Three and a half years ago — well before ChatGPT cracked open the distribution conversation — HubSpot made a contrarian bet. With paid getting more expensive and search getting less reliable, the answer wasn't to pour more money into rented channels. It was to build an audience that compounds.

Jonathan Hunt leads owned media at HubSpot, where he's quietly built one of the most ambitious in-house media operations in B2B software: 17 YouTube channels, six newsletters, more than a thousand short-form clips a month, and a bench of 150 creators — reaching over 50 million people every single month. To staff it, he didn't poach from other software companies. He hired journalists from Axios, Business Insider, Morning Brew, and The Onion.

In this conversation with LeanScale co-founder Anthony Enrico, Jonathan walks through the entire playbook: how to make the economic case to a CFO, when to build vs. partner vs. acquire, why you never touch the editorial after you buy a media brand, the video-first flywheel that turns one asset into ten, and why HubSpot is officially calling time on inbound marketing.

WHAT YOU'LL LEARNWhy HubSpot bet on owned media years before AI blew up the top of the funnelHow to make the economic case for content to a CFO who wants last-touch attributionThe build vs. partner vs. acquire framework for launching media brandsWhy injecting product messaging into a media brand you acquired destroys the thing you boughtThe video-first flywheel: how one recording becomes a podcast, a newsletter, clips, and an SEO postWhy LinkedIn is 'a video product but not yet a video platform' — and what to do about itHow to use YouTube as a testing ground before you expand anywhere elseWhere an early-stage media team should report (hint: not under marketing)Why HubSpot hires journalists from Axios and Morning Brew instead of software marketersWhat 'loop marketing' is and why HubSpot says inbound no longer works the same way

CHAPTERS00:00 — Cold open + intro02:06 — What HubSpot saw before ChatGPT03:25 — Making the economic case (and the measurement problem)08:09 — Structuring media around product SKUs09:32 — Build vs. partner vs. acquire11:27 — Why you never touch the editorial after an acquisition14:30 — Where a Series A/B company should start17:32 — The video-first flywheel: human, AI, human20:38 — The LinkedIn reality check22:25 — YouTube as the testing ground23:28 — Hiring journalists, not marketers26:32 — Should the founder be the face — and where media should report33:09 — The biggest mistake founders make38:01 — Surprises, experiments, and where owned media goes next46:42 — Inbound is dead: enter loop marketing

ABOUT THE GUESTJonathan Hunt leads owned media at HubSpot, where over the past three and a half years he has built one of the most ambitious in-house media operations in B2B software: 17 YouTube channels, six newsletters, and more than a thousand short-form clips a month — reaching over 50 million people every month. He staffed the operation with journalists from Axios, Business Insider, The Information, Morning Brew, and The Onion, and built a bench of 150 creators HubSpot partners with monthly. The portfolio has grown through acquisitions including Starter Story and My First Million. He and the HubSpot team are publishing Loop Marketing (Simon & Schuster) on September 22, available for pre-order at loopmarketingbook.com.

ABOUT THE LEANSCALE PODCASTThe LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale.

▶ Learn more: https://www.leanscale.team▶ Follow Anthony on LinkedIn▶ Follow Jonathan on LinkedIn

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