How Clay Christensen’s failure helped me process my own

On Thursday, January 23rd one of my intellectual heroes, and one of the all-time great thinkers in business strategy passed away.

It feels weird to eulogize someone I never met—but that’s the power of writing. I spent so much time with his words, I feel like I know him, and the impact he made on my life couldn’t be more real.

So, to honor Professor Christensen, here’s a little-known story from his past that helped me grow as an entrepreneur.

When I think about Clay Christensen, I think about the warmth of the basement studios at the old Gimlet Media office in Gowanus, Brooklyn.

I joined Gimlet in the summer of 2017 after my startup ran out of cash. It was called Hardbound. We had thousands of paying subscribers that loved our visual “tap stories,” and Apple even called our app “beautiful,” but, ultimately, we weren’t growing fast enough to raise money or cover production costs.

So, the company failed.

After I joined Gimlet, I missed making stories every day, and went on the hunt for a new creative outlet. Graciously, my boss Matt Lieber allowed me and my friends to commandeer a spare recording studio for our own purposes in the evenings.

Our plan was to create a podcast exploring Clay Christensen’s work. We’d prepare by reading chapters from his books, and gather over beers every Monday night to have a conversation about his ideas, to try and relate them to our own experiences building businesses.

I soon realized I had a lot to talk about.

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Shutting down Hardbound was painful. I had to lay everyone off, which was surreal. I tried to help them find new work, but I still felt terrible for the hardship I knew my failure was causing. Personally, I was also running out of cash.

A week later, I realized I had to break the news to all our customers and friends, so I wrote a dazed post on Medium explaining the situation. That elicited a helpful flood of support, but I still had a lot of unresolved emotions weighing on me.

In the recording studio, I was finally able to let them out. 

We’d sit down to talk about integration vs modularity, which would lead me down a rabbit hole talking about the value of integrating stories with design and interactivity, which would pull us into a bigger discussion about managing cost in a media business. After a couple hours and a couple beers, I’d take the subway home happy and exhausted.

When we decided to start the podcast, we didn’t know what it would become. We just wanted to spend time with each other and to learn theories of business strategy, like “disruptive innovation,” “the conservation of modularity,” and “jobs-to-be-done.”

But those conversations turned out to be much bigger than that. Yes, they helped me understand strategy and markets in a deeper way than ever before. But more importantly, they gave me energy. They reconnected me to my love of startups. And they even added a new layer to my identity: before, I only really cared about designing great products. After, I cared about designing great businesses.

I didn’t know how badly I needed this space to figure out what happened to Hardbound. But once we got rolling, I was all-in. I turned to theory as a way to understand my defeat.

Turns out, so did Clay.

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As our sessions continued, I delved into Christensen’s deeper cuts. I read his earliest case studies, learned more about his biography—and a surprising story emerged. I don’t think many people know about it. For me, it’s been pivotal for my understanding of his life and work.