Brand-Safe Comedy Targeting
Make brands entertaining by targeting power, processes, trends, products, or yourself.
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 93%
Create an entertaining brand voice by defining both a recurring comedic persona and a safe target map. Humor can repeatedly challenge business rituals, organizational habits, trends, products, and other inanimate targets without singling out ordinary people. Self-deprecation is especially useful because it demonstrates vulnerability and places the company inside the joke rather than above its audience. Public figures with exceptional power may be fairer subjects for punching up, but the material should still avoid needless cruelty. When a premise works, reuse its underlying structure as a running joke so followers recognize that they are part of an ongoing bit. The result is a voice that can generate attention and affinity while reducing the risks associated with impulsive personal ridicule.
Origin
On Marketing Against The Grain, Trung Phan described his anti-LinkedIn persona, recurring jokes about founder culture, and boundaries for whom or what a brand should mock.
Core principles
- 01Humor can attack a convention without attacking a vulnerable person.
- 02Self-deprecation builds trust by placing the brand inside the joke.
- 03Powerful public figures carry different targeting risks than private individuals.
- 04Processes and trends offer repeatable comic material.
- 05A recognizable comedic persona makes recurring jokes compound.
How to run it
- 1
Define the comic persona
Describe the perspective from which the brand makes jokes and the conventions it naturally questions. Keep the persona connected to the product and audience.
Pro tip A clear contradiction, such as an anti-corporate business founder, can produce durable material.
Watch out A persona that conflicts with the company's actual behavior will feel manufactured.
- 2
Map acceptable targets
Create explicit categories of safe targets, including processes, organizations, products, trends, and the brand itself. Define stricter rules for jokes involving people.
Pro tip Use power and public prominence as part of the risk assessment when punching up.
Watch out Do not treat notoriety as permission for harassment or hateful material.
- 3
Start with self-deprecation
Find honest frustrations, mistakes, or absurdities in the company's own experience. Frame the brand as a participant in the joke.
Pro tip Use a real operational truth so the humor also signals candor.
Watch out Do not joke about failures that materially harmed customers unless restitution and accountability are already clear.
- 4
Build recurring bits
Turn a successful premise into a recognizable format that can accommodate new examples. Preserve enough repetition for recognition while varying the punchline.
Pro tip Use recurring bits to reward followers who understand the accumulated context.
Watch out Retire a bit when repetition becomes predictable or detached from the brand.
- 5
Apply a prepublication risk check
Review who bears the joke, whether the target has meaningful power, and whether the audience can identify the intended premise. Remove material whose entertainment value depends on humiliation or ambiguity.
Pro tip Ask whether the same joke could target a process or the brand itself instead of an individual.
Watch out Short-term engagement does not compensate for avoidable reputational damage.
In the wild
Trung repeatedly flips polished founder content by portraying himself as an inexperienced operator, including joking about how to calculate MRR when revenue is zero. The premise reinforces his anti-LinkedIn persona while mocking startup posturing rather than a private individual.
→ A recurring self-deprecating bit generates recognition and high engagement around his founder identity.
Trung joked that he raised at a $100 million valuation by issuing 100 million shares and selling one to his mother for one dollar. The joke parodied startup financing announcements while linking naturally to his product.
→ The post reportedly drove 2,000 clicks and dozens of paying users.
A fictional SaaS company posts a recurring series about needing six internal meetings to simplify its meeting software. The joke targets the company's own bureaucracy and a recognizable business process, not an employee.
→ The brand appears candid and memorable without creating an external victim.
Common mistakes
Punching down at individuals
Targeting ordinary people can make a brand appear cruel and expose it to risks far beyond the joke's potential value.
Using random humor without a persona
Disconnected jokes may earn isolated engagement but do not build a recognizable relationship with the audience.
Mistaking controversy for comedy
Provocation that lacks a clear comic mechanism or safe target can attract attention while eroding trust.
Is it for you?
Best for
It is best for brands and founders seeking a distinctive, entertaining social voice within clear safety boundaries.
Not ideal for
It is not ideal for regulated communications or serious situations where humor could trivialize harm.
From the transcript
“I mean, now that you mention it, this is my running joke, is I don't take anything about business seriously.”
“Go after trends, go after other products, and go after inanimate objects.”
From the episode
How I Grew To 600,000 Twitter Followers Using Reddit with Trung Phan (#108)
Trung Phan