Five Years Working for Myself

Five years working for myself. In a couple of months this will be the longest stretch I've ever worked anywhere.

Lots has changed, especially in the past year. AI is doing a number on the economics, planning, and budgets of pure software companies which is where I've spent most of my career. The private equity + venture capital investment thesis for most pure software companies has been blown up.

It's been the most wildly productive software building year of my career, and the toughest sales environment since I hung my shingle as a solo consultant.

My bet is that good software is just as needed and valuable as it ever was, but maybe in different places than it has been for most of my 20+ year career.

Specialized agents and the agent native software that's designed to be used by them and the big harnesses can be applied more widely and effectively than ever before, at a lower per capita investment cost.

The addressable market is getting a lot wider and going to many other companies where it would not have made sense to have built their own software before.

I don't think everybody is going to write their own CRM, etc. I think combining custom agent native software and workflows that are fit for purpose with SaaS products that keep up with how companies are rewriting their workflows is the key.

Efficiency is there for companies who want it, but focusing only on efficiency for ways of working that already exist is a serious mistake.

Ambition is where the real opportunity is. Figuring out how to leverage this new paradigm into capturing demand that didn't pencil out on the spreadsheet before is the way forward. More ambitious competitors will come for the companies that think they can just get more efficient, cut headcount, and grow the bottom line sustainably.

I'm grateful to be wrapping up 10 days in the sunshine with my family to lay off bossing robots around and recharge a bit. It feels like momentum is building into something new and I'm fired up to help some more folks capture this wave, even outside of pure software companies.

LFG. Here's to the next five years.

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