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, CEO of Dotdash, discusses the success of reducing ads on their sites to increase engagement, focusing on contextual advertising. He also emphasizes the importance of great content for SEO. The podcast delves into Dotdash's strategic evolution, premium content opportunities on Investopedia, vertical expansion, and the future of Dotdash within IAC.