Newsletter #22 (3/24/2025)

Goodbye to Southwest Airlines, car notes are crazy expensive, Dick's Sporting Goods is making that cash

Back after taking last week off for Spring Break!
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Goodbye to Southwest Airlines.

…..at least in the sense of what used to make it stand out versus other airlines. Bowing to activist investor pressure, and the reality of its balance sheet, Southwest recently announced it would institute bag fees for the first time.

And now, for the first time, Southwest finds itself at odds with how it was founded: a cheap, no frills airline designed to get you from point A to point B with remarkable efficiency and obsession on customer service. Now? Just another airline.


Another week, another troubling sign for the economy, this time in late car payments.

Recent news shows that late car payments are the highest they have been in over 30 years. 1994, the first year such records were kept, was the last time so many car notes were behind their due dates.

A number of factors can be attributed to 2025’s situation, chief among them the cost of new vehicles. Check out the average car note now:

This is a key data point to keep an eye on the weeks ahead.


Dick’s Sporting Goods continues to re-invent their company.

On their recent quarterly investor call, Dick’s Sporting Goods discussed their quarterly earnings results and how they plan to expand initiatives on RFID tags in their stores and employee training.

For what used to be a sleepy uninitiated competitor of retail sporting good stores like Academy, Big 5, or even Walmart, what Dick’s has done the last few years is remarkable.

Their stock price has nearly doubled in the last few years. They ignored the “let’s be like Amazon” trends, and double-down on ways to woo shoppers back into their stores. They closed some stores to free up capital and have made a number of other moves to completely overhaul how they were seen in the marketplace, and it has paid off handsomely. While they are forecasting some rocky economic times ahead, they have done well in a crowded marketplace by focusing on the customer experience.


AI project failure rates are on the rise.

Which makes sense, given all the rage, hype and interest in figuring out what AI can do for most any company in the market. This process will take some time to play out, as executives at any company out there will launch projects to harness AI’s capabilities, only to find out it just doesn’t work for their needs. Like any new technology, assessing whether AI can impact your organization is not a cookie-cutter approach.

Unfortunately, the hype the last 2+ years has seemingly been exactly that: cookie cutter.

The large-scale reporting of AI project failure rates, though, seem surprising. From the article’s information, the data indicates the “average organization scrapped 46% of AI proof-of-concepts before they reached production.” In other words, half. In general and on average, half of all AI POC projects are cancelled before they hit production.

There’s a much more in-depth writeup here if you are interested, but suffice to say as I’ve written many times, each company’s use case is going to be unique. Take the time to decide what is right for your company. Not everything is going to work, and that’s OK.

Software startup Rippling sues competitor Deel, claiming James Bond infiltrated their company.

Well, not exactly I suppose, but it reads like that!

In short, a software company called Rippling hired the person it called “the Deel spy” in 2023. This “spy” allegedly and repeatedly accessed information “about Rippling customers, quotes, sales calls, demos and support requests in internal Slack repositories, and found and downloaded Rippling's guidance on how to go up against Deel for prospective business, too.”

Guarding against corporate espionage is difficult to do when you largely have to bestow a large amount of trust in most employees to do their job, but this case seems like a straight up a spy story.

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© March 2025, Brandon Caldwell. All rights reserved. Hyperlinks are used frequently for proper credit to source material on respective websites, news articles, social media or other sources. Images are used with and in credit to rights reserved to their respective owner(s). While it can be a useful tool, no ChatGPT or other generative AI was used in the production of this newsletter. Opinions are mine and do not reflect the opinion or policy of others including employers past or present.