books_118_365_-4f14cbc-introTextbooks — especially college textbooks — is one of those industries that’s so obviously broken from the outside that entrepreneurs can’t help themselves but try to fix it. But most of them, once they get knee-deep in venture money and product, realize the industry might actually be too far gone.

It’s similar to the music industry, which could have bought Napster for $3 million and monetized it. Instead they chose to sue the pants off of it to teach it a lesson. Now we’re left deciding between cumbersome iTunes, and Pandora and Spotify, both of which are unprofitable and plagued by complaints and hearings that they’re screwing over the artists and labels. Great job, all.

Big Textbook and Big Bookstore are not terribly different. Many startups that nobly set out to disrupt textbooks have realized they quickly needed to change course. Several built businesses in the hopes they’d sell to Apple; the company’s partnerships with Cengage and the rest of the textbook sellers have signaled that Apple will go into textbooks on its own, thank you.

Chegg, one of the oldest, largest and most well-funded of the group, has had to branch into new, non-book revenue streams. The company is using (or exploiting, if you prefer) the most valuable thing it has — an audience of college kids — to get brand dollars from the likes of Taylor Swift and Home Depot. The site now does banner ads on its commerce pages (a huge no-no in the world of ecommerce) and sends coupons along with its its orders. That’s not a book business, it’s a media business that uses textbooks as a gateway drug. And like Kno and Inkling, two other well-funded, straight-to-the-consumer textbook companies that are mostly focused on their supplementary interactive learning tools, Chegg has rolled out its own supplementary products to the actual books.

Flat World Books was meant to revolutionize textbooks with its free, printable books. That hasn’t worked — last month the company announced that free was dead. And now founder and CEO Jeff Shelstad has stepped aside for the adult CEO Chris Etesse, for CTO of Blackboard Student Services.

Which leaves two companies that seem to be fighting the good fight. Bookboon, a Denmark-based company that provides free ebooks and expects to have 50 million downloads this year. The company’s solution is arguably the most successful of the group, and it’s also the most basic and low tech. The ebooks are free and monetized entirely with ads. Funnily enough, Europe doesn’t even have the textbook price-gounging issues we have in the States.

That leaves us Boundless, a very early stage Boston company that, until it was sued by three of the four big textbook companies (lawsuit ongoing), did “free textbook replacement.” Meaning, it used open source documents and information to recreate college textbooks for free. A revolutionary concept, I thought. It still does that, but since being sued, like all others (except Bookboon) in the industry, Boundless has expanded into study guides and tools. Now the company pimps its tools to help students “Learn Faster.” The reason co-founder Ariel Diaz told me at the time was because “Students aren’t excited by textbooks, so we won’t want to be viewed as just a textbook. We want to be viewed as useful.”

The company has today rolled out more usefulness in the form of more beyond-the-textbook features. Tools that condense your notes and highlights, allow you to edit and share, and view notes on full screen are now available for students before finals. It’s all very useful stuff. But the tools obscure the real value of Boundless, which is its fight to make information free and open. The company is being careful not to mess up its future by losing this lawsuit so early in its life. But stories like its hackathon last month are, I think, more exciting than study tools, no matter how well-designed and useful they are.

At the hackathon, the company gathered 30 Boston-area academics to curate open educational resources to create a free, open physics textbook from scratch. “Though it typically takes two years for authors to complete a textbook, we finished about one-third of ours in a weekend,” Diaz says. The textbook industry might never be fixed, disrupted, or revolutionized, but I’m glad that someone is at least trying.

[Image via Casey Fleser]