The Rebooting is launching paid memberships. All the details are on therebooting.com . In this episode, I speak to my collaborator Reid DeRamus, founder of Caddie Labs, which is working with me on implementing and growing memberships. Rather than discuss the benefits, we talk through the strategic and tactical decisions we made. Among the topic we cover: Why sequencing your business is important – and realizing your “unfair advantages” is critical in that The importance of first-party data in a ...
Feb 06, 2024•56 min•Ep. 111
Digital media veteran Scott Messer discusses the structural changes to the publishing business, from the deprecation of the third-party cookie to the critical role search plays in many publishing businesses. Scott is a longtime digital media exec who understands the mechanics of the digital ad industry as well as anyone I know.
Jan 30, 2024•45 min•Ep. 110
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 model and more. Listen on Apple, Spotify and other podcast services.
Jan 23, 2024•47 min•Ep. 109
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 online video was still mostly about webisodes nobody watched and YouTube’s famed dog on a skateboard videos. Tastemade has been at the forefront of many trends, as it is now with its focus on everything from IP to subscriptions with Tastemade+ and recre...
Jan 16, 2024•42 min•Ep. 108
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 The unrealistic expectations of the ZIRP/scale era Cyclical challenges vs structural changes The wasteland of general interest publications The existential threat of AI to many publishing businesses AI’s impact on the non-content aspects of the pub...
Jan 09, 2024•23 min•Ep. 107
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 subscription exists subscriptions as a force function to be customer centric what publishers should and shouldn’t learn from the success of The New York Times The struggles of many streaming services what publishers can learn from subscription companies outsi...
Dec 21, 2023•57 min•Ep. 106
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 think everything else now lacks nuance. And I actually still care about nuance. There are shorter attention spans, which I completely understand. Where do you actually get time to hear someone talk about opinions that aren't scripted? Is it proper...
Dec 12, 2023•47 min•Ep. 105
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 BuzzFeed-like culture publication. Big Cabal has raised $2.3 million in venture capital as it builds an independent digital media company in Africa’s largest economy that's geared to shifting consumption patterns. Tomiwa and I discuss how Big Cabal ...
Dec 05, 2023•46 min•Ep. 104
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. “One of the reasons I call it a forever business is to call out the fact that there is going to be ongoing work,” Patrick told me, “but also that it sets you up to play a very sustainable game.” Among the topics covered: The shifting role of stee...
Nov 28, 2023•38 min•Ep. 103
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 Rebooting Show, we spoke about the progress toward a sustainable business model for Hearst news outlets like The Houston Chronicle, The San Francisco Chronicle and others around the country. All told, Hearst newspaper properties have 400,000 digital sub...
Nov 21, 2023•48 min•Ep. 102
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 contributions, either one-off or recurring. On this week’s episode of The Rebooting Show, I spoke with Steve Sachs, The Guardian’s U.S. managing director and veteran of non-profit news models, about this approach and how extensible it is for news publisher...
Nov 16, 2023•45 min•Ep. 101
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 The Rebooting Show to discuss what we’ve both learned on the independent path. We discuss the transition from editorial to sales, why treating “lifestyle business” as a pejorative is strange, and fighting the pull to rebuild what you left behind....
Nov 09, 2023•55 min•Ep. 100
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 source of information, analysis and research beyond an anonymous Twitter account with a monkey avatar shooting lasers from its eyes. As crypto recovered and headed into a bull run that accelerated during the pandemic into what I’d consider a bubble...
Nov 02, 2023•45 min•Ep. 99
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 sturdy business.
Oct 26, 2023•36 min•Ep. 98
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.
Oct 19, 2023•47 min•Ep. 97
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.
Oct 18, 2023•52 min•Ep. 96
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 them up. Yet for many publishers, the costs associated with video creation are certainly high but the revenue while potentially big is uncertain. Tom Pachys, CEO of online video platform Ex.co, joined to discuss the challenge “The publishers that we...
Oct 17, 2023•48 min•Ep. 95
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 spent by medium. The message was clear: the internet would win, it was just a matter of timing. The time spent gap did close, although a disproportionate amount of gains went to tech platforms rather than web publishers. The chart was always wrong,...
Oct 16, 2023•43 min•Ep. 94
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 expenses of its 14-person team, the profits are then invested back into growing 1440’s subscriber base with paid marketing campaigns through Facebook and Instagram, newsletter ads and other channels. That “flywheel” has enabled 1440 to enter an exc...
Oct 10, 2023•53 min•Ep. 93
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 business model (advertising) and makes it even more difficult because you’re taking a cut of a cut, after YouTube gets its taste. Most MCNs fizzled. Whistle shifted its focus to building its own properties, producing franchises like “No Days Off,” a ser...
Oct 03, 2023•44 min•Ep. 92
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 people more say on data collection and pushes advertisers and ad tech companies to operate differently. In this episode, I had a conversation with Joe Root, CEO of Permutive, an audience platform that's used to deliver privacy-safe digital advertising....
Sep 26, 2023•46 min•Ep. 91
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 real conversations.
Sep 25, 2023•18 min•Ep. 90
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 with the legalization of sports gambling in 33 states and the District of Columbia. A giant industry would need customers, and sports media was there to help. That's led the Sporting News, which Rich joined as CEO last year, to raise a $15 million...
Sep 19, 2023•55 min•Ep. 89
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 rewarded didn't turn out to be a durable model. Now, Bustle is looking like a different entity, as its CRO says typical ad campaigns are now just 15% of the company's revenue Instead, it is focused on using its stable of brands for bigger efforts more a...
Sep 12, 2023•46 min•Ep. 88
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 focus lends itself well to a strong direct-sold ad business. Other topics we cover: What ails legacy publishing models Raising $10 million in a rough funding climate The pendulum shift from institutions to individuals The enduring value of scarcity T...
Sep 05, 2023•46 min•Ep. 87
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 topics. But most importantly, he completely understands the challenges of being a CFO because he’s a CFO. In this episode, we discuss how he built Mostly Metrics, as well as getting into the weeds of why media is often a terrible business and what ...
Aug 15, 2023•45 min•Ep. 86
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 events. Literally Media CEO Oren Katzeff explains the approach, along with Literally's emphasis on IP-based video franchises and more.
Aug 08, 2023•45 min•Ep. 85
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 leaders without a clear understanding of how to make that leap.
Aug 01, 2023•50 min•Ep. 84
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 Google's rise to be the dominant distributor of internet traffic. The opportunity is to use the AI tools to create better experiences and more resilient business models. "There's no use in crying over spilled milk," Scott advises.
Jul 25, 2023•49 min•Ep. 83
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, picking up on an eight-year run as president of Hearst Magazines from 2010 to 2018. He was group president at Condé Nast for many years, as well as the founding publisher of Smart Money. Some highlights from our discussion: The broad view of content...
Jul 18, 2023•54 min•Ep. 82
