4 unhinged founders that accidentally built brands (and what you can learn from them)

If you think you can build a great founder brand by sharing generic "value" on social media, you probably just got back from doing the Harlem Shake and have your ringtone set to Gangnam style.

But if you take the time machine forward to 2024, you'll realize successful founder content can't just be advice people can get anywhere. Nowadays, people want two things:

1. Personality: You can get information everywhere. People need to find you interesting.
2. Trust: There are too many people who've never done what they give advice on. People want to know they can trust you.

When you check those two boxes, you build cult-like followings, drive massive engagement, and become the micro-celebrities of your space.

You can't do this without taking risks. Some of the best at it look outright unhinged. Like the four we're featuring in this article. They're honest, transparent and speak their mind (whether or not people agree with them).

If you’ve got strong opinions and you’re not afraid to share them, this is your playbook. In this post, you'll see how they do it - while driving sales, growing their audiences, and creating brands that people can’t help but rally around.

Perhaps the hardest part of learning from them is that they're not trying to build a brand. They're just being themselves. Still, I think we can learn a lot from them about building a non-bullshit brand.

The $2.7m/year solopreneur: Pieter Levels

Pieter Levels is a serial entrepreneur who has shipped dozens of products (up to 70, depending on how you count). Most of them failed, but those that succeed are now bringing in almost $3m a year.

That'd be great money for a startup, but it's even better when it's just you. And that's exactly Pieter's reality. Pieter is the prototype indie-hacker. Just a guy with no employees, building cool things from his couch, basement or wherever else he wants to be.

Here's how he builds his brand:

Specific critiques

Pieter isn't afraid to call out companies he dislikes, products he hates or even criticize the entire European Union (which even got him invited to chat with former European Central Bank chief Mario Draghi, who recently put together a report on boosting European productivity).

What I think is most interesting about how Pieter does this is that his critiques are never generic. It's rarely things everyone already agrees with, like "sales is annoying", it's always specific.

Look at this example of him calling “Google APIs as the worst APIs” lol 

Well, that’s what makes Pieter, Pieter – his willingness to say what others won’t. 

Real knowledge from experience

One of his existing startups is called Photo AI – an AI photo generator. 

See how he shares in detail what he thinks the future holds for AI photography. It’s really well thought out. This shows his readers that Pieter really does know how shit or at the very least certainly thinks about it. 

Maybe he's right, maybe he's wrong. But in a world where countless Twitter/X threads predict the future with zero authority, we're starved for people sharing specific knowledge from real experience.

One of his most unhinged moments came when he critiqued Europe for its anti-tech sentiment and outdated policies. It was polarizing, sure, but it also sparked conversations that needed to happen.

Another unhinged moment came when he hilariously criticized the tech industry’s obsession with over-complication and inefficiency.

Whether you agree with him or not, you can’t ignore him, and that’s exactly the point.

The key takeaway for you here is don’t be afraid to be authentic & be opinionated. 

It’s scary to share opinions especially when you know it won’t be taken favorably but it can help to show off your authentic self. 

Jason Fried – How to hate your industry and still be popular

Jason Fried is the co-founder of Basecamp, the project management tool that's been fully remote since 2009. Jason has many axes to grind with the software industry.

He's both beloved and controversial because he's willing to call out "best practices" and the assumptions others accept as true.

Take this tweet:

He critiques over-management & bureaucracy. But not only that: His company Basecamp ran this as a real billboard campaign. Committed to the bit! Just like Pieter Levels, Jason Fried doesn't just talk about it, he does something.

One of his most unhinged stances? He hates much of SaaS, aka the best way humans have found to monetize software.

Again, Jason didn't just complain about it on Twitter. He launched a new line of pay-once-own-forever software products.

He launched once.com by sharing his PoV on the state of software. He crafts a compelling launch narrative around how once users owned what they paid for, controlled what they depended on, and privacy and security were the users’ own business. 

This is a common thread for founders like these. They don't just talk about things, criticize and lament how things are and how they should be instead.

Again, when he and his team hated email, they built a better way to do email:

Jason has many other controversial takes. He's mostly against raising venture capital, thinks prices should be low, companies should be small, you should be immediately profitable, etc. Not everyone agrees with this.

And if he was just complaining about it in public, he'd probably be far less popular. But Jason is always constructive, always building something to remedy the problem. He has skin in the game.

This has turned Jason into his companies' no. 1 marketing asset. Because if you agree with his philosophy, you'll probably enjoy the types of prodcuts that company leads to .

The man who sold the same app twice: Nikita Bier

Nikita Bier is the founder of teen polling apps TBH and Gas, acquired by Facebook and Discord, respectively. He's a notorious Twitter/X shitposter, but also one of the world's foremost experts on making apps go viral.

But he's also not afraid to be a curmudgeon and call out things he finds wrong or weird.

His takes aren't limited to tech, though. Just like Pieter Levels, he also comments on more cultural issues.

That’s the vibe of Nikita - he’s full of hot-takes & unpopular opinions. 

One of his most talked-about moments was the “sushi controversy.” Nikita didn’t just criticize Japanese sushi—he went to Jiro, one of the world’s most revered sushi restaurants, and didn’t hold back. 

And he made a claim that conspiracy theorists would be proud of – “best chefs in Japan go abroad and improve on international dishes and the OK chefs continue to make Japanese food”. 

This might sound odd as an example of building a founder brand. It doesn't sell any product or strengthen your brand. But the reason we love people like Nikita is precisely because they don't hide behind a polished or ghostwritten front. They say what comes to their mind, which makes them authentic.

Nikita capitalizes on this too – he charges $4000/hr to consult companies on how to go viral.

Unraising VC: Sahil Lavingia

Sahil Lavingia, the founder of Gumroad and @shl on X, shares a few traits with Pieter, Jason and Nikita. He, too, is willing to be controversial, shares honest opinions and follows his personal interests, even when they're not about the software business.

Some of Sahil’s most memorable moments come when he challenges the very foundations of the industry. 

Like this tweet: Calling product managers (PMs) and Venture Capitalists (VCs) low-status jobs when they're some of the most coveted roles in tech.

Whether he's right or not, questioning "truths" certainly gets attention. But just like the rest on this list, Sahil is constructive, builds products and runs his companies in ways that align with his heretical beliefs.

The people who agree are likely to use his products. For example, he positioned his latest startup Flexile as an “upgrade to capitalism”.

But here’s the thing: even when Sahil ruffles feathers, his message lands because it speaks to something deeper. 

Like this tweet:

or this one:

This one definitely made me think. And that’s Sahil’s jam. He makes you think things you never thought were worth thinking about. 

If you’re trying to take a page from Sahil’s book, it’s this – talk about things that people know they should think about but don’t. Whether that’s about the future of work, or how tech is shaping our lives – the takeaway here is to think deeply about fundamental assumptions & challenge them from a first-principles perspective. 

Conclusion: How to be unhinged

The frustrating truth about these 4 founders is that they're not doing anything particularly advanced. They get attention and are beloved precisely because they're not strategically "building their brand", but instead saying what comes to their mind.

A second characteristic they all share is that they're building things that align with their opinions on what's wrong with the (tech) world and how it could be better. Plenty of people complain on social media, but only few build real businesses that fix those problems.