Special Guest: Ben Fox, Founder of Shepherd

Len: Hi I’m Len Epp from Leanpub, and on this episode of the Frontmatter podcast I’ll be interviewing Ben Fox.

Based in Portugal, Ben is a serial entrepreneur and founder of Shepherd, a unique and popular book discovery platform connecting readers to books and authors to readers.

You can follow him on Twitter @bwb and check out his website at shepherd.com.

In this interview, we’re going to talk about Ben’s background and career, professional interests, building Shepherd, and at the end we’ll talk about some trends in the book publishing industry generally.

So, thank you Ben for being on the Frontmatter Podcast.

Ben: Thank you for having me.

Len: I always like to start these episodes by asking people about their origin story. So, I was wondering if you could talk a little bit about where you grew up, and how you grew a love of reading - and how you found your way into the world of entrepreneurship?

Ben: I grew up in Fayetteville, Arkansas. My parents moved there from Texas. They were hippies at the time, and wanted to get some place with more nature, I believe. My mom read to me while growing up, me and my brother. She was a book buyer in another life. And, I - to be honest, I’m not quite sure what that means. But she worked at the university bookstore. I need to talk to her about that.

My house had walls and walls of books. I think a lot of the books, where they were given as demo copies, or something like that, where they weren’t technically supposed to be sold. So we had an amazing library to dig through.

And also, both my parents are big readers. So it was just part of my life at all times. And when I was little, it just clicked. It was just a wonderful thing. And I found that I can read really fast, so it just became a huge part of my life early on.

And in terms of entrepreneurship, my dad is a bit of an entrepreneur, and he’s an engineer. So at a very early age, I was seeing some of those things. He started a small ISP in a different town in Arkansas while he was working, and he had some of his projects going up. That was kind of in front of me.

Then I got involved with computers through him, because he’s a system admin. I started playing with Linux when I was probably twelve or thirteen, and QBasic and Turbo Pascal. All those things kind of came together and led me down this track.

Len: It’s really interesting. Typically the guests on the podcast are Leanpub authors, who are often computer programmers and people with a background in that, and you’re a special guest, because you’re not a computer programming book author. But I was surprised when I was doing research for this interview, to learn about that you’ve actually got like a similar kind of experience that a lot of our typical guests have, where a parent brought technology into the home. And that story goes back 70 years now for some of our guests sometimes. So, you actually started a company, I think, in university?

Ben: Yeah, actually in high school. It was an emulation website that got very popular, and ended up having a small collective group of people that were putting together different emulation projects. I was running it day to day. It grew fast. Then, I eventually ended up with a web hosting company in college, and was in that industry for like fifteen to seventeen years, somewhere in there.

Len: That’s interesting. You say emulation - you mean video game emulation?

Ben: Yeah. It was a way to play NES on your computer, to play arcade games. It’s a way to save the old games, before the hardware gets lost. At the time, there was a bit of a revolution going on, and people could play modern N64 consoles on their computer as well. That kind of thing. That was very interesting.

Len: Without admitting to breaking any laws, I may have a few ROMs on my computer. But for anybody who’s into gaming and the history of gaming, a lot of the early games, like from NES and stuff like that,, if you don’t have one, they can be lost. But if you’re resourceful enough, you can find ways to play them on any machine that can emulate them. It’s just a fascinating technology.

I’m curious, what that was it like - the experience of like having something succeed that way, when you were so young?

Ben: It was nice. I had some nice amounts of money coming in. A lot went back into the project. But for a kid, I was doing pretty well. I remember I bought like Vietnam-era night vision goggles. All this stuff that a kid wanted out of weird catalogues. I was like, “I can buy that and then sell it back on eBay. Try it out for a few months.” A lot of good stories from there. But, yeah - nothing too crazy, I guess.

Len: You mentioned that you grew up in Arkansas, and now you live in Portugal. But you’ve also travelled around a bit in your life, I gather?

Ben: Yeah. I love to travel. That also came heavily through my parents and my grandparents. I - Gosh, I think I went digital nomad back in 2005? I moved over to Ireland for a while, came back, did a lot of trips for two three months out of the country, and then eventually, years. I’ve lived in Egypt for a year, Australia for a year. Bummed around South America for six months. This was all while working. I really like combining the two - it was a little bit easier when I was single. But it’s much nicer when I have company as well.

Len: The work that you were doing as a digital nomad, can you just give us a little bit of a flavor? I’m looking at your LinkedIn profile here - I know you’ve done a bunch of different things. But if you can just give people a little bit of a sense of what the early digital nomad life was like, and what work you were doing?

Ben: In the early days I was actually working for somebody else, for a brief moment in my career. I was a weird firefighter-type figure who was doing odds and ends. I was running the sales department. I was sometimes training tech support, sometimes fraud detection, other types of weird little jobs for Hostgator. Actually, I was their first official employee.

Then, after that, just a number of different companies I either started or bought. I had a good, long seven-year stretch, where I did a lot of those travels, where I was running a company that eventually grew to about 130 people. A web hosting company, our largest brand was [?]. I was CEO. Operations and marketing were my purview.

Len: It sounds like a very start-up style life, where you just wear all the hats.

Ben: Yes, and I enjoy that.

Len: This has come up on the podcast before, because so many people who get into books and publishing often have a independent streak. But do you have an EU passport, for example, that’d make it a bit easier to travel around like that?

Ben: I’m a dual citizen.

Len: Okay. I’m on the list of jealous people, for those who have those kinds of passports.

Ben: It’s nice.

Len: It must’ve been - so, when did you move to Portugal?

Ben: At the very end of 2019, my son at the time was about to turn three. We decided it was a good time to spend a couple of years abroad. We actually moved to Spain first. We landed in November. Then, of course, 2020 hit. We were in Spain for a year. Then towards the end of 2020, we decided to move to Portugal, just to be a little closer to greenery and some other complex reasons. We loved Portugal, and that’s how we ended up here, where we actually decided to stay for the foreseeable future, because my son starts school next year.

Len: Was that around the time that you decided to found Shepherd?

Ben: Yes. I actually had another startup that had just pivoted about six months before COVID hit. It was trying to help people optimize meetings at a company level - to get people out of meetings, and try to get bigger blocks of deep work time. Something probably a lot of the software engineers who write books that you talk to would love to have. But we just hit some walls. When COVID hit, we had just pivoted, and we were getting some good traction on the new direction we were doing.

We just had everything get swept out from under us. We lost our first couple of paying clients, either delaying by five months, or disappearing. One didn’t, and they’re fantastic. But we basically decided that we needed - or, I decided that it wasn’t good to pursue it right then. Because it was just not going to make it, with everything going on. Because everybody was pulling their budgets at the time and freaking out. I shut that down in late April. I took some time just to relax with everything going on. I haven’t really had much downtime over the last nine years with different projects.

I took six months off, and I’d been wanting to do something in books for a very long time, but I could never find a hook or a way that I was really helping, besides just mimicking functionality that already existed. Then, I had this idea to create something that helped people see what other people’s favorite books were, and why. Because I think, at some point, I’d been in several bookstores where they put Post-it Notes or little index cards, and the staff would say, “Hey, this book is one of my favorites, and here’s a short sentence on why.”

I always loved that, because I walk up and down the aisles, and those catch my attention, and they connect me to the person. That was the birth of the idea. I started sending out some emails to authors that I loved, to see if they would take part. I’d done a mockup with a great designer I work with. It was getting some good responses from the author community. I decided, “I think this will work,” then proceeded from there, and tested it more. Then started zooming forward.

Len: Let’s zoom in on Shepherd. You’ve got Shepherd For Authors as well, right? Because what you’re trying to reach is both authors and readers with this project. It’s really great. I mean you talk movingly, and quite extensively on a couple of posts about why you’re building Shepherd and how it works, and what the marketing program is, and what the business plan is, and stuff like that.

The basic idea is that you contact authors, or authors find you, and they write write-ups of their favorite books. Then you post affiliate links basically to either Amazon, or is it bookshop.org, where people can then buy those books.

But for the author’s benefit, you actually link to the author’s website. People get to know the author by reading their very personal write-ups about the books that they love. That way, as a reader, you get to discover not only books that you might like, but authors that you might like, who like books that you like.

Ben: Yeah. We’re trying to really solidify that five-book list around a topic, theme or mood that gets the author making a list in front of readers who are most likely to read their book. That’s key, that if I wrote a nonfiction book about the Battle of the Bulge, I might do a book list about, “The best books on the biggest battles of World War II.” Or something like that, that the readership who’s coming to that list and attracted to it, is also going to be interested in the book that I wrote. It’s a way to get in front of your target audience, and give them something of value. You’re giving them personal recommendations. They’re also connecting with you when you give those.

Now that varies, depending on the type of person you are. But we do try to pull that from authors. In a sense of, why do they love the book? Then the reader is going to connect more with the author through that recommendation, I believe from - this is based on some psychology for some groups I’ve been part of in the past. And, yes, the hope is that it, in addition to giving them those great book recommendations, it also attracts interests in them and their book over the long term.

Len: This is a specific question, but do you find that authors and readers are connecting personally? That people like will actually go to the author’s website, and then contact them about their books?

Ben: You know what? That’s a hard one to track. We do track links to the author’s website, and other things they give us. Because we allow that, we want them to do social media and newsletter, we try to focus them on the three most valuable actions a reader can take. We are very early in the process.

My hope is, as we grow and have more financial resources to create those things, we will create ways to help engage readers with their favorite authors. Or even authors they’re most interested in. But right now, we are pretty basic. I have had a few emails from authors who -

Actually I’ve had readers contact me, asking to contact authors, because it’s not always easy. I’ve had a few of those, that kind of thing. We do track clicks separately. We can see that interest is here for promoted book, and interest here for all the other books. We’ve done one case study, and I’m hoping to do one later this year - but a lot of the features, I think it’ll help make that connection more long-lasting. Those are having to come later on, because we’ve tried to be very lean. Because we don’t have Goodreads financial resources. That requires a user system and some other things that are coming down the road. Because we are only fifteen months old, since our launch.

Len: That’s really interesting. I think we’ll maybe take the opportunity to talk a little bit about Goodreads a little bit later.

But in the meantime, rhat’s really interesting that you’ve made a lot of progress in that time. I think you’ve got over 5,000 authors who’ve already participated?

Ben: Yes.

Len: And you’ve got a really great blog, where you talk about building Shepherd, where you talk about a lot of the interesting initiatives that you’ve taken, including the use of natural language processing, to help people find the right books. I was wondering if you could talk just a little bit about what that is, and how you actually managed to build that into the site?

Ben: The core belief, and why I’m building this as a reader, and I think, as I’ve talked to other readers, it resonates, authors, to some degree as well - is, I love to explore and find books. To do that, you don’t know what you’re looking for. Currently the internet is really designed to get you to what you know. It’s a big fundamental problem with what’s going on right now with it, in a lot of ways.

What I’m trying to do, especially with NLP, is to find more ways to help readers bump into books that they might be interested in. This concept, some authors do understand it, and others, I’m still trying to help them understand it. But we try to give people multiple points into meeting a book. NLP is a huge swath of different things. We use it to try to analyze a book, and tell you what it is about. We actually piggyback on Wikipedia. There’s a lot of technical reasons for that. But we use their topic suite, because it gives us a base. I don’t have to manage what topics or like -

So, for example, if somebody gives us a list about the best books on the founding fathers, we use a lot of the data that people give us on those books. We give some data that we pull down. We say, “Okay, what is this book about?” If the book’s about George Washington, we might have George Washington, we might have his wife. We might have other topics that are tagged through that. That helps us create both a better recommendation engine for seeing how different topics relate, but also the bookshelves around those topics.

If somebody’s browsing the site, and they go to “founding fathers,” they can also go to a George Washington page that has that book, where they are at the “founding fathers” page, it has that book, or anything connected to that. It’s trying to help build more of a spider web type approach, where people can move in different ways to the site.

Really, I think that search provides a lot of meaning for what you’re looking for, and so that’s what I’m trying to play with. It also eventually will have some other ramifications, in terms of cool things we can do with that information as we get further along. But that’s hard - is that a decent explanation or,?

Len: That’s really good. Thank you for sharing that. You broached one of the big motivations that I gathered behind Shepherd, which is your view that - you said how the internet keeps you in your bubble, for example, is a real thing, and it’s a big topic of conversation in the last few years, for all kinds of obvious reasons. You write quite movingly about it on your site. I’m going to just quote you back at yourself, if you don’t mind for a second here?

Ben: Okay.

Len: In addition to saying things like, “I am incredibly frustrated with online book discovery,” you also say, “One of the biggest global problems is that people are losing trust in the institutions that run our society. Politicians are telling us that there are easy and simple solutions to large and complex problems. Politicians are pandering to this simplistic nonsense to gain power. It is reminiscent of the rise of fascism in the early 19th century and is terrifying.”

When I came across that, I was researching an interview with someone who founded a book discovery platform, and it was bracing. I was very glad actually, to see that there was this motivation behind it.

Just as an exercise, I mean, you brought up, you’ll use Wikipedia’s labeling and search and stuff like that, as a part of your platform. But I actually, I’ll do it again now, but I did it last night, if you go to Wikipedia and you search for “Ben Fox,” you find the footballer, and then you can find links to soccer and soccer teams, and stuff like that, right? But if I go on YouTube, and I just put in “Ben Fox,” just a few scrolls of the mouse down, and it’s -

Ben: I changed my name too.

Len: Oh.

Ben: I mean, last year. Because when I got married, my wife and I picked a new last name.

Len: Oh did you? Okay.

Ben: Yeah. My name used to be really unique. It was Ben Welch-Bolen, and with a hyphen.

Len: Okay.

Ben: My parents eventually didn’t get along, which maybe that was a sign, and they got a divorce. It was Welch-Bolen. But yeah, my wife and I picked a new last name for after we got married. Because we wanted to have the same one, and for some reason we didn’t take my wife’s, because her dad was a little weird about it.

Len: That would explain why it was a little bit more difficult for me to do my research than it is for most interviews.

Ben: Yeah.

Len: But I guess I’m just bringing it up, because, if I search for “Ben Fox” on YouTube, a few scrolls with the mouse, and it’s like Ben Shapiro and Jordan Peterson, and Alex Jones even.

Like, I just searched for someone’s name. It’s obvious that what I’m being shown, is not being shown based on any like smart analysis of my search. It’s because that platform wants to show me that content.

Ben: It’s engaging.

Len: It’s engaging. I actually don’t know exactly how to get into talking about this, but it’s hard to talk about, because this experience is so pervasive. But one thing that I love about, say, Wikipedia, is that Wikipedia’s there for you to find what you’re looking for. Even though you’re not quite sure what you might be looking for yet. But there’s a very common and very popular and successful form of content discovery, which is just, you’re basically on a rollercoaster. You’re like, “Take me somewhere.” People seem to really be okay with being taken anywhere.

I just wanted to ask in general, what are your thoughts about that? Why is that, for example, so popular with so many people? To just be kind of - I don’t mean this in a condescending way. Do people love being led around? Why is that?

Ben: I think about it a lot as well. I think there’s a difference between pull and push. That’s some marketing terms for how it’s done. Each one has a certain type of power. But I honestly think that people are so stressed out and exhausted, that when they’re on the couch, and they want a dopamine hit or whatever else, it’s so easy to pull out TikTok or YouTube, and go into that bubble. Those companies are not paid to challenge you, they’re paid to put you in a nice warm room with your perfect pillows and other things. They don’t want to cause you discomfort, where you break off from the ad revenue and the other bit.

It’s very hard, because there’s a lot of things broken in the US. There’s a lot of things broken globally in a lot of countries, in terms of just life. I’m trying to figure that out.

But I think when you are stressed, you’re much more susceptible to those type of things. Especially - I don’t think our brains are good at handling these big problems and these big threats, especially when media does amplify them. I don’t think that anything’s really changed for media. But I think, some people, it’s very hard to ignore these big threats they can’t do anything about. They turn to comfort areas, and simple answers. It’s not working. It’s not working well for society and people, I think.

Len: It’s interesting, one of the things I think you write about as well is that the form of the book is something one could be optimistic about when it comes to facing these challenges, right? Because, I mean, there’s all kinds of terrible books that have been written, that we’re all familiar with. But at least the book presents one with the idea that difficult things need to be engaged with at length, and that doing a lot of work to address them is important.

Ben: Yeah. I even think, if you’re reading a, even a science fiction book or something, it’s about putting you in somebody else’s life, from different perspectives. I think that’s so valuable. Because I think over time, it helps rewire your brain to recognize that, in different ways - it just responds in different ways. I mean, if you’re reading sci-fi books about aliens and relations between aliens and people, I have to think that that also helps you understand racism or different discrimination going on, and recognize that in a different way. Because you’ve seen it in a book, and you’ve been put in that person’s place.

Even with fiction, I just think it’s so powerful. There’s obviously more practical examples of nonfiction - of somebody reading about what it’s like to be an immigrant, to be an illegal immigrant. I think that you can still disagree and want different solutions, but at least you’re more empathetic to the challenges of that person.

I think a lot of those things help to soften the debate. It’s so much easier just to fear people and that kind of thing. I do think a book is very powerful, as long as it is written with authenticity, and not darker motivations. Because there are, of course, as you know, books that go the wrong path, because they’re written to scare people. Or to announce what they’re going to do exactly.

Len: It’s interesting you brought that up. I guess this isn’t going to be the podcast of easy questions either, sorry about that.

Ben: Yeah.

Len: But you bringing up motivation is very important, actually. Because it has to do - I mean, if you’re hosting content, you do have to think about the motivation behind the content that people are producing, right?

I was listening to a podcast that you did, I think not too long ago, where you talked about a very specific example. Not that you’ve necessarily had to engage with this specific one on Shepherd. But if someone were to do a writeup of Mein Kampf, because they’re like, “This is a very important book to read, to understand World War II,” that’s one thing. If they’re like, “Because I’m a believer,” that’s another thing.

Ben: Yeah.

Len: So, what’s your approach at Shepherd? Just generally speaking to that problem, that basically all sites have?

Ben: It’s hard, it’s super hard. Because the line is not clearly defined. So, the first thing we look at is motivation, and where somebody’s coming from. I think the example I often get is, if somebody’s writing in positivity about white supremacy, that is not going on the site, of course. But if it’s a professor who studies it, and they want to include a book from the head of the KKK, and their explanation is about “understanding where this person is coming from, this is worth a read” - because we do have some of those type of takes on the site. That’s something we look at, a case-by-case, and we’re going to put it out there. There’s some debates that are not -

There’s some things that I will say, “As a society, these are not acceptable.” White nationalism. There’s some things like that, that I won’t get into. But we want to make sure people are coming from the right place. Who gets to speak to abortion-type things? This is a very sticky one. We want to make sure that, “Okay, who can speak to this?” Well, somebody who has had an abortion, they can probably speak to it. A professor who studies the legal and history of abortions, they can speak to it. If it’s a religious leader, a male religious leader, probably not, if they have like a real motive around it. Whereas, if they’re trying to come at it from a religious point of view, that might be allowed if it’s, “Understand what these books actually say about it.” It’s very hard sometimes to discern what we’re going to put.

Len: I wanted to bring it up, because it is such a very difficult challenge. Finding people who are willing to talk about it openly, is not the easiest thing. But, for example, one can - and, again, motivation, analysis of motivation comes in. For example, if someone is writing about theology, books about theology, for example, that’s very different from actually promoting a theology, trying to convert people, right?

By the way, there are places for that. But not every place is for everything. When you publish stuff, you do have to decide where you’re going to be. One thing that’s particularly tricky, is that, just the nature of language is ever-shifting, right? A word that’s benign one day, can become very coded the next.

So, you can imagine, well, for example, just to pick a very specific thing to our moment, the name “Brandon.” All of a sudden it’s loaded with all this significance. You have to start watching for that. And, so, words that are okay one day, might be something you have to think about the next day, because it’s just shifting. And that’s the reason that you can’t actually have straight and final rules about what’s acceptable, and what’s not. Because there’s no such thing as like a kind of - language just is an - words are arbitrary signifiers. What their content is, is up to people’s actions. That can change every day.

Ben: I actually had one a few days ago, where an author used the - somebody making a recommendation used the word “retarded,” and that is something we check now. Because society is moving away from that. We had to look at it. In that case, it was allowed, because it was a quote from the book, which was addressing the issue and using it the correct way. Because they were addressing the issue, and it was done in a great way. But, yeah, we do watch out for those things, and it is a very hard line.

There’s some things I do that are easy, like I do not allow people or books on the site that advocate against democracy. I take a very hard line that democracy is the best form of government we have, because people have a say, and there’s obviously better-run democracies than others. But that’s one. We have some that we take a very hard stance on. But, yeah, it’s a very difficult time right now.

Len: It’s really difficult. For anyone who hasn’t seen it, there’s a great Spike Lee movie called Bamboozled, which addresses the problem of like - this isn’t exactly what Bamboozled does, but it talks about blackface minstrelsy, and stuff like that. The way these images exist and persist in American culture. But, basically, you could have a very scholarly book analyzing racist jokes, right, from an anti-racist perspective. But for the racist person, now they’ve got a book of racist jokes. For some things, there’s really just no way around a paradox that just needs to be engaged with as transparently as you can, when it comes to the challenges of being any publishing platform.

Maybe on a bit of a lighter note, when it comes to book discovery, you brought up science fiction, and stuff like that. Often, we’re sometimes reading to be sort of - we have things brought to our attention, that we otherwise wouldn’t pay attention to, and that’s good. Sometimes we’re just reading for fun and for entertainment, and for pleasure, which is great. You’ve talked about how, just to bring up the truly controversial point, you don’t like the Lord Of The Rings books.

Ben: Get it out there.

Len: Which has actually come up on the podcast before. I’m not as much of a strong believer in this as my brother, but his claim is that they’re just badly written, so -

Ben: Yes, and it’s mine, yeah.

Len: I think you said, “It’s like reading an encyclopedia,” or something like that. But I mean, I would say that, yeah, I mean, I’ve got to say, to just throw the controversy around, I feel that way about most science fiction.

Just pick the big names, and I just can’t read more than a page. It’s just bad writing, often.

Ben: Have you done The Expanse?

Len: No I haven’t done “The Expanse.”

Ben: Okay - I, every year I do a present for my family, and I got my wife to read book one of The Expanse and she did like it, and she is not somebody who would touch science fiction with a ten foot pole.

Len: Okay, okay.

Ben: I think we might have a good list on the site, which is “Science fiction books for people that hate science fiction.” I’m pretty sure we had an author do one that was quite nice that way.

Len: I mean, this is getting to the heart of it, but like, about how difficult it is - but I want to ask you about your approach to helping people find the books that they want to read next, which is so interesting.

I love science fiction, it’s science fiction writing, that I often find is terrible.

But like, for example, if someone like me were to go to Shepherd, and look up science fiction, what do you do so far, I know you’ve got plans for what to do in the future. But what do you do so far, that would help me find something new, that is also something I would probably like?

Ben: That’s a good question. Right now, we don’t even know if books are fiction or non-fiction. When I started the site, we started with manually setting up each book. We set it up with a book title, ISBN codes, author information, author relationship and book cover image. We were doing it all manually. Because we looked at APIs, and they were just horrible, they would’ve required a lot more work for us at the time. We decided, this is partially some of the marketing reasons, but we wanted to get the list out first, start engaging authors. Get that piece in place, because that is going to feed all the other pages.

The next thing we launched after that was the topic pages, that are based around Wikipedia topics. Because we get a lot of people that are used to looking for books by genre. They come to our site, and they look for science fiction, and nothing is there about science fiction. If they search - I think that there might be a few broken topics we haven’t banned yet around science fiction. That is really what we’re building, as we move towards winter.

Right now, we are shipping an entirely new recommendation engine, that’s quite good. Right now, if you were looking for books you like, I would go to the site, and you can look for one of your favorite authors. You can look for one of your favorite books, or you can look for a topic that you are interested in. This can be galactic empire, this can be space warfare, it can be NASA. Anything you can think of, pretty much. When you search for those, we don’t do a search traditionally, it’s really about exploring. What we return, is we recommend five book lists by authors, and we recommend bookshelves.

If you go to a bookshelf, it’s the same thing, where you can see what interests you, and what calls you. You might see a book that sounds interesting, and below it you see that it’s a list that sounds very interesting to you. That’s how we currently have it.

We are moving towards adding genre pages towards the winter, and age-specific pages towards winter. We’ll add filters as well. This is all the base step I want. Because I want to be able to go to the World War II topic page, and, “Show me all World War II historical fiction.” But I don’t want to leave spaces. Or science fiction, “Show me all science fiction that has to do with artificial intelligence.” Or other combinations like that, or “For age nine,” or for “YA,” or, “For middle schoolers.”

This is really the most basic step we can take on the exploration. It’s something I’ve been wanting for years. I don’t understand why Goodreads doesn’t want it. Because I want to be able to go to Goodreads and say, “Show me all science fiction books in -“ or, “Military science fiction, that are rated 3.5 or above, and were published in the last two years.” Things like that are just not possible, and I don’t understand why. I’m going to quickly find out. But that is the first step we’re taking at the end of this year. Then we’re going to slowly start moving into more unique approaches.

I should note, the thing we’re going to ship between those two things, is a “books like” page. That’s pretty common right now. But the reason we are much different, is the heart of our recommendations are human beings. Not algorithms, not ads, anything like that.

One of the awesome things we get from authors, is they give us a human grouping of books. Humans are so diverse on how they think about things. What we’re getting is, if somebody liked Dune, they probably liked it for wildly different reasons. I think we have probably ten book lists that pick Dune. But they also pick a lot of other books that they have sorted in some way around a topic, theme or mood with Dune.

Our upcoming “books like,” and a lot of our recommendations - we actually shipped a new section this last week. That’s all driven by human recommendations. Then, it’s going to get better, because it also is driven by topics.

Then this winter, we’ll also add a filter over the top for genre and age group. Not only can you see, “Okay, humans recommended these books with Dune, but what sci-fi books do they recommend, or other books?” It’s a long spiel, but that’s where we’re working towards. It’s human recommendations that are the heart of everything, and then sprawling out to provide more discovery points.

Len: That’s a really great explanation. I’m just looking at an example right now. If you look up like “watercolor” on the site, you’ll go to shepherd.com, put in a term, then you’ll see a bunch of really nicely-presented books, and then a explanation of a book, and why someone picked it. But then you click onto that, there’s a link. Then you go to the author’s page, right? They all look great. At the top is a “Who am I?,” and then the author’s book. Then there’s their list. It’s all just so thoughtful, and it’s clear that there’s a person behind it, with all the richness and complexity that comes from being a person and having preferences, and the choices that they’ve made.

It’s just completely different from a like, the experience of like I was saying, the sort of, I mean, to be pointed about it, the totally gross experience for me of YouTube. The kind of, I don’t know how to put it? It’s not like “gross,” it’s maybe “icky?” That’s a fine distinction. But that you get on Amazon, for example, where it’s like, “Why is this showing up in my search? Is it because someone paid for it to be there?” I mean, often there seems to be very little connection between what you type in, and what you see. But with Shepherd, the person explains, here’s who I am, and here’s why I picked what I picked.” It’s just so great. There’s the a sense that like it’s just people who genuinely care about books, writing about the books that they care about.

You mentioned, actually - so, Goodreads has come up a couple of times, and I wanted to talk about that, and maybe shift towards the next part of the interview, where we talk about the book publishing industry more generally.

For those listening who might not know, Goodreads is nominally a book discovery website, that I believe Amazon bought, oh, I don’t know? Quite a few years ago now, for quite a bit of money. Then, apparently, just left it to wither. People still use it, because people are desperate for community being built around books and book discovery and things like that, and this appears to be the main place to go, even though it appears to have been abandoned. Is that - I mean, and, again, this is getting into the weeds. But is that your view? Do you think that Amazon’s abandoned Goodreads?

Ben: No, I don’t think they’ve abandoned it. They have a ton of people working on it, from all I can tell. This is outside looking in.

Goodreads was awesome when it started. The founders are awesome. They did awesome work to create something to share their love of books.

When they sold to Amazon, what I think happened, and what I’ve heard on some podcasts that they’ve done, is, Amazon is an ecommerce company. Amazon can’t look at anything and not see ecommerce. It’s the same as a surgeon. If a surgeon knows you’re sick, the answer is to cut you open. So, Amazon has done some really great stuff to integrate Goodreads with the Kindle. Because that’s where they saw the power of, “Let’s get them on the Kindle platform.”

From my outside perspective, they are starting now to trim down Goodreads. They also ended a lot of programs that had some promise for helping authors.

I am just super frustrated. Because really the only thing I found that readers use Goodreads for, is tracking what books they’re reading, and even that’s gone by the wayside.

But that’s really it. I haven’t found a reader yet who is using it to find books. Occasionally they’ll get something, but it’s not actively been thought of that way, it’s a book-tracking website. The authors I talk to are not - they just find it utterly useless. They changed some of the pricing for book giveaways. They don’t really offer anything. Their ad platform that they were doing, doesn’t work. People deposit money in, and it just doesn’t spend it.

There’s a lot of things like that, that I don’t know what they’re doing. I mean, their LinkedIn says, I think they have 300 employees? They have been, this last year, doing some fixing to the design, and they’re cutting some features. Which also is frustrating people. Because they just killed off their API, which means a lot of people doing work to try to make cool book ideas, were suddenly in trouble. Because they had no access anymore.

There’s a lot of things like that, that I can only see on the outside, and guess at. As a reader, I just grew more and more frustrated that I couldn’t do power searches, or anything else to try to help me find stuff.

Len: I’m curious about that, about the API for Goodreads that they took away access to. Would people be using that to do research about like, what book to write next?

Ben: They could, but I mean, it’d be like software programmers who write a book, who are getting really savvy with it. Most authors are not super technical, I’ve found. I think it was a lot of people doing some cool little apps, to use the API to analyze what you’re reading, things like that.

Now, I think they might’ve not cut off people who are active. But it was also people doing a thesis. I saw one guy who was doing, I believe, his Master’s thesis, was analyzing what people were reading, and suddenly he’s in trouble, because he can’t finish it. There’s some things like that. But it was smaller sites for book discovery and other things they were trying to do around that ecosystem, and suddenly got pulled out.

Len: This is a bit of an out of nowhere question, but are you planning on doing anything like that for Shepherd down the line? Opening up the data, basically?

Ben: Well, and this is - how I would love to - but here’s the problem, is, we have manually created 25,000 book entries. It’s expensive. We have a couple of people doing part-time data entry. Other sites go a crowdsourcing approach, which I hoped to use. But we hit a point where we had to license data.

So, in April, we licensed data, so that we know where books - we can do fiction genres and other things, and we’re slowly integrating it in the platform. Because we licensed that data, we now have stipulations for of course who owns that data. We have a license to use this data. We are careful that it doesn’t mix into what we’re doing. But legally, that’s what prevents a lot of people from doing much. I think we will be able to do some, but that’s just one of the big problems.

I’ve talked to our API provider, for example, it’s Neilson, they’re fantastic. There’s a couple of others, Ingram, and so on. But Neilson’s great people. They love their work, and so on, but they’re selling that API for money. I’ve tried to talk to them about lowering the price and standardizing at a certain level, so that they can unleash programmers’ creativity. I don’t think they got that, because these are mostly big companies, and they’re just not used to that type of thinking. They want to keep the pricing private. They want to renegotiate every year, and all that fun stuff. It’s something I’m keeping an eye on. I would love to do it one day, I’m not sure legally how. Because we have licensed that data, and it’s not necessarily ours.

Len: That’s really interesting. Again, in the interests of getting into the weeds, so you’re running this company, and you said you have a couple of people doing part-time data entry. You must have developers as well? I know you’ve got at least one.

Ben: One part-time freelance developer. One part-time freelance designer. Then we have one full-time person who helps me with emails, and just all communication. One part-time editor, who is awesome, and does all the editing and formatting for the pages. We have one person who does the data entry, and we’re about to hire another.

Len: I imagine, like you, they’re people who are just distributed wherever they want to live?

Ben: All remote, yeah. The designer’s in Serbia, the developer’s in Berlin. The editor is in Spain. Then data groomers are in the Philippines, and Cathy who helps with emails, and she’s also in the Philippines.

Len: Speaking of email, a lot of the way you’ve built up your cast of authors, is by contacting them directly.

Ben: Yeah.

Len: I’m very curious, for anyone who’s sort of, I mean, there might be more people than we know listening, who’ve undertaken projects that involved cold emailing people to ask them to participate in new initiatives. What was your approach to that at the beginning, and how has it evolved? Like, emailing authors and asking them to provide you with book recommendations for your idea, that they may not have heard of Shepherd before?

Ben: Oh, yeah. I mean, I started and there was no website. There was just a mockup that I made with the designer about the core idea. Then I would email them, pitch the idea, and show them, or attach the mockup. They could take a look and see if they’d take part.

We had an amazing response rate. I will say, the first authors I responded, or I emailed, were the authors that I’ve read over the years. Because I have a blog, where I track all the books I read. I have, I think going back to 2011, a giant list of all the books I loved, a little note about them - or disliked, in some cases.

I started by emailing my favorite authors. Which is maybe not the way to do it. But I emailed them with this crazy idea. I started emailing in December of 2020, and I think I got a “yes” within a couple of days, and more, and so it was really gratifying. That’s how I did it in the early days. I reached out, I personalized everything. Because I knew their book. Because I can pretty much remember them all. I think that helped me to understand what they’re getting. But this is also a very easy thing to do. Because authors are in such pain, I think, in this industry, to really do any type of marketing or sales. It’s such a weird industry.

My offer - I get an amazing response rate. I mean, now that we’re proven. We have a case study up that at least can show them ratios on one thing, it was nonfiction, and we’re trying to get more out there. But at this point, it’s easier.

Then, I have a lot of operations and marketing experience, so I just had to scale that up. At first we just asked friends and family, “Who do you want to recommend books?” We still get some of those every so often. Readers reach out and say, “Hey, these five people, I want to know what this person thinks about this.”

Then eventually we started looking at Goodreads, and who was recommended there. We get a ton of referrals. Once authors are in the system and they like the process, and they liked how it turned out, they’re not only sharing it on social media, because we encourage that - they’re also telling their friends. That really helps us a lot.

Len: I’m curious if you know what proportion of the authors that have written reviews on Shepherd are self-published, or have engaged in self-publishing at some point in their career?

Ben: That I don’t know. Since we’re doing all manual data entry, we’re very careful about data points, so that’s not something I know. I know that there is a decent chunk, but there’s a lot that are traditional. But I couldn’t guess at this point, because the process is pretty systemized.

I did everything, in the early days, like every single piece was just me. I could tell you up to 600 authors. I would think the split was like 70% traditional, more established, 30% are probably self-published. But that line is getting so blurry, I think.

Len: That’s one thing I wanted to ask. I mean, it’s baked into your project that the line is blurry, right? Because what you’re not doing is writing to the publishers and saying, “Can you find some staff to give me write-ups, to contact the author?” and then arrange it that way, right? Which is actually the way something like this might have been done in the past. You might’ve got in touch with an author’s agent or their publisher. Then there would’ve been middlepersons between you and them. But in 2020, you just reach out directly to authors. Authors respond themselves. This is just the way that book marketing works now.

Ben: Of course, once we started, that’s exactly what we want to do. Because in order for these to be authentic, it has to be the author doing it, ultimately, anyway. We did eventually make contact with - publishers see what we’re doing. Especially some of the ones that are getting modern marketing. We do work with a ton of publicists. But it’s a very distinct group of - publicists get it, because that’s their job. They’re a joy to work with. Because they’re like, “Let’s get them out there, let’s get them with the books they should be comparing themselves to. Let’s make sure that they know what they’re doing.” Because we do have to walk authors through the process, because sometimes they don’t understand that what they’re doing is really honing in on their target readership.

Because they don’t even think about, “Who is my target reader?” A couple of publishers we work with are an absolute joy, because they want their authors to do these. Because it’s one more place that they can get sales from. It’s just another source in a wide array. They do a really good job of it.

Then, we’ve talked to publishers who don’t even want to publish in Kindle. They don’t want to do any ebooks. They just want paper. They don’t do marketing. That always blows my mind, because my background has been marketing for a very long time. But, yeah, sometimes they just don’t get it, when we have talked to them. Because we have gotten intros at high levels to certain publishers and so on, and they just don’t get it.

Len: You bring up something that’s pervasive in the book industry, but that is hard to talk about - is that people come at it from so many different directions. There might be some people for whom, it may seem strange when you come from a certain perspective, it’s like you’ve written something for other people, but you don’t want to try and reach them. Like why?

Ben: Yeah.

Len: Why is that? It’s like, well, because if you really care about something, having it attached to the aesthetic of promotion, you know what I mean? Can feel like it corrupts - to speak of intentions, it corrupts the sense of what the intention might be behind it. There is this tension with some book projects, or even entire book publishers, with achieving their mission and marketing.

Ben: Yeah. I talk to more authors, I do a lot of interviews, because this industry is so insane to me, that I was like, I have to figure out a little more of what’s going on, and understand the diversity. Because the authors are so diverse on where they’re coming from, and what this book means to them. I have a better handle on that. I have an author who wrote a historical fiction, that I ended up reading his book, because I was on a YouTube show.

I really liked the title, I liked the first chapter, and I couldn’t believe it, I read it, I couldn’t believe it’s not published yet. Couldn’t believe an agent hasn’t - it’s in an area of historical fiction that I read a ton in. I was blown away. It needed a little work, but not much, it’s fantastic. I talked to him, and I was like, “Well, why not self-publish this? I think this can make good money. It’s got a unique approach, it’s got a unique time period.” For him, I hear this more, I’m using him as a case study - for him, it was a lot about the time and the complexity, and having to learn all this stuff.

He has a full time job. He loves the act of writing. He doesn’t want to go learn formatting, and all this other stuff. He would like the prestige of going through one of those gatekeepers, because it is a seal of quality. He doesn’t want to have to go get a book cover that’s high-quality that hits the right notes, those things are just not part of what he wants to be doing.

I have learned a lot about how the different authors approach it, and that is helping me to understand, eventually, how we’re going to help different segments. But it has been really interesting over the last 15 months. I’ve interviewed a lot of authors, to try to get more info.

Len: It’s super interesting that, it is an insane industry, book publishing. As you put it, that seal of quality element to it, is one of the things that makes it so crazy. We haven’t had the moment - in the early nineties, there was this moment in both movies and music, at least in North American culture, where indie became the seal of quality, right? Getting a big label to back you - which everybody, most people secretly wanted it anyway - that was selling out.

Len: But this has not happened in the book publishing industry, for all kinds of complicated reasons. It’s one of the things that I reflect on. Because when you read - I found out about Shepherd from Jane Friedmans Hot Sheet newsletter. Which I read for the sake of my own sanity, because everything you read in the mainstream news media about book publishing, is crazy. It’s because the people who write about it seem to be guardians themselves of the publishing industry’s seal-of-quality magical power.

So, when you read about the book publishing industry, you’ll get, I mean, you talk about data and numbers. The numbers often just completely exclude self-publishing. Or they’ll completely exclude ebooks, or something like that. You’ll read like, oh, “Downturn in author earnings.” It’s like, not from Leanpub’s perspective. But they don’t ask us. That’s not a complaint, it’s just, we’re not one of the people viewed to be having the magic staff of, “I declare you sealed with quality now.”

It’s just super interesting that there’s - we brought up the the form of the book. We should probably be glad that there’s an element of this idea of an ideal of quality. It’s problematic, but sanctioned quality, behind the book.

Ben: Yeah. I think it gets back to the discovery problem. Because it was a gatekeeper, again, in the bookstores back in the day, before the internet. Now, you can find those books in online stores, which is fantastic. But yeah, I think it gets back to, how do you find those books? It’s becoming blurry, because, I mean, I had a writer I loved who was indie published. The book was amazing, I loved it. The second book was amazing.

Then he got a traditional deal. The books stayed pretty good, but then they started going down, because they switched to the schedule of where they’re publishing four books a year, or something like that.

I was so frustrated. Because he’s a great writer, but they also changed how he writes the books. The first ones were a little more denser, and there was like more heart in them. They’ve stripped that out a little bit. It’s a little too commercial now.

There was one thing that I noticed, where it went backwards. Because I knew him before he got his traditional market publishing deal.

I think about it a lot right now. Because there’s some publishing companies, that when I interact with them, I see how much they care about their books. I mean publishing companies, in the sense of anybody that’s helping an author get their product out, in a way that facilitates that author. Some of the publishers I talk to are an absolute joy. Because they’ve picked that book, because they love it. Those publishers are doing an amazing job, because usually they have a specific focus, and they just are passionate about it. They’re picking what they want to work with.

Then you meet some publishers that are purely commercial, and they’re looking purely from the money standpoint. It’s a much different interaction. Authors on the first one get along a lot better. Because I think that falls into a lot of the stuff you’re doing as well.

Len: That brings up the matter of push and pull, right? When recommendation engines are out there, and there’s a very commercially-minded publisher, they’re looking at what recommendation engines are working, and then they’ll decide what to publish next, and who to publish next, and how, what advice to give them, the authors, about what to write, will be based on those recommendation engines. You get this self-fulfilling prophecy.

But there does seem to be an element to these things, where like, they just, I don’t know what the right metaphor would be, but they end up eating themselves. You know what I mean? Like it’s sort of, there’s too much werewolf romance out there, at a certain point. Maybe “saturation” might be the right image, or something like that, right? Where too many people are chasing the same formula. Then something else just has to emerge.

Ben: That’s really eventually what I hope Shepherd is helping on, and that’s a big part of what I’m hoping to cover for authors. Right now, what I’m focused on, is getting authors 50 to 150 sales from people they don’t know. Because this is such a big challenge for a lot of people coming into it. It’s, how do you get in front of people who are willing to buy your book? Because I figure at around 50 to 150 sales, that gets them around fifteen reviews on Amazon, if they’re doing some things right. That starts the organic growth machine.

That’s our base pyramid that we’re doing right now. Then, we’re going to slowly start moving up. Because I want to give more of a meritocracy, so that - because I feel like we’re leaving generations of authors right now behind, the more I look at this industry. It’s either like a random lottery, and then there’s all these authors I think that are getting left behind. But I want to do this base, because you need that base to get in the game.

Then I want to find ways to help people from a cheap standpoint, get up to the thousands and tens of thousands, and maybe hundreds of thousands, as we grow. That’s really what’s occupying my mind. Is, “What are the ways that we can get people dependable, 50 to 150 sales a year, just to get them over that hump, with minimal work?” Then, “How do we recognize the books that have that magic spark, to zoom them up to thousands?” That’s what we will be working towards, yeah.

Len: Just to wrap up, for any readers out there interested in finding great books recommended by authors, you can go to shepherd.com. But for any authors out there who might be interested in joining the Shepherd community, where can they go?

Ben: They can go to forauthors.shepherd.com. There’s a link in the footer at shepherd.com. It has a big FAQ, and it talks about some of the other formats. Because we are going to - next year, early next year, and starting late this year, we’re going to do two new formats as well. We’ve got one which will be like online dating, but with book characters. We’re going to start collecting from authors a profile of their main character, or characters, if they so want. We’re going to try to find ways to help readers bump into those, based on other books/characters they like. If you like Jack Reacher, who else might you like? Instead of going into a book description, it’ll go into like a, I use this jokingly, but an online dating profile.

Then the other thing we’re doing is sharing interesting facts to meet books. The idea being that, if somebody is looking up “ant facts for kids,” then you wrote a book about ants for kids, and you have expertise, we want to show you off. Share five or six facts, and help give them a little nudge towards a book. Whether it be on ants, insects, like that. Those are two new formats we’re working on as well.

Len: That’s a super interesting idea of online dating for characters. You can like put in your profile for the character you might like to read about. Then swipe right, or swipe left, based on what you’re shown.

Ben: Yeah.

Len: That’s a super interesting and entertaining idea. Then discover books and entire fictional universes along the way.

Well, Ben, thank you very much for taking some time out of what I’m sure was a beautiful evening in Portugal, to talk to me, and to talk to our audience about shepherd.com.

Ben: Thank you so much for having me, that was a lot of fun.

Len: Thanks.

And as always, thanks to you for listening to this episode of the Frontmatter podcast. If you like what you heard, please rate and review it wherever you found it, and if you’d like to be a Leanpub author, please visit our website at leanpub.com.