The Rebooting Show

This week on The Rebooting Show, I spoke to The Juggernaut’s founder and CEO Snigda Sur. We discussed the need she saw for a publication focused on South Asians, going through Ycombinator as a media company, using subscriptions as a base of a business ...

This week, I caught up with Larry Fitzgibbon, the CEO of Tastemade. I think of Tastemade as an original digital video brand, ahead of its time in many ways since it was founded back in 2012, before streaming was even a thing. This was an era when onlin...

The media business in 2024 To kick off the year on The Rebooting Show, I spoke to Axios senior media reporter Sara Fischer about the main themes of the year ahead. Among the topics we covered: The value of identifying patterns from the torrent of news ...

I spoke to Matt Cronin, founding partner of House of Kaizen, a consultancy that works with publishers on their subscription and recurring revenue products. Among the topics we covered: fixing misaligned incentives in publishing whether peak subscriptio...

Matt Reustle, CEO of Colossus, a business-focused podcasting network that’s home to Invest Like the Best, Business Breakdowns and Founders, sees podcasting as an antidote to many of the ills of algorithmic media. “To me, it's the highest trust media. I...

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...