to discard will be harder than they imagine, but possible.

To the insurgents. Partnering judiciously with the incumbents will enable you to learn faster, avoid a bunch of obvious mistakes, build credibility with the enterprise buyer and figure your own path to longevity. Find your Robert Smith. Get prepared for the difficult second album.

The difficult second album.

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February 17, 2025

Now that I retired my Otter Advisory blog, I’m going to be reposting some of my favourite posts here. Some I’ll edit, reflecting what’s changed. This post was from 2021 and it still holds up well. I added one AI related sentence, and left the rest as is.

Sometimes the very best things come from combining things that you never thought could be combined.

Here it is. Thank you Olivia and Robert for creating something wonderful. This is one for the ages.

And a live version of them singing together.

My usual more curmudgeonly fare will return soon.