“Once in a while, a pirate can beat a soldier.” – Mike Leach
496 days after publishing their first episode, TBPN has been acquired by OpenAI.
What Jordi, John, and the team have built is inspiring. I’ve been tuning in since the Technology Brothers Podcast days, and have watched them iterate, build chemistry, and lead a cult. I saw their set improve, formats adapt, their skills as co-hosts sharpen, and their hair game reach levels I didn’t know existed.
This reportedly low-hundred-million-dollar outcome was a combination of creativity, strategy, nimbleness, and brute force. There are no shortcuts to going live three hours a day, five days per week, sometimes with a dozen guest appearances.
Enough glazing, though. Losing independence comes with real risks and people are rightfully skeptical of what this means for their objectivity going forward. That’s real, and admittedly I was kind of sad when I first read the announcement tweet. The whole value of the acquisition is that the audience trusts these guys — but that trust was built on independence, and independence is exactly what got sold. There’s a version of this where OpenAI is smart enough to keep their hands off the wheel. Owned media tends to drift toward house organ.
It’s worth understanding why this keeps happening — because while this is one of the splashier corporate media acquisitions, it ain’t the first.
I started following this “New Media” evolution during Covid. I remember being struck by a tweet from HubSpot CTO Dharmesh Shah back in 2020, and I’ve referenced it in multiple pieces since then.
HubSpot has put its money where its mouth is — buying The Hustle in 2021, Mindstream in 2024, and launching the HubSpot Media Network. Erik Torenberg’s Turpentine, which formally launched three years ago, was acquired by a16z and Erik became a Partner and Head of their New Media team in April 2025.
Just last week, Plaid bought This Week in Fintech, a company with a variety of industry newsletters and events. In February, Benchmark brought Jack Altman and his Uncapped Podcast aboard.
No doubt the phones of people like Molly O’Shea () and Dwarkesh Patel () have been ringing for many months now, too. One to keep an eye on: Ti Morse (Relentless podcast).
The pattern is unmistakable: everyone wants a jungle guide. Nobody wants to sort through endless waves of information within a sector — people want someone smart to tell them the what, the how, and the why. Businesses have figured this out. They can spend all the money they want on traditional advertising, pleading with rented audiences to become customers. Or they can own the audience outright — and owning the audience means owning the guide. Distribution, authenticity, insight (very different from information), commentary (very different from reporting), and tight content-audience fit is a combo worth paying for.
That’s what makes TBPN’s ad book so telling. They partnered with companies so niche there is zero chance you’ve heard of the majority of them unless you work in tech — and sometimes not even then unless you’re, say, an ML engineer managing GPU clusters.
And here’s the thing about who will continue to win in this industry media landscape. It won’t be trained journalists. It’ll be real enthusiasts – insiders who have actually been in it. Authentic storytellers and pro-industry people, not snarky gotcha reporters. John and Jordi ooze enthusiasm and passion for technology and Silicon Valley, and there is no faking that.
Look at sports media. There are many people who are ball-knowers, but they’ve never touched a ball...and it’s always easy to tell. On the flip side, there are also great athletes who aren’t sharp or likable enough for media. The people who can bridge both worlds — credibility and charisma — are the ones who get rewarded these days.
TBPN’s format itself isn’t new. Three-hour daily live show, banter between hosts, guests rotating through, inside jokes, a loyal audience that tunes in at the same time every day. That’s PTI. That’s Mike & Mike.
Coogan and Hays have said it themselves — they were inspired by Pat McAfee, a fellow pirate who built a media empire out of pure force of will.
TBPN did the same thing for Silicon Valley, and paired it with high-volume clipping, written commentary, and their compressed ‘diet’ offering. They turned a three-hour live show into endless pieces of content.
It’s not shocking that the VCs and Silicon Valley leaders are the first movers on the acquisition side of this — it’s their job to see the future. In the sports business world, my friends Sid Balaga and Suraj Peramanu (The 4th Quarter) joined forces with Courtside VC late last year — more of a partnership than an acquisition, but a smart move by Courtside. They see the value of distribution and owning the conversation. Hell, even I’ve had a few groups sniffing around Under the Number — and I’m just getting this ball rolling.
The TBPN guys are pirates. They placed an ambitious bet — one that clunky, bureaucratic legacy media would never have dreamed up, let alone executed on. They did it with an incredibly lean team undoubtedly fueled by lots of caffeine and nicotine. The soldiers of the old guard, with their layers of management and committees and consultants, simply aren’t nimble enough to compete.
Congrats to the TBPN crew for getting the bag. Here’s to hoping the fellas stay pirates, and don’t become soldiers.
Essays normally go out every other Wednesday, not Thursday, but it was a busy week of travel. Lots of great content on deck!
Stay tuned and share this with someone who should be paying attention to where sports, media, and entertainment is headed.
If you’re building, investing, or advising within this space — please reach out!
Email: [email protected]
– Brent
