Brilliant piece, Kyle 👏 — conviction-led contrarianism isn’t just an investing lens, it’s a leadership imperative. In startup culture, the real contrarians are the founders who quietly prioritize trust, safety, and long-term team health—especially when it’s not the loudest thing on the pitch deck. Some of the hardest, most important bets are the ones no one applauds (yet).
This was such a fantastic read. Thanks for putting together this type of content - really helpful for someone junior in VC building their toolkit and mental models!
Great piece. To your point about being "contrarian and right," Peter Thiel offers a similar insight in Zero to One arguing that individuals on the autism spectrum often have a comparative advantage precisely because they're less responsive to social pressure:
"The hazards of imitative competition may partially explain why individuals with an Asperger’s like social ineptitude seem to be at an advantage in Silicon Valley today. If you're less sensitive to social cues, you're less likely to do the same things as everyone else around you. If you're interested in making things or programming computers, you'll be less afraid to pursue those activities singlemindedly and thereby become incredibly good at them. Then when you apply your skills, you're a little less likely than others to give up your own convictions: this can save you from getting caught up in crowds competing for obvious prizes." —Peter Thiel, Zero to One, Chapter 4: The Ideology of Competition
In other words, not all contrarianism is consciously chosen—sometimes it's just hard wired into our brains.
about how often we conflate deviance with defiance, when the real challenge isn’t in being oppositional,it’s in being foundational. So many of the people I’ve seen succeed in building new systems (not just new products) weren’t trying to be different. They just couldn’t not follow what they saw as truth. You captured this tension perfectly with the story of the village and the hurricane. That blind confidence built on collective ego, not evidence, reminded me of how easily groups use consensus as a proxy for correctness.
One angle I’d add is that many “Layer 1” dependencies are now being monetized and industrialized by platforms. Social feedback is no longer just personal,it’s algorithmically reinforced. That means the courage to be disliked today isn't just a personal battle, it's one against engineered psychological feedback loops. We talk about deviance and conviction like internal traits, but they’re now also functions of platform architecture.
Another amazing piece Kyle ! Conviction-led contrarian founders are the best. Finding such founders is extremely difficult as they are not so easy to be identified as contrarians.
Brilliant piece, Kyle 👏 — conviction-led contrarianism isn’t just an investing lens, it’s a leadership imperative. In startup culture, the real contrarians are the founders who quietly prioritize trust, safety, and long-term team health—especially when it’s not the loudest thing on the pitch deck. Some of the hardest, most important bets are the ones no one applauds (yet).
Brilliant piece, Kyle 👏 — conviction-led contrarianism isn’t just an investing lens, it’s a leadership imperative. In startup culture, the real contrarians are the founders who quietly prioritize trust, safety, and long-term team health—especially when it’s not the loudest thing on the pitch deck. Some of the hardest, most important bets are the ones no one applauds (yet).
This was such a fantastic read. Thanks for putting together this type of content - really helpful for someone junior in VC building their toolkit and mental models!
This was a rollercoaster and a fantastic read. Thanks for taking the time, it is reflected in the quality of your output.
Great piece. To your point about being "contrarian and right," Peter Thiel offers a similar insight in Zero to One arguing that individuals on the autism spectrum often have a comparative advantage precisely because they're less responsive to social pressure:
"The hazards of imitative competition may partially explain why individuals with an Asperger’s like social ineptitude seem to be at an advantage in Silicon Valley today. If you're less sensitive to social cues, you're less likely to do the same things as everyone else around you. If you're interested in making things or programming computers, you'll be less afraid to pursue those activities singlemindedly and thereby become incredibly good at them. Then when you apply your skills, you're a little less likely than others to give up your own convictions: this can save you from getting caught up in crowds competing for obvious prizes." —Peter Thiel, Zero to One, Chapter 4: The Ideology of Competition
In other words, not all contrarianism is consciously chosen—sometimes it's just hard wired into our brains.
This was amazing! Thank you!
about how often we conflate deviance with defiance, when the real challenge isn’t in being oppositional,it’s in being foundational. So many of the people I’ve seen succeed in building new systems (not just new products) weren’t trying to be different. They just couldn’t not follow what they saw as truth. You captured this tension perfectly with the story of the village and the hurricane. That blind confidence built on collective ego, not evidence, reminded me of how easily groups use consensus as a proxy for correctness.
One angle I’d add is that many “Layer 1” dependencies are now being monetized and industrialized by platforms. Social feedback is no longer just personal,it’s algorithmically reinforced. That means the courage to be disliked today isn't just a personal battle, it's one against engineered psychological feedback loops. We talk about deviance and conviction like internal traits, but they’re now also functions of platform architecture.
Another amazing piece Kyle ! Conviction-led contrarian founders are the best. Finding such founders is extremely difficult as they are not so easy to be identified as contrarians.
Brilliant piece, Kyle 👏 — conviction-led contrarianism isn’t just an investing lens, it’s a leadership imperative. In startup culture, the real contrarians are the founders who quietly prioritize trust, safety, and long-term team health—especially when it’s not the loudest thing on the pitch deck. Some of the hardest, most important bets are the ones no one applauds (yet).