Joshi Herrmann is the founder of The Mill , a newsletter focused on Manchester – England, not New Hampshire, for those who call it “soccer” – as well as sister publications in Sheffield and Liverpool . Joshi started The Mill in June 2020, and across the three newsletters, the company has 45,000 email subscribers and has converted over 7% to paid subscribers. The Sheffield Post has 12,000 email subscribers and has managed to convert an impressive 950 to paid, according to Joshi. The company is ne...
Dec 06, 2022•54 min•Ep. 51
The Athletic started in 2015 with a simple proposition: It would produce the highest quality sports journalism with a subscription model that would align incentives with producing quality work vs chasing traffic. The approach wasn't without its flaws -- The Athletic consistently lost money -- but it did produce a differentiated, high quality product. In January, The New York Times bought The Athletic for $550 million. Nine months later, the Times, which has proven that advertising can co-exist i...
Nov 29, 2022•39 min•Ep. 50
Ari Paparo is a longtime ad tech veteran, not to mention holding the disputed title as Funniest Person in Ad Tech. Some highlights from our conversation: Innovation requires fragmentation. Ad tech’s complexity is a longtime talking point. And it is undeniably a convoluted supply chain that’s given the veneer of plausible deniability to all kinds of corner cutting, at least in my experience as an observer for many years. But Ari points out that “innovation requires fragmentation,” and besides, ma...
Nov 15, 2022•48 min•Ep. 49
Isaac Saul saw knee-jerk distrust in media firsthand as a political journalist at outlets like Huffington Post, where what he wrote would end up being distrusted based on the place it appeared rather than the substance. Three years ago, Isaac started Tangle with the idea that presenting both sides to news stories would appeal to a wide group of people. And that’s proven true. Today Tangle has 8,000 paying subscribers and nearly 50,000 free email subscribers – a 16% conversion rate is amazing. It...
Nov 08, 2022•54 min•Ep. 48
Alex Kantrowitz is the founder of Big Technology, an independent publication focused on he immense impact of tech companies on business, politics and society. A reporter covering tech for BuzzFeed News, he wrote a book on the tech industry called “ Always Day One ” and became one of the early trailblazers to decamp to Substack in 2020. Since then, Big Technology has amassed nearly 100,000 subscribers. We spoke about his independent journey – and plans to start a paid tier to his newsletter – as ...
Nov 01, 2022•49 min•Ep. 47
Semafor, backed by $25 million in private investment, has (finally) launched, marking possibly the most ambitious attempt in recent years to build a new global news brand. At the heart of the effort is an attempt to restore trust in media by rethinking the journalistic product. Despite the long history of failed attempts to "reinvent the article," Justin sees a glaring need to unbundle the article to clearly delineate factual news from analysis and opinion, while providing the context of the new...
Oct 18, 2022•28 min•Ep. 46
6am City is turning to the newsletter to build out a network of 25 local news publications it says have 1 million cumulative subscribers and an open rate around 50%. After starting in Greenville, South Carolina, in 2016, 6am has expanded to markets like Madison, Wisconsin; Austin; Portland; and Indianapolis. The 6am formula is to keep new publications’ costs under $250,000, staff them with two-or three editorial staffers and four total employees, mostly making money from ads, both local and regi...
Oct 11, 2022•48 min•Ep. 45
In 2014, Bonnie Kintzer was named CEO of Readers Digest Association, becoming its fourth CEO in three years as it emerged months earlier from its second bankruptcy. After renaming the company Trusted Media Brands, recently shortened to TMB, Bonnie set out to decisively shift the company to a digital model while diversifying its focus to include its other lifestyle brands, such as Taste of Home and the Family Handyman. TMB added Jukin Media, bringing its streaming and video capabilities as well a...
Oct 04, 2022•33 min•Ep. 44
Casey Newton, a former writer at The Verge, started Platformer to cover the societal impact of the most powerful tech platforms. He’s used a subscription model, charging $100 a year. With 75,000 free subscribers and what he’ll only call “thousands” of paid subscribers – Platformer is the No. 2 most popular paid newsletter in tech on Substack – Casey has built a successful solo business that’s he’s expanding by bringing on Zoe Schiffer as Platformer’s managing editor. (He’s also got a new podcast...
Sep 27, 2022•44 min•Ep. 43
This is a preview of a new weekly podcast I’m doing with Troy Young. The People vs Algorithms podcast will focus on patterns in media, business and culture. Each episode will revolve around themes. This week, we tackled the theme of whether media is better now than in the past, along with an exploration of the type of media that’s winning in this kind of environment. It’s narrower, more focused, more niche . Subscribe to People vs Algorithms on Apple or Spotify ....
Sep 20, 2022•35 min•Ep. 42
Flying , a 95-year-old magazine publisher focused on amateur pilots, is on this path. Craig Fuller, CEO of Freightwaves, bought Flying in July 2021 and a key part of the growth plan he and COO Preston Holland have begun is a massive bet on so-called air parks, basically resort communities with ample space to park your plane at your home. The Fields is a 1,500-acre development in Tennessee’s Sequatchie Valley that’s due to open next year. Plans call for 800 homes, 180 “vacation villas,” a runway ...
Sep 13, 2022•43 min•Ep. 41
Future is a collection of over 200 specialist titles that range from gaming and tech (Tech Radar) to homes (Homes & Garden) to beauty and fashion (Who What Wear) to B2B (SmartBrief), Future has established itself as one of the UK’s most successful publishers. (Its current market capitalization puts it at 8x the value of BuzzFeed.) But for its future growth, Future is betting heavily on the U.S. market, which CEO Zillah Byng-Thorne noted to me is five times the size of the UK. The U.S. alread...
Sep 06, 2022•31 min•Ep. 40
The business of hip hop is often overlooked, even though it's a massive business with outsized cultural influence. Dan Runcie saw this as an opportunity, starting Trapital in 2018. I wanted to talk to Dan about his approach to building an independent media brand. He’s already established himself and Trapital as an authority on the hip hop business. Trapital now has over 16,000 subscribers, with the publication supported almost entirely through sponsorships. Dan had earlier done a paid model, but...
Aug 16, 2022•41 min•Ep. 39
Begun as a meme account in 2017, Litquidity has amassed 1 million social media followers across Instagram, Twitter, LinkedIn and TikTok, specializing in the dark arts of “dank memes” that poke fun at the weird world of finance. The account, run pseudonymously by a former trader who goes by Lit, has spawned a daily news summary email ( Exec Sum ) with 160,000 subscribers, podcast ( Big Swinging Decks ), investment fund, merch and more, as part of a $2 million business. Some key takeaways: Find un...
Aug 09, 2022•47 min•Ep. 38
In February 2021, marketing software company HubSpot bought popular business newsletter The Hustle. Jordan DiPietro, a veteran of The Motley Fool, joined HubSpot to run The Hustle just after the acquisition, after having spent time advising the company. The Hustle now claims 2 million subscribers to its daily email, which gives a meme-friendly dive into business news topics. DiPietro said being part of the marketing operation of a brand helps The Hustle take the long view. “Being in the publishi...
Aug 02, 2022•1 hr 8 min•Ep. 37
One of the most solid areas of digital publishing is what’s become known as intent media. In the old days, we called this “SEO.” The basics are taking service content and applying it to algorithmic distribution (usually Google) and marrying it with performance advertising models like affiliate marketing programs that pay for sales leads. Ad Practitioners is another intent-based publisher in expansion mode.In late 2019, Ad Practitioners bought Money.com from Meredith with the plan to run its inte...
Jul 26, 2022•46 min•Ep. 36
Adam Ryan, former president of The Hustle and cofounder of Workweek , wants to rethink the B2B model. Workweek is banking on finding individuals – creators, if you will – to build audiences around. The bet is that individuals, particularly but not exclusively those who are practitioners in the field, can build deeper connections with audiences while benefiting from the infrastructure, services and halo effect of a parent media brand. Some highlights from our discussion: Don’t raise too much mone...
Jul 19, 2022•1 hr•Ep. 35
The pendulum always swings. Media regularly oscillates between periods of bundling and periods of unbundling. Bundles tend to rub people the wrong way because they feel they pay for stuff they don’t want. The downside is unbundling can be a complete hassle and the supposed savings quickly evaporate. Just look at what you’re paying now for various streaming services (themselves mini-bundles) instead of cable service. Inevitably, whether it’s the proliferation of newsletters or the many streaming ...
Jul 12, 2022•57 min•Ep. 34
Everyone loves a comeback, but few companies get them in the consumer internet business. ( Most companies have peaked and then set course on inevitable decline, with new owners either milking the asset on the way down or floundering unsuccessfully to reinvigorate the asset. That’s why it’s noteworthy what IAC has done with Internet 1.0 stalwart About.com. It was a company long past its peak in the first phase of digital publishing, having begun all the way back in 1994 as a place to find “expert...
Jun 28, 2022•47 min•Ep. 33
Katie Vanneck-Smith, formerly president of Dow Jones, co-founded Tortoise Media , a UK-based publisher dedicated to “slow news.” The problem she and her co-founders diagnosed: “The problem isn’t just fake news or junk news, because there’s a lot that’s good – it’s just that there’s so much of it, and so much of it is the same. In a hurry, partial and confusing. Too many newsrooms chasing the news, but missing the story.” The slow approach means that Tortoise confines itself to producing one podc...
Jun 21, 2022•28 min•Ep. 32
Outsider is a media and commerce brand focused on a particular view of “the American lifestyle” that, to me, takes its cues from the South, emphasizing college football, hunting, fishing, wraparound sunglasses and the like. Recently, Deirdre Lester moved from CRO of Barstool Sports to become the CEO of Outsider. The goal is similar to Barstool: Use personality-driven publishing – former NFL QB Jay Cutler is chief design officer at Outsider – to build a deep connection with a like-minded communit...
Jun 14, 2022•44 min•Ep. 31
The crypto winter has pitched the giddy excitement over the endless possibilities of Web3. The drumbeat of negativity hasn’t shaken Time president Keith Grossman’s confidence in Web3 providing a new path to sustainable business models. Time, now under the ownership of billionaires Marc and Linda Benioff, has become the most aggressive large publishing brand in exploring the possibilities of Web3. To date, Time has: Minted iconic covers as NFTs and generated nearly $500,000 in proceeds Collaborat...
Jun 07, 2022•50 min•Ep. 30
Morning Brew is a breakout success in digital media, turning an email newsletter of business news delivered with a witty tone, into a robust digital media business that now has over 4 million email subscribers, with another 1 million to its growing stable of vertical industry email newsletters .Now, Morning Brew is focused beyond its original product, the daily Morning Brew publication, by building a roster of five B2B offshoots, with two more in the works, in addition to podcasts and video show...
May 31, 2022•47 min•Ep. 29
Since its founding eight years ago, Permutive has bet on privacy being a key consideration in the future of ad tech. Permutive CEO Joe Root delves into what privacy-conscious advertising looks like – and if it’s possible. Highlights: The GDPR was a harbinger. Most U.S. companies didn’t understand how far-reaching the General Data Protection Regulation would be to them. The landmark move to rein in the collection and use of user data without consent is not without its critics, but it set in motio...
May 24, 2022•39 min•Ep. 28
Forbes is a unique brand that has global cultural cachet that’s managed the transition from being a magazine business to a mostly digital business, with an emphasis on building its direct revenue as well as its brand extensions. Now, it's looking to plot a future business in which consumer revenue take a far larger role.
May 17, 2022•36 min•Ep. 27
Why The Dispatch outgrew Substack Many would assume the most popular political publications on Substack are culture war agitators like Matt Taibbi and Glenn Greenwald. In fact, the top two slots are much milder publications: Letters from an American and The Dispatch . Taibbi and Greenwald will be moving up a slot soon, since The Dispatch is leaving Substack. Steve Hayes, one of the founders of The Dispatch in 2019, said the conservative news and commentary publication has outgrown the tools that...
May 12, 2022•49 min•Ep. 26
Quick request: Please take this 10-question audience survey that will help me better understand the makeup of The Rebooting’s readership in order to grow it as a sustainable business. I’ve already gotten many useful insights from the first wave of responses. Thanks to all who took the time. This week, I spoke to Anand Sanwal, CEO of CB Insights , about how it uses its popular email newsletter as a customer acquisition tool for a software business. Also: Where Quartz went astray and how access is...
May 03, 2022•42 min•Ep. 25
I decided to mix up the days for this newsletter and the format. You’ll now get The Rebooting twice a week, Tuesday and Thursday. The Tuesday email will continue with a new format that is a mix of topics, along with highlights from the podcast. I think this is a better approach than my original podcast-centric approach. But let me know your thoughts: [email protected] . Human ad products Building a good media product is endlessly difficult, particularly when it comes to advertising. Math give...
Apr 26, 2022•43 min•Ep. 24
The future of work is one of the most fertile topic areas out there. The pandemic caused a reset, when combined with the labor shortage coming out of Covid, and it’s not going back to normal. The Atlantic’s Derek Thompson cited statistics that show basically every industry halted by Covid – from restaurants to cruises – has more or less returned to normal, except ones like movie theaters and offices . I’ve long thought the boss class is kidding themselves about strongarming people back to dreary...
Apr 18, 2022•42 min•Ep. 23
Check out the full episode on Apple Podcasts or Spotify . Let me know what you think: [email protected] . The war in Ukraine is now six weeks old, likely to drag on even longer. It’s important to consider how vital an independent and free media is to a free and independent Ukraine. I visited Kyiv in the fall, and I wrote about how the media operates in a far more complicated context there than in a place like the U.S. This challenge got greater in the wake of an invasion that’s mostly ground ...
Apr 11, 2022•36 min•Ep. 22
