I love the commentary about investment in operations. They hire a finance-oriented CEO who doesn't invest in building out tooling and infrastructure. This was the key paragraph for me:<p>> But as time went on the operation began to deteriorate. There was little investment in upgrading technology (after all, how do you measure the return on investing in infrastructure?) or the tools we needed to operate efficiently and consistently. As the frontline employees began to see the deterioration in our operation we began to warn our leadership. We educated them, we informed them and we made suggestions to them. But to no avail. The focus was on finances not operations. As we saw more and more deterioration in our operation our asks turned to pleas. Our pleas turned to dire warnings. But they went unheeded. After all, the stock price was up so what could be wrong?<p>I see this in tech all the time. It is indeed very hard to measure the return on investment for tooling and infrastructure in tech! Any infra work, whether it's splitting up your monolith into components, improved developer tooling, or fixing flaky builds has a vague and hand-wavy return on investment and has to compete with "Well customer FooBar will sign a $10M contract in Q2 if we build feature BashBaz instead," and now good luck as an engineer explaining how and when exactly your investment in developer tooling is going to make the company $10M in Q2.<p>But if you never invest in these, then the machine comes to a grinding halt and everyone's hair is on fire, and there is no quick fix because the solution was to invest in the problem proactively starting 2 years earlier, and now that you're so late it's going to take <i>4 years</i> to solve the problem because you have to first deal with all the debt you accrued.<p>This is a place where leadership really can have 100x impact by establishing a dual-route for evaluating projects. The first route is the traditional "how much money will this make us", but the second is based on principle ignoring $$$ returns, "what is the most impactful operational improvement that our front-of-the-line staff is recommending?" You have to simultaneously run both strategies!