Southwest Airlines has made headlines in recent days for all the wrong reasons: bad weather impacted air travel, which required Southwest to adjust plane and crew schedules. Those adjusted schedules were often logistically flawed because the planes and crews matched at a specific place and time didn’t make sense in the real world. Making matters worse, those adjusted schedules had to be re-(and re- and re-)adjusted every time either the weather changed or operations changed (ie., more flight cancellations), and both the weather and operations were changing throughout Southwest's route network. The culprit, according to people at Southwest quoted by the Wall Street Journal, was scheduling technology that could not sufficiently scale and is nearing end-of-life. Whether a problem of rapid growth or neglected investment, everybody seems to agree that Southwest has been living on borrowed time.
The neglect of core technology is an all too common a practice by virtually every company: the technology becomes more complex than its foundational architecture was ever intended to support, the team familiar with the technology erodes through layoff and attrition, and as a result a technology become more vulnerable to failure. But it still works day in and day out, so there is no incentive to invest in repair or replacement.
Unfortunately, vulnerability of an aging technology isn't a financial statement phenomenon; it is at best one risk mentioned among many in the 10-K. However, money spent on the labor to reduce that vulnerability is a financial statement phenomenon. Add to that the opportunity cost: every dollar spent on risk mitigation is a dollar that doesn't go toward a net new investment in the business, or a dollar that can't be returned to investors. While it doesn’t cost anything for a technology to fall into a state of disrepair, it sure costs a lot to rehabilitate it. Conversely, neglect is not only free, it’s cash flow positive: i.e., the company can claim victory for streamlining tech spend.
But as mentioned above, neglect creates business risk. And risk is a peculiar thing.
There have been dozens of massive macroeconomic risks realized in the past 25 years - acts of terror, acts of war, financial crises, environmental disasters, viral pandemics - that have made a mockery of the most sophisticated of corporate risk models. Yet risk is still no better an investment proposition than it was a quarter of a century ago: investing to be prepared for "black swan" events (i.e., robustness) is still an uncommon practice (n.b. perhaps inventory build-up and multiple sourcing practices in response to supply chain disruption in recent years will change this, but it remains to be seen how durable this turns out to be). And anyway, dilapidated internal systems are self-inflicted exposures: even if they can talk about such risks publicly, CEOs aren't paid for their acumen at developing and executing remediation strategies. Plus, just about every company will accept exposure to technology risk as business as usual. Business is risk. If a company spent to mitigate every last risk, it would be wildly unprofitable. There's an amount the company budgets annually for maintaining the status quo and every now and again the company will try staffing some up-and-coming manager or hire some hotshot consultants to figure out a way to make things a little less bad. This is great, but it amounts to pennies spent mitigating very large dollar amounts of exposure. In other words, hope is all too often the insurance policy against having a huge hole blown in the income statement by the failure of a high-risk technology.
While risk is generally not an investible proposition for technology (unless business operations are being wildly disrupted because of it, such as is happening to Southwest this week), sometimes there is a golden ticket that promises to make the risk simply go away, such as when a company has a legitimate case to make that it can reposition itself as an ecosystem if only it were built on a cloud-based platform. With consistent cash flows and an existing - and under-leveraged - network of partners, the right leader can motivate investors to pony up to make a wholesale replacement of existing technology. It's a growth story with a side order of risk mitigation through modernization. And with the appropriate supporting data, this is an attractive proposition to risk capital.
Investible, yes, especially since it is more than just an investment that makes the business less bad than it need be. But the headline doesn't tell the whole story. Switching from one technology to another is not a trade of one set of business parameters (the company's current business and operating model) for another (the company's future business and operating model). It is more accurately a trade of risk profiles: exposure to a current technology (the tech and operations supporting current cash flows) versus exposure to aspirational technology (the tech and operations supporting aspirational cash flows).
The magnitude of the technology risk between the two is really no different. It is, optimistically, an exchange of current system sustainability risk for the combination of development risk and future system sustainability risk. System fragility and key person risk may make the status quo highly unattractive, but software development has long track record of cost overruns and failure. In practice, of course, development risk and current system sustainability risk are carried at the same time, and current system risk may be carried for a very long time if it proves difficult to fully retire some legacy components. The true exposure is therefore far more complex than current versus future technology. In practical terms, this means is that just because “reinventing the business” makes legacy modernization more palatable to investors doesn’t mean it offers the business a safe way out of technology risk.
It bears mentioning that a business electing to mitigate existing technology risk through reinvention is taking on a new set of challenges, especially if that company has not made such an investment in recent years. It must be ready to deal with contemporary software delivery patterns and practices that are much different from those of even a decade ago. It must know how to avoid the common mistakes that plague replatforming initiatives. It must be prepared to deal with knowledge asymmetry vis-a-vis vendor partners. It must know how to set the expectation for transparency in the form of working software, not progress against plans. And it must be prepared to practice an activist form of governance - not the bullshit spewed by vendors passed off as governance - to make those investments a success.
Reinvention promises freedom from the shackles of the status quo, but while going about that reinvention, exposure to technology risk vastly increases and stays at an elevated level for a long period of time. The future awaits the replatformed business, but do be careful what you get investors to agree to let you sign up to deliver.
