Connecting the Fragmented Tech Stack of Independent Bookstores

Many independent bookstores run on a disconnected patchwork of essential systems. Nearly every bookstore I’ve talked to has mentioned some version of this problem:

So many silos! Everything is disconnected! Nothing talks to each other! It’s all very painful!

You have a point-of-sales with inventory that may or may not be connected to your e-commerce website. You also have a wonderful collection of rare books you want to sell online but you have zero time to take on the overwhelming chore of listing them on each of the different marketplaces. You have multiple data sources each with different features, but none of your tools work with bibliographic data. Payment processors, gift cards, subscriptions, memberships, etc. Every piece of software that you use for selling books is your bookstore’s “tech stack”, and your tech stack is only getting more difficult to manage as the tools multiply.

I first built Bookhead to be another one these services. My goal was to create an e-commerce platform designed for independent booksellers because I saw a need for something different, but I’ve decided that adds to the fragmentation problem.

Instead, why don’t I connect what already exists?

Introducing… Bookhead Connect!

It’s very simple. Bookhead Connect is a collection of book-smart services that connect the different systems you use to run your bookstore. The first version connects the inventory from your point-of-sales with your existing online website, that way you can keep using your familiar tools while solving the very important problem of syncing your inventory to your website.

I swear, it’s simple. This chart describes this very first iteration:

The chart represents a data pipeline that combines a bookstore’s local inventory with bibliographic data and then lists the products on an e-commerce platform. Bookhead will work tirelessly in the background to keep your local inventory synced on your existing website. It doesn’t care what point-of-sales provider or e-commerce platform you use. It just wants to connect the two dependent yet unconnected pieces.

I have a basic beta version that is ready to be tested by stores right now, and it includes inventory syncing from Basil to Squarespace, eBay, and Biblio. Once I’ve finished integrating the inventory syncing with the rest of the bookselling point-of-sales systems and some popular e-commerce platforms, I can take this concept and it apply it to other components of your store’s technology. I want to be the data pipeline for the parts of your bookstore that need it. Your bookstore’s central nervous system that connects to the brains behind your bookstore. Zapier for independent bookstores.

Bookhead Connect is the missing part of a bookstore’s tech stack. If you are interested in learning more about using this service for your bookstore, email me at sam@bookhead.net. Otherwise keep reading about the background of this decision.

An Uncertain Future

The recent progress of AI has drastically changed the landscape for a software business in many ways. I don’t care to get into the AI debates, but importantly for Bookhead’s concerns:

• AI lowered the barrier for creating software. People without technical backgrounds can use AI to create custom software unique to their business. The idea that "software is becoming a commodity because of AI" has floated around the entrepreneurial tech world for the past couple of years, and it's led me to question my choice of building an e-commerce platform if it will become a cheap commodity or even obsolete because of AI.
• Some believe that AI will remove the need for web browsers and apps, and instead we'll be interacting directly with an AI to do everything, like buying books.

I have no idea what the future holds, except I will still be reading books bought from independent bookstores and recommended to me by people. In this uncertain world Bookhead’s mission is to help bookstores use technology to promote literature. With Bookhead Connect, positioning Bookhead as the connection layer for a bookstore’s fragmented tech stack is the best way to do this in 2025. I can help bookstores sell online by creating software that solves problems they have right now with their existing platforms.

I’m not abandoning the existing e-commerce platform because Bookhead Connect complements the e-commerce platform. If the all of the competing e-commerce platforms race towards the bottom in price because software becomes a commodity due to AI, then Bookhead might be in a good spot to weather that. We will be alongside everybody else racing to the bottom with our own e-commerce offering while Bookhead Connect provides value to stores who prefer another platform.

Commoditize the Complements

An early stage business is fun because I get to build new features like the inventory sync while also coming up with the messaging and positioning for the new feature while I make it. It’s this unique combination of listening, creation, problem solving, design, engineering, strategy, marketing, communication, and sales. But with creation comes self-doubt; the constant critic in my head telling me that I’m going the wrong way spiraling into bleak existential thoughts about an imminent future with AI.

Then I happened to read an essay by Gwern called “Laws of Tech: Commoditize Your Complement”, where he riffs on an idea first identified by Joel Spolsky: a tech business can find a strong market position by embracing and accelerating the commoditization of complementary products in their space.

The essay fit perfectly into my brain with what I’ve been thinking about bookstore tech. E-commerce platforms are becoming commoditized — they’re getting cheaper, more interchangeable, easier to spin up, etc. Instead of fighting this trend by building another e-commerce platform, Bookhead can embrace it. By making it easy for stores to use any platform they want, Bookhead becomes more valuable as the connection layer.

The same principle applies across a bookstore’s tech stack. I don’t need to build my vision of a point-of-sales system or bibliographic database etc. Let those become commodities. Bookhead’s value comes from being the essential layer that helps all of the systems work together, making the existing platforms even better for the bookseller. Because that’s what I’m here for, serving booksellers.

This strategy turns Bookhead into a collaborator with everybody in the bookstore tech industry, rather than a competitor. This fits my disposition: I like to collaborate instead of trying to compete. Much more natural for me. Competition feels bad!

What’s Next

I’m starting with the first crucial connection that a lot of stores need right now: syncing inventory between your point-of-sales and website. I have some ideas that I’ve come up with over the years of being a bookseller and seeing firsthand some of the pain points, and I’m eager to work on them. I’m excited about the future of bookselling technology!

If you’re a bookstore dealing with disconnected systems, I’d love to talk. You can email sam@bookhead.net or book a meeting with me at this link: https://calendly.com/sam-gw9b/30min.