To a hammer, everything is a nail. As the world continues to become ever more screwy as AI eats everything and formerly solid frameworks lose their foundations, those with a toolbox will outperform those reliant upon singular tools.
Great post Charles! Very thoughtful examination of venture capital's evolution. While the industry's maturation has brought needed structure, your observation about trading "metrics for taste" really resonates. The focus on algorithmic approaches and investment themes seems to prioritize pattern-matching over genuine innovation discovery.
Curious - How do you personally maintain your investment taste when the industry pressures push toward conformity? Any practices you've developed to identify those "weird and wonderful" ideas that don't fit neatly into established metrics or themes?
👏 Spot on, Charles! In a world where capital is more accessible, VCs who evaluate a team’s culture with the same rigor as other metrics will be the ones to thrive.
To seed, build, and nurture timeless, intangible human capitals — such as resilience, trust, truth, efficiency, evolution, fulfilment, quality, peace, patience, discipline, relationships and conviction — in order to elevate human judgment, deepen relationships, and restore sacred trusteeship and stewardship of long-term firm value across generations.
A refreshing take on our business world and capitalism.
A reflection on why today’s capital architectures—PE, VC, Hedge funds, SPAC, Alt funds, Rollups—mostly fail to build and nuture what time can trust.
Built to Be Left.
A quiet anatomy of extraction, abandonment, and the collapse of stewardship.
"Principal-Agent Risk is not a flaw in the system.
Amazing piece, I feel VC is losing its courage, moving always more on PE model to de-risk investment, but at the end of the day VC is "betting" on an a worldview that is hard to imagine at the moment of the investment.
Great piece, Charles 👏 As VCs become more institutionalized, the human side of building companies risks getting lost. Founders aren't just managing metrics—they're shaping culture 💡 The best investors support both. Thanks for sparking this important convo 🔁
"This job used to be about hunting for the most revolutionary, high-risk ideas."
YES. I've been thinking about this a lot over the past few years. I get that B2B SaaS is a sexy (and safe) category, but so much of it just doesn't seem hard or high-risk to build anymore.
Big congrats, Charles 🎉. Would love to learn how you’re thinking of keeping committed to your mission within the changing environment. It’s something I’m really struggling with, and would appreciate some advice. Ben (ben@chasingrainbows.vc)
a) charles is the best
b) ok ok i'll write my 'self-commodization' post, which mirrors your feelings here, and our discussions for the last few years
c) thanks for having me in this fund
To a hammer, everything is a nail. As the world continues to become ever more screwy as AI eats everything and formerly solid frameworks lose their foundations, those with a toolbox will outperform those reliant upon singular tools.
thank you for this! if everyone's focus is on the same themes and metrics, we will miss out on unique companies that change the way we operate.
I hope the ecosystem is listening! This is so insightful, and I hope this piece helps VC reflect on the real job. Congrats on closing Fund V, Charles.
love this! super insightful :)
Great post Charles! Very thoughtful examination of venture capital's evolution. While the industry's maturation has brought needed structure, your observation about trading "metrics for taste" really resonates. The focus on algorithmic approaches and investment themes seems to prioritize pattern-matching over genuine innovation discovery.
Curious - How do you personally maintain your investment taste when the industry pressures push toward conformity? Any practices you've developed to identify those "weird and wonderful" ideas that don't fit neatly into established metrics or themes?
👏 Spot on, Charles! In a world where capital is more accessible, VCs who evaluate a team’s culture with the same rigor as other metrics will be the ones to thrive.
Hello there,
Huge Respect for your work!
New here. No huge reader base Yet.
But the work has waited long to be spoken.
Its truths have roots older than this platform.
My Sub-stack Purpose
To seed, build, and nurture timeless, intangible human capitals — such as resilience, trust, truth, efficiency, evolution, fulfilment, quality, peace, patience, discipline, relationships and conviction — in order to elevate human judgment, deepen relationships, and restore sacred trusteeship and stewardship of long-term firm value across generations.
A refreshing take on our business world and capitalism.
A reflection on why today’s capital architectures—PE, VC, Hedge funds, SPAC, Alt funds, Rollups—mostly fail to build and nuture what time can trust.
Built to Be Left.
A quiet anatomy of extraction, abandonment, and the collapse of stewardship.
"Principal-Agent Risk is not a flaw in the system.
It is the system’s operating principle”
Experience first. Return if it speaks to you.
- The Silent Treasury
https://tinyurl.com/48m97w5e
Amazing piece, I feel VC is losing its courage, moving always more on PE model to de-risk investment, but at the end of the day VC is "betting" on an a worldview that is hard to imagine at the moment of the investment.
Great piece, Charles 👏 As VCs become more institutionalized, the human side of building companies risks getting lost. Founders aren't just managing metrics—they're shaping culture 💡 The best investors support both. Thanks for sparking this important convo 🔁
"This job used to be about hunting for the most revolutionary, high-risk ideas."
YES. I've been thinking about this a lot over the past few years. I get that B2B SaaS is a sexy (and safe) category, but so much of it just doesn't seem hard or high-risk to build anymore.
thanks for sharing!
Big congrats, Charles 🎉. Would love to learn how you’re thinking of keeping committed to your mission within the changing environment. It’s something I’m really struggling with, and would appreciate some advice. Ben (ben@chasingrainbows.vc)
Does your company offer grants for startups?