The best ideas are wrong at first
Contrarian hypotheses and how to spot the good kind
There’s a mental model I keep coming back to—one that sits at the root of breakthrough startups, market-beating products, and the best founders I know.
It’s this:
If everyone agrees with you, you’re probably too late.
But if no one does—and you’re right—you’ve found leverage.
This is the power of the contrarian hypothesis.
The best ideas often sound bad at first.
Not because they are bad—but because they go against assumptions everyone else is too comfortable to question. These are called contrarian hypotheses, and they’re the starting point for some of the most legendary companies in tech.
Today’s note: what they are, how to recognize a good one, and how I’ve used them across my own projects.
What’s a Contrarian Hypothesis?
A contrarian hypothesis is a belief that goes against popular consensus—but turns out to be true.
It’s not about being different just to be edgy. It’s about noticing something non-obvious before it becomes obvious.
It sounds weird or naive at first.
It’s rooted in a sharp observation of reality.
If you’re right, it opens up a unique opportunity.
“The best startup ideas are the ones that look like bad ideas… but are actually good.”
— Paul Graham
It’s uncomfortable to hold a contrarian belief. Because if you’re wrong, you look dumb. If you’re right, you look early—until everyone else catches up.
How This Played Out in Big Wins
Here are a few contrarian bets that shaped tech history:
Uber (2009)
Belief: People will get into strangers' cars using an app.
Status Quo: Taxis are the only safe, regulated option.
Result: Multi-billion-dollar company and a new category: rideshare.
Discord (2015)
Belief: Gamers need a new chat tool, even though Skype exists.
Status Quo: Voice chat is a solved problem.
Result: Became the default community platform for a generation.
Shopify (2006)
Belief: Small businesses want their own store, not just a listing on Amazon or eBay.
Status Quo: Centralized platforms already “won” e-commerce.
Result: Empowered millions of independent sellers and built a $100B+ company.
Notion (2016)
Belief: People want an all-in-one productivity workspace.
Status Quo: Everyone is using separate apps like Trello, Evernote, and Google Docs.
Result: Created the modular productivity movement and a fanatical user base.
5 Contrarian Bets I’m Making
Here’s how this mindset shows up in the projects I’m building:
supply.tf – Fashion isn’t about fitting in—it’s about standing out and creating opportunity.
Most brands sell status, we sell action. supply.tf is for those who refuse to wait for the future to happen to them. We believe the future isn’t given—it’s created by the bold, the outliers, and those who aren’t afraid to carve their own path. Every drop is a call to act: to take risks, challenge norms, and transcend the ordinary.
updatenight.com – This newsletter
The best tech and business insights don’t make headlines.
Mainstream newsletters recycle Twitter. This one zooms in on the edges—small creators, overlooked tools, early shifts, and unsexy innovations that end up mattering most.
Division Null ∅ – A Discord for the curious elite
The best ideas don’t come from big public threads—they come from tight-knit collisions of curiosity.
Division Null isn’t a server for everyone—it’s for those who see the matrix. Engineers, founders, artists, and hackers jam together in a calm, trusted space without clout games or surface-level discourse. It’s not about access. It’s about alignment.
decosmic.com – Trusted AI agents
The future of AI isn’t scale—it’s usefulness grounded in trusted context.
Big models aren’t enough. We’re focused on agents that don’t hallucinate—because they know where their data comes from.
been.place – Track where you've been and want to go
Travel isn’t about what's trendy—it’s about what matters to you.
While everyone builds recommendation engines, we’re building a memory engine. A tool to track where you’ve been and where you want to go—not for likes, just for yourself.
What’s Your Contrarian Bet?
Ask yourself:
What do you believe that most people around you don’t?
What seems like a bad idea now, but could be obvious in five years?
Where is everyone zigging—so you can zag with purpose?
That might just be your unfair advantage.
A Framework to Find Your Own
Want to apply this yourself? Try this 3-part prompt:
What’s the default belief?
What “everyone knows” in your space or niche.What if it’s wrong?
Or what if the truth is more nuanced, more interesting, or shifting?What would I build (or bet on) if I believed that?
That’s your contrarian wedge.
Start small. Ship something. Share it. Watch what happens.
Final Thought
If everyone agrees with your idea, you might be too late.
If nobody does—and you’re right—you have edge.
Most people chase trends.
The brave ones chase tension.
The rare ones chase truth that hasn’t scaled yet.
What’s your contrarian bet?
Until next time,
Jay