Holiday Special 2022
Ben Gilbert (host), David Rosenthal (host)
In this episode of Acquired, featuring Ben Gilbert and David Rosenthal, Holiday Special 2022 explores acquired hosts recap 2022, trade-offs, growth, and 2023 plans Ben Gilbert and David Rosenthal deliver a freeform holiday special reviewing Acquired’s biggest episodes and moments of 2022, including Taylor Swift, Sony, NVIDIA, Walmart/Amazon, Benchmark, and Enron.
Acquired hosts recap 2022, trade-offs, growth, and 2023 plans
Ben Gilbert and David Rosenthal deliver a freeform holiday special reviewing Acquired’s biggest episodes and moments of 2022, including Taylor Swift, Sony, NVIDIA, Walmart/Amazon, Benchmark, and Enron.
They reflect on what makes Acquired distinctive—deep research, long-form storytelling, and selective partnerships—while acknowledging missteps like legitimizing FTX by hosting Sam Bankman-Fried.
They discuss show growth (doubling again to ~250k monthly listeners), the challenges of podcast shareability, and the pros/cons of live events and multi-part “big tech” series.
They preview potential 2023 topics (OpenAI, luxury/brand power, Epic, Intuit, Nike, Sears) and share personal updates and end-of-year “carve outs” (books, podcasts, shows, products).
Key Takeaways
Acquired’s differentiation comes from strategic trade-offs, not just “working harder.”
They emphasize Michael Porter’s distinction: operational excellence (more prep) isn’t a strategy; enduring advantage comes from choices like long episodes, fewer releases, and staying a small team.
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Live shows are memorable but often degrade the core product for most listeners.
In-person and audience constraints (sound artifacts, breaks, logistics, equipment failures) can make episodes less “listenable” afterward, even if the room experience is special.
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AI feels like an App Store moment—obviously transformative, but unclear “killer apps” yet.
They compare ChatGPT-era excitement to early iPhone/App Store days: the leap is clear, but the breakout, category-defining businesses are still emerging.
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Podcast growth is sticky but structurally hard because audio is hard to share.
They echo Ben Thompson’s point: podcasts lack natural forwarding mechanics; growth often comes via step-change distribution (Spotify promotion) and network effects inside companies.
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Selective sponsorships can be a strategic moat when relationships go deep.
Acquired avoids programmatic ads and agencies, choosing season-long partnerships with a few companies, enabling better-integrated sponsor segments and real relationships with CEOs.
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The show’s platform can create investment leverage—community capital + sponsor insight.
They describe investing meaningfully in Vanta via an SPV (largely backed by the Acquired community), combining sponsor proximity, audience feedback, and access to capital allocators.
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FTX highlighted the cost of platform-legitimization and the importance of “what can we add?”
They apologize for lending credibility to SBF/FTX and explain why Acquired avoids real-time drama: it prefers evergreen, research-heavy work (e. ...
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Notable Quotes
“Taylor is a rock star in the internet… the markets are bigger than you can ever imagine.”
— David Rosenthal
“I think there’s a little bit of a crypto moment here… ‘Whoa, this unlocks a whole world of possibilities.’ And someone says, ‘What is it?’”
— Ben Gilbert
“There’s operational efficiency and there’s strategy… real strategy is trade-offs.”
— Ben Gilbert
“We lent our platform to Sam and to FTX… and yeah, I do feel bad about that.”
— David Rosenthal
“Forced consistency is the hobgoblin of little minds.”
— David Rosenthal (quoting Peter Fenton)
Questions Answered in This Episode
On the FTX episode: what concrete changes (if any) will you make to guest vetting or framing to avoid “legitimizing” future bad actors?
Ben Gilbert and David Rosenthal deliver a freeform holiday special reviewing Acquired’s biggest episodes and moments of 2022, including Taylor Swift, Sony, NVIDIA, Walmart/Amazon, Benchmark, and Enron.
Get the full analysis with uListen AI
You argue live shows are often a worse product for the broader audience—what criteria would justify doing one anyway (size, venue support, topic fit, audio plan)?
They reflect on what makes Acquired distinctive—deep research, long-form storytelling, and selective partnerships—while acknowledging missteps like legitimizing FTX by hosting Sam Bankman-Fried.
Get the full analysis with uListen AI
For a 3+ part Microsoft/Apple/Google series, what structure could prevent listener drop-off—interleaving specials, or splitting eras (founding vs platform shifts)?
They discuss show growth (doubling again to ~250k monthly listeners), the challenges of podcast shareability, and the pros/cons of live events and multi-part “big tech” series.
Get the full analysis with uListen AI
In your AI discussion, what’s the first “Uber-scale” use case you think will emerge from ChatGPT-like interfaces—enterprise workflow, consumer search, dev tooling, or something else?
They preview potential 2023 topics (OpenAI, luxury/brand power, Epic, Intuit, Nike, Sears) and share personal updates and end-of-year “carve outs” (books, podcasts, shows, products).
Get the full analysis with uListen AI
You mention podcast shareability as a limiter—would you build transcript deep-linking and “moment URLs” on acquired.fm, and how would you measure success?
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Transcript Preview
How do I open again? Welcome.
Wait, what is this show? What are we doing? [laughing]
Welcome to How I Built This.
Welcome. [laughing] No.
[laughing]
No, nothing against How I Built This, but that's not us.
All right, let's start. [laughing]
Okay. [laughing]
Who got the truth? Is it you? Is it you? Is it you? Who got the truth now? Is it you? Is it you? Is it you? Sit me down, say it straight. Another story on the way. Who got the truth?
Welcome to this special episode of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert, and I am the co-founder and managing director of Seattle-based Pioneer Square Labs, and our venture fund, PSL Ventures.
And I'm David Rosenthal, and I am an angel investor based in San Francisco. But today, Ben, you are hosting me at your lovely home here in Seattle.
Welcome to the studio.
[laughing] It's great to be here.
And we are your hosts. Ho, ho, ho.
Ho, ho, ho, happy holidays.
Happy holidays. [hip hop music]
Man, I, uh, I don't know about you, but, uh, I'm ready to put a bow on 2022. [laughing] Well, we have much to talk about.
Yep. Well, listeners, normally I have, like, a script, like, a thing that I'm looking at in front of me to know what to say now, but I don't really on this one, other than to say join the Slack. There are great people there-
Yes
... including probably you, if you're listening to this episode. We don't think this is an entry point for a lot of people into Acquired. We think this is probably if you're a fan, you're gonna listen to this, but I don't think this is gonna be anyone's sort of first show, so we're gonna try and go a little, uh, a little deeper and nerdier than normal.
We've got a little agenda. We're gonna recap 2022 for the show, for tech, for us, talk a little bit about what's ahead in 2023. We've got some extra, extra fun carve-outs.
Indeed. Well, we would be remiss if we did not thank our good friends at Vanta. So before we dive in, over to our conversation with founder and CEO Christina Cacioppo.
One of the things we've talked about over the season, Christina, is how security and compliance has really evolved in these few years that Vanta has been, uh, really pushing the market forward, and it's no longer just about, like, check the box, playing defense as a company, and especially as a startup. It's actually about playing offense. Given all that and the kind of central role that Vanta is now playing in this space, how do you see security and compliance evolving?
Really excited about the future, so I think a handful of things we're seeing. This concept of, you know, security and compliance and basically proving the security you have to your buyers has just become table stakes to B2B companies. When raising the seed round for Vanta in 2018, walked around and totaled the VCs that were gonna SOC 2 all their startups, and many of them very reasonably looked at me perplexed and said: "But my startups don't get SOC 2, so what are you talking about?" But now we serve a majority of the current YC batch, so people in YC right now, and again, like, YC is all about just getting revenue, but these reports just help you unlock that, and they do that by, like, opening up new markets, whether it's international or enterprise or healthcare or regulated industries. And I think particularly in the 2022 funding environment, so much is about revenue growth from secure, trusted sources, and so I think we're gonna see more companies move upmarket faster than we might have otherwise, and these big companies know that, you know, they're only as secure as their vendors are. If your vendor gets breached, looks like you did. It doesn't matter it was them, and so there's just... I think we're gonna see more and more scrutiny here over time, and that's gonna filter down into higher expectations for startups. So having stable customers that aren't gonna go out of business on you and hopefully are gonna expand over time, and one of the things these security and compliance certifications and reporting helps you do as a founder is sell to those big companies and prove your credibility. And, you know, you might not have the tenure of a kind of more established competitor, but you have their practices. You are taking good care of the customer data that you've been entrusted with and are ultimately gonna be a good and trusted business partner for the long run.
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