One of my favorite thinkers is Morgan Housel, investor and author of The Psychology of Money. He writes a lot about “margin of safety” and “room for error”. Housel talks about how in business, a lot of bets fail not because they were wrong, but because they were mostly right in a scenario where they needed to be exactly right.

As we design experiments for AI in our companies, I think we could all benefit from some more margin of safety thinking. It’s easy to get so AI-pilled that we want to inject it into every part of the business as soon as possible. Unfortunately, AI can compound our mistakes just as fast as it can do anything else. Here are some examples of low-risk experiments where the cost of being wrong is low:

All of these tools exemplify margin of safety because they don’t leave room for AI to compound an error if one is made. They’re largely for internal use and they all require a human review step. These are tools that build internal capability and fluency with AI tools, which sets the foundation for everything else.

The ultimate low stakes AI tool for any new business isn’t flashy. It doesn’t replace an entire role wholesale. Based on my own discovery work with clients, the task that people are universally using AI for is writing emails. Most people agree that it’s never quite ready to send after AI writes a draft, but it’s getting close.

Construction is one of the most complex business endeavors that exists. It’s the coordination (and sometimes collision) of countless trades, vendors, legal entities and supply chains. I strongly encourage people to be thoughtful when using AI to write. But for the volume of communication that building requires, we could all benefit immensely from a tool that helps us communicate faster. And not only faster but with vastly better recall. AI can augment the capabilities we already have, so that professional tone, writing quality and detail tracking no longer hold builders back.

A simple email assistant trained on company/individual tone guidelines, writing examples, and desired format can massively improve speed and quality of communication. As the builders I’ve spoken to understand, communication is what makes or breaks most jobs. For contractors wondering where to start, this is a great jumping off point. It’s not often you encounter an experiment that can be low-cost and low-risk with such high upside.

If you've ever printed a vendor invoice just to scribble cost codes on it with a Sharpie, this one’s for you.

upmarkPDF lets you upload a PDF bill and overlay your job costing details directly on top of it. Cost codes, job names, chart of accounts, sales tax breakouts. It allows your whole team to pull from the same shared backend, with simple dropdowns for all of your relevant details. When you're done, you can email the marked-up PDF straight from the app.

It's collaborative and affordable, including a free tier.

This is exactly the kind of tool I love seeing in construction tech. Small, focused and built by someone from the industry who really understands the problem. If your team is still printing bills to mark them up or just needs a smoother process, I would highly recommend you check out upmarkPDF.

*This is not a sponsored post.