The Business of Content with Simon Owens

Visit SparkLoop: https://sparkloop.app/partner-network?utm_campaign=simonowens   If you’re aware of Morning Brew, it’s probably because of its daily business newsletter. Since its founding in 2015 by two college students, it’s grown to over 4 million subscribers, and its news digest format has been copied by dozens of other media startups.   But since getting acquired in 2020 by Business Insider, Morning Brew has expanded into new niches in verticals. Not only has it launched several B2B industry newsletters, but it also invested heavily in podcast and video production.   That’s where Dan Toomey comes in. After graduating college in 2020, he pitched Morning Brew’s founders on the idea of him coming on board to create video, and to his surprise, they went for it.   After experimenting with several different formats, Dan started creating sketch comedy videos for TikTok, and it worked. Every morning he woke up, scanned that day’s business news, and chose a topic to parody on video.    In our interview, Dan talked about how he came up with the format, his daily routine for writing scripts, and Morning Brew’s strategy to grow beyond TikTok and launch new video series.

Visit SparkLoop: https://sparkloop.app/?utm_campaign=simonowens If there’s one thing Twitter’s known for, it’s character limits. It famously only allowed 140 of them and then later expanded to 280. In some ways, that forced brevity made Twitter what it is today: a real-time commentary on what’s going on in the world. But for years, Twitter has been trying to expand beyond its own character limits, first by launching features like photos, gifs, and videos. It launched a threading tool that allows you to string several tweets together. In 2021, it acquired newsletter platform Revue. And then just recently, it debuted a new tool called Notes. Though it’s still in the testing phase, Notes will allow users to publish longer blog posts within their Twitter feed.  But is this something users actually want? Or will it eventually join the very large graveyard of social media features that never caught on?  To answer this question, I brought on Ernie Smith. Not only is Ernie one of the foremost experts on publishing platforms and newsletters, he also got early access to Twitter Notes and tested them out for himself. He gave me his initial reactions to the tool and we discussed whether it would usher in an era of longform writing to Twitter.

Visit Video Husky: https://bit.ly/vh-simon-owens-pod   When Nick Meacham first joined SportsPro in 2010, it mainly existed as a B2B print magazine that monetized through advertising. The editorial staff was tiny and it didn’t have much of a web presence.   But after taking over the business operations, he rapidly expanded it into new ventures – first by launching a series of lucrative conferences that targeted multiple industries within pro sports, and then by rapidly building out its digital operations.   In an interview, Nick explained to me why he made such a big bet on events, how the company adapted during the pandemic shutdown, and where he sees more opportunities to monetize the outlet’s digital content – including his plans to launch a subscription paywall. 

Visit Video Husky: https://bit.ly/vh-simon-owens-pod   During their combined 20 years at The Wall Street Journal, Bradley Hope and Tom Wright covered some of the most momentous stories to hit the financial world, but none were as consequential to their personal careers as their reporting on Jho Low, a Wharton grad who was caught stealing billions of dollars from investment funds. Their dogged investigation led to the publication of the book Billion Dollar Whale, an instant bestseller that transformed them into A-list writers, on par with Michael Lewis and Malcolm Gladwell.   Rather than simply returning to their newspaper jobs, they partnered on a new media entity called Project Brazen. Unlike most digital media companies, Project Brazen has no ambitions to churn out large quantities of web content. Instead, it only focuses on ambitious, investigative storytelling that can be adapted into multiple mediums that include podcasts, books, film, and television.   How does Project Brazen go about vetting and staffing these projects, and what are the best ways to monetize serialized storytelling? Those are some of the questions I put to co-founder Bradley Hope in today’s interview.   

Visit https://theygotacquired.com/newsletter   When everyday people hear about space-related news, it’s usually in association with an organization like NASA or SpaceX. But while Elon Musk is great at grabbing headlines, the space industry actually comprises a vast constellation of companies that generate hundreds of billions of dollars a year. And it’s only set to expand; Morgan Stanley projects it’ll reach $1.25 trillion by 2040.   Given the size and growth of this industry, it’s probably a surprise to no one who listens to this podcast that there’s an enormous opportunity for the B2B media outlets that cover it. One of the most exciting entrants into that space is Payload, a daily newsletter that launched in 2021.   Though Payload was bootstrapped for its first several months, it announced a $650,000 seed round last year that was led by Winklevoss Capital, the venture firm run by Cameron and Tyler Winklevoss. It’s since hired an editorial staff and landed its first major sponsors.   Payload was founded by Mo Islam and Ari Lewis, and in December 2021 I interviewed Mo about the newsletter’s origin, its audience development strategy, and its plans to monetize its influential readership.

Visit https://www.transizion.com/ There were a lot of media companies that were vulnerable to the pandemic shutdown, but perhaps none more so than Pop Up Magazine. Not only was its content delivered through live performances, but the hosts made special care during each event to tell the audience that nothing that night would be recorded. Part of the magic, in other words, was the show’s ephemerality.    Of course, there was no way Pop Up Magazine could continue delivering on that promise once all in-person events went away. Instead, it had to adapt by somehow taking the magic of a live performance and delivering it over the internet.   Not only did the magazine succeed in this endeavor, but the new restraints forced it to diversify revenue and expand its audience. With live events now returning, it’s arguably stronger than ever.   How did its staff accomplish this? In an interview last year, founder Chas Edwards walked me through Pop Up Magazine’s pivot, from the hellish first weeks of the pandemic to its recent return to live events.

Sign up at https://cex.events/ and use coupon code "Simon" David Kushner had the kind of mainstream success that most writers dream of. His writing regularly appeared in glossy print magazines like Wired and Rolling Stone. Several of his books became national bestsellers. And his work has even been adapted into multiple TV shows and movies.    But in 2021, David decided to bypass legacy media entirely and start publishing his work to a Substack newsletter. What drove him to do this? In our discussion, David explained how the changing norms over IP rights and his own desire to experiment with serialized storytelling motivated him to make the move.

Sign up at https://cex.events/ and use coupon code "Simon"   When Patrick Trousdale launched his newsletter The Daily Upside in 2019, he didn’t have much of a personal brand to build from. In fact, even today, his personal Twitter account has fewer than 300 followers.   What he did have was several years of experience in finance and the willingness to grind out the newsletter each day, even when it didn’t have much of a following. That kind of persistence netted him his first few hundred followers, and it also helped him get his foot in the door so he could pitch The Motley Fool, a popular finance website, on a content partnership.   That partnership paid off in a big way, and The Daily Upside quickly grew by tens of thousands of signups. Today, the newsletter has over 300,000 subscribers and has sold out its ad inventory for months in advance.   In our interview, Patrick walked me through his initial launch strategy, his business model, and how he convinced editors at The Motley Fool to take a chance on a partnership with an unknown entity.

Sign up at https://cex.events/ and use coupon code "Simon"   When Adam White graduated from the University of Miami in 2017, he had every intention of getting a job in sports administration. In fact, he went through several rounds of interviews at a major organization and was sure he’d get an offer.   But the job never actually materialized, and instead of applying to more open positions, Adam decided to double down on Front Office Sports, a website he had founded during his freshman year in college. For the next year or so, he worked part-time jobs while also spending his mornings, nights, and weekends interviewing top executives at the largest sports franchises all around the world.   His bet paid off in a big way. Not only did he manage to secure angel investment, but the site also started to attract major sponsors. Today, Front Office Sports is a powerhouse in the B2B sports media space, and it’s using its momentum to expand into new verticals.   In my interview with Adam, he explained to me what sparked his initial idea, how he became a better interviewer, and why he’d rather embrace slow growth than accept large VC investment.

Get your tickets at https://cex.events/ and use coupon code "Simon"   Pat Walls’s most successful startup to date was born in the wake of a previous failed startup. Back in 2016 he and a couple other co-founders had been operating a B2B SaaS platform, but after it struggled to gain traction, they were forced to shut it down.   But Pat never lost the entrepreneurship itch, and in 2017 he started interviewing other startup founders on the phone and converting those interviews into case studies for a website called Starter Story. After a few of those case studies blew up on Reddit, Pat knew he was onto something, so he started publishing them with more frequency.   Flash forward a few years, and Starter Story now attracts over a million visitors a month, many from Google Searches. It also generates half a million dollars in annual revenue through a mixture of advertising, membership, and affiliate marketing.