Ben Clymer on Building Media & Commerce at Hodinkee

Jacob Cohen Donnelly: Can you talk about where the idea for Hodinkee came from? The genesis of that name and how you got started?

Benjamin Clymer: Sure. The genesis of Hodinkee is really completely organic. There was no idea for it. I had no idea what I wanted to do with my life to be totally frank. I grew up in upstate New York, I went to school for Business and Information Studies. I knew that I wanted to be in business of some kind, I didn’t think media was the answer, to be totally honest with you. I started my career after undergrad in New York in management consulting, and then finance at work at UBS. That was during the first financial crisis of my lifetime in 2008.

I saw the way that not only myself, but similar folks, and even those senior to me, were treated during that really strenuous time on the financial industry and it rubbed me the wrong way. At the time, I had a small blog going about watches called Hodinkee. That was inspired by a watch that my grandfather had given me. My maternal grandfather was an entrepreneur, not in the media world. He gave me his omega and that inspired me to start writing about it. I really wanted to learn about it and it was my little creative outlet. I started writing more and more, and then more people started coming to it.

When layoffs hit at UBS, I was perfectly happy to take a severance package and say, “You know what, I want to go do something completely differently.” I then started writing for a few other publications and ended up going back to journalism school. It was again, no business plan, then much to the chagrin of many of my investors. Still no business plan now, I’m proud to say, but it was one of those things where this was purely born out of passion. We’re an e-commerce player, as well as media for sure. That just came to us because we felt that our advertisers weren’t rightfully respecting, or dutifully respecting the power that we had with our audience.

In terms of where the name Hodinkee came from. Hodinky, with a Y on it, H-O-D-I-N-K-Y, actually means wristwatch in Czech of all things. It sounds silly to say now, but in 2008-2009, it was actually really common for people starting websites to add a double vowel to any name that they were creating for our website. Google would be the big one, of course, but look at what Gwyneth Paltrow did, Goop, the double O in the middle. Hodinkee was a spin-off of Google and Goop, I guess, back in the day, and it just worked.

It was one of those things where we don’t take ourselves too seriously and I think that’s why Hodinkee works. We’re talking about very expensive, often perceived to be pretentious things with a name like that. We people know that we don’t take ourselves all that seriously.

Jacob: Originally, Hodinkee, was just your blog for you to talk about watches. At what point did it make that pivot from Ben is writing about watches to Hodinkee as a watch publication for people?

Benjamin: Yes. When I got into graduate school for journalism, I realized I used Hodinkee as basically the foundation of my application to journalism school. Somehow got into a good one, and realized then that, “Hey, maybe there is something to it,” and around the same time, larger watch companies, very large for me, said, “Hey Ben. We love what you’re doing. Would it be possible to advertise alongside your content?” I said, “Sure. It’s completely passive income, why not?”

That happened probably around 2009-2010. Then when I graduated from journalism school in 2012, I hired my first one or two employees and really went off to the races, but it was still an advertising-based business. That started to change around late 2012.

Jacob: I want to talk a little bit more about those early days. It’s interesting, a lot of the people I’ve talked to started the project out on their own, and then just fell into this opportunity and then started hiring people. Thinking about those first two hires, what was the composition of the team, when it was just you and the two other people?

Benjamin: Yes, sure. The first two people I hired, I’m extremely proud to say are still with Hodinkee and still actually now in very senior roles in the company. The first was named Stephen Pulvirent. We hired him effectively right out of grad school. A young guy that was doing some freelance work for a few luxury publications as well as Businessweek. He was a mini-me. He was an editor, a photographer, a one-man show that could do just about anything. He could host events, still can, eventually get into video work and not on the production side, but on the talent side. He was tasked with basically everything that I was tasked with which at the time was literally everything.

Then Will, I had met at a journalism school. I remember I had this idea of doing video and I had done quite a bit of video before I met Will. On my own when I was shooting myself and I would cut it in iMovie, or some such program, and then I met him at journalism school, and he was in one of my digital media classes. I was like, “Wow, this guy is just way better at video production than I am” Certainly he would give it more time than I would.

I actually asked him to edit something that I had shot for the site. I think I paid him $100 or something like that and he did an amazing job. I said, “Hey, let’s take this a little bit more seriously.” My second hire ever was a full-time videographer and photographer, of course, but I would say video was his specialty and certainly what allowed us to jumpstart into the mainstream is with our video work. It was myself who was a photographer, writer, editor, et cetera, and then Stephen who was effectively the same thing, and then Will who was really purely a videographer and photographer.

Jacob: I want to pivot and talk a little bit about the business, because there are quite a few lines of business. We’ll talk about e-commerce in a second but I want to start with a simpler one, which is the media business. You said that early on, advertisers started coming to you asking to advertise around the content, which makes perfect sense, it’s a contextual ad play. Today, what are the products that you offer to advertisers and what is the audience story that you sell them on it?

Benjamin: Sure. The audience is the thing that I’m the most proud of. Our audience is me, is you, is somebody that is educated, that is thoughtful about their purchases, that in many cases actually want to pay more for something with a great story. They care about the craft, not the cost, but they are capable of paying the price when they want to. Our demographic, and psychographic are really very, very important that our brand and that is a young, intelligent, affluent, thoughtful person that, again, is interested in things. I think we’ve been able to validate that many times over, which is why we actually launched e-commerce.

Our products right now range from everything from basic display ads on the site and app and et cetera to print publication. We still get an amazing value for our print advertisers relative to what else is out there. We have two podcasts that we sell ads against, and we do a significant portion of our business now in native advertising, which is Brand X says, “Hey, this is what we want to promote. How would you tell that story?”

Effectively what we’re doing is taking a story that we would love to produce, and giving it the time, money resources that we simply just don’t have. We couldn’t afford to give everybody the time of day that we do with the sponsor packages or the native packages, simply out of a resource strain concern. Brand X says, “Hey, we want to do something awesome with this watch up in the mountains of Montreal,” or something like that. “Let’s do it.” Then they basically allow us to style it and craft it and then also develop special landing pages with it. Native advertising is definitely a bigger thing for us over the past few years.

Jacob: Why did you decide to launch a print publication?

Benjamin: Yes, that’s a great question. Here’s the thing, I’m slightly older than maybe some of your listeners, and certainly some of my listeners and readers, and that I really love and hold in high regard traditional media and print media. The GQs, the Vogues, the Esquires were the stalwarts and still are the stalwarts of traditional opulent media. We always wanted to do it, Stephen and I, from the earliest conversations his first day, I bet we probably talked about it. We wanted to do it the Hodinkee way, which is finding a wonderful printer in Canada, that’s carbon neutral, and also has the best stock of paper you could possibly imagine.

Then we also wanted to give it the right creative services, et cetera. It just took us a long time to get to a point where we thought we had the bandwidth to do it but more than that, we wanted to do something that would act as a prestige funnel into our world, that would get people that was slightly different than who would come to our site on the internet. Hodinkee online is watches, it is pure watches all day every day, and that’s great, and the majority of our audience loves that. We also have the interest and ability to tell stories about watches, about art, architecture, design, style, fashion, you name it.

The magazine is actually far more wide in what we cover and with that we’ve been able to get distribution through American Express Centurion lounges in all their lounges around the world back when people used airplanes. It’s in Soho houses, is in several hotels, very high-end hotels around the world. It’s in FBOs, that’s your private jet terminals. It has really become an interesting way to get people into our brand in a very organic way. They’ll pick up the magazine at a private jet terminal or wherever and say, “Oh, what is this thing? It’s beautiful.” Then they’ve discovered that there’s this whole other world that lives online from there.

The other thing I’ll say is we’ve been able to crack advertisers in print that we were not able to crack online. We’re dealing with a hyper-conservative, in many cases, really backwards thinking industry. We said, “Hey look, if they don’t believe in the internet that’s fine. We’ll give them a program. We’ll give them a package that they do believe in.” Crazily enough, they actually do still believe in print. Especially print that is beautiful and print that speaks to exactly their audience.

I think beyond that, we often do things that reward us in certain ways. Hodinkee, as I’ve said, was really an outlet for me. The idea was never to really serve a community in the beginning, it was to give me the opportunity to be creative and produce something. I think the magazine is just another example of that, where we wanted to flex certain muscle that we don’t get to use all that often in the online world. It’s been a lot of fun to produce, for sure.

Jacob: Now, the major part of the business is the e-commerce business. You are one of the few, online entities that has direct relationships with some of these luxury watch brands. How did that happen? Because from my understanding of the watch world, and you’ve alluded to it, they are very resistant to selling watches online. You figured out how to convince them to do that. How did you do that?

Benjamin: I’ll start from the beginning. The first thing I’ll say is one of the very first conversations I had with a very, very senior, he was French, luxury executive, and some reason– This is when I was in journalism school, a publicist said, “Hey so and so, you should meet this guy. He’s online. He’s a blogger”. His response was, “Oh, very nice to meet you. I think the internet is for poor people.” That was said to my face. This was no more than 11 years ago, probably 2009 or so.

That’s the foundation with which we’re working. We’re working with a foundation that is just so ridiculously, really prejudiced, against online and again, digital. It’s always been that way and things have been getting better since, of course. Basically, how we convinced these folks to go online was by playing the straight and narrow. By saying, “Hey, we are going to do things at the highest quality. Yes, we happen the be online but our content, our video, our photography, our everything is going to be so much better than anything else you see, print or digital, around the globe, that you will be forced to hold us in high regard.

Then that led us to working with well-known people like JayZ and John Mayer and well-known folks in the watch world. That certainly helped. It allowed us to grab the attention of the GQs and the Esquires and Vogues and Vanity Fairs of the world. Those guys were nice by covering us. New York Times wrote about us significantly in the early days. Then, we were on the jury of the Grand Prix of watchmaking, which is like the Oscars of watchmaking.

All these barriers that existed to, not only Americans but also digital players, were broken by us first, in most cases. That allowed us to say, “Look, we’re going to do this, but we’re going to do this the right way.” I think that is what the Swiss and European luxury really cares about most. It took a long time, but going back to this idea that– We had this incredible audience, this wild, shockingly engaged audience. I would get emails from people saying, “Hey, this article that you wrote about this Patek Philippe”, which is a very expensive watch, “caused me to spend $200,000 on this thing.” I said, “Wow, that’s amazing.”

I would show these marketing folks that the brand said, “Hey, this guy spent $200,000 because of our story.” Instead of saying, “Hey, here’s $100,000 in advertising dollars,” they would either say, “Thank you very much” or “That’s great, here’s $5,000” or something like that, “for the next year in advertising.” Just as a way to placate us.

I was like, that just doesn’t seem right. We are truly turning people on to their products, at scale. By this point, it was at scale. We’ll see 1,000,000 people a month or something. It just felt unfair to me. I said, “Look, if you don’t feel like our audience is transactional, let us put our money where our mouth is. We will buy some product from you. We will design a product and we will sell it only online, which is kind of shocking to people back then.

We did that. We did Limited Edition watches for the first few years. They would sell out often, within minutes, sometimes maybe an hour or two. We’ve made a few million dollars within 20 minutes, with certain products. People were just forced to take notice and said, “Wait a minute, these guys are really doing things a different way. They’re doing it online.” With that came some prominent investors in 2015, then some prominent employees a little bit later. Then, we went off to the races.

Jacob: I guess, a few follow-up questions on that. The first is, when you started originally, you did not intend for this to be an e-commerce play?

Benjamin: Correct, and then it’s so funny. There’s actually a story or an interview, rather, from Reuters in, probably, 2015 and I say verbatim, “We will never sell watches online.” I said that, expressly. It may have been actually much earlier than 2015, maybe ’12 or ’13. Probably when I was in journalism school. That sounds like something I would say when I was in journalism school. What’s funny is, that’s, obviously, no longer the case. We’ve in fact reversed that completely. The gentleman that actually wrote that story for Rueters now works for us.

Coming full circle, it’s one of those things where you have to be adaptive. You have to be willing to change your opinion based on new inputs. In 2012-2013, there was this idea that media was going to come back, it was just going to be online. Then as time went on, it just said, “Wait a minute. Even online media might be a race to the bottom. Who wants to pay for banner ads anymore?”

It’s just one of those things where it’s so difficult to be held accountable for the statements you make. In situ, they make a lot of sense. Had I known what was going to happen to the world, the media world, the digital world, the e-comm world in the years to come, I never would have said that, for sure. Yes, there was no intent at all to an e-commerce player. In the early days, we did start selling straps like leather goods and small accessories in 2012. That really validated this idea that our audience was more than engaged. They were transactional. They really wanted to spend with us.

Jacob: Going from being just a media company to now being an e-commerce company, what had to change about the structure of the business, both from a technical perspective, but as well as a staffing perspective?

Benjamin: Look, we’re still going through those changes right now. I think we will be for some time. We are, from a legacy perspective, a media company. Such a good chunk of our team is based on the media side, ad sell site, video site, et cetera but as you’ve alluded, a good, good chunk, more than half of the revenue comes from the commerce side. What we’ve had to do is rethink the way that we hire, rethink the way we prioritize things. We were able to bring over a man that I’ve truly admired for the longest time, and it’s Russell Kelly. He was actually the president of a watch brand that we work with very closely, here in the United States. Worked for Rolex, really just a star all-around.

We brought him in as our Chief Commercial Officer, and this is what he does. He knows how to sell watches. He knows how the industry works, frankly, in a way that I don’t. We gave him the authority to really build out his team in a meaningful way. That will only expand with time. Bringing in somebody that has experience in that space was a game changer for us, no question about it.

Jacob: Correct me if I’m wrong, but you also create unique co-branded watches. How does that work.

Benjamin: Sure. That was actually how we first got our start, because we wanted to say, “Hey, our audience is different from everybody else’s. Our products that we want for our audience are also different than everything else.” We got out and we take the DNA or the heritage that already exist within any great brand, take Omega for example or Vashron, yes, these high-end watch brands, and we put our own little twist on it. We say, “Hey, let’s call this a Hodinkee Limited Edition. Let’s make 500 of them. We’ll take 300, you take 200. We’ll sell them online. Then we do it. We’ve done this very successfully for a long time.

It’s a little bit like, if you’re familiar with Supreme, the streetwear company, or Kiff which is another streetwear company, they’ll do Supreme X Louis Vuitton or whoever. It’s the idea that there’s this special conjoining of two distinct brands, and they put their own spin on these legacy products. Those have been wonderful brand-building moments. We’ve worked with everyone from Hermes, arguably the most prestigious luxury house in the world, with Leica cameras. Again, a very, very high-end German-made, handmade camera, to Omega the watch company.

We do this, and it’s a wonderful way to extend our brand, get new people, get people talking about what we’re doing and also show just how meaningful Hodinkee has become to this space. I really think– This is not just me saying this, somebody has said this about us. I really think in many ways that we represent the future of what a brand could be and what a media property could be in that we’re much more than just journalists. We have journalists, I think the best in the world in our space, but I think beyond that, we are our own brand. We are creating something that is much more than commentary on product. We are actually shaping product.

Jacob: Are the economics better on these co-branded watches, versus just like selling an Omega or a Breitling?

Benjamin: The economics are not better, to be totally honest with you. The economics are sometimes even worse. We get involved with these products as much as possible and in many cases we say, “Hey, we want this to feel great for our audience.” If the brand wants the product to be “X,” we want it to be “X,” minus 20%. We really push to get these numbers down.

In many cases the brand says, “Hey, if you want to sell it for “X” minus 20%, that 20% is coming from your side, not ours.” In many cases, we’ll just say, “Okay, fine. We’d rather do something that is meaningful and great, than slightly overpriced. The economics are not better, but they are quicker. I can tell you that, these limited editions sell out in, I think the longest one is ever taken, which was a very, very high-end chronograph. I think it took four or five days, something like that. The majority of them go within, I’d say three hours, four hours at most. These are just amazing little revenue bursts every time we do them.

Jacob: That’s remarkable. I’ve not done commerce, but I’ve done events and when the day a ticket price is supposed to increase, suddenly you see a burst in people buying tickets and it’s a dopamine hit. I’ll be honest.

Benjamin: Yes, I mean, off the record or not, we sold 500 Omegas in 19 minutes for $3.4 million. We had like the Shopify screen up on our TV in the office, and just to see it go from zero to $3.5 million in 20 minutes is just wild. These things are flying all over the world. It was really a neat experience.

Jacob: Moving away from the e-commerce part, but still you selling something, you’ve recently launched insurance as a product. What made you move into this industry and how does Hodinkee make money on this?

Benjamin: Sure, yes. Our insurance product is something I’m actually super proud of. It’s something that I believed in for a long time. We actually worked on the product with Chubb who’s a world-class insurer for many years. I mean, truly like over two and a half years. What we do with Hodinkee is we try to solve problems that exist.

I’m a watch collector, which should not come as a surprise. Ensuring your watches, no matter where you live, is a freaking pain in the ass, man. I mean, it really is annoying. You have to put it on a home insurance, a homeowner’s policy, or a renter’s insurance policy, you have to call the agent. It’s really very convoluted and also just not fun at all. If you’re really into watches, you’re probably active.

You might take, you’re wearing one at a time. There are some people that wear two, but that’s another story. They’re wearing one at a time, and so you don’t need to be paying for insurance for things that are sitting in your safe or in the bank vault or whatever. We wanted to create something that was incredibly user-friendly, that was dynamic so that you could change your policy from your iPhone. We wanted to build something that was really crafted for our audience, which is younger.

Chubb as many of you may or may not know, is really a very premium service. The average, I’m sorry, the starting point for a Chubb policy before Hodinkee for wristwatches was $10,000. Not a premium of 10,000, but underwriting. We said, “Hey, we want to get these guys into your service young.” We said, “Instead of a $10,000 minimum, let’s do a $1,000 minimum, which means you’re basically paying $50 a year or less.” On top of that, we want to integrate this completely with the Hodinkee app, which is fairly robust.

We also want to integrate it into something called the Hodinkee Community, which is a digital platform that we built three years ago that allows people to comment and create conversations and profiles and collections. You can say, my name is Ben, he’s got 10 watches, they’re X, Y, and Z. From there, insurance is integrated perfectly. People have been able to store their watches for a little while, and now they can have them insured instantly. On top of that, you can take a picture of your watch from your phone and share it in under 30 seconds. If you sell a watch to your friend, you can remove it from your policy instantly from your phone.

It’s super dynamic. It is an amazing app. Truly something I’m so proud of, and with it, we’re more than an insurance broker. We created this policy with Chubb, it’s something of a JV, and we go out and we said, “Hey we’re going to basically be your sales agent and get people in our community in, and then Chubb takes over.” These are Chubb clients now via us. Basically, there’s a revenue split there. Chubb frankly makes the majority of it, as they should. I mean, they’re taking on all the risk. It’s a great recurring revenue stream for us and also it solves a problem, and I think that’s what I really feel Hodinkee is best at in this space. We are not for everyone, for sure, but in the watch world, we think we can be for everyone there. We can be a one-stop shop for new authorized watches on our shop side, vintage watches, accessories, and also demand creation on the media side as well as insurance.

Jacob: Moving to your audience as one of the premium communities dedicated to the watch market, how do you and the team think about audience development and introducing new people, either newbies or watch experts to the Hodinkee ecosystem?

Benjamin: Sure. I think that’s a great question. I mean, the way that we do it is we don’t try to suck people in. We try to make them believe that they’re coming there on their own, which they are. We do these videos called Talking Watches, which is either myself or Steven or one of our editors with a well-known person. That might be John Mayer, it might be a Zee Zon Sori, or a professional athlete or whoever.

Those videos we just put up on our site and we put up on YouTube, and most of them do exceptionally well. I mean some of them are in the millions of views, and what it does, it says, “Hey I’m a quiet guy from upstate New York, I love this stuff, but I don’t really like– Is it okay to be interested in these material things? Are people going to judge me for this?”

That’s everyone’s self-doubt about this. Then you see a video with somebody like a John Mayer who’s just a cool guy that is hyper-successful, that likes this stuff for the right reasons, and it validates. It says, “Hey, wait a minute, it is okay to be into this stuff for the right reasons.” Again, this is the cost versus craft kind of thing.

We create these videos, nothing is sponsored, nothing is paid for. We don’t pay them, they don’t pay us the talent. We just do these things with people that love watches and that encourages a lot of young people to get into the space themselves. Then we know that they’llbegin to start reading Hodinkee after those videos and going on from there. Again, we often do– Those are our best examples.

Some of the more easy ones that we do are let’s say I don’t know, Tiger Woods win the Masters or something like that. Tiger Woods is a paid Rolex ambassador, so he legally has to wear Rolex when he wins a professional event. Nobody knows about that, and frankly, nobody cares. Let’s say Tiger Woods wins the Masters next month, if he wins, we’re going to say, watch spotting. Tiger Woods seen wearing Rolex so-and-so at the Masters, and people will absolutely love it.

People will say, I guarantee you, they’re going to see Tiger on TV and they’re going to Google exactly what watch he’s wearing. I think that is one of those things that, our core audience rolls their eyes at, but is an amazingly effective way to get people into our audience and into our brand.

Jacob: I want to expand on the Hodinkee community, and you said you made that big investment a few years ago. One of the products, like you said was the collections feature where users keep track of all the watches that they own. How have these various community features helped you cement deeper relationships with the audience? Also, how does it help inform either editorial or new product decisions?

Benjamin: Yes, look, I mean, I think any real relationship, whether it’s with a man, a woman, a friend, an employer, an employee like it’s got to go both ways. I think one of those things we’re like, we feel that we don’t exist without our audience. They buy things from us, we sell ads against them, et cetera. We need to pay them back with something. What we do is we give them tools, we give them opportunities to purchase things that others don’t have. We give them access to information others don’t have. The way that we view it it’s a trade-off. We give them this, they give us that. The idea that people can track their collections on our platform, like that is a tool that people want. That’s a tool that I would want if I were just a collector in the community. I think insurance is another example of that but we really feel that everything we do should equally serve them as much as it serves us.

Jacob: With everyone in media losing their minds over subscriptions, is there a paid component to the community that you could see in the future?

Benjamin: In the future? Look, our magazine is subscription, obviously, but that’s a slightly different thing. That just covers the hard cost. Right now, no, I think Hodinkee and watches, in general, are such a narrow, we’re a subset of a subset of a subset, you know what I mean? I think trying to limit it, even more, would be detrimental. Even though we have some very, very affluent, crazy affluent folks in our community it just doesn’t feel right. We want to keep this thing as open as possible.

I think there’s an opportunity to do hyper-premium content. What I mean by that is, like, for the person that’s about to put $500,000 into a watch at auction or pay for a watch at auction, do they want special information about said object before they bid? That I could see us doing. It wouldn’t be a true subscription model. It would say, Hey, it’s like it would be like a research subscription as opposed to a content subscription. In the foreseeable future, I don’t see subscriptions as something that I think makes a lot of sense for us when our goal is really to become a household name. We want to be synonymous with watches. For now, I think we’re going to head in the direction that we’re in.

Jacob: Media, business, commerce business, magazine, you offer insurance through a joint venture, premium community. That’s a lot to do when you started with three employees.

Benjamin: [chuckles] You’re telling me my friend.

Jacob: What does the team structure look like today?

Benjamin: I’m the CEO which may or may not make sense, we don’t really know. That was a joke kind of, but also I’m the CEO, we have a Chief Operating Officer who oversees everything that is not related to the shop. Then we have Russell, who I mentioned, the Chief Commercial Officer who oversees everything on the shop, and then several VPs and et cetera, beneath those two.

We are still heavy on the edit side, we will not be letting anybody go. We’ll simply be adding people that are slightly more in tune with commercial objectives. I think these people will be editors, they will be content creators. They might just understand that the future of this business as well is basically every other media business. The food, 52s of the world, the meat eaters, things like that is commerce. It just is. I think the structure I don’t think will change dramatically. I think it’ll happen over time where this will become more geared like a commercial play as opposed to an editorial.

Jacob: Let’s build on that a little bit. Over the next few years, where do you see Hodinkee going? To expand on that, could you see the company expanding into new luxury market or are you just going to continue going deeper and deeper with watches?

Benjamin: We’ve thought about that last question ad nauseum. We’ve been approached by one of the biggest wine collectors in the world and one of the biggest car collectors in the world. To do the same thing for those verticals, and look, we’ve given it thought, we have this– Once you succeed at one thing, you think it’s very easy to do it again. I think we’re smart in that we know that that’s not necessarily the case.

We also have a wonderful stranglehold on the watch world. We are the outlet for watches right now. This is a massive market, a massive, massive market. We’re talking billion, probably $20 billion a year in watches go out the door if not more. We’re still a very small company. I think there’s a long way to go in a vertical where we have a massive amount of influence. For the foreseeable future, I can say without a doubt, we will stay to watches. That’s not to say we won’t cover other things. We might expand upon the base of what we’re writing about, even online. What we sell in our core business will remain watches for sure.

Jacob: I own a decent number of watches. I don’t think anything that is quite as luxurious as an Omega or a Rolex, but–

Benjamin: You’re better off that way. Trust me.

Jacob: [laughs] But I never wear them because it’s A, quarantine, but B, they always get in the way when I’m typing and I type a lot. You obviously love watches. What is your favorite watch and what’s the story behind it?

Benjamin: My favorite watch as I mentioned really briefly in the beginning of this conversation is the Omega that my maternal grandfather gave me when I was 16 years old. It’s one of those things where you never really can understand how meaningful the slightest bit of kindness or gesture could be. My grandfather, when I was 16, who was my hero, he just took this watch off of his wrist. There was no circumstance or pomp around it. It wasn’t my birthday or Christmas or Hanukkah. He just said, “Here, I want you to have this,” and gave it to me. I said, “Holy– That’s just unbelievable.”

That watch is what I first started writing about on Hodinkee, and it first got me to understand why a mechanical watch could be so compelling to a young man or a young woman. That watch quite literally that gift gave me the life that I have today. The one that which I’m very proud of. That is for sure my most valuable watch from a sentimental point of view for sure.

Jacob: Now it’s, through the math 12 years, I believe since Hodinkee has has been in existence. That’s a very long time to do a single thing. I imagine you have made mistakes because we all make mistakes. What is a mistake that you have made either individually or Hodinkee overall that you wish you hadn’t made and what did you learn about it?

Benjamin: The number of mistakes are countless, as any honest entrepreneur would tell you. I think I held on to power too long. I don’t mean actual power. There was no power struggle or anything like that. I was the sole proprietor of the business until 2015. I was making most of the decisions in a silo. It wasn’t until 2015 that I brought in folks that had done something before.

What I mean by that is people that have run a business at least witnessed somebody running a business, invested in businesses, et cetera. I wish I had brought on investors earlier because that was a real turning point for me as a professional, for me as a person. Then certainly for Hodinkee as a business. I would definitely have looked to bring in smarter people or more smart people earlier in the business for sure.

Jacob: How can somebody be aware that it’s time to do that? Obviously, when you first started you were the solo guy writing about watches, probably not ready to bring in a 6 figure COO but at some point, you had to recognize that. How would you advise other people to recognize they’re at that inflection point where it makes sense to do that?

Benjamin: I think we were lucky enough in that we had people approaching us all along to invest. I was like, “Ah, it doesn’t make sense, I’d rather just keep it small and have a nice life.” Then in 2014, a very large media group, one of the big boys came around and said, we wanna buy you. They wanted to acquire the whole thing. It was a 3-person company and it was basically an aquire. I was like, “Wait a minute. These top top top-tier guys think enough of us to give us a little bit of money. It is probably time to start thinking about the future of this business. Do I want to work with them? Do I want to raise our own money, et cetera?

I think not everybody’s lucky enough to have people come knocking saying, “Hey, we want to buy you,” or, “Hey, we want to invest.” I do think most people are lucky enough to have somebody who might at least show a little bit of interest in investing. If you’re in the investment world at all, you know it’s about supply. It is actually competitive to find deals to invest in. Most people would say, “Oh, I only want to work with X, Y, and Z.” There are a lot of people out there that are constantly looking to give people money to invest. This isn’t no such thing as a free lunch. It’s a real investment.

I think that if you have something worthwhile, you’ll start to get those random cold emails from so-and-so in Boston or so-and-so in Philadelphia or New York or Greenwich or wherever, saying that, “Hey, I’d love to take you to coffee and hear about your business.” What that means is they’re kicking the tires on if they want to invest or not. I think once you start getting a steady stream of those, and it doesn’t have to be a ton, a small handful, you might have something that is worthwhile because then all of a sudden you’re approaching people’s radars, you’re in people’s purviews and then that is a good sign that you’re headed in the right direction.

Then of course, I think once you hit a certain number of dollars per year and whether it’s $1,000,000 or $100,000 or $5 million, that’s up for debate. Everyone’s different. Once you hit 7 figures in revenue, you just need people. You just need people around to support and make sure that that things are running the right way. I think for me, I was always anti-VC in some ways because I didn’t know why I had no experience, but I just didn’t like what it represented. Now I’ve got some of my best friends are venture capitalists. Some of our greatest investors are for sure. They’ve helped us change this business for sure.

Jacob: My last question builds on that last one. Hodinkee is clearly an example of what Web Smith from 2PM would call a linear commerce business, which is you build a great audience through the media side, and then you develop products and sell. For entrepreneurs or current media operators that are thinking about going down this path of building a media company that will also be a commerce company. What is some advice that you would give them to try to streamline that execution for them?

Benjamin: I think first and foremost, stay the hell away from watches for sure. Kidding but not. I think the idea of hyper-specialization is everything. I think I’m a columnist for GQ. I just did a Facebook or an Instagram live with them earlier today. I adore them. I think there’s no more room for magazines like GQ. We have GQ, we have Esquire, we have Vanity Fair, we have enough common interest, general interest publications on this planet. That is not the future of media, that is not the future of business. The future of business and media are hyper-specialized publications.

I use this example often, but if you want to know about let’s say cars. You don’t read GQ, Vanity Fair, or Esquire, you read a car blog or a car forum. Even from there, if you want to read about, let’s say early air-cooled Porsches, there’s an even more dedicated forum for that. If you want to read about watches, you come to us. If you want to read about shoes, you go to The Shoe Block. I think picking something that is really hyper-specialized and already has an unofficial community forming it could be in forums. I think that that’s a really good way to figure out.

If you’re going to do this from a strategic perspective, a really good way to figure out if there’s a market is like, “Is there an organic rinky-dink forum that has a huge user base?” I think that was interesting with watches. Is like there were two or three big, big forums back in the day in the watch world prior to Hodinkee, but they were talking inward, they were talking– It was insular. They were talking to themselves. I think what we did is we took that mentality that you would see in these forums and started broadcasting it outward and said, “Hey, everyone would love to know about the ins and outs of a Philippe Dufour Simplicity and what it’s like to get a handmade watch or whatever.”

My chief piece of advice for anybody looking to do this is hyper-specialization. Become an expert. No matter what. It annoys me at this point 12 years in after we built this business into what it is to be called a watch expert. I am. You know what I mean? Many of the people that I respect the most, and I think respect me the most in my life, came to me first because they wanted my opinion on a watch. You know what? That’s okay.

I think, again, I’m at that point where I can get annoyed by that because I think we’ve done so much more than that. Having a specialization and understanding is something that is not very commonly held is really an amazing way to meet some very interesting people and potentially build a great business.