In today’s post, I look back on the developments of ecommerce and my role in covering this technology. I was recently reminded of this history after writing last week about Paypal — this motivated one of you to recall events that happened in the early 2000s, back when the “internet bubble” was rising and then bursting.

I last took a long look back at ecommerce in 2014 with this blog post. In it I highlighted a series of other works:

• Back in the late 1990s, I tested many ecommerce products and also lectured at conferences around the world on the topic. One piece was an op-ed that I wrote for ComputerWorld back in 1999 here.
• In 2010, I looked at how hard it was to take credit card payments online in my blog.
• Then for ITworld in 2011, looking at the crop of mobile payment apps such as Square.
• And in 2013, I looked at the frustrations surrounding eWallet technology.

While the web came of age in the 1990s, it took a while for ecommerce to get into gear. The technologies were bare-bones: back then, you could learn basic HTML coding in a couple of days and easily put together a static series of web pages. The key operative words in that sentence were “static” and “basic.” The 1990s era of HTML was waiting for the language to catch up with what we wanted to do with it, but eventually the standards process got there. The real stumbling block was making a site dynamic and being able to support online inventories that were accurate, checkout pages that were secure, and having access to software interfaces that were pretty crude and simplistic. All of that required other tools outside of HTML, which is somewhat ironic. Now if you look at the code behind the average webpage, it is almost impossible to parse its logic at first glance.

Yet, here we are today with ecommerce being a very sophisticated beast. HTML is no longer as important as the accompanying and supporting constellation of web programming languages and development frameworks that require lots of study to be competent and useful. Connecting various databases and using a web front-end is both easier and more complex: the APIs are richer, but how they are implemented will require a deft touch to pull off successfully. Payment processing has numerous vendors that occupy sub-markets. (Stripe, Bill.com, and Klarna are three such examples of companies that are all involved in payments but have taken different pieces of the market.)

You might not have heard about Klarna: they are one of more than a dozen “buy now, pay later” services that pop up at checkout. No purchase is too small to be spread across a payment plan. Back in the pre-internet times, we had layaway plans that had one important aspect: you didn’t get the item until you completely paid for it. Now items arrive in days, but attached to a stream of loan payments stretching out several months. The downside is that there are potential late fees and 30% annualized interest charges too.

And then there is Amazon and Google. The former has both made it easier and more complex to do online shopping. It used to be both free and easy to return merchandise purchased on Amazon. Now it is neither. If you don’t pay attention when you are purchasing something, you could end up using one of their contract sellers, which complicates the returns process. And the cost of Prime continues to climb.

Google’s Lens technology has also transformed online shopping. If you have a picture of what you want to buy, you can quickly view what websites are selling the product with a couple of clicks on any Android or iPhone. My interior designer wife uses this tech all the time for her clients.

Before I go, I want to mention that Cris Thomas, known by his hacker handle Space Rogue, has a new book out that chronicles his rise into infosec security, including his time as one of the founders of the hacking collective L0pht. Its early days were wild by today’s standards: the members would often prowl the streets of Boston and dumpster dive in search of used computer parts. They would then clean them up and sell them at the monthly MIT electronics flea market. Dead hard drives were one of their specialties — “guaranteed to be dead or your money back if you could get them working.” None of their customers took them up on this offer, however. There are other chapters about the purchase of L0pht by @stake and Thomas’ eventual firing from the company, then taking eight years to get a college degree at age 40, along with the temporary rebirth of the Hacker News Network and going to work for Tenable and now at IBM. I review the book in this post, and highly recommend it if you are looking at reliving those early infosec days.