- 2026-03-24
- Work-in-progress/scrappy
- Role models
Following on from the thread of Holding myself and other men to high standards - 2026-03-24, Milan has been on my mind in the last week or so as a key archetype of “successful provider with lovely wife and great life”.
Context
When I was at Ship It Week in August 2025 at Casa Tilo, there was a guy there, Milan (Twitter, blog)
I barely spoke to him, because I was very intimidated by him. He seemed like a real adult. He’s a venture capitalist, for crying out loud. (Another real adult who I barely spoke to was Andrew Conner, who I spoke to slightly more, and he messaged me a few times afterwards, after I stopped replying1).
Since Ship It Week, Milan has remained in my brain as a role model. My model of him:
- A venture capitalist → a very cool sounding job, high status, high skill (it’s only today that I learned that his firm, Lionheart, is doubly cool in that it is “focused on the wise development of transformative technologies.“)
- Very grounded, competent-seeming, unhurried, masculine, provider energy. Seems like someone who has gained a huge amount from the ~spiritual path, whilst remaining a highly competent actor, rather than the typical stereotype of a very Yin, woo, hippyish dude. It’s very rare to meet men who remain very masculine and seem very competent, in the post-rationalist space. I remember seeing a tweet from Sasha Chapin when he was at VibeCamp, decrying the lack of traditional masculinity on display there.
- Speaking of provider energy, I connected with his lovely wife, and was struck by the fact that, as a VC, I’m sure he could easily provide for both of them. And wow, this woman is so amazing that he must also be amazing, for them to have recently married.
I’ll talk to him
- I’d like to talk to him, but I think I can do a bunch of thinking asynchronously first
- The question, really, is: what is it that you do, that I don’t do, that I should start doing, if I want to have a lovely life and a lovely wife, like you?
Obvious thing is: dude, he’s been writing stuff like this, since 2014 !!! 12 years dude !!!
Like, he wrote this post, “Heuristics for evaluating performance”, all the way back in fucking 2015. This IMO shows that way back then, he was a way better thinker than I am right now, at 29, in 2026. I’ve been thinking well for 0 years, he’s been thinking well for at least 10, but realistically, longer than that.
This brings me back to Recommended readings from one of my mentors, 2026-03-13. Sprinting on “learning how to think”. Jacobus book, logic primer, getting feedback (this is a huge one!). And Attila has said that he’ll set my critical essays to write, and critique them. So. Onwards!
(I could email Milan (and Andrew) with a quick “hey, how do I learn how to think like you?” thing, but really, Attila is a much higher context person here. I should trust his guidance. The thing from Donna Tartt’s A Secret History: “It is is better to know one book intimately than a hundred superficially.”. But you know, substitute “book” for “mentor” (?))
Another thing here is that he’s American. He’s presumably lived in the Bay area for 10+ years, literally at the centre of the entrepreneurial world, with all the most interesting people. He’s probably middle class, plausibly (probably) has ~knowledge worker parents, etc. Exceptional people typically have relatively stable & supportive childhoods.
Appendix
As an aside, I’m having fun conceptualising Milan as an alternative universe version of me. He has blog posts about Kendrick Lamar and D’Angelo. He’s existed in the same spaces as me (Effective Altruism, post-rationalism), but in a way more leveled-up way. I’m just now learning to think, I started writing on this site in June 2025, and he’s been doing it for 10+ years. Maybe I should consider him a rival (who is over a decade ahead of me and who I have barely any chance of catching up to. Kind of fun to have a Great Adversary in this way, and very humbling/clarifying).
Footnotes
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There’s a pattern of people who are above my “power”, mentor-types, “More Knowledgable Other”-types, who engage with me for a bit, but I get into procrastination spirals re: replying to them because I think surely there’s nothing in it for them. I can see through this when I think about it clearly, and engaging more with MKOs is a clear way for me to level up. It’s the reason I wanted to work at Longview Philanthropy, and the reason that I’m now at the EA Hotel, to get mentorship from Attila ↩