I recently started a new role. Evidently, part of the initiation is receiving a flood of unsolicited emails from SaaS companies looking to sell me their latest-and-greatest. To my surprise, it’s now the norm to offer to pay me personally “just to hop on the phone”. I’ve received multiple emails from companies (the two that I was able to find quickly in my inbox were from Galactic Fed and Premier Soft)¹ telling me why I should sign my employer up for their services.…

Living in a house that’s in need of repairs and upgrades over the last few years has presented me with a wealth of learning opportunities. Just in the last year I’ve had to: repair our dishwasher, fix a leaky washing machine, rewire our dryer to work with our electric system, replace some doors, install new walls, and a thousand other smaller fixes along the way. Fortunately, I’m quite handy and for the things I don’t already know how to do, I’m able to YouTube-tutorial my way to success.…

We live in a world of monotone software. It isn’t all the same, but it sure does feel that way. Go look at the Wayback Machine for, say, 2005. Different websites felt different. Today, though, you can jump between a dozen different sites and feel like you’re wandering different aisles in the same grocery store. The inventory might be different, but there’s no change in how they make you feel. Why is that the case now when it wasn’t the case a decade ago?…

When I was a kid there weren’t any technical limits on what I could get our computer to do. There were parental limits, common sense, and skill limits - but the computer that sat in our living room let me do whatever I wanted. That included everything from being able to use the OS to delete the OS (that’s how I learned what hidden files were) to the freedom of sliding open the side of the box to unplug things (that’s how I learned that you shouldn’t unplug cards while the computer is running just to see what they do).…

Back when I worked for a mortgage startup we had a peculiar growth mandate that came with a number of constraints. These made sense at the time (we weren’t profitable, we weren’t trying to scale yet, and we were still figuring out our internal operations), but which also lead to more cautionary lessons in how not to scale a startup than in how to do it well. When it came to bringing in new leads in a highly competitive market, we had three main curbs to keep in mind:…