Dan Runcie is the founder of Trapital, a publication dedicated to the business of hip hop. In this conversation, we discussed how he had to put his CEO hat on to make the decision to shut the paid subscription down versus listening to the emotional side, how he thinks about the brand evolving in connection with him, and where he sees the business growing from here.

Scott Gerber is the co-founder and CEO of Community.co, which partners with media companies to create high-priced professional communities. In this conversation, we discussed what goes into making a great community, why it has become such a big buzzword in the market today, and how people should think about growing.

Arsalan Arif is the co-founder and publisher of Endpoints News, a media company that covers the massive biopharma world. During this episode, we discussed the unique subscription they offer, the various events products they bring to market, and why his advice to media operators is not to get into media unless you really love it.

Adam Ryan is the co-founder and CEO of Workweek, a new media company that brings together creators in different industries. During this episode, we discussed how the business got started, the long-term vision for the business, why new entrants into the newsletters space will likely never be able to compete with Morning Brew or The Hustle and so much more.

Amanda Hesser is the co-founder and CEO of Food52, a media, and commerce brand dedicated to the wonderful world of food. With a blend of content and commerce, Food52 has become one of the most impactful brands in the food industry and is now growing to touch more parts of the home.

Naomi Shah is the founder and CEO of Meet Cute, an audio romcom media company. With a focus on creating consistent 15-minute episodes versus trying to aim for hits, Meet Cute is building a robust catalog of IP that the company could use in the future for exciting opportunities.During this episode, we talked about a lot, but a few things jumped out to me…On consistency vs. hitsFor many studios, the goal is to create a hit. They create a few big projects every year with the hope that when one is released, people will flock to it and it’ll be an economic success.That’s not Meet Cute’s approach. Instead, the team strives to consistently deliver on its proposition: a 15-minute romcom audio episode. It doesn’t deviate from consistently delivering that product to people.The benefit here is that the listener builds a relationship with the Meet Cute brand while the company is less dependent on any one piece of content being a savior of the business. I like the consistency over hits approach.On IP and monetizationThe easy road for monetizing would be throwing a quick ad in the beginning of an episode. But for a 15 minute show, a 30-60 second ad eats up a lot of time.Instead, they are looking at all the IP they’re creating as an opportunity to monetize down the line. Consider opportunities like merchandise tied to specific characters. As people fall in love with them, they’ll want to represent those characters.Another opportunity is taking these audio stories and turning them into videos. Could they take their IP and partner with Netflix to create a movie or limited series? When you own valuable IP, your means of monetization are endless.On using data to inform decisionsWhile there is definitely a limited amount of data in audio, some of what they look for is how far into an episode a user got, how many actually completed the full episode, and how many went on to additional episodes.With that limited data, they are able to push that back into their writing flywheel. For example, if they’ve found that cliffhangers often work, that might become part of their strategy going forward.

Mario Gabriele is the founder of The Generalist, a tech publication that tells stories about companies from idea to IPO. The company is new, but he has learned quite a bit about launching a paid subscription and the early days of building a community.

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.