ExpertsFMNot Boring (with Packy McCormick)
Acquired · December 3, 2021
5 Selected Lessons:
heuristic · 3 priority · 1 reasoning_pattern · 1
Assume the audience is smart
Source
Acquired — Not Boring (with Packy McCormick) (December 3, 2021) · at 1:10:42 ▸
When this applies
when creating any product, content, or communication for a mass audience and deciding how much respect/transparency to extend them
The takeaway
Optimizing for the intelligent subset of any audience, even at the cost of alienating less discerning members, compounds into a higher-quality audience and brand over the long run.
Why it works
Treating the audience as smart forces you to write well-reasoned, non-condescending material; over time this selects for a smart, loyal audience who reward quality, compounding your credibility and reach.
One level up
Long-term audience/brand quality is shaped by what behavior you select for, not by the size you chase in the short term.
Where it stops holding
This stops working when your business model actually depends on maximizing the dumbest common denominator of attention (e.g., pure ad-clicks-driven content) rather than durable trust.
Detail
hierarchy:
- Respect the audience's intelligence above short-term engagement tactics
- Accept smaller reach in exchange for a smarter, more loyal audience
- Never hide the ball even when it would be more profitable short-term
rationale: Both Ben/David and Packy state that assuming audience intelligence has direct trade-offs (can't hide incentives, can't write fluff) but compounds into attracting exactly the kind of audience that rewards quality long-term.
In their words
David and I text ourselves this phrase all the time or text each other this phrase when one of us is straying from it. But rule number one, it acquired is assume the audience is smart.
Grading a solo-founder business using the Seven Powers framework
Source
Acquired — Not Boring (with Packy McCormick) (December 3, 2021) · at 2:14:01 ▸ · at 2:15:52 ▸ · at 2:19:47 ▸ · at 2:23:02 ▸
When this applies
when trying to identify the actual durable competitive advantage of any business, especially one that looks unconventional
The takeaway
Use a structured taxonomy of competitive advantage types to diagnose an unconventional business, rather than assuming either 'it has no moat' or 'it has some vague moat' — explicitly test and rule out each type.
Why it works
By systematically testing the business against each of the seven canonical power types (scale economies, network effects, counter-positioning, switching costs, branding, cornered resource, process power), the group isolates that Not Boring's advantage is primarily counter-positioning (doing what incumbents structurally can't/won't) plus a form of process power (an unreplicable, undocumentable creative process), with only weak network effects.
One level up
Rigorous frameworks applied honestly (including admitting weak or absent powers) produce more useful diagnosis than either blanket skepticism or blanket enthusiasm.
Where it stops holding
This stops working when the framework's categories don't map cleanly onto genuinely novel business models, forcing analysts to stretch definitions (as happened when trying to decide if 'process power' truly fit).
Detail
approach: Walk through each of the seven powers (scale economies, network effects, counter-positioning, switching costs, branding, cornered resource, process power) and test whether it applies.
signals:
- counter-positioning identified on both journalism side (transparency vs. traditional media's wall) and venture side (low-diligence transparent investing vs. traditional VC)
- weak/uncertain network effects acknowledged honestly rather than overclaimed
- process power identified as the strongest: the creative process literally cannot be written down or handed to someone else
rationale: The group explicitly rejects forcing a 'flywheel diagram' narrative ('you can make an Excel spreadsheet say anything... but no one has Amazon's flywheel') in favor of rigorously testing real power sources.
In their words
it's funny. We get it a lot too. Like, what's your process? You're like, well, I can tell you mechanically, but it's not going to sound like
Report bad news honestly rather than hiding it
Source
Acquired — Not Boring (with Packy McCormick) (December 3, 2021) · at 11:02 ▸
When this applies
when results fall short and there is a temptation to misrepresent performance to someone who trusts you
The takeaway
Owning and disclosing shortfalls immediately, loudly, and without spin builds long-term credibility that is worth more than looking good in the short term.
Why it works
The punishment wasn't for underperforming but for lying about performance; honesty preserves trust and allows course-correction, while concealment compounds the failure into a trust violation.
Where it stops holding
This stops working when excessive self-flagellation about failures becomes performative rather than genuinely informative, or when radical transparency exposes information that materially harms stakeholders without benefit.
Detail
rule: If you're not going to do well, at least be honest about the fact that you're not doing well.
threshold: Applies any time there's a gap between stated performance and actual performance.
rationale: He now 'blares from the rooftops' when he gets calls wrong in Not Boring (e.g., crypto winter, shorting bill.com), which he ties directly back to this childhood lesson about honesty mattering more than the underlying mistake.
In their words
that if you're not going to do well, at least be honest about the fact that you're not going to do well. And so now I think, you know, when I get things wrong and not boring, I blare it from the rooftops and probably comes back to that moment.
Don't raise money or sign a lease before proving community/demand exists
Source
Acquired — Not Boring (with Packy McCormick) (December 3, 2021) · at 35:18 ▸ · at 39:00 ▸ · at 43:29 ▸
When this applies
when about to commit to fixed costs (capital raised, leases, long-term contracts) for a business whose hardest unproven part is building genuine user/community engagement, not the operational logistics
The takeaway
Sequence commitments so that cheap, reversible tests of the riskiest unknown happen before expensive, irreversible ones.
Why it works
Fixed costs (leases, large raises) lock you into a specific execution path before you've validated the actual hard, uncertain part of the business (community formation), so premature commitment increases downside risk without proportionally reducing uncertainty.
One level up
Spend first on de-risking your biggest unknown, not on the parts of the business that only look hard.
Where it stops holding
This stops working when the capital or lease itself is needed to generate the very signal you're trying to test (e.g., physical space is required before anyone will show up at all).
Detail
rule: Don't raise money and don't sign a lease before you actually try to build a community.
threshold: Test with free/cheap tools (Slack groups, dinners, debate nights) before committing capital.
rationale: Packy followed this advice, started a Slack group and small dinners instead of raising money or signing leases — which let him pivot cheaply when COVID hit and when Not Boring Club underperformed (e.g., 7 people at trivia night).
In their words
But I got a bunch of advice from a bunch of other people who were like, don't raise money and don't sign a lease. Please, for the love of God, don't sign a lease before you actually try to build a community because it sounds like the other stuff is hard, but what's really hard is actually building a community around this kind of stuff.
Be consistently yourself online rather than playing a scalable persona
Source
Acquired — Not Boring (with Packy McCormick) (December 3, 2021) · at 43:29 ▸ · at 46:50 ▸
When this applies
when building any personal brand or public-facing identity for long-term, high-frequency output
The takeaway
For high-frequency, long-duration personal brands, authenticity is the lower-effort, more sustainable strategy because it eliminates the overhead of maintaining a fictional identity.
Why it works
A performed persona requires constant extra cognitive work to maintain separately from the real self, doubling the effort of content creation (inventing both substance and in-character voice) and creating a mismatch between the audience's expectations and the creator's actual preferences over time.
One level up
Sustainable systems minimize ongoing maintenance cost; adding a layer of performance to a high-frequency process multiplies effort compounding over time.
Where it stops holding
This stops working when the creator's authentic voice/opinions are illegal, harmful, or fundamentally mismatched with what any audience would want, or in contexts that are not sustained/high-frequency where maintaining a persona is cheap and useful (e.g., single viral campaigns).
Detail
rule: Be as close to yourself as possible in public content creation; dropping a persona reduces cognitive overhead and audience mismatch.
threshold: Applies once you're producing content frequently enough (weekly) that maintaining a separate voice becomes unsustainable.
rationale: He explicitly says adopting a persona would double the work (figuring out content AND in-character voice) and that if authenticity doesn't find product-market fit, that's an acceptable outcome rather than forcing a mismatched performance.
In their words
I realized really early on that I just needed to like kind of be as close to myself as humanly possible, or else it was just going to be too much work. And once you admit that, you're kind of like, okay, well, if it works, it works.