Ben Fox is a serial entrepreneur and avid reader whose latest venture is a new platform for book discovery, www.shepherd.com. I was curious to know more about what drove him to pursue this new venture, and he kindly agreed to be interviewed.

Phil: You have a number of businesses behind you already, mostly very tech focused. What attracted you to starting a new business focused on authors and books?

Ben: I love books and I love reading. I think books are half the reason for my tremendous optimism about humanity. I wanted to do something that helped readers bump into books they might not otherwise find. I love wandering through a bookstore and seeing what catches my eye. I want to build an experience like that, but the online version (nothing replaces a bookstore). 

A bookstore is a great example of a commercial entity that can also form a sense of community. Some bookstores, like Shakespeare and Company in Paris, are legendary for supporting writers and readers.

Yep, and I would like to see if I can create a new version of that same community and support for writers and readers online. A big part of this is I want to help authors meet more readers. The pressure being put on authors to build and grow their own audience is insane. My hope is I can help them as the publishing world evolves.

And evolving is something that the publishing world has been doing a lot of in the past twenty years. Between the aggregation of publishers worldwide, and the same happening with vendors online, power is shifting within the industry. It’s becoming both more democratic (with a boom for self-publishing) and also less so (with fewer viable sales channels).

A lot of people might expect an entrepreneur to have a business degree or a similar education. How does your liberal arts degree impact your approach as an entrepreneur?

I think my liberal arts background is a symptom of my curiosity for the world and how things work. And being an entrepreneur is a natural extension of that. I love trying to figure out how things work and try to find new approaches to challenges. 

That’s a great way to describe entrepreneurship. It’s that “try-fail-try again” mentality that seems to be a big predictor of success.

The pandemic has also changed a lot about how we shop for and consume books, accelerating existing trends towards digital. How does the Shepherd fit into this “new normal?”

Shepherd is focused on helping readers discover books. This is our entire focus, and we will be trying to find new ways to do this (what you see now is just the first step). I think book discovery is something Goodreads and Amazon do very poorly. And so, my goal is to replace them in this capacity. 

I hope to eventually help local bookstores by freely licensing our book lists and book recommendations to use in their physical stores. I think local bookstores do discovery very well and this is how they are going to compete against Amazon and other changes in the publishing industry. 

This is something that I love to hear, because as much as I love the convenience of “one click” shopping for a book that has caught my eye, I will always love bookstores. 

Agreed, nothing will replace the magic of bookstores. My hope is to reimagine online book discovery and create a more serendipitous experience. 

The world seems to be heading towards more AI driven processes that promise to “know us better than we know ourselves.” Certainly, Amazon’s algorithms already doing that for a huge percentage of book shoppers. Why the focus with Shepherd on hand curated lists?

We live in a time where social-media and shopping algorithms serve only to reinforce our world view. I want Shepherd to play a role in combating that. A book is one of the best ways to help someone see the world through different eyes. We need a lot more of this right now. 

I couldn’t agree more. Books can open new vistas for people.

This is why I am doing hand curated lists by people who are passionate about a topic. I’ve found that the recommendations I receive from an individual with passion/expertise are a hundred times better than any machine. And, getting their reason why they love the book is more powerful than any marketing description. It also has the side effect of exposing their voice to the reader which drives even more interest in their book.

That is so true. We typically look to friends for these kinds of recommendations, but I gravitate to bookstores that I know are really well curated by their owners or staff. I know that they can help me find just the right book in whatever category they have expertise in, and so depending on what book I want to buy, I go to a different store. (I’m also lucky to live in a big city where this is possible). I love the idea of being able to access authors and their recommendations as well.

All of this makes me curious, though – are you a writer yourself?

Writer yes, author no. I’ve kept a very detailed personal blog since 2008 and that process of writing has helped me in so many ways. When I feel stuck, I love to sit down and write out a few pages of thoughts. It has been a very good habit to build. I do hope to one day write a children’s or YA book. I love to make up stories for my 4-year-old son Calico.

I identify much more as a storyteller than a writer, so that makes sense to me. Writing is just one way to convey those stories and telling them to my kids has been an outlet for me for years too.

Finally, a question I ask nearly everyone I meet, much less interview: what are you reading right now that you’d recommend?

Yep, so far this year my favorites have been Fatherland by Robert Harris, The Girl and the Bombardier by Susan Tate Ankeny, the Empires of Bronze series by Gordon Doherty, and Achtung Baby by Sara Zaske. Last year my three favorite books were Barbarian Days: A Surfing Life, Who Is Michael Ovitz, and the Dresden Files series. 

Barbarian Days is a favourite of mine as well! I wonder what books William Finnegan would recommend!