Listen Now

Jesse Jacobs and Mike Kerns are co-founders of The Chernin Group, an investment firm known for their involvement in companies including Barstool Sports, Food52, MeatEater, and so many more. Part of the reason they have found such success is because they have been diligent with executing their thesis.

David Nemetz is the GM of Culture & Innovation at Bustle Digital Group, overseeing brands including Inverse, Input, and Mic. He is also the former co-founder of Bleacher Report, which unlike many digital media companies that started at a similar time, actually had a successful exit.

Elizabeth Bramson-Boudreau is the CEO and Publisher of MIT Technology Review, the oldest technology magazine in the world. Over the past few years, the business has been going through a transformation of building out the tools and processes to run a digital-first media business.

Jason Yanowitz is the co-founder of Blockworks, a media and events company covering the crypto asset space. Originally, the plan was to create an advisory, but multiple iterations later, it is now has a newsroom, a podcast network, and an events business that plans to go physical again in 2021.

Scott Brodbeck is the founder, editor, and publisher of Local News Now, a network of hyperlocal media properties. What started as a single guy with a camera and a police scanner has turned into a media company with a small staff serving the D.C. area through multiple websites, both owned and through partnerships.

Nick Friese is the founder and CEO of Digiday Media, a company with three verticals: Digiday, ModernRetail and Glossy. Friese started the company during the Great Recession and has gone through a tremendous journey building this company with events, membership and marketing services.On building membershipThe membership product at Digiday started primarily as a print product. As Friese explained it, people were comfortable paying for a magazine, so that’s what they sold. And despite costing nearly $200 for four issues, it sold.But as time went on, they started adding other features to the membership, including member-only content and then the metered paywall until now, it’s a much more expensive product at the company.The lessons they’ve learned has been applied to the other verticals where now Glossy and ModernRetail actually have more robust membership offerings that the original at Digiday.On equal numbers of buyers and sellers at eventsA solid number of Digiday’s events are hosted buyer events, where the buyers typically come for free. In exchange for that, the sellers get guaranteed meetings with decision makers.According to Friese, this boils down why people really want to attend events. They’re looking to do business. It’s about meeting your contemporaries.This is also how they think about verticals over all. If you can clearly define the buyers and sellers in an industry, you’ve got the potential for something.On their structure of verticalsFriese has a different approach to the various franchises than other vertical media companies. Each publication has its own writers, editors, marketers and sales people.This is different than how others have done it where the editors and writers are unique to the publication, but everything else is centralized with services spread across all the verticals.In Friese’s mind, each brand has its own very unique image, so he believes it’s important for the majority of the people working on it to be focused exclusively to those brands.

Sherrell Dorsey is the founder and publisher of The Plug, a publication focused on the Black innovation economy. While it started as a morning newsletter she did before going to work, it has now morphed into a media company with original reporting, data, research, events and podcasts.In this show, we discussed a variety of important topics, but a few things jumped out...On quarterly, not monthly pricingThis was an important topic to me. The Plug's membership is sold quarterly or annually, but not monthly. As she said, this runs counter to the habit so many of us have formed paying for subscriptions every month.In her mind, though, a month is just not a long enough time to form a relationship. By extending it to a quarter, she feels that The Plug has enough opportunity to demonstrate value to a reader.It's an important distinction because if we look at when most subscribers churn, it's after the first month. By extending to a quarter, you have more time to form a habit with them and, ideally, keep them engaged for much longer.On not charging a CPMFor most media companies, charging a CPM is how they do things. But in niche media, it's harder. As Dorsey explained, because they don't have scale, they need to price things based on value.Whether it's their podcasts, newsletter sponsorships or other content initiatives, they try to determine how valuable a sponsorship is worth to a partner and then work on pricing from there.On being diversifiedAlthough we didn't explicitly talk about this, The Plug generates revenue through advertising, events, membership fees and has received grants to create new content initiatives.This embodies a core ethos of successful media companies. Those that are overly reliant on a single source—or a single property—carry more risk than those that are well diversified.While The Plug has gone on to raise some money, it's clear in our conversation that Dorsey continues to think very diligently about not overextending the business and ensuring there are multiple streams of revenue.

Mike Orren is the Chief Product Officer at The Dallas Morning News and has called this the pivotal year for local media. With Orren leading, Dallas Morning News has been undergoing a digital transformation, using the revenue generated from the print operation to invest in the online business. In this episode, we talked about a wide variety of topics that you'll find informative and interesting.

John Yedinak is co-founder and President at Aging Media, a vertical media company focused on the business of aging. With so many people retiring every single day and few b2b companies covering the space, John and his brother have grown into multiple verticals over the years and have even more growth ahead of them.

Julia Beizer is Chief Product Officer & Global Head of Digital at Bloomberg Media. While Bloomberg is primarily known for its terminals, the digital team has built a robust media operation that has now added hundreds of thousands of paying subscribers.In this episode, we discussed quite a few different topics, but a few things jumped out to me...On program managers vs. product managersA big mistake that media companies make is that they hire product managers because they need someone to "get stuff done." But as Julia explained, "everyone can get stuff done."What companies are actually looking for is a project or program manager. This is a person who is very focused on the delivery of certain features or initiatives getting out the door.Product management is more expansive. These are people that sit at the intersection of competing business interests: user needs, commercial interests, editorial vision and resources. Product managers synthesize all of these ideas and figure out the best thing to do.On building a revenue optimization systemI call this a revenue server and Julia calls it a revenue optimization system, but they are effectively the same thing. How can media companies look at their users and determine the right way to monetize each visitor?Bloomberg is in the early stages of this and it's pretty manual. A few of her people meet with the subscriber and advertising sides in a meeting called "Project Needle" because they are trying to thread the needle of maximizing revenue on both sides.This refocuses the conversation from RPM (revenue per thousand) to the lifetime value of a user. It's not just about understanding how much a single page makes, but how much a user across the website generates for the business.On advice from Jeff BezosSoon after Bezos acquired The Washington Post, they were discussing a product that was being preinstalled on Kindle Fire devices across the country. They mentioned that they were going to bring the product to user testing.Bezos’ response was, “hey, that’s great and you should obviously get that user feedback, but you also want to think about, do we love it? Do we love this product?”This goes against everything taught in product school, but the lesson Julia has taken to heart is, “if you deeply, deeply understand your customer and get in the mindset of your customer, you’re a good barometer of what the right thing to do is for the business.” 

Ryan Selkis is the co-founder and CEO of Messari, a crypto data and market intelligence platform. Ryan and I go way back with him hiring me at CoinDesk nearly four years to the day. Since then, he has gone on to build an exciting and well respected data and research company in the rapidly evolving world of crypto assets.

Packy McCormick is the writer and creator of the business strategy newsletter, Not Boring. Although he has only been doing this full time since April, it has quickly morphed into a project with a loyal audience and an advertising-driven business model that bucks the trend of many of the newsletters launching today.We discussed a lot about what goes into building these solo products, but a few things jumped out to me...On building a referral systemThe referral system in newsletters has become a favorite way to grow audiences; however, for Substack writers, it doesn’t exist. Packy decided to go around that and build his own, hacked together version of it.The way it works is straight forward… They use a system called GrowSurf that is plugged into a Webflow landing page. GrowSurf manages the whole process of giving unique codes to everybody.When people sign up, he has to download a CSV of the email subscribers and upload them into Substack so they can start receiving the newsletter. So, as Packy says, it’s a manual process.On going ads vs. paid subscriptionMost people who have launched newsletters over the past year have gone all in on subscriptions. I, too, have leaned heavily into subscriptions. Packy, though, opted not to go that direction.Instead, Packy does what a lot of media companies do and sells advertising. He has a couple of different products that range from sponsorships in newsletters to outright, dedicated sponsored content emails.His logic? He wasn’t sure if an audience would be able to justify expensing his newsletter and he preferred seeing the list grow faster with the free newsletter. And so far, he’s been very pleased with the results.On staying focused on your passionEarly in his attempts at building Not Boring, he tried to lean heavily into community. But what he found was this wasn’t the right play for what he was trying to do because he didn’t enjoy it. He preferred to focus on the business strategy side of things.His advice for others is to be very specific about what you want to focus on and continue leaning into this. It allows for more informed conversations with readers and allows you to meet a lot of new people, which is integral to these one-person operations.However, he also advised creators to experiment with different things. There are a variety of ways your specific focus can manifest itself, so be comfortable with those different potential options.

Neil Vogel is CEO of Dotdash, a series of brands across verticals like food, technology finance and others. What started as About.com has morphed into an incredibly profitable, fast-growing media company. Although Neil has poor taste in sports teams, when it comes to running this network, I have to tip my hat.In this episode, we discussed a variety of topics, but a few things jumped out to me…On ad strategy at DotdashWe all have been to that website that causes the fans on our laptops to go into overdrive. Whether it’s popups, pre-rolls, interstitials… You name it, we’ve likely all experienced it.Dotdash bet that by reducing the number of ads on the site—2/3rds of what their competitors might have—that the sites would load faster and that would make people happier. That, in turn, would result in people engaging with the content and ads more.The other part of the strategy is focusing in on contextual advertising. An example Neil shares is if someone is coming for the site on July 2nd and looking for BBQ recipes, they know exactly what type of advertising to deliver to them.On creating great content & SEOThere is no denying that Google drives a decent percentage of traffic to the various Dotdash sites, though Neil qualified that it’s no more or less than most other publishers on the web.However, the way he sees it, the only real “secret” to SEO is doing exactly what Google wants: delivering the absolute best content out there. That’s Google’s business. And so, Dotdash invests millions in creating the absolute best content.But it’s more than just that… In his mind, creating great content is fundamental to the quality of the brands they’re building. I wrote about this on Friday, but because of the quality of the brands built on the great content, he believes people would miss the brands if they went away.On not chasing the shiny thingsSome of the biggest mistakes that they made early on at Dotdash was seeing what other people were doing, knowing that it was the wrong approach, but still trying to do them anyway.The advice that Neil has for prospective operators is to stay focused on what you know works. It’s easy to get distracted by the shiny things and the press other people are getting, but it’s about staying focused on what works. 

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.