Every Startup Needs a Designated Hater
Someone who rips bad ideas before they escape into the world.
Every startup’s got cheerleaders.
What they actually need is one person who ruins the mood.
A designated hater.
Not another useless “brand guardian” or another strategy guru with 100 slides.
Just one person who says what everyone’s thinking.
“This is dumb. Please stop.”
Then go back to sipping their coffee.
Founders love to fight the wrong enemy. They’ll blame the market, the economy, or a competitor with deep pockets. But that’s rarely what kills you.
Most startups die from the inside out. From bad judgment disguised as creativity. From the “clever” ad nobody asked for. From the rebrand that made customers wonder if you’d lost the plot.
You need someone who’ll stop you before you press publish. Call that person the Designated Hater. Your human airbag.
Harvard Business Review calls this approach “structured dissent.”
In Make Decisions with a VC Mindset, they argue that assigning a devil’s advocate early in the decision process helps teams expose blind spots before they become expensive mistakes.
The Vasa Lesson ⚓
The first cringe ship didn’t sink online. It sank in Stockholm nearly 400 years ago.
In 1628, Sweden launched the Vasa, the most expensive warship in the world.
And it sank within 20 minutes. Why?
Because no one dared tell the king the design was unstable. Too many cannons. Too tall. Everyone knew but nobody spoke. Plus too many vested interests.
Founders repeat this every day. A leader gets excited and everyone in the team nods out of fear.
No one dares say “This will sink us.”
Modern shipwrecks
Even the big players do cringe.
But here’s the difference. These big companies can afford it. But as a startup you can’t. What’s even worse is you can humiliate yourself for free.
– The deck that opens with “We’re the Uber for…”
– The landing page stuffed with verbs and buzzwords that say nothing
– The founder video that tries to start a movement when you’re selling software
– The proposal post where someone turns a marriage into a sales lesson
Why smart people ship dumb things
Fear.
The boss talks and everyone feels compelled to agree. Silence feels like the best option. And that’s how dumb ideas survive.
You’ve already sunk weeks into a project. You hate it, but killing it would mean admitting the waste and worse that you were wrong. So you push it out anyway.
Sometimes it’s conformity. You don’t want to be the difficult one. So you smile, pretend to like it, and hit publish.
That’s where cringe lurks.
What it costs
Bad ideas are expensive. They burn money, time, and trust.
Every pointless campaign drains survival cash. Every tone-deaf post chips away at credibility. Investors can forgive missed targets. They rarely forgive bad judgement.
Great people don’t leave because of coffee or salary. They leave when they’re forced to ship nonsense. Once customers decide you don’t get it, every promise sounds hollow.
The higher you climb as a founder, the less truth you hear.
Without a Designated Hater you end up trapped in your own hype, mistaking polite nods for consensus.
I wrote about a similar problem in Dear Prince, You Are Not the Founder how unchecked ego and power dynamics quietly kill execution. The pattern’s the same, too many nods, not enough truth.
“But isn’t taste subjective?”
Not really.
Most people feel when something’s off. They just don’t say it out loud. That awkward rebrand. That “clever” caption. The fake-humble funding post.
Nobody debates it. They just cringe and move on.
Good taste isn’t special. It’s just seeing patterns and knowing when you’ve missed one.
If you want the deeper take, I wrote about why taste becomes the real moat when execution gets automated in When AI Makes Everything Good, Taste Becomes Everything. It’s the same problem from a different angle, when everyone can ship polished work, judgment is what separates signal from slop.
The misunderstood hater
The hater’s not negative.
They care enough to stop you from making a fool of yourself. Their job is to protect you from self-delusion.
They don’t attack people, they attack the idea.
Pixar has the Braintrust. A group that picks holes in everything. But only the director decides what to change. That’s how they stay sharp.
Every good team needs someone who tells the truth. Even when it stings.
As HBR advises in Making Dumb Groups Smarter, you must appoint a devil’s advocate to prevent hidden knowledge and self-silencing from wrecking your best ideas.
The Devil’s Advocate Problem
Of course, not every critic deserves a badge. There’s a difference between dissent that sharpens ideas and dissent that kills momentum.
The danger is the devil’s advocate or false hater the person who shoots everything down out of ego, boredom, or fear of change. They’re not protecting the work. They’re protecting their own status.
Real haters are evidence-driven. They don’t enjoy saying no. They just can’t stand watching avoidable mistakes.
The goal isn’t to create friction for its own sake. It’s to stop bad ideas early so the good ones can breathe.
A proper Designated Hater makes things better, not slower.
Negativity isn’t the problem
People think negativity kills morale. It doesn’t.
Watching something stupid go live does.
Toxic positivity is far more dangerous. Because everyone can see when something’s dumb, they just stop saying it out loud.
The Designated Hater is a release valve.
They absorb the frustration, channel it, and protect the rest of the team from groupthink. Their job is not to say no to everything. It’s to say “wait, prove it” before you waste months and millions chasing the wrong idea.
Install the Designated Hater
Here’s the system.
Give one person explicit permission to stop anything going live. Protect them from retaliation.
They can pause, not veto. The owner must either fix it or defend it with evidence. No “because I feel like it.”
Run a ten-minute preflight for every public thing.
Ask these out loud:
Would a smart customer share this with a colleague for the right reasons
Is the claim specific, provable, and in plain language
Are we borrowing status from brands, trends, or life events we didn’t earn
If a rival posted this, would we quietly laugh
What breaks if this goes viral for the wrong reason
What would we cut to make this simpler
Who is going to hate this and can we live with that
If you can’t clear that list in ten minutes, you’re not ready.
Who it should be
Not the CMO. They’re too close to it.
Not the founder either. They’re too high on their own story.
You need someone who doesn’t care about politics.
An advisor.
A senior operator who isn’t afraid of being unpopular.
Even a brutally honest customer.
Think of it like a red team for reputation. Security teams hire hackers to break into their own systems. You need someone to break your campaign before the public does.
And they need job protection because the first time they call your baby ugly, someone will want to fire them.
The mirror effect
Every founder thinks they want honesty until they get it.
The Designated Hater isn’t there to humiliate you. They’re there to hold up a mirror before the public does.
Love the people who make you uncomfortable.
The north star
The longer you work in startups, the more you realise it’s not the market that breaks you. It’s pretending to like ideas you hate.
Great founders don’t need hype teams.
They need someone who says
“This will embarrass us.”
What I’m reading 📚
Good judgement starts with what you consume.
These stood out this week:
The death of the corporate job. by
Corporate jobs haven become hollow shells that workers now exploit as platforms to build their real lives elsewhere.
SEO is Dying. AI Engine Optimization by
The battle has shifted from ranking on Google to being cited by AI engines.
How Revolut Turned Referrals into a $4B Growth Machine by
Revolut’s referral engine wins because it’s engineered around activation and defensibility, not vanity sign-ups as a referral only counts when it drives real product use.
Got something I should read? Hit reply, I actually read every suggestion.
Until next week, keep building. No fairytales required.
Martin, Chief Ranter at Uncharted
P.S. this week’s track is Fashion by David Bowie.
Love how you reframed ‘negativity’ as protection. It’s about care, not cynicism!
I write about surviving the corporate jungle using animal archetype to break down complex human behaviors and situations. If this resonates, please connect and lets support each other.
Here is my latest post:
https://corporatejungle.substack.com/p/ambition-vs-survival-mode-slow-down
Spot on. I use premortems for the same reason. I find they give people explicit permission to point out the problems before they happen. It shifts the conversation from defending ideas to strengthening them. When you make it safe to call out risks early, you trade surface alignment for real alignment. It’s one of the simplest ways to turn potential landmines into learning moments and ultimately make execution smoother and faster.