The Rebooting Show

On this week’s episode of The Rebooting Show, I spoke to Tomiwa Aladekomo, CEO of Big Cabal, a Nigerian digital media company that’s home to a pair of properties: Tech Cabal, which I describe as similar to TechCrunch but with more memes and Zikoko, a B...

The Rebooting recently wrapped up its second research project in collaboration with BlueConic. Patrick Crane, vp of sales at BlueConic, joined me on The Rebooting Show to discuss the state of subscriptions at publishers and the maturation of the market...

Bridget Williams is a veteran of the industry. I first got to know Bridget when she was at Business Insider prior to heading to Food52 before landing at Hearst Newspapers in tk, where she is chief commercial officer. On this week’s episode of The Reboo...

The Guardian has used voluntary reader contributions as a bulwark of its unique model that blends philanthropy, advertising and voluntary contributions. In the U.S., The Guardian now generates 57%, or $33 million, of its revenue from voluntary contribu...

Jeff Selingo spent eight years at the Chronicle of Higher Education, serving as editor in chief and editorial director, before setting off on his own path. Jeff and I have traded notes on the independent path over the years, and I wanted to have him on...

Blockworks, founded as a crypto events company in 2018, has rode these ups and downs. It began in the face of a crypto pullback with the thesis that crypto would become a major asset class and as it grew, institutional investors would need a credible s...

Defector is a worker-owned media company that was born out of disillusionment with the tradeoffs the digital media ecosystem often requires (or at least incentivizes). Instead of chasing traffic, Defector relies on a subscription model for a small but ...

My former colleague Mike Shields of Next in Media joins me to discuss what to make of Advertising Week, which is mostly a PR vehicle but a useful gauge of the prevailing winds of the media and advertising worlds.

On a crossover episode of The Rebooting Show and People vs Algorithms, Alex Schleifer and I discuss the end of the zero-interest rate policy era and how it will lead to cascading changes in tech and media.

Video is viewed paradoxically by publishers. They see budgets shifting to sight, sound and motion. Video ads, formerly known as TV spots, were always valued by advertisers far more than a standard display ad, no matter what efforts were made to gussy t...

Before the Lumascape, there was another go-to conference and pitch deck slide for anyone betting on what was then called web advertising. The slide, updated annually by the financial analyst Mary Meeker, showed twin bar charts of time spent and budget ...

Five cents. That’s how much general-news newsletter 1440 makes each time one of its 3 million subscribers opens one of its daily emails. Say what you want about scale, but nickels can add up when the multiplier is in the millions. After paying for the ...

Founded a decade ago, Team Whistle is a survivor. It sprang to life as a wave of multichannel networks that filled the need of aggregating YouTube properties to make buying easier. The biggest problem of the MCN model is that it takes a difficult busin...

The digital advertising system is in the midst of a shift, from an over-reliance on collecting vast amounts of data to crunch to do one-to-one targeting – dog owners getting dog food ads, cat owners get cat food ads – to a new landscape that gives peop...

This is a bonus episode of The Rebooting Show, featuring a conversation I had on the People vs Algorithms podcast. We discuss why the conventions of media are giving way to new formats that dispense with the artifice in favor of something approximating...

Rich Routman is a veteran of the sports media industry. He recalls how if an advertiser discussed a cost-per-action deal with a major sports media company as recently as five years ago, the media executives would "run out of the room." That all changed...

Bustle was founded a decade ago in a far different media environment, as big digital media companies, flush with VC cash, scrambled to acquire the biggest audiences possible. The supposition that those with the biggest uniques would be handsomely rewar...

Puck launched two years ago, heralded as Vanity Fair for the Substack era. A big part of the pitch was a subscription model. But like others, such as Punchbowl, Puck has found that its subscription business, with its direct connections, and vertical fo...

CJ Gustafson is one of the rare people who is both immersed in his field but does not suffer from the tyranny of knowledge. CJ uses memes and a conversational style with Mostly Metrics to address what those outside corporate finance would consider dry ...

Literally Media -- home to Cracked, I Know Your Meme and Cheezburger -- isn't going to fight creators. Instead, it's partnering with them to do everything from launch channels on new platforms, get access to brand partnerships and be part of live event...

This week, I spoke to Parquor’s Andrew Rosen, a former Vicom exec turned media analyst, to unpack Hollywood’s weird summer of transition. The challenge for media companies is moving from a wholesale model to a retail model. Andrew sees a group of leade...

Bloomberg Media CEO Scott Havens sees AI as both challenge and opportunity for publishers, who at this point are used to rapid changes to how their content is distributed. The challenge is how AI is poised to have the biggest impact on search since Goo...

On this week’s episode of The Rebooting Show, I was joined by Hearst’s David Carey to discuss the resilience of so-called legacy media businesses. David returned to Hearst in 2019 as svp of public affairs and communications after a stint at Harvard, pi...

At Dotdash Meredith, CEO Neil Vogel remembers sitting around with his management team, after $2 million in “incremental” ad revenue appeared, and wondering, “Have we hit peak Dotdash?” “We had a really great formula: make incredible content, make reall...

Last week, at The New Attention Economy in Cannes, I discussed the notion of “influencer journalism” with Semafor co-founder and editor-in-chief Ben Smith and Puck co-founder and COO Liz Gough. Some highlights from the session: The creator economy is a...

Christine Cook joined Bloomberg Media in March as global chief revenue officer. We spoke about reasons for media optimism, how AI is an opportunity (and a threat), and how Bloomberg is approaching programmatic as the data landscape changes.

At The New Attention Economy’s final day in Cannes, we turned the spotlight on AI with a closing session featuring Rei Inamoto, CEO of I&Co, and Myra Nussbaum, chief creative officer and president of Havas, assessed the impact AI will have on creativit...

For Hearst global chief revenue officer Lisa Howard, the shift to focus mostly on subscriptions at many publishers obscures the reality that advertising will continue to be the dominant monetization form for most media, including Hearst. Lisa discussed...

In a live recording of The Rebooting Show from Cannes, Kirk McDonald, CEO of GroupM North America, seemed to wonder whether we’ve all talked ourselves into a downturn that wasn’t, "For the first half of this year, we saw behavior that anticipated a cra...

Anna Palmer is a journalist turned startup CEO. Along with Jake Sherman and John Bresnahan, she founded Punchbowl News in January 2021, just in time for the assault on the Capitol. Punchbowl’s obsessive focus on the Capitol, and business model that com...

This episode is sponsored by Kerv, which uses artificial intelligence to identify objects within video and match them to databases, enabling for, among other uses, the creation of interactive “shoppable video” that embeds commerce in entertainment Kerv...

The Rebooting show is sponsored by Kerv Interactive, an AI-powered video creative technology that creates shoppable and immersive experiences within any video content. Learn more...... On this week’s episode of The Rebooting Show, Bob Guterma, CEO of T...

⁠Thanks to Kerv ⁠ for sponsoring this episode. To see Kerv's technology at work, ⁠check out Peacock's MustShop TV⁠. If you’ll be on the Cote d’Azur next month. The New Attention Economy, presented by Kerv, will have speakers from the Financial Times, U...

Last week, I was in Chicago to attend the Omeda OX6 conference, where I recorded a live version of The Rebooting Show podcast. Jessica Sibley, CEO of Time, joined me to discuss her first six months at the 100-year-old publishing brand. Among the issues...

Will Hayward, the CEO of Private Media, an independent publishing company in Australia that publishes several titles, including politics-focused Crikey, recently faced the intriguing and likely slightly terrifying experience of being the subject of a d...

When I sent over topics for the latest episode of The Rebooting show to Axios’s Sara Fischer and Vox’s Peter Kafka, Peter replied with an editorial note: “maybe something deliberately upbeat to counteract a very gloomy pod.” Listeners, we tried, but jo...

The Bitter Southerner began as a passion project for a group of natives to the South who were, well, a bit bitter about how it was often caricatured or reduced to its historical legacy as the birthplace of American slavery. That’s a past that is unfort...

News on its own is often not a great business. Advertisers want to avoid it, and the humans required to recreate the product every day drive up costs, and subscriptions can only go so far. New York University journalism professor and media analyst Jay ...

Brian Hanly, CEO of Bullish Studio, is creating media brands from memes, working with a stable of finance meme accounts in particular to build media properties. I got to know Brian over the pandemic, and quickly became fascinated by Bullish’s business....

Last Thursday, I spoke to Substack CEO Chris Best to get a better understanding of where the company is going. We recorded the interview before Elon Musk threw a temper tantrum over Substack's coming Twitter competitor. Chris and I spoke about a couple...

Joe Ruffalo was recently named senior vice president and general manager of Nexstar's NewsNation digital operations and The Hill. At both, Nexstar is looking to occupy a lane of "non-partisan" news outlets, betting on a middle ground that seems to have...

Claire Atkinson, chief media correspondent at Insider, has long experience covering the ins and outs of the media industry. In this episode, we discuss the state of affairs as different parts of the media business are between eras. What’s next for Vice...

Dave Finocchio was CEO of Bleacher Report, one of the success stories of the last era of digital publishing. Dave is back in publishing with The Cool Down, which aims to be a mainstream publishing brand for climate conscious consumers. We discuss the l...

Patrick Trousdale started The Daily Upside in 2019 after working in investment banking at Guggenheim. Patrick saw the success Morning Brew and The Hustle had with newsletters that produced business, finance and entrepreneurial news for younger audience...

Axel Bard Bringéus is co-founder of Informed, a Berlin-based company with $5.3 million in backing that’s building a service for subscribers to pay for access to paywalled content from top tier publishers like Bloomberg, The Economist, The Financial Tim...

On this week’s episode of The Rebooting Show, I spoke to Darren Samuelsohn, a longtime politician reporter who was most recently head of Insider’s ill-fated DC bureau. Darren and I spoke about his new newsletter devoted to journalism, the decision to t...

Bill Bishop likes to make clear he’s not a journalist. Instead, he’s a China analyst who brings his deep understanding of the country to an English-speaking language through his newsletter, Sinocism. In 2017, Bill became the “original Substacker” after...

The Dispatch is a three-year-old publication focused on bringing fact-based politics news and analysis from a center-right perspective. Steve Hayes, CEO of The Dispatch, joined the podcast to discuss how it's managed to climb to near 40,000 paying subs...

I had a conversation with Krystal Olivieri, global chief innovation officer at GroupM, about whether advertisers would conveniently forget all those promises they made during flush times to support local news. The takeaway: Advertisers will cut here an...

Substack’s Reid DeRamus talks about growing newsletter audiences. Reid and I have spoken for the past two years on this topic, going back to before Substack bought his company Yem, which was focused on building a growth engine for newsletter writers. T...