Ben Clymer is founder and CEO of Hodinkee, a media and commerce company dedicated to the luxury watch market. What started as a personal blog thanks to a watch from his grandfather has turned into a highly respected business that can sell millions of dollars in watches in minutes.In this episode, we went through the many different facets of the business, but a few things jumped out to me…

Jarrod Dicker is the VP of Commercial at The Washington Post, which puts him in charge of a variety of products, but most specifically, the Zeus ad suite. But in his free time, he has become somewhat obsessed with the creator economy and the evolution of media. In this episode, we discussed quite a few topics, but a few things jumped out...Where media went wrongJarrod got his start in media at The Huffington Post, working on products to help the business be, well, a business. One of the early products that they launched was digital native content. While HuffPo ultimately sold to AOL for a successful exit, one of the things Jarrod talked about was that the story of media got screwed up. It was no longer about building a great brand, but rather, about being the first and fastest to get a story out, irrespective of outcome. Additionally, many of these media companies saw the scale that platforms were getting and assumed that was the only way to grow and succeed. Since then, of course, that narrative has changed. On record labels & media companiesThe ease in which individuals can launch their own business is becoming easier than ever before, but we still operate in a very black and white world. You either work for a media brand or you are on your own. In Jarrod's opinion, media companies need to start thinking about themselves as record labels, which should focus on brand, distribution, services, etc. Rather than letting talent walk away to start their own thing, partner with them. It's a different notion for media companies to come to terms with. However, in the current state, media companies are acting like factories where they help a journalist build their brand and then that journalist starts anew (see Politico Playbook writers leaving). On the renaissance creatorIn that same breath, this idea that all the very best writers are going to suddenly quit their jobs and go solo is not actually a reality. The reason? It's actually a lot of work. The promise of going solo is that you can focus on writing what you want to write. That sounds great. However, you also have to edit, design, do audience development, track finances, etc. All the things a media company typically did. The real benefactors of this new era will be the renaissance creator: an entrepreneurial operator that also wants to create. These are people that understand building a business and then opt to build a creative entity.

Sean Griffey is co-founder and CEO of Industry Dive, a network of business publications covering a wide variety of topics including retail, biopharma and waste management. When I think about a successfully scaled b2b media company, Industry Dive comes to mind first.In this episode, we discussed a ton, but a few things jumped out…On expanding into new marketsIndustry Dive has a specific playbook that they use to determine what verticals they want to expand into it. It starts with a very simple question: does this fit the business model?Because Industry Dive is marketing driven, it needs to find industries with high capital spend. That means the executives are buyers that control budgets. A mistake Sean sees many operators make is that they in industries that don’t have this.The other very important question they ask is whether the industry is being disrupted by technology or regulation. What they’re trying to identify is whether people’s jobs require them to keep up to date on what’s going on day-to-day. If that exists, you’ve got something.On media’s sweet spot with content studiosIndustry Dive recently acquired the content studio from NewsCred in what appears to have been a match made in heaven. NewsCred was moving away from its content studio business while Industry Dive was doubling down on it.What this reinforces is the sweet spot that media finds itself with regarding to producing content for partners. As Sean explains, any agency can create great content. That’s not the hard part.They might even be able to create great content and distribute that content to an audience (though not as easily as a media company can.)Only a media company can take it a step farther and consult their clients on when the narrative has shifted. Industry Dive was able to tell its partners, “hey, the audience is moving away from covid-related coverage” far faster than an agency ever could, which allowed their partners to start creating new content in the new narrative.On data being the most important thingSean offered his big piece of advice for prospective media operators and it’s something that I whole heartedly agree with as well.Operators need to start collecting user data immediately. You’ll never feel bad having a better understanding of who your audience is. More importantly, the sooner you have it, the better it’ll be when you decide to use it.And using it doesn’t have to mean advertising products. Having better user data can also mean making better product and editorial decisions.In Sean’s opinion, too many media companies wait to determine their user data strategy and they’d be smart to start sooner.

Dan Shipper and Nathan Baschez are the founders of Everything, a bundle of business newsletters. What started as their two respective publications, Superorganizers and Divinatons, has expanded to include multiple newsletters.A few things we discussed in this episode...On revenue sharesWhen a user signs up for the Everything bundle and after all the fees are taken out, Everything sends a survey to the subscriber to ask them what newsletter was the primary reason they signed up. Whatever the answer is dictates which newsletter writer gets paid for that newsletter subscriber. From there, each writer has their own agreement. Some are licensing deals whereas others are built entirely within the network. So, the revenue shares might be different depending on the situation.The plan is to then resurvey the subscribers and determine whether the primary newsletter has changed. If it has, then the money gets allocated to this new newsletter. This way, the writer is rewarded for keeping the subscriber subscribed. On writing & audience developmentBoth Dan & Nathan agree that one of the most important things they can do is create the best possible writing possible. In their words, this is the best way that they can help create a successful publication. They also see the current newsletters as a good way of helping to incubate different newsletters that may join the newsletter. An example, Shipper explained, could be adding a new productivity newsletter to the bundle. Superorganizers could then drive audience to it with the goal of getting people to convert. Where it goes from hereThe future looks a lot like where they are now, but with many more newsletters in the bundle. They could expand into industry verticals, such as waste management or space (their examples) to job roles (marketing and product management) and to newsletters focused on specific companies. What they are also trying is finding the people that have that "twinkle in their eye" about a very specific topic. The idea is that, even if they don't write, they can be paired with great writers. It's unknown if it works, but the idea is that the team of expert/writer could create a great product. Ultimately, they want to try and figure out ways to identify some of the "best business knowledge that's locked inside people's heads."

Snigdha Sur, Founder & CEO of The Juggernaut, always knew she wanted to be in media. She now runs a subscription media company that is dedicated to creating "smart journalism for the South Asian diaspora” called The Juggernaut.In this episode, we discussed a ton, but a few things jumped out…Niche can scaleUnder normal circumstances, you wouldn’t expect to see a media company in Y Combinator, an accelerator for traditional tech startups. However, for a variety of reasons, they decided to have Snigdha join the program.One of the things she said that resonates with me is that niche can actually scale. We think of niche as small, but these verticalized media companies have the potential to really grow into something robust. Part of the way to think about that is about content appearing in multiple places, including on the website, newsletter, podcasts, video & TV deals and various other opportunities.A classic example that she used is BET, which serves a specific community. Viacom bought BET in 2001 for $3 billion. It was a niche play, but that didn’t hold it back from reaching incredible scale.On lifetime subscribers & Thursday customer callsUnlike many media companies, The Juggernaut offers the option for people to purchase a lifetime subscription. For $249.99, you will never not have access to The Juggernaut. It’s an interesting experiment and one that Snigdha is really a fan of in a limited sense.As she explained, these are the most die hard of supporters. They’re people that really care about the brand and what it stands for. They’re also people that she sometimes uses to bounce ideas off, whether that’s sharing content ahead of time or perhaps taking a look at the upcoming app.The other part of this is her ritual of taking 5-10 customer calls every Thursday. She wants to hear from people and get their thoughts on how The Juggernaut is doing; the good and the bad.Audience development with InstagramI teased this out on Twitter, but I am a big fan of The Juggernaut’s Instagram strategy. Using a tool called Link.bio, they are effectively able to create a clone of The Juggernaut’s Instagram page. Every time they share a new photo, they include three paragraphs of text and then a “link in bio.”That link in bio is a link.bio URL that then shows all the same images the user had seen previously. This time, though, when a user clicks one of those images, it takes them to the individual story page. It’s a great way to distribute content on a platform that is otherwise not very friendly with distributing content. 

Craig Fuller, Founder & CEO of FreightWaves, didn't have a clear path to media. His background was in the trucking business. But when he identified an opportunity to launch a futures market around trucking, he recognized that there were major gaps in the news & data around trucking. So, he launched FreightWaves.In this episode, we discussed a variety of topics, but a few things jumped out.On pivoting post CovidEvents were a big part of the business, accounting for half of the revenue in 2019. It was expected that it'd be another major component in 2020, but due to Covid-19, it was forced to pivot.The company had already started introducing TV-quality content from its studio in Tennessee. It shifted its event to fit within the TV experience. The majority of the sponsorship dollars were absorbed into commercials on the show. On the attendee front, FreightWaves was able to keep the majority of its revenue by shifting them all to research subscriptions.Ultimately, FreightWaves was able to give sponsors exposure to nearly 100,000 viewers rather than the 2,500 that they expected to have at the physical event.On being valued as a data companyMore than half of the revenue at FreightWaves comes from traditional media sources: advertising on the site and video and subscriptions. However, the company has been able to raise tens of millions of dollars because FreightWaves is also in the data business.When investors look at the business, they see the entire community across media, data and events and were willing to value the business much higher than if the company had just been a traditional media company. Data multiples are higher than media.That has then allowed FreightWaves to play a bit of an arbitrage game where it can acquire smaller pure-play media companies at lower multiples compared to the multiples it raises.On media creating negative net CACs for dataCustomer acquisition costs (CACs) is effectively the amount of money that a company spends to acquire a new customer. For traditional SaaS companies, these can be incredibly high, but it's worth it because the retention is high enough that returns accrue over time.However, FreightWaves has a new metric it tracks called net CACs. Because users are being monetized with the media business before they get a subscription to the SaaS data platform, FreightWaves actually generates strong cash flow while also earning free advertising for its data products.This is the unique opportunity that a media/data blended company can offer that a true SaaS company can't. The media brings the audience in, FreightWaves monetizes with traditional advertising and then it also promotes the data business to those same users.

Austin Rief is cofounder and COO of Morning Brew, a 2,000,000+ subscriber newsletter company with additional vertical brands covering various niches. It started while he and his cofounder were in college and it has been growing incredibly fast over the past couple of years, generating eight figures of revenue.On the differences between the newslettersIn the early days (and still to this day), the Morning Brew team was incredibly focused on the growth of the number of subscribers and fanatical about the open rates. As Austin explains, he doesn’t know any newer media company that has thrived without an obsessed audience.However, with the vertical newsletters, they dive much deeper into the numbers. They don’t just want to know that a lot of people are opening, but are specific about understanding who is opening.Additionally, they see these vertical newsletters as an opportunity to dive much deeper in the types of offerings they provide to readers and advertisers.On the future of Morning BrewMorning Brew has changed quite a bit over the years, from being a single newsletter to now sporting a podcast and multiple verticals. The company intends to expand into a couple of additional verticals over the next year, but Austin made it clear that they’d only expand if they could cover something to the utmost degree.Looking forward, Austin also sees Morning Brew being a hub with a variety of different spokes across podcasts, newsletters and subscriptions. He expects users that fit within their target psychographic to come to Morning Brew to choose what they want: marketing, personal finance, podcast, newsletter.On creators being sheep following the herdAustin has been unabashedly outspoken about the fact that too many creators are sheep following the herd when it comes to subscriptions. What he’s most excited about is operators turned creators building businesses that rely on models that work for their brand versus just trying to slap on a subscription.One of the main points that Austin did mention is that the best products that do launch will come from people that used to work within the industry they write about—operators that understand how to run a business. They come with a baked in network of people that can help with the early growth of the product. 

Adam White, Founder & CEO of Front Office Sports, is as unlikely a media operator as there ever was. FOS started as a college project that Adam hoped he would be able to leverage into a job. When that failed, he figured he might as well see where this could take him. So far, that strategy is working.In this show, we discussed a variety of important topics, but a few things jumped out.On building for a prosumer audienceThe business of sports as a core topic is a multi-billion dollar business, but there are so many adjacent industries that intersect with sports. This intersection is where Adam believes his company is able to excel the most. Additionally, there are so many job functions outside of core sports that his audience comes from because of a general interest in sports.This opens up an opportunity for Front Office Sports to generate revenue from more than just endemic and non-endemic b2b advertisers; specifically, he's talking about brand advertisers. In one deal, Anheuser-Busch sponsored one of their awards shows, which would likely never have been heard of from a b2b publication.The Politico of sportsOne of the reasons Adam believes this is the right approach is because he believes he can build the Politico of sports. If you look at Politico's business, it has 100 million people visiting its website, but only about 30,000 are paying subscribers. The secret is that each of those subscribers is incredibly high priced.The same hopes to be true for FOS. Presently, it hopes to serve this broader audience that works around sports. But at some point in the future, it might identify a new product opportunity that could benefit from a high priced subscription. However, as Adam said, if that's just slapping a paywall in front of their content, he'll be disappointed.Young startups need to constantly fight for a dollarWe discussed a great story about how FOS launched a podcast that had a crypto advertiser. It had a football player who was a fan of bitcoin that was supposed to be the host. At the last minute, the player backed out of the project, so Adam had to take over because it was a high ticket sponsorship that the company couldn't afford to lose.Looking at the Anheuser-Busch deal, Adam talked through the execution for the Rising 25 sponsorship that included creating their own soccer team with original kits. The flywheel of media is such that any dollar you bring in ensures that you can reinvest it back into producing better content for your audience, so they’ve had to consistently be creative with their opportunities.While Covid-19 has certainly had an impact on the business (sports did shut down after all), the business is still expected to grow revenue by 100%. And depending on how Q3 and Q4 goes, it should be profitable.

Brian Dolan, Founder & Lead Writer at Exits & Outcomes, is the first guest on the show and for good reason. He has had multiple careers in media, first working for Fierce Markets (which seems to have trained multiple future operators), then launching MobiHealthNews, which was then sold and, most recently, creating Exits & Outcomes. In this show, we discussed a variety of important topics, but a few things jumped out. Having an advisory committeeAs Brian explains it, the acquisition of MobiHealthNews was something they hoped would happen, but was certainly not a given. Multiple times he and his co-founder would go out to lunch with executives from HIMSS, but it was only after a few years that the conversations turned more serious. One thing that Brian admits would have helped was having people that he could call on to help him out. Having people that could relate to the situation would have made things simpler when going through the exercise of getting acquired. By and large, a tight network of advisors can be invaluable for discussing ideas and getting a gut check on whether an idea is good. Pricing for subscriptionsThe blend of art vs. science for pricing subscriptions was certainly alive during this discussion. The way he did it was straight forward: what were other people charging for similar content? By finding comparable rates, he knew he was in a good place. One thing Brian doesn't offer that I do is a monthly rate. His logic makes sense: the value of his market research is too high to let someone access it for a month for only $20 and then unsubscribe immediately afterward. At $200 a year, it's still a good value. What comes next with an idea toward bundlingThere are two potential paths he has thought about taking...The first is that he could go the route of replicating the success he has had with Exits & Outcomes and expand into other verticals outside of digital health. That would require bringing on additional writers and effectively taken a script from FierceMarkets and Industry Dive. The second (and more likely course) is to find more niches within digital health. Healthcare is a huge industry, so there are plenty of niches within that. It's a more likely way to go that he could continue operating as a solopreneur without needing to bring other people on board. This second approach would result in a sort of bundle for his subscribers, providing multiple different high-quality digital health insights that would keep his subscribers from leaving.

A Media Operator is a new podcast that expands on the newsletter, found at AMediaOperator.com. This is a trailer to give you a hint of what's to come, but in the coming days and weeks, we'll have additional episodes from leading operators, entrepreneurs and investors in the digital media space. Excited? Subscribe now!