> We were brought in specifically do to the rewrite.

That's the key difference. The stakeholders should always be in on the rewrite.

> It sounds like less about the refactor itself and more about the skills of the team doing the refactor. You certainly can't expect a refactor to go well if the team makes poor decisions to begin with.

This has been my biggest struggle with rewrites where I’m currently working. We have several large, messy old codebases that everyone agrees “needs a rewrite” to (1) correct for all the early assumptions in business needs that turned out wrong, (2) deal with old PHP code that is very prone to breakage with every major new PHP version released, and (3) add much needed architectural patterns specific to our needs.

I’ve seen rewrites of portions of the project work when they involve myself and one other mid-level dev who has a grasp on solid sw engineering practices, but when the rest of the (more senior) team get involved on the bigger “full rewrite”, they end up quickly making all the same mistakes that led to the previous project being the mess that it is.

Sure, it will be using fancy new PHP 8 features, and our Laravel framework will force some level of dependency injection, but the you start seeing giant God classes being injected over here, but duplicated code copy-pasted over there, all done by “senior” devs you feel you can’t question too strongly.

To that end, an open and collaborative culture in which you start the rewrite with some agreed upon principles, group code reviews and egos kept in check, are all necessary for this to work.

You have a great experience and did a great job indeed. My only question is how does one get 20 years of such experience without horrific flashbacks of “let’s just rewrite it” decisions. Do you do rewrites/redesigns often? What’s your success rate?

I've done what I would consider as four rewrites that I can remember as large events in my life (although not fully what you'd expect). But all are good stories in my opinion.

First one was the above example. It was for the largest hardcore porn company on the planet. Myself and my good friend Jeff rebuilt an already successful business IT department from the ground up and made it even more successful. Ever heard of 'the armory in sf'?

Second was that jeff and I were hired as contractors by Rob @ Pivotal Labs (ceo) to help the CloudFoundry team rewrite itself after he had bought the team and trimmed it down to only the good people. That one was a huge mess. We spent a lot of time deep in shitty ruby code using print statements trying to figure out what 'type' of an object something was and, of course, backfilling tests. It was a fun project and both Jeff and I learned the Pivotal way, which was probably the most enlightening thing I had ever learned about how to develop software correctly from a PM perspective. If you want to improve your skills beyond just slinging code, spend some time figuring their methodology out. Much of it is documented in Pivotal Tracker help documentation and blog posts.

Third one was not really a rewrite, but the original two founders, who were not technical, had tried to hire a guy and got burned because the guy couldn't finish the job. Sadly, they had already paid the person a ton of money and got really nothing functional out of it. We (jeff and I again!) just started over. We did a MVP in 3 months (to the exact date, because we both know how to write stories using pivotal tracker and do proper estimates) and ended up doing $80m in revenue, in our first year with an initial team of 5 people.

Fourth one was three guys (who were also not technical) I kind of randomly met after I moved to Vietnam. They were deploying litecoin asic miners into a giant Vietnamese military telco (technically, they are all military). They had hired another guy to do the IT work and he was messing it all up. They invited me out to help install machines, I came out, rebuilt their networking layout and then proceeded to eventually fix their machines because the software 'firmware' that was on them was horrible. I also added monitoring with prometheus so that I could 'see' issues with all these machines. That first day on the job, they fired the other guy and made me CTO. We ended up deploying in another datacenter as well. It was a really wild experience with a ton more stories.

Life has been, um, interesting. Thanks for reading this far.

Please tell me that you've retired now due to your incredible billing rates and track record of success.

Not everything has been a success. For example, unless you're stupid rich and can afford years of losses, never start/own a night club or you might end up working for the rest of your life to pay off your debts.