Here's the trick-or-treating haul. Shrimp chips. Octopus paste. And a Kumon coupon. That's Halloween (aka Week 8) of our Family Gap Year™️. This was a hard one, because no one does Halloween like an American suburb. For the kids, it's probably the 2nd holiday (behind Xmas) in terms of excitement. And it's just not a big deal in Tokyo. Once again, Lisa was deep in Facebook groups to try to find things to do. She carried a pretty big emotional burden of getting it "right" for them. We start at an international school at 10:30 am that has a "haunted house." It turns out it was mostly 6 year olds speaking French and Japanese. Our 12 year old didn't even want to go inside (but we met the head of schools, who made a pitch to enroll there). Next we went to a "mask building" event in Roppongi Hills. Turns out that you needed tickets and it was sold out. Kids are dejected (but not that much since it was like a Santa photo shoot). Third stop (also a ChatGPT recommendation) was another street where you get tickets and the stores set up stands to hand out one piece of candy. Tons of kids (mostly little ones), all Japanese and just a very surreal scene. It was super orderly and the closest thing to trick-or-treating. That's where we got the Octopus Paste. We then needed a break so went to our safe space (the Park Hyatt roof bar) for some drinks and French fries, then headed to Shinjuku (aka Times Square) to see the paraders. I did run into a random group of westerners rapping 2Chainz' Birthday Song, so it felt a bit like home. Ended up in a big arcade playing Japanese video games as a family and failing to win prizes with the mechanical claws. My eldest wrote in her notebook, "it was so random, that it was really fun."

The big difference I've seen here is in people's networks. Not "I have 1,000 LinkedIn connections" but there are people who understand my full body of work, who I am, how resourceful I can be and will vouch for me. This latter group usually lands (and tbf, usually finds themselves in this position)

"Dad, can you move your company to Japan?" That was not on the bingo card as we wrapped Week 7 of our Family Gap Year™️. Everyone is really digging it here. We've found our groove (subways, workouts, almond butter and Whispering Angel). The entire family can even navigate Shinjuku Station without Google Maps. And in 3 weeks we're hitting control-alt-delete and heading over to Seoul. It is a nice fantasy to consider living here (tl;dr, way too hard for a solopreneur) and we've got a lot of the world left to see. I suspect the question will come up again. We also got hit with a gut punch of nostalgia this week. Our old house (rental) of 8 years came onto the market. Someone sent us the listing. It was empty, the tacky fixtures had been upgraded and the floors restored. "I miss our house," said our 9 year old. I didn't clarify that it was no longer "our house." Plus, they re-listed it at a 25% rent increase, which is a painful reminder of the re-entry tax that awaits us next summer. But it also validated the reason we're able to do this trip. We've been renters for 14 years (6 in Dumbo, 8 in Manhattan Beach). It's given us a ton of flexibility and financial liquidity to make bold life decisions. There are many peers who have said they would try this but a massive mortgage just breaks the math. Another side benefit of being renters for that long is that we accumulated way less stuff. Heck, we only had one car in LA. And we never fell into the trap of "you can own your stuff, or your stuff can own you." With kids aged 9 and 12 we were at that next phase of life where you dump all the baby shit. The milk-stained couches, the Ikea desks and that one dresser from when you were single. We were at the phase when we could've done an upgrade - heck we were overdue for one - but kept putting it off because of the possibility of this trip. There were moments where we were embarrassed to have certain people over, but had we done a 6-figure upgrade of all our stuff, we'd probably still be in LA. Today, our stuff sits in 4 storage cubes and we'll do the upgrade when we get back. But as of today, the thought of buying more stuff just doesn't even register. After all, the adventure bug does hit you pretty hard.

"Dad, can you move your company to Japan?" That was not on the bingo card as we wrapped Week 7 of our Family Gap Year™️. Everyone is really digging it here. We've found our groove (subways, workouts, almond butter and Whispering Angel). The entire family can even navigate Shinjuku Station without Google Maps. And in 3 weeks we're hitting control-alt-delete and heading over to Seoul. It is a nice fantasy to consider living here (tl;dr, way too hard for a solopreneur) and we've got a lot of the world left to see. I suspect the question will come up again. We also got hit with a gut punch of nostalgia this week. Our old house (rental) of 8 years came onto the market. Someone sent us the listing. It was empty, the tacky fixtures had been upgraded and the floors restored. "I miss our house," said our 9 year old. I didn't clarify that it was no longer "our house." Plus, they re-listed it at a 25% rent increase, which is a painful reminder of the re-entry tax that awaits us next summer. But it also validated the reason we're able to do this trip. We've been renters for 14 years (6 in Dumbo, 8 in Manhattan Beach). It's given us a ton of flexibility and financial liquidity to make bold life decisions. There are many peers who have said they would try this but a massive mortgage just breaks the math. Another side benefit of being renters for that long is that we accumulated way less stuff. Heck, we only had one car in LA. And we never fell into the trap of "you can own your stuff, or your stuff can own you." With kids aged 9 and 12 we were at that next phase of life where you dump all the baby shit. The milk-stained couches, the Ikea desks and that one dresser from when you were single. We were at the phase when we could've done an upgrade - heck we were overdue for one - but kept putting it off because of the possibility of this trip. There were moments where we were embarrassed to have certain people over, but had we done a 6-figure upgrade of all our stuff, we'd probably still be in LA. Today, our stuff sits in 4 storage cubes and we'll do the upgrade when we get back. But as of today, the thought of buying more stuff just doesn't even register. After all, the adventure bug does hit you pretty hard.

My investing philosophy in 5 bullets: 1. Start buying S&P index in 2000 (age 20) 2. Keep your job during 2008, buy more 3. Quit finance, reduce income by 90% and use some margin to bridge cash flows 4. Realize that you can easily clear funding rates (and maintain 10% lvg) 5. Don't pay capital gains (ever). Maybe pay back the loan when I'm 6 feet under

My investing philosophy in 5 bullets: 1. Start buying S&P index in 2000 (age 20) 2. Keep your job during 2008, buy more 3. Quit finance, reduce income by 90% and use some margin to bridge cash flows 4. Realize that you can easily clear funding rates (and maintain 10% lvg) 5. Don't pay capital gains (ever). Maybe pay back the loan when I'm 6 feet under

Companies need more AI Champions. And those aren't the same as Power Users. I'd probably be the latter, focused on experimenting, leaning on vibes and not focusing on the actual ROI of what I've been building. There's the unsexy work of cataloging use cases, expanding them beyond just making things faster and then thinking hard about the actual deployment. Furthermore, Power Users aren't always good communicators and teachers, so knowledge stays suck in their heads. via @nlw Daily Brief

"Get under the table and cover your head," I told my 9 year old. She was shaking and had tears in her eyes. Our phones were buzzing like an Amber Alert on steroids. There were sirens wailing outside. Our first earthquake warning. Week 6 of the Family Gap Year™️. 12 hours later the government apologized for the mistaken warning. Turns out there wasn't a 9.9 heading our way. (And yes the earthquake advice came from ChatGPT... but now we know.) This week has been a good one with a nice dose of social interactions (including a small Yale reunion). A few other highlights: 1. Attended the Tokyo Derby Our first football game (off the heels of the World Cup). It was a beautiful brisk day at Ajinomoto Stadium where our (adopted) FC Tokyo won 4-nil. We followed it up with a nightcap at the Fairmont with views of the Tokyo Tower. 2. Two very Japanese encounters We were out to dinner with another couple and when the bill came, we split it. The staff went out of their way to inform us (3 times!) that the bill was an odd number, so one person would be paying one extra yen. (Half a penny.) We walked by protesters at the US embassy. I don't know the back story about what happened at one of the bases, but the chant was loud and angry. It also was polite, "USA, please go away." 3. We love the subway here Once you get over the fact there are 4 different subway systems, it's so clean and quiet. You can hear a pin drop, even during rush hour. It's seriously meditative, especially when you're outside the city center on the outdoor lines. 4. Wrapping up a hard work stretch I've had calls at 4:45 am all week (and a few calls ending at 11pm). It's probably the most physically tired I've ever been, but the work and clients are awesome. Once November hits, things quiet down for a few months. It's wearing on my family that I'm continuously sleep deprived. (I haven't drank coffee in a decade, but have transitioned to Coke Zero - can't believe I discovered this at 47) 5. What's the best thing we've eaten? We've been getting that question a lot, but tbh we haven't gone down the foodie route (especially with the kids and everyone still being on a slightly different schedule). Also, reservations here are surprisingly hard to come by. But the baseline of pretty much every meal (except Mexican) is just so high. And it's hard to spend > $50 (no alcohol) for a family of 4. We've got under a month left in Tokyo before Taiwan, Seoul and HK. Those will probably be shorter trips and starting to think about a longer stint in January (Vietnam?). Thanks for reading, friends 🇯🇵

"Get under the table and cover your head," I told my 9 year old. She was shaking and had tears in her eyes. Our phones were buzzing like an Amber Alert on steroids. There were sirens wailing outside. Our first earthquake warning. Week 6 of the Family Gap Year™️. 12 hours later the government apologized for the mistaken warning. Turns out there wasn't a 9.9 heading our way. (And yes the earthquake advice came from ChatGPT... but now we know.) This week has been a good one with a nice dose of social interactions (including a small Yale reunion). A few other highlights: 1. Attended the Tokyo Derby Our first football game (off the heels of the World Cup). It was a beautiful brisk day at Ajinomoto Stadium where our (adopted) FC Tokyo won 4-nil. We followed it up with a nightcap at the Fairmont with views of the Tokyo Tower. 2. Two very Japanese encounters We were out to dinner with another couple and when the bill came, we split it. The staff went out of their way to inform us (3 times!) that the bill was an odd number, so one person would be paying one extra yen. (Half a penny.) We walked by protesters at the US embassy. I don't know the back story about what happened at one of the bases, but the chant was loud and angry. It also was polite, "USA, please go away." 3. We love the subway here Once you get over the fact there are 4 different subway systems, it's so clean and quiet. You can hear a pin drop, even during rush hour. It's seriously meditative, especially when you're outside the city center on the outdoor lines. 4. Wrapping up a hard work stretch I've had calls at 4:45 am all week (and a few calls ending at 11pm). It's probably the most physically tired I've ever been, but the work and clients are awesome. Once November hits, things quiet down for a few months. It's wearing on my family that I'm continuously sleep deprived. (I haven't drank coffee in a decade, but have transitioned to Coke Zero - can't believe I discovered this at 47) 5. What's the best thing we've eaten? We've been getting that question a lot, but tbh we haven't gone down the foodie route (especially with the kids and everyone still being on a slightly different schedule). Also, reservations here are surprisingly hard to come by. But the baseline of pretty much every meal (except Mexican) is just so high. And it's hard to spend > $50 (no alcohol) for a family of 4. We've got under a month left in Tokyo before Taiwan, Seoul and HK. Those will probably be shorter trips and starting to think about a longer stint in January (Vietnam?). Thanks for reading, friends 🇯🇵

hi brett, big fan. here's a less glib version of my take. i agree w/ your definition of judgment, weighing unique views/insights and comparing ur view to what the market thinks. my personal view is that the next big unlock is probably not finding more creative ways to use excel with ai, it is finding a more sophisticated way to automate the judgement. to step back quickly, to me, ai represents everyone having the same facts with zero friction, when everyone has the same facts, the near term gets priced faster and more accurately and the edge moves further from the facts at hand, and closer to what those facts will mean. the problem is that the tree branches the further out u go, competitors respond, capital comes in, discounts go up, regulators show up, mgmt manages to the stock, small changes have time to compound and rip up your base case and, oh, don't forget about timing, an excel model and its variations are usually just one path w/ have baked scenarios stapled on and the pm's gut is doing the weighing.... my view is that simulation could be the answer to how you actually map the distribution in a rigorous, auditable manner. before ppl say 'excel can already do monte carlo sims' that is not what i am saying. the paths should interact. right now excel doesn't have a way to represent that. it was built for ppl typing assumptions into cells, and on occasion they would do a nice side build, and it was good enough for what investing was in the past that we just kind of accepted it because it got us 95% of the way there, now i think that excel has become a bottleneck for what investors can do, so we should probably start to think of ways to get rid of that bottleneck. other industries/fields that deal with predicting complex systems moved past this a long time ago. weather guys run different models and read the spread, epidemiologists and supply chain ppl simulate agents to see how stuff plays out, i actually don't know what they do if i am being honest, but i know that there is massive toolkit out there that finance bros are not tapping into. fundamental investing really hasn't touched any of that bc building it took a team of engineers, and all of the good engineers have gone into tech for the last decade. w/ coding agents that should change right? if i were you I would literally rebuild excel from scratch, keep what you mentioned (auditable, transparent, easy to visualize), and then find a way to let fundamental analysts leverage all of the advanced forecasting techniques that have been developed over the last 20 years. i.e. how can you build a system to start to understand the all of the interacting paths (where the scale comes in), you can see where outcomes cluster, where they split and how the whole distribution compares to what the price implies, which is exactly what you are talking about with weighing insights. great investor's heuristics work alright, but they are becoming commoditized quickly now that they can be hardcoded. like in chess, everyone can see the entire board now. the edge is reading further ahead, and past a few moves u can't calculate by hand. simple example. today most analysts probably model a restaurant chain as some drivers for same store sales hopefully they have a thorough unit economics build and they plug in data sources to get their estimates for the next 2-4 quarters, AI can do that in 5 minutes, but the analyst doesn't have an easy way to do much more than that. they should be able to model the actual business: every store, local demographics, compare that to demographics with other ramps, what is the spread of the ramp curve, how does timing effect the PV, local wages, how traffic reacts when menu prices go up (for this demographic how much of their wallet share does it eat into, etc.), how much a new store steals from the one down the road on a product by product basis, and with all of that information all stuff that is very easy to build, but you have to build a platform that lets analysts do audit, check, etc. but who knows, maybe jane street just builds a massive model and trains it on every source of information that a l/s investor would ever use and any extra work to codify an investor's inductive bias is useless! and maybe i was being too harsh on the talent point, you just need to actually want to try to do stuff like this, very easy with AI. hope this is somewhat helpful and not just jibberish, always happy to chat/dms are open

Same thing happened in the early days of Grok Bot with computer use. After 2 weeks of magic, it seemed like the sites figured something out and kept signing me out or blocking. Brought me back to local Codex sessions (plus dot)

Are you still using projects? All year, I was meticulous in curating context in folders for Cowork/Code. Grok Bot made me realize how good the models are at dynamically grabbing context via connectors. Now in Claude, I've just been loosely describing where the files/folders live in the cloud and there doesn't seem to be any performance degradation. A month ago, I thought this would have been unthinkable.

"I really want to talk to someone besides you and mom." We just finished Week 4 of our Family Gap Year™️ and this was probably the first hard week. It basically feels like we're in a Covid pod. For the past 28 days, the four of us have spent 15 hours a day together. 420 hours. In LA, we'd probably need 140 days to spend that much time together. (And it still wouldn't be the 4 of us at the same time.) It's gotten to the point that we even do the most mundane activities together. I finally got my haircut (at a tatt'd up hipster barber shop) and the entire clan was going to come with me. At the last minute, they bailed and so I walked by myself. Between the walk, haircut and a burger after I was alone for a little under 2 hours. It was literally the first alone time I had (besides work and going to the gym) in a month. In LA, I have probably 4 hours to myself a day! It felt glorious. And also scary. Is this really sustainable for another 9 months? Or is this actually how the trip is supposed to go? After all, when we planned it we made a conscious decision to not enroll in any programs. We wanted flexibility. 2 months in one place. 1 week here. Random weekday trips. Lots of sleeping in (as the 4 of us are big sleepyheads). But with that flexibility comes the huge trade-off, where we become the child care (and teachers). Even downtime is spent being with the kids (since we're not throwing them iPads). This week we realized that while us parents *might* be able to deal with this isolation, it probably wouldn't work with our eldest. (Last night I had a dream that we aborted the trip for this reason!) So here's the current game plan. We're getting them in some dance classes. We are having a "family date" with some expats this Sunday. We're going to a "halloween" barbecue on October 10th. And the whole family comes to my networking meetings! Admiteddly, Japan is a harder place for connection given the language and local culture. When we go to Hong Kong in December, it probably will be different. So for now, we'll continue to savor ANY interaction with someone who's not from our family.

"I really want to talk to someone besides you and mom." We just finished Week 4 of our Family Gap Year™️ and this was probably the first hard week. It basically feels like we're in a Covid pod. For the past 28 days, the four of us have spent 15 hours a day together. 420 hours. In LA, we'd probably need 140 days to spend that much time together. (And it still wouldn't be the 4 of us at the same time.) It's gotten to the point that we even do the most mundane activities together. I finally got my haircut (at a tatt'd up hipster barber shop) and the entire clan was going to come with me. At the last minute, they bailed and so I walked by myself. Between the walk, haircut and a burger after I was alone for a little under 2 hours. It was literally the first alone time I had (besides work and going to the gym) in a month. In LA, I have probably 4 hours to myself a day! It felt glorious. And also scary. Is this really sustainable for another 9 months? Or is this actually how the trip is supposed to go? After all, when we planned it we made a conscious decision to not enroll in any programs. We wanted flexibility. 2 months in one place. 1 week here. Random weekday trips. Lots of sleeping in (as the 4 of us are big sleepyheads). But with that flexibility comes the huge trade-off, where we become the child care (and teachers). Even downtime is spent being with the kids (since we're not throwing them iPads). This week we realized that while us parents *might* be able to deal with this isolation, it probably wouldn't work with our eldest. (Last night I had a dream that we aborted the trip for this reason!) So here's the current game plan. We're getting them in some dance classes. We are having a "family date" with some expats this Sunday. We're going to a "halloween" barbecue on October 10th. And the whole family comes to my networking meetings! Admiteddly, Japan is a harder place for connection given the language and local culture. When we go to Hong Kong in December, it probably will be different. So for now, we'll continue to savor ANY interaction with someone who's not from our family.