

The Rebooting Show
Brian Morrissey
The Rebooting Show gets into the weeds with those building and operating media businesses, giving an open view into how the smartest people in the media business are building sustainable media businesses. https://www.therebooting.com/ (www.therebooting.com)
Episodes
Mentioned books

Sep 6, 2022 • 31min
The Future playbook for sustainable publishing
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. already represents 35% of Future’s audience as well as 38% of its revenue. Byng-Thorne is something of a newcomer to the media business. An accountant by training, she joined Future in 2014 as its interim CFO and soon was appointed CEO, tasked with turning around a magazine publisher that, like its peers, was struggling to make a transition from print to digital. Her turnaround plan – she initially cut 40% of employees as the company was recording a £35 million loss in 2014 – has become something of legend, setting the stage for a remarkable financial turnaround as Future became an early adopter of using its niche focus in high-intent categories to drive transactions. The shift to commerce – it is now 34% percent of Future’s revenue – was informed by her previous time at Auto Trader, which made the leap from car magazine to marketplace. Zillah recounted how her first year at Future, which was on what she describes as a decade-long decline, the key question to answer was: “What’s our right to exist?” Her conclusion: Put the company on firmer financial footing, double down on the expertise embedded in the brands. Future was struggling with the transition from print to digital when Byng-Thorne took over. Beyond that, the diversification needed to be done on the digital side as well since many publishers were overly reliant on digital advertising. Commerce was a way to make money from audiences without the ups and downs inherent to the ad business. Future’s revenue is now roughly split in thirds among advertising, commerce and direct revenue from the audience. Having an acquisitions playbook. Future has spent over £1 billion on acquiring companies since Byng-Thorne took charge. In the past year alone, it has acquired four companies, including Who What Wear and Dennis Publishing and MarieClaire.com. “We integrate fully. I know some of our competitors don't all integrate fully, but for us, it was really important that it's one Future, one tech system, one sales team, one way of working.” This episode was produced by Jay Sparks from Pod Help Us. If you have podcast production needs, get in touch with Jay.

Aug 16, 2022 • 41min
Trapital's Dan Runcie on building a brand at the intersection of business and hip hop
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 pivoted to free when realizing he could reach far more people without the friction of a paywall – and a value proposition that appeals to sponsors like Moonpay, Convertkit and Alts..Some takeaways from our conversation:Hip hop punches above its weight. There’s a school of thought that niche business publications are best in “unsexy” areas, as Industry Dive showed in its focus on big nuts-and-bolts business sectors. But cultural industries have influence beyond their size. Trapital isn’t about news. Dan has made a point of saying what he does is not journalism but business analysis. Part of that is to be clear the product isn’t a tool for keeping up to date on the ins and outs of the industry. Instead of the play-by-play, Trapital focuses on the context with Stratchery-like essays on topics like “how The Weeknd mastered his brand” and “Beyonce’s streaming strategy, explained.”The pivot from subscriptions. For the past couple years, all roads have led to subscriptions in publishing as the travails of the big digital publishers have cast a pall on the ad model. But as Industry Dive, Axios and others have shown, advertising can be the great focal point of a publishing business model – if the audience is a group that’s hard to reach and valuable. In 2018, Trapital scrapped its initial paid model. Often subscriptions are painted as a set-it-and-forget-it option, but making money is hard no matter the model, and subscriptions require constant selling and marketing. Dan saw as a one-person operation this was cutting into his focus. Instead, Trapital focused on an “influence” model that initially treated the newsletter and podcast as lead gen for consulting, while adding in advertising and moving into investing.Going beyond solo. Trapital is working as a one–person business, but Dan wants to expand beyond just himself. The challenge is how to do this without losing the personal touch since Trapital’s brand is very tied into Dan’s perspective.

Aug 9, 2022 • 47min
How Litquidity memed his way to a $2m media business
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 underserved audiences. The world is not short on finance news. But what Lit found as a young investment analyst is that little of the coverage captured the experience of being in the (well-compensated) rank and file of finance. “One thing that I felt was lacking was real insider baseball-type humor,” Lit said. “You look at CNBC or Bloomberg, it's probably people who aren't insiders that are reporting on the news or talking about the stock markets.”Memes are top of the funnel. Litquidity began as a meme account, attracting advertisers as its revenue source. But Lit felt that could only go so far – “I don't think they're like the highest value monetization paths to go through because you'll saturate your audience with ads, and people hate ads” – so he spun off Exec Sum, a newsletter that pithily summarizes the days finance and markets news. And more importantly, provides valuable surface area for high-value ads. “I really thought of how can I provide value to my audience in a way that would also make sense monetarily.”Publishing and investing mesh. Like Packy McCormick and Anthony Pompliano, Lit sees the opportunity to use his publishing reach as a way to expand his investmenting by raising a fund. Eventually, he sees Liquidity as more of an investment fund with a publishing arm rather than vice versa. “That's how I want that to be viewed going forward as I continue to build out the credibility and the track record.”Expanding beyond a personal brand is hard. Recently, Litquidity lost its “only employee” – there are a handful of part-timers – when Mark Moran split to focus on an investor relations play, Equity Animal. Expanding a media company tied to a person, even one who uses a pseudonym, is tricky. “One of the things that I found difficult was having the entire brand being ied by my humor and my voice,” he said. “If you start to introduce other creators or elements who don't fit that, then it starts to dilute that brand.”

Aug 2, 2022 • 1h 8min
The Hustle's Jordan DiPietro on being a publisher inside a software company
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 publishing game, when you're focused on ad dollars, that is a grind. The Hustle had [subscription service] Trends and, and certainly our plan was to accelerate the growth of Trends, but still a lot of our revenue came from advertising and that's just a different beast. Once it was acquired by HubSpot, the pressure to sell external ads was off, but instead to focus on being our own media buyer was attractive, especially knowing the business model behind HubSpot and the capital and the resources that HubSpot had.”Thanks to Bombora for supporting The Rebooting and sponsoring this episode.

Jul 26, 2022 • 46min
Money's Greg Powel on intent media
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 intent playbook with the personal finance brand. That means more lists of the best credit cards, best savings accounts and, yes, the best pet insurance companies. The entire company, which is based in Dorado, Puerto Rico, is 160 people and generates over $100 million in annual revenue.Some takeaways from Ad Practitioner CEO Greg Powel:Arbitrage works. Paid acquisition is an important part of the Ad Practitioners model – it has spent about $500 million on Google ads in its history. Search for “best credit cards 2022,” and you’ll see why. This kind of high-value intent traffic is very valuable – credit card leads can fetch $100 – that it makes sense. Bad sites are a business model problem. Publishers with terrible websites do not have a tech problem; they have a business model problem. The attention-based ad model for general audiences is hard to make work without adopting, well, adversarial tactics. The performance ad model of intent media aligns incentives better since the publisher wants people to get the information they need rather than hijack their attention elsewhere.Algorithm dependence is a manageable risk. To put it mildly, there’s a checkered history of publishers relying on algorithms for the overwhelming majority of their distribution. Ad Practitioners look to mitigate that dependence with its paid acquisition as well as licensing deals with the likes of MSN and others. While new channels like TikTok could catch on to eat into Google’s search share, Greg sees the biggest threat of disruption coming from Apple, since its devices are the originator of a big chunk of Google searches.

Jul 19, 2022 • 1h
Workweek's Adam Ryan on why B2B shouldn't be boring
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 money. Adam spent part of his career at Spiceworks, a professional network for IT professionals. The company identified an underserved community and executed on the opportunity, only to have an unsatisfying outcome. “It was a great company, bad cap table,” Adam said. “They actually made a ton of money. They didn't need to raise that much money. And then because they did, they made terrible decisions, long term.”You can be professional and have personality. Workweek is leaning on its network of 19 creators to be front and center. It doesn’t have an editor-in-chief and instead relies on its newsletter writers to chart their own path that hews closely to what motivates them. Nicole Casperson, for instance, writes WTFintech and focuses often on diversity and inclusion issues that are important to her personally.Sector expertise is critical. Not all Workweek creators worked in the fields they cover, but many do. Workweek writer Nik Sharma, for instance, is a DTC marketer. This hands-on familiarity with the issues in these fields in invaluable, so long as it is also married with the ability to clearly communicate and consistently produce valuable pieces. “The reason why [B2B content] is kind of boring is because you have a lot of people that have never done those jobs,” he said . “They're just like listening and regurgitating. They're not like coming from a point of action.”Paid acquisition is more than a shortcut. Publishers used to have an aversion to admitting to buying traffic. I can remember BuzzFeed making sure to point out it only bought ads for its sponsor content, not editorial. But Adam saw how an effective paid audience development strategy can accelerate growth. For instance, Workweek’s The Marketing Millennials property grew by 7,000 newsletter subscribers organically in seven weeks while paid acquisition added 20,000. So long as a company is confident in its cost per subscriber number, and is focused on quality of acquired subscribers, paid acquisition is an important tool. Overall, Workweek pays to acquire nearly half its overall list at an average cost of $10 per subscriber.You need connective tissue. Workweek has cast a broad net in its first eight months of existence, with newsletters focused on everything from cannabis to fin tech to memes to franchises to marketing. It has since refined the model around “pods” of core categories. Workweek has clusters around areas like startups and investing, health, marketing and fintech. “It just allowed the business to focus on marketing allows our business to essentially have more efficiencies,” Adam said.

Jul 12, 2022 • 57min
Human Ventures' Joe Marchese in defense of the bundle
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 products, we’ll see rebundling take off.“The bundle was the absolute worst form of entertainment delivery, except for every other one,” said Human Ventures executive chairman Joe Marchese. “Consumers are looking for a rebundle and these streamers are gonna have some sort of rebundle coming. News and Substack has some sort of rebundle coming. Everything that's old is gonna be new again over the next couple of months.”Other topics:Media is often a terrible standalone business but is good support for other businesses. The TV business is now dominated by tech companies, a trend likely to continue. That isn’t particularly new. “Media has historically been owned by non-media businesses,” Joe notes, going back to early radio and then cable systems owning TV networks. “The business of media has outsized influence but undersized monetization.” The result: “I don’t know the media business works at scale without alternative models.”The "permission to curate" is powerful. In a world of near-infinite media choices, people need some way to make sense of what’s good and what’s bad. That’s where trust comes into play. People can turn to algorithms like Google’s or Facebook’s to make sense of what’s important to them, or they can turn to publishing brands and individual brands. “Brands matter for the curation of goods and services so that people don't have the paralysis of infinite choice,” Joe said.Not everything is performance advertising. With ample data, sophisticated targeting and analytics, it can sometimes seem that brand advertising is an anachronism as the media world shifts firmly to “performance advertising,” or what used to be known as direct response. “In a world where we have dynamic targeting and we know what each household is watching, the advertising experience is actually worse,” Joe said. “How did we get worse at advertising in a CTV advertising environment than broadcast television 40 years ago?”

Jun 28, 2022 • 47min
Neil Vogel on Dotdash Meredith's best, fastest, fewest strategy
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” answers. Some takeaways from our conversation:Having a good user experience doesn’t have to come at the expense of the business. Media is hard. I always mention how difficult it is to satisfy different constituencies: audience, advertisers, algorithms. Dotdash has proven that you can have fewer ads, faster sites and better content and still make more money.Print still has an important role. Everyone likes to call things dead, and print isn’t going to be the driver of many media businesses going forward. But it still plays a role. I think it’s a good sign that someone like Neil is bullish on print, run efficiently, doing the job of being a statement of the brand.Driving transactions is critical, but maybe not building products. There’s lots of talk of commerce media here in Cannes. Publishers have seen their commerce businesses as bright spots. Dotdash has a large chunk of their business in driving transactions. Still, Neil strikes a note of caution when discussing turning that into actually making products versus passing on customer to product companies. These are often different businesses.

Jun 21, 2022 • 28min
Tortoise Media's Katie Vanneck-Smith on slow news
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 podcast episode a day, one daily newsletter (in email and audio), one multi-part series per month and one book a quarter. Katie discussed the Tortoise approach in an on-stage conversation at the FIPP World Congress in Cascais, Portugal.

Jun 14, 2022 • 44min
Outsider CEO Deirdre Lester on building a lifestyle brand
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 community, then complement the media with commerce operations. Some key takeaways from our conversation:Finding the sweet spot between individuals and institutions is a big opportunity. The unbundling of publishing has put the focus on individual creators, but there are only so many Mr. Beasts in the world. The more tangible opportunity is the Goldilocks approach with institutional brands that can tap into the power of individuals to establish tight ties with an audience. Outsider is doing that with Cutler and popular podcaster Marty Smith.Lifestyle publishing brands are more about AOV than CPM. Publishing has been stuck in a default mindset that the audience either pays with data and attention to ads or with money through subscriptions. Commerce – real commerce, not just affiliate links – offers a third way to build product companies with media used for efficient distribution and, ideally, premium pricing power based on the credibility established with customers.Doing both media and products is hard. These are different businesses with different dynamics. The rough patch hit by Food52, a prime example of publishers pivoting to product, shows how difficult it is to manage both publishing and products. Publishing is all about managing conflicts, and that can get even messier when publishing is in the service of moving products.


