Media product in the ‘more with less’ era

The heaving Fontainebleau lobby and a half dozen dueling happy hours at this week’s Possible conference is a reminder that AI is not going to wipe away everyone’s jobs. Humans will continue to find things to do – and plausible reasons to go to sunny places for meetings. See you in Cannes?

We held a marketing leaders dinner last night in Miami in partnership with 1440. It was a great gathering to discuss the role of human curation in the age of AI. Thanks to 1440 for its support in bringing together a great group. The hopeful consensus: Real human curation as a form of "anti-personalization."

In today's newsletter:

• The Rebooting is releasing its latest research report. We surveyed media product leaders to understand how they’re navigating the pressures and opportunities of the more-with-less era. 
• A conversation with HubSpot Media’s Kyle Denhoff on why the go-direct mantra is simply good marketing.
• On PvA: who is best positioned in the chaos economy.

Inside Hearst’s personalization strategy

See how Hearst UK connects with millions of readers daily using personalization that feels one-to-one. From onboarding to retention, read to learn their winning strategy.

Media product in the ‘more with less’ era

The Rebooting partnered with WordPress VIP to survey 131 media product professionals on how they're adapting to today’s cost-constrained reality. 

Key insights from the report:

• 55% of respondents say audience engagement is their top priority
• Nearly half spend less than 10% of their budgets on product and tech
• AI is being embraced for workflow automation but remains off-limits for editorial use
• Product innovation today means fixing brittle infrastructure, not chasing flashy new tools

This report includes proprietary survey data and interviews with product executives. It's a clear-eyed view of how media teams are trying to modernize without the benefit of deep pockets.

Download the full report to see what’s working—and what’s not.

Inside HubSpot's go-direct playbook

The "go-direct" movement is framed as a reaction against the  unfairness of traditional media. In Silicon Valley, it's fueled by a belief that the media can't be trusted, with Andreessen Horowitz's growing media portfolio as the clearest example. But the broader shift isn't just ideological. It's a practical marketing strategy. HubSpot shows why.

CRM software maker HubSpot's content push wasn't about grievance but effectiveness. Kyle Denhoff, head of audience growth for HubSpot Media, joined me on The Rebooting Show to discuss how the CRM software company has built a full-fledged media arm with brands like The Hustle, My First Million, Masters in Marketing, and Mindstream. It expanded with a creator network that funds business-oriented independent media, with a particular focus on YouTube. As the publisher of The Hustle with 2 million subscribers and My First Million with 700,000 YouTube subscribers, HubSpot has its own distribution muscle.

What it’s found is these media assets are best used not to flog the product features of HubSpot but to gain a top of the funnel audience that can then be nurtured by lead-gen spinoff content. For example, a Hustle video about Midwestern gas station pizza businesses can be complemented with downloadable asset that goes deeper. This kind of approach is rare in B2B marketing, which tends to focus on dry white papers and webinars. 

"We've completely allowed our editorial teams to focus on just building great media products for the audiences we serve," Kyle told me on this week's episode of The Rebooting Show. "And then it's on us, the audience development and monetization team, to figure out how do we add additional value, how do we move those audiences down the funnel."

HubSpot's DNA is built around inbound marketing — the idea that the best customers come to you because you offer something valuable. First it was SEO-optimized blog posts, then newsletters, podcasts, creator partnerships. After acquiring The Hustle and its My First Million podcast, HubSpot focused on building real media products with independent editorial sensibility — not thinly veiled sales collateral.

Venture firms like Andreessen Horowitz and Founders Fund have embraced the go-direct playbook. A16z has hired podcast hosts from The Hustle and bought Erik Torenberg's Turpentine network, a portfolio of podcasts and founder communities for entrepreneurs and tech insiders. Founders Fund has invested in media properties that align with its worldview, recognizing media's influence on market narratives. Media is no longer just marketing collateral — it's becoming strategic infrastructure to build influence and bypass legacy intermediaries.

The arbitrage opportunity is clear. Media remains powerful — look at how Trump weaponized it to rise to power — yet it's undervalued due to a broken distribution and monetization system. Companies don't need traditional newsrooms; they just need to reallocate a slice of their vast communications and marketing budgets to own direct audience relationships. Hiring more PR people isn't the answer — they already outnumber journalists six to one.

"A lot of companies revert back to short-term thinking and make content about the product itself," Kyle said. "Our approach is to build a media product that people want to come back to every week."

HubSpot's model shows the future of go-direct isn't about ideological warfare. It's about building durable audience assets in an environment where those assets are more available — and more valuable.

The biggest challenge for these companies is their short-term thinking about marketing as a customer vending machine.

"We may sell to that audience in the next 90 days," he said. "We may sell to that audience 36 months from now, but we're building an audience of folks who engage with us, start to introduce them to HubSpot the business, and they get to know us through the content and the value we provide them."

Listen to my conversion with Kyle

The chaos economy

America’s economic future is being reshaped by chaos. On PvA, we talk about how innovation is shifting from big, centralized corporations to small, nimble operators empowered by AI and global platforms. The traditional advantages of scale and hierarchy are eroding, replaced by speed, creativity, and resilience in a fragmented economy. It’s a messy but dynamic new reality that rewards initiative, the willingness to get your hands dirty, and the propensity to quickly “get to start.”

Plus: the rise of alternative tech media, the economics of small but influential audiences, and why Twitter might matter more than YouTube for distribution.

Watch on YouTube; listen on various podcast services

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