Inn this episode, The Daily Upside's Patrick Trousdale explains how niche products like Advisor Upside and ETF Upside are helping... more

Stakeholder media is how a media company can stay influential and build a real business—especially now, when scaled ad models... more

An enduring challenge of the media business is finding leverage in models. This used to be fairly straightforward. Newspapers had... more

Morning Brew CEO Robert Dippell joins me to break down the fundamental differences between consumer and B2B media, why so... more

Adam Ryan, CEO of Workweek, joined me this week to discuss his recent warning that the newsletter sector is overheated.... more

Sean Griffey, until recently the CEO of Industry Dive, joined me on The Rebooting Show to discuss the big things... more

BuzzFeed has always been a company that plays with the boundaries of media, technology, and internet culture. From its early... more

The worlds of TV and internet publishing operated separately. The platforms, the dynamics and even the language used was completely... more

This week, I'm joined by Pete Pachal, a publishing veteran who writes The Media Copilot newsletter that focuses on the... more

This is set up to be a banner year for alternative media. Axios senior media reporter Sara Fischer joined me... more

On this week’s episode of The Rebooting Show, I was joined by Alex Kantrowitz, who writes the Big Technology newsletter... more

Mike Mallazzo, writer of the reliably excellent Zero Clicks newsletter from Martech Record and a veteran of digital publishing and... more

In this live podcast, I spoke to Imtiaz Patel, chief consumer officer; Kristin Roberts, chief content officer; Jason Taylor, chief... more

At Metro, the free London newspaper, the comedown from the traffic era was jarring. At the end of 2022, with... more

Stagwell CEO Mark Penn is a veteran of politics. In this discussion, he examines how shifting audience behaviors and trust... more

AI-powered search engines have clawed a foothold in the critical search market that controls distribution on the open web. Media... more

Blockworks CEO Jason Yanowitz discusses how Blockworks has evolved the company from an events business to podcast network to news... more

Defector Media, the sports and culture publication launched four years ago by former Deadspin writers, is an example of the... more

I was joined by Reid DeRamus to discuss the strategic and tactical decisions that go into building an independent media... more

In this Spotlight episode, Josh Brandau, CEO of The Rebooting partner Nota, discusses how AI can be a critical tool... more

Fitt Insider, a media brand for the fitness and wellness industry, is a good example of the type of media... more

This week, I was joined by one of my favorite media entrepreneurs, Adam White. Adam has built Front Office Sports... more

Adam Mendelsohn operates at the nexus of sports, media, business and culture. Adam is a longtime advisor to LeBron James... more

This week marks an important moment in the history of digital advertising as the U.S. Department of Justice presses its... more

Scott Messer is founder of media advisory firm Messer Media and former svp of media at Leaf Group. Scott is... more

In a spotlight episode of The Rebooting Show, I spoke with Affinity Global CEO Lavin Punjabi for his view of... more

On this week’s episode of The Rebooting Show, I was joined by Ana Andjelic,  a veteran brand executive and writer... more

This week, we are wrapping up a series on The Rebooting Show that examines the role of product at a... more

At the Media Product Forum earlier this month, I spoke with Gannett head of product Renn Turiano, Hearst Newspapers chief... more

At last week’s Media Product Forum, which The Rebooting held in collaboration with WordPress VIP, I had a discussion with... more

In a session recorded at The Media Product Forum in NYC, Bloomberg Media global head of product Marissa Zanetti-Crume shares... more

In a discussion held in Cannes, I sat down with Jason White, chief product and technology officer at The Arena... more

In a session recorded at the Cannes Lions, Hearst Magazines CRO Lisa Ryan and Jen Dorre join the show to... more

In this episode recorded at the Dotdash Meredith villa in Cannes, Dotdash Meredith CEO Neil Vogel and Axios senior media... more

This episode from Cannes of The Rebooting Show, presented by Outbrain, features David Kostman (CEO of Outbrain), Kate Scott-Dawkins (Global... more

Semafor editor in chief Ben Smith sees a fragmenting media landscape and impatient owners running headlong into the peculiarities of... more

In the wake of Jeff Bezos buying The Washington Post in 2013 and the heady “Democracy Dies in Darkness” days... more

Publishing is shifting from prioritizing breadth to rewarding depth. That starts with understanding the audience — and its segments —... more

Scott Porch, founder of Big IP, which operates the business side of several popular lifestyle podcasts like The John Campea... more

Detailed.com's Glen Allsop breaks down the massive Google update roiling the publishing world as Google attempts to gain control of... more

Emma Tucker was named the editor-in-chief of The Wall Street Journal (and Dow Jones Newswires) in early 2023. She was... more

Jay Rosen, a professor of journalism at NYU, discusses the diminished state of the industry, promising nonprofit models and new... more

I’m joined by Matt Cronin, founding partner at House of Kaizen, which works with publishers and other companies with recurring... more

On this week’s episode of The Rebooting Show, I spoke to writer John McDermott about his recent expose of self-help... more

Stephanie Kaplan Lewis founded Her Campus in 2009 with Annie Wang, and Windsor Western as college undergraduates. They saw a... more

Matt Cronin is a founding partner at https://www.houseofkaizen.com/rebooting (House of Kaizen), a consultancy that works with publishers and other... more

Mosheh Oinounou, a broadcast news veteran, started posting summaries of the news of the day during the early days of... more

The Rebooting is launching paid memberships. All the details are on therebooting.com. In this episode, I speak to my collaborator... more

Digital media veteran Scott Messer discusses the structural changes to the publishing business, from the deprecation of the third-party cookie... more

This week on The Rebooting Show, I spoke to The Juggernaut’s founder and CEO Snigda Sur. We discussed the need... more

This week, I caught up with Larry Fitzgibbon, the CEO of Tastemade. I think of Tastemade as an original digital... more

The media business in 2024 To kick off the year on The Rebooting Show, I spoke to Axios senior media reporter... more

I spoke to Matt Cronin, founding partner of House of Kaizen, a consultancy that works with publishers on their subscription... more

Matt Reustle, CEO of Colossus, a business-focused podcasting network that’s home to Invest Like the Best, Business Breakdowns and Founders,... more

On this week’s episode of The Rebooting Show, I spoke to Tomiwa Aladekomo, CEO of Big Cabal, a Nigerian digital... more

The Rebooting recently wrapped up its second research project in collaboration with BlueConic. Patrick Crane, vp of sales at BlueConic,... more

Bridget Williams is a veteran of the industry. I first got to know Bridget when she was at Business Insider... more

The Guardian has used voluntary reader contributions as a bulwark of its unique model that blends philanthropy, advertising and voluntary... more

Jeff Selingo spent eight years at the Chronicle of Higher Education, serving as editor in chief and editorial director, before... more

https://blockworks.co/ (Blockworks), founded as a crypto events company in 2018, has rode these ups and downs. It began in the... more

Defector is a worker-owned media company that was born out of disillusionment with the tradeoffs the digital media ecosystem often... more

My former colleague Mike Shields of Next in Media joins me to discuss what to make of Advertising Week, which... more

On a crossover episode of The Rebooting Show and People vs Algorithms, Alex Schleifer and I discuss the end of... more

Video is viewed paradoxically by publishers. They see budgets shifting to sight, sound and motion. Video ads, formerly known as... more

Before the Lumascape, there was another go-to conference and pitch deck slide for anyone betting on what was then called... more

Five cents. That’s how much https://join1440.com/ (general-news newsletter 1440) makes each time one of its 3 million subscribers opens one... more

Founded a decade ago, Team Whistle is a survivor. It sprang to life as a wave of multichannel networks that... more

The digital advertising system is in the midst of a shift, from an over-reliance on collecting vast amounts of data... more

This is a bonus episode of The Rebooting Show, featuring a conversation I had on the People vs Algorithms podcast.... more

Rich Routman is a veteran of the sports media industry. He recalls how if an advertiser discussed a cost-per-action deal... more

Bustle was founded a decade ago in a far different media environment, as big digital media companies, flush with VC... more

Puck launched two years ago, heralded as Vanity Fair for the Substack era. A big part of the pitch was... more

CJ Gustafson is one of the rare people who is both immersed in his field but does not suffer from... more

Literally Media -- home to Cracked, I Know Your Meme and Cheezburger -- isn't going to fight creators. Instead, it's... more

This week, I spoke to Parquor’s Andrew Rosen, a former Vicom exec turned media analyst, to unpack Hollywood’s weird summer... more

Bloomberg Media CEO Scott Havens sees AI as both challenge and opportunity for publishers, who at this point are used... more

On this week’s episode of https://pod.link/1595625177 (The Rebooting Show), I was joined by Hearst’s David Carey to discuss the resilience... more

At Dotdash Meredith, CEO Neil Vogel remembers sitting around with his management team, after $2 million in “incremental” ad revenue... more

Last week, at The New Attention Economy in Cannes, I discussed the notion of “influencer journalism” with Semafor co-founder and... more

Christine Cook joined Bloomberg Media in March as global chief revenue officer. We spoke about reasons for media optimism, how... more

At The New Attention Economy’s final day in Cannes, we turned the spotlight on AI with a closing session featuring... more

For Hearst global chief revenue officer Lisa Howard, the shift to focus mostly on subscriptions at many publishers obscures the... more

In a live recording of The Rebooting Show from Cannes, Kirk McDonald, CEO of GroupM North America, seemed to wonder... more

Anna Palmer is a journalist turned startup CEO. Along with Jake Sherman and John Bresnahan, she founded Punchbowl News in... more

This episode is sponsored by https://kervit.com/ (Kerv), which uses artificial intelligence to identify objects within video and match them to... more

The Rebooting show is sponsored by Kerv Interactive, an AI-powered video creative technology that creates shoppable and immersive experiences within... more

⁠Thanks to Kerv ⁠for sponsoring this episode. To see Kerv's technology at work, ⁠check out Peacock's MustShop TV⁠.If you’ll be... more

Last week, I was in Chicago to attend the Omeda OX6 conference, where I recorded a live version of The... more

Will Hayward, the CEO of Private Media, an independent publishing company in Australia that publishes several titles, including https://www.crikey.com.au/ (politics-focused... more

When I sent over topics for the latest episode of The Rebooting show to Axios’s Sara Fischer and Vox’s Peter... more

https://bittersoutherner.com/ (The Bitter Southerner) began as a passion project for a group of natives to the South who were, well,... more

News on its own is often not a great business. Advertisers want to avoid it, and the humans required to... more

Brian Hanly, CEO of Bullish Studio, is creating media brands from memes, working with a stable of finance meme accounts... more

Last Thursday, I spoke to Substack CEO Chris Best to get a better understanding of where the company is going.... more

Joe Ruffalo was recently named senior vice president and general manager of Nexstar's NewsNation digital operations and The Hill. At... more

Claire Atkinson, chief media correspondent at Insider, has long experience covering the ins and outs of the media industry. In... more

Dave Finocchio was CEO of Bleacher Report, one of the success stories of the last era of digital publishing. Dave... more

Patrick Trousdale started https://bit.ly/3Is4kDu (The Daily Upside) in 2019 after working in investment banking at Guggenheim. Patrick saw the success... more

Axel Bard Bringéus is co-founder of https://www.informed.so/ (Informed), a Berlin-based companyhttps://www.startupreporter.eu/informed/ ( with $5.3 million in backing) that’s building a... more

On this week’s episode of The Rebooting Show, I spoke to Darren Samuelsohn, a longtime politician reporter who was most... more

Bill Bishop likes to make clear he’s not a journalist. Instead, he’s a China analyst who brings his deep understanding... more

The Dispatch is a three-year-old publication focused on bringing fact-based politics news and analysis from a center-right perspective. Steve Hayes,... more

I had a conversation with Krystal Olivieri, global chief innovation officer at GroupM, about whether advertisers would conveniently forget all... more

Substack’s Reid DeRamus talks about growing newsletter audiences. Reid and I have spoken for the past two years on this... more

Scott Brodbeck got into local news a dozen years ago, after working in local broadcast news in Washington DC. “I... more

In 2016, Max Kabat and Maise Crow moved to Marfa, a small arts town in west Texas, and a couple... more

There’s the understandable urge to “do something” to fix the difficult situation the news business finds itself in. Government intervention... more

Joshi Herrmann is the founder of https://manchestermill.co.uk/ (The Mill), a newsletter focused on Manchester – England, not New Hampshire, for... more

The Athletic started in 2015 with a simple proposition: It would produce the highest quality sports journalism with a subscription... more

Ari Paparo is a longtime ad tech veteran, not to mention holding the disputed title as Funniest Person in Ad... more

Alex Kantrowitz is the founder of Big Technology, an independent publication focused on he immense impact of tech companies on... more

Semafor, backed by $25 million in private investment, has (finally) launched, marking possibly the most ambitious attempt in recent years... more

6am City is turning to the newsletter to build out a network of 25 local news publications it says have... more

In 2014, Bonnie Kintzer was named CEO of Readers Digest Association, becoming its fourth CEO in three years as it... more

Casey Newton, a former writer at The Verge, started https://www.platformer.news/ (Platformer) to cover the societal impact of the most powerful... more

This is a preview of a new weekly podcast I’m doing with Troy Young. The People vs Algorithms podcast will... more

https://www.flyingmag.com/ (Flying), a 95-year-old magazine publisher focused on amateur pilots, is on this path. Craig Fuller, CEO of Freightwaves, bought... more

Future is a collection of over 200 specialist titles that range from gaming and tech (Tech Radar) to homes (Homes... more

The business of hip hop is often overlooked, even though it's a massive business with outsized cultural influence. Dan Runcie... more