September 2025 Random Ramblings
Andrew Walker sees a switch from quarterly to semiannual reporting as a market-structure event, not a long-term-compounding event. If Q1 and Q3 releases disappear, May and November options could lose embedded earnings volatility while August and March gain it, creating potentially “free alpha” for quant shops and larger post-earnings overshoots for patient stock-pickers.
Elon Musk’s roughly $1 billion open-market Tesla purchase was extraordinary less for its bullish message than for its unprecedented scale. Walker could find no comparable corporate-insider transaction: Dustin Moskovitz accumulated roughly $1 billion of ASAN over time, while Berkshire’s $3 billion OXY Form 4 reflected its status as a greater-than-10%-owning financial buyer rather than a corporate insider.
The historical record of enormous insider purchases is surprisingly poor, so conviction should not be confused with foresight. ASAN fell from near $100—Walker thinks Moskovitz began buying in the $80s—toward $14, OXY lagged, and Patrick Soon-Shiong’s $45 million NantKwest investment was disastrous. CEOs can be “getting high on their own supply.”
Sector-wide insider buying is a lens Walker increasingly prefers to one spectacular transaction. He highlights regional banks after the 2023 failures and busted biotech earlier in 2025, where directors and executives bought meaningful amounts across the group: “You could throw a dart at any regional bank” and find insiders purchasing.
Time spent investing is not automatically improvement. Walker contrasts years of “mindless practice” in golf and video games with writing, publishing, and revisiting old work, arguing that embarrassment at something written two or five years ago is welcome evidence that the learning curve remains alive.
September 2025’s meme-stock surge raises a process-versus-outcome problem: how seriously should one take an investor whose implausible thesis has produced a five-bagger? Walker admits he discounts people who own companies whose technology appears to be “smoke and mirrors,” alongside ATM issuance and insider selling, yet worries about judging an entire investor by one “pot of magic beans” position.
1. Semiannual reporting would redistribute volatility—and create alpha opportunities
Walker would prefer quarterly reporting, partly because the UK’s semiannual regime can produce “BS trading updates” with selective disclosures. Yet for genuinely long-term investors, he does not believe quarterly versus semiannual reporting materially changes the value of a great compounder.
The investable question is how a moderate rule change alters the game. His analogy is basketball’s three-point line: teams that adopted it faster gained a structural advantage, and even moving the line by two feet changed strategy. Reporting frequency could similarly create alpha opportunities as the market structure changes.
His proposed trade: if Q1 and Q3 reports disappear, sell May and November call options whose prices still embed those earnings events, then buy August and March options before six-month Q2 and full-year disclosures. Those releases would cover six months rather than three and could be “lit,” while the removed quarters would lose volatility.
The second-order effects could reach multi-manager “pod shops” built around whisper numbers, pre-earnings positioning, and four annual catalysts. Even without trading options, Walker would hold more dry powder: when a favored stock next reports after six months of information, a miss and bad guidance update could make it “more likely to overshoot to the downside.”
2. Musk’s Tesla purchase sits in a category of its own
Musk bought roughly $1 billion of Tesla on the open market on September 12 and filed on September 15. Walker accepts the standard interpretation—“people don’t do that if they’re bearish”—but stresses that token insider buying and a billion-dollar personal commitment are entirely different signals, even given Musk’s wealth. Musk’s earlier Tesla purchases were smaller and generally alongside equity offerings.
The nearest comparison he found was Dustin Moskovitz at Asana, ticker ASAN: a $350 million purchase directly from the company in 2022 plus roughly $1 billion of open-market buying under 10b5 plans from late 2021 through the end of 2022. Even that total accumulated over about a year rather than in one transaction.
Berkshire reported a $3 billion OXY purchase on one Form 4 in early 2022 and may have bought $6 billion to $7 billion overall, but Walker rejects it as a direct comparison: Berkshire was a financial buyer filing because it owned more than 10%. Musk’s purchase was the largest corporate-insider transaction Walker could identify.
3. Giant insider conviction has often produced poor results
Moskovitz began buying ASAN near $100, Walker thinks in the $80s; by the recording it was around $14. Walker calls the program “some of the worst capital allocation of all time,” a warning that founder conviction does not guarantee a good outcome.
Berkshire’s OXY investment looked less disastrous but still unimpressive: the shares were roughly flat since early 2022 and had underperformed both the S&P 500 and the largest oil and gas stocks. Buffett may be “the goat,” Walker says, but the purchases do not exactly “cover him in glory.”
Patrick Soon-Shiong’s NantKwest transaction was another cautionary specimen. He invested $45 million through a private placement near $12 per share while the accompanying public offering priced around $9—a roughly 30% premium—yet the company subsequently performed terribly.
There are important winners. Jamie Dimon’s $26 million JPM purchase in early 2016 compounded to almost 7x with dividends versus roughly 3x for the indices; Harold Hamm bought $200 million of CLR around $17 during 2020 and later took it private in the low-to-mid $70s. Tilman Fertitta’s roughly $27 million Wynn purchase in late March or early April 2025 also looked well timed, though Walker says it is early and Fertitta is not really an insider. Walker’s conclusion remains deliberately mixed: “Big insider buys don’t always mean super-bullish stuff.”
4. Sector-wide buying is Walker’s preferred lens
Walker increasingly prefers clusters of transactions across a distressed sector to a celebrated purchase at one company. After Silicon Valley Bank failed and First Republic was absorbed by JPMorgan in 2023, regional banks traded below book value while directors and CEOs bought across the group.
The individual purchases were smaller but personally meaningful: multiple directors sometimes committed a full year of board fees, often making their first-ever open-market buys, while CEOs invested hundreds of thousands of dollars. That across-the-board insider buying reinforced his bullish regional-bank view.
He saw a similar pattern in busted biotech earlier this year, another of only two examples he says worked well, while conceding he “wish[ed] I had leaned harder into it.” He presents the broad pattern as a lens worth following rather than treating one billionaire’s confidence as decisive.
5. Deliberate feedback separates learning from repeated activity
Walker’s personal warning is “mindless practice.” In grade school he visited the driving range three or four times weekly, played 18 holes once a week, and walked nine holes once or twice a week, yet remained worse than peers practicing comparable amounts. Video games produced the same realization: time accumulated without much improvement.
An old Todd Combs–Ted Weschler interview sharpened the question. One of them, already in his mid-50s, described joining Berkshire and working with Buffett for a year or two as the steepest learning curve of his career. Walker wants to know the mechanism—perhaps the depth of Buffett’s questions—so he can model it rather than merely admire it.
The unresolved social challenge is pushing oneself and collaborators without becoming “a completely condescending know-it-all butthole.” Berkshire appears both demanding and collaborative; Walker is searching for a way to reproduce that combination, where people feel challenged, happier, and demonstrably better.
His best existing mechanism is public output. Preparing ramblings forces clearer thought, while rereading blog posts from ten, five, or even two years ago often embarrasses him. He welcomes that discomfort: the investor and writer he is now “would write something better” and think more rigorously.
6. Meme-stock winners still have to defend their process
September 2025 is, in Walker’s phrase, “shitco stock season”: companies with no revenue, a bad or nonexistent business model, and high short interest have gone parabolic, leaving short sellers despondent. He jokes that if he owns such a company, its stock has been getting killed.
He distinguishes legitimate controversy from situations where the technology appears to be “smoke and mirrors,” insiders continually sell, the company hits the ATM, accounting looks shady, or controlling managers appear to be bad actors. When serious investors own those names, he instinctively takes them less seriously.
Walker knows that response may be unfair. If nine positions support intelligent discussion but the tenth depends on “magic beans” growing into a beanstalk, should that single thesis discredit the investor—especially after it becomes a 5x, 10x, or 20x winner? “Maybe it’s a failure of understanding on my end,” he concedes.
The harder problem arrives with Q3 letters and victory laps, from retail claims of turning a YOLO position into 100x in 24 hours to serious investors saying they are up 400% or more. Outcomes cannot settle whether the original reasoning was sound, so Walker returns to disaggregating track records: separating repeatable judgment from one spectacular result.
Full transcript
This podcast is sponsored by Portraitan Analytics.ai. Portrait Analytics is a whole new way to use AI investing. They've got a unique set of AI tools that will help you discover, research, and monitor new investment ideas with unprecedented depth, including allowing you to automatically screen and monitor your portfolio while creating summaries of trends and tailwinds that are driving your stocks. But don't just take my word for it. I had a listener email me and tell me, "I've never thanked anyone for helping me to spend thousands of dollars before, but I never would have heard about Portrait Analytics without your podcast, and I'm just thrilled with how much time it's freed up for me to do highle analysis and portfolio management. It's super accurate and reliable. It's been a complete game changer for me. Like my listener said, Portrait is simple to use, super fast, and really intuitive. Check out Portrait Analytics today and see how they can improve your research process." That's Portrait Analysts at portraitanalytics.ai. All right. Hello and welcome to the yet another value podcast. With me today, I'm happy to have on myself. It is Saturday, September 20th. The longtime listeners know that once a month I get on and I just ramble for about 30 minutes and talk about everything I've been thinking about for the past month. I really enjoy it. Hopefully you enjoy it, too. We'll get to the ramblings in a second. Quick disclaimer, remind everyone nothing on this podcast is investing advice. That's always true, particularly true today because you know I'm just going to ramble for 30 minutes. So let's hop into everything.
The first thing I want to start by talking about is Trump suggesting that companies change their reporting requirements from quarterly to semiannually. Why? Because I think it’s a lot of fun to talk about and think about, and I think there are some interesting nuggets there.
Look, if you’re telling me you’re investing in companies for the long term—you’ve got great compounders, you’re buying great AI companies, you’re buying great data companies, whatever it is—do I think it matters if companies report quarterly versus semiannually? No, absolutely not.
I will say, if you look at the UK, I think it’s been really tough where they do semiannual reporting and then the companies come out with these, to be honest, BS trading updates every quarter where they selectively disclose stuff. I don’t like it. I would rather companies report quarterly, but I don’t think it matters hugely whether companies report semiannually versus quarterly.
However, I do think it’s a really interesting thing to change because it’s a structural change in the market, and moderate structural changes can present alpha opportunities. I like to use sports analogies a lot. In basketball, the 3-point line was introduced, and if you were faster to adopt the 3-point line, your team benefited. In hindsight, NBA teams were very slow to adopt it. If you were faster to adopt the 3-point line, then your team benefited.
If you look at the 2010s, the teams that were pushing the envelope on taking 3-pointers were getting huge structural advantages in the game. Comparing 3-point shots with quarterly versus semiannual reporting, maybe we’re being a little bit facetious. But in the 1990s, they moved the 3-point line in by 2 feet, and I think that really changed a lot of the strategy, too.
Think about quarterly versus annual reporting. If I told you tomorrow that all companies were going to report semiannually instead of quarterly, you could make alpha really fast. One way you could do it is by thinking about options.
Option prices tend to be highest right after quarterly earnings. Why? Because there’s volatility around earnings. Everybody knows—if you follow Netflix, the stock is up 10% or down 10% after every earnings report. If you’re buying an option that includes an earnings release, it’s going to be more valuable because there’s more volatility associated with the quarterly earnings.
If you told me tomorrow that all companies were going to switch from quarterly to semiannual reporting, you could make alpha by going and selling a bunch of May and November call options. I initially said April, but I think it would be May and November. Most companies report their first-quarter earnings in late April, so May options incorporate that first-quarter earnings volatility. Most companies report third-quarter earnings in late October or early November, so November options include that third-quarter earnings volatility.
If first- and third-quarter reporting goes away, will the volatility on those options come down? And then there’s going to be more volatility in the second- and fourth-quarter updates because, instead of getting 3 months of information, companies will be giving you 6 months of information.
If you think of a company that reports first-quarter earnings, misses or beats, and gives guidance, that takes away some volatility from the second-quarter earnings because now you know how things are going. Well, second- and fourth-quarter earnings are going to be lit in this scenario, right? Companies might be coming out and giving you 6 months of information instead of 3 months of information.
You could make alpha by selling the overpriced options that incorporate first- and third-quarter earnings. That would be the May and November options, and buying options that don’t incorporate the heightened volatility of the second- and fourth-quarter earnings.
Most companies report their second-quarter earnings in late July, so you’d probably want August options. Most companies report their full-year earnings somewhere between February and early March, so maybe you want March options. That could be a systematic trade that would generate insane amounts of alpha if you believed it.
Please go see the full disclaimer. I’m not saying anyone individually should put this trade on. This is the type of thing that quant shops would do. They would really monetize that. But it’s an example of what would be, quote-unquote, free alpha that you could systematically make if you really thought about and understood how the structure of the markets changed.
The other thing I do think about is that, right now, around earnings, it’s not lost on some people that a lot of the pod shops’ model is a little overwhelmed. A lot of the pod shops’ model is figuring out that Company X is reporting earnings, getting our position 3 days in advance of it, having the whisper numbers, having views on the quarter, and then the quarter happens and there’s lots of changing and positioning.
You do wonder: if that happens 4 times a year, that’s one thing. If that happens 2 times a year, how does that affect the pod shop model? How does that affect all of us who are trading against them? It’s really interesting to think about, and you could imagine lots of bolt-on effects.
Twenty years ago, there was lots of alpha around index changes. The S&P would drop something, and there was just all this forced selling.
Today, a lot of quant shops make a lot of gains off anticipating the index changes. If they think a stock is going to get booted in June, they start shorting it in April, and they’ve got up-to-the-minute models of what’s likely to be included, deleted, and all this sort of stuff. You could imagine lots of ways moderate structural things like this could create a lot of alpha for someone who’s thinking about it.
I just wanted to mention it and think about it. I think it’s been a little under-discussed that, yes, if you’re a value investor, if you’re doing long-term investing, and if you’re not doing crazy quant models, it probably doesn’t matter for the long term. But it could matter for game selection, where you can pick up alpha, and things that are mispriced. I could imagine lots of ways it could do that.
I’ll just give one more example. If you get more volatility around earnings, that could be a lot more opportunity to buy stocks, even if you’re not trading earnings. A company comes out with Q1 earnings, they miss; they come out with Q2 earnings, it’s the first time they’ve heard from the company, and they miss badly and update their guidance badly. If that’s a company you really like, the stock is probably more likely to overshoot to the downside.
Even if you’re not playing the quarterly earnings game, you could imagine how it changes things. You might say, “Hey, it’s more important for me to wait for a company to report earnings, because if they slightly miss, I’m going to get my shot to buy really good companies. They’re more likely to overshoot to the downside.”
I just wanted to mention that. I think it’s really fun to think about. I’m not saying I’m doing anything there. I don’t know if the change is going to be implemented, but anytime you have a structural change, I do think it’s useful to think about it and start incorporating it into your thinking: “Hey, how can I use this structural change to my advantage?”
I’ve laid out the ways I think I would probably use it, particularly maybe a little more dry powder, waiting for more volatility around earnings. I think that’s very interesting to think about. Let me move on to the second thing I want to talk about.
Now, if you read the blog, I’m recording this September 20th, and I’m actively working on a blog post that I’m probably going to put up September 22nd. This might duplicate the blog a little bit, or it might not. Who knows?
Elon Musk bought $1 billion of Tesla on the open market last week. I think he technically did it September 12th and filed the form on September 15th. I was a little surprised. Everybody mentioned it—I saw lots of mentions, CNBC covered it, everyone covered it. It’s Elon, it’s Tesla, it’s a huge, $1 billion buy, and it’s a really nice round number.
There was a lot of coverage of it just saying, “Hey, this signals Elon’s bullishness,” and all this sort of stuff. That’s probably true. The old adage is that insiders sell for a lot of reasons, but they only buy for one reason: they think the stock is going up.
Say what you will, I think a lot of insiders started to understand, “Hey, we buy a token amount of stock, it signals confidence in the business, and it gets our investors off our back.” I’m pretty dismissive when I see, “Oh, a CEO who’s making $4 million per year buys $4,000 of stock on the open market.”
A billion dollars is a really big number, and it is curious. In the wake of Elon being worth so much money, is a billion dollars a token amount to Elon or not? I don’t fully know the answer, but it’s still $1 billion. It’s a big purchase.
All that kind of got covered. What I was surprised by was that I don’t think people understand quite the scope of how big this is. I spend a lot of time following insider purchases, and my favorite way to use insider purchases now is actually not looking at individual company insider purchases. I do think those are important and useful signals and all that type of stuff.
I’ve actually come to have really good success, to be honest with you. I wish I had leaned harder into it, and I’m going to lean harder into it. It’s one of the reasons I’ve been thinking about Elon Musk: following sector-wide transactions.
What do I mean by that? I’m not looking at, “Hey, is the CEO at Bank X—is their stock down, and is he buying the bank stock?” That’s nice. But in mid-2023, in the wake of Silicon Valley Bank failing and First Republic getting taken over by JPMorgan, all the regional banks got crushed. They were all trading below book value, and I was very bullish on banks when all this happened.
I’ve got the post to prove it. I wish I had been more bullish on banks. One of the reasons I was bullish on banks was just that, across the board, across the spectrum, you could throw a dart at any regional bank and you would find directors buying on the open market and the CEO buying on the open market.
Often, these weren’t enormous sizes. We weren’t talking about a CEO going and buying $1 billion of stock. But you were talking about directors buying multiple directors’ full year’s worth of their board fees on the open market, for a lot of them for the first time ever, making insider purchases. CEOs were putting hundreds of thousands of dollars here and there into the stocks.
You were seeing it across the board, and I’ve come to believe that type of across-the-board insider buying is really interesting. I can really only point to 2 places where it’s happened for me, and both of them have been great successes. Maybe it’s N of 2, but one was banks in mid-2023, and the other was busted biotech, which I was pounding the table on earlier this year.
Again, I’m not tooting my own horn. I’ll be happy to throw my nose into the myriad mistakes I’ve made in the past. But I do think those are interesting signals.
I follow these closely because of those signals. What I think is getting underreported on Elon Musk is just the pure size of this. I cannot find another insider transaction that comes anywhere close to this size.
Part of that is just because there aren’t a lot of people with $1 billion lying around, and there aren’t a lot of companies that can take $1 billion of insider buying on the open market. The closest I could find—and, by the way, the SEC’s website is not easy to track on this—would be Dustin Moskovitz at Asana. The ticker there is ASAN. He bought $350 million of Asana stock in 2022.
That was directly from the company, so even that was not on the open market. Dustin Moskovitz, if you go and look at Asana—again, the ticker is ASAN—has a very interesting history, because I actually believe he has made the most aggressive insider purchases of all time.
He did that $350 million slug directly from the company, but he also filed a bunch of 10b5 plans to buy stock on the open market at Asana. I believe from late 2021 till the end of 2022, he bought $1 billion of stock on the open market, including multiple hundred-million-dollar open-market slugs. So, I think that’s the largest insider buy of all time before Elon.
That one’s interesting because the stock has been a disaster. So, I think that’s interesting. You get through a year’s worth of 10B5 buying on the open market, and you get to $1 billion, including a $350 million slug directly from the company.
The only other one I could find that even rivals this size is Berkshire buying $3 billion of Oxy stock on the open market in early 2022. That was 1 Form 4; they bought $3 billion of Oxy stock. They actually bought more than that. People remember Buffett used to have something like a $60-per-share or $55-per-share limit, and if it went below that, Berkshire would make huge purchases of Oxy.
I think they probably bought $6 billion or $7 billion of Oxy on the open market back in 2022. Why is that interesting? It’s not a direct comparable, because Berkshire is a financial buyer, not an insider. They’re only filing a Form 4 because they own more than 10%. That’s the only other one of a similar size that I can find.
If we’re talking about Form 4s—just straight insider buys—Dustin Moskovitz at Asana would be the one. Harold Hamm bought $200 million of CLR at the depths of COVID in June and July 2020, late June and early July 2020. That was $200 million across a couple of $50 million slugs around that time frame.
Outside of those, Jamie Dimon bought $26 million of JPMorgan on the open market in early 2016. Tilman Fertitta, who is not an insider at Wynn but does own over 10% and is a gaming CEO, bought—I think he’s got the largest insider purchase of 2025 before Elon—it was $27 million of Wynn stock in late March or early April of this year.
Aside from that, that’s it. I just listen to these guys. The biggest ones are $25 million. There’s a $100 million or $250 million one, but I think it shows the pure scope. This is insane, and I don’t think it got talked about enough.
It would be like if Wilt Chamberlain came and scored 180 points in today’s NBA, where the top NBA scorer might get 50 to 60. You’d be like, “What?” It’s so much higher than anyone else is scoring. Teams aren’t scoring this much, and the man dropped something. I have just never seen anything of this scope.
So, I think that’s interesting. The size has been underreported. But here’s the other interesting thing: most of the reporting centered on this being a bullish signal from Elon Musk, and it is. He dropped $1 billion of his own money on the company. People don’t do that if they’re bearish.
But the other interesting thing is that the history of these types of open-market insider buys is actually really poor. The first one I’d mention is Asana. Dustin Moskovitz starts buying Asana when the stock price is closer to $100 per share—I think he starts buying in the 80s. Asana today, as I’m pulling it up while you and I speak, is trading for $14 per share.
I mean, this has been some of the worst capital allocation of all time. It’s been a disaster. The other ones don’t look great. Jamie Dimon buys JPMorgan, and that does very well. Tilman Fertitta’s purchase of Wynn looks like it’s doing pretty well. I’d say it’s early, but it looks like he timed it well. Again, he’s not really an insider, so I don’t know how to think about that.
Berkshire’s $3 billion of purchases of Oxy haven’t done that well. Oxy has been about flat since early 2022 and has underperformed the S&P 500. You can say, “Oh, it was oil and gas. There was a lot of macro stuff that happened since then.” Yes, you’re correct. But go pull up the largest oil and gas stocks since Berkshire was buying Oxy back in 2022. Axon is about in line with the S&P 500, and Chevron and all these other guys are, too. Oxy has been a huge laggard.
So, Berkshire—you know, Buffett’s the smartest guy in every room he walks into. He’s a legend. He’s the GOAT. But the Oxy purchases don’t exactly cover him in glory, right? I think the history of these huge insider purchases is not just mixed; I think it’s actually kind of negative. It’s not great.
I’ll give you one more. Patrick Soon-Shiong, who runs the Nant companies and bought the L.A. Times, made these investments in a lot of biotech firms back in 2020, right when Harold Hamm was purchasing Continental Resources. Patrick put $45 million into NantKwest, which traded under the ticker NK at the time. This was through a private placement, but I think it’s a really interesting private placement because, if you go back and read the filings, he put money into NantKwest at about $12 per share.
Alongside his $12-per-share offering, the company went and did a public offering that priced at $9 per share. So, he put money into the company at a big premium—a 30% premium to where the public equity offering went off—and it was $45 million, so it was huge. The company has been a disaster since then.
Again, I don’t know how this turns out for anyone, but I was just surprised. I saw lots of people say, “Hey, this is Elon’s biggest insider buy of Tesla ever,” which is 100% true. He’s done a little bit of insider buying of Tesla in the past, but it’s normally been alongside equity offerings, and it’s much smaller than this.
This is huge. It’s orders of magnitude bigger than anything he’s ever done, but it’s also orders of magnitude bigger than anything else I can find in the public markets. I just think that size is really interesting. I saw a lot of bears who got real quiet when Elon bought $1 billion of stock on the open market, and I saw a lot of bulls who got real excited—and probably rightly so.
This is a really good signal value, but I think if you look at the history of these big purchases, it’s actually CEOs who are kind of getting high on their own supply. Again, that’s not to say that this can’t turn out well. If I go look at Jamie Dimon’s JPMorgan purchase, JPMorgan is up almost 7 times, with dividends reinvested, since he made that purchase in 2016. The indices are up 3 times, right?
If I go back, I mentioned Harold Hamm. That’s a really interesting one. The founder of Continental Resources bought $200 million of CLR in the depths of COVID, in late June or early July 2020, for about $17 per share. He took CLR private a few years later—I think it was late 2022—for somewhere in the mid- to low-$70s per share. So, he kind of set his own marks on both sides, but he’s got a 4- to 5-bagger in his hands.
I’m not saying it’s all a disaster, but the history of these things—you think about the NantKwest investment I mentioned, you think about the Moskovitz investment, and you think about the Berkshire investment—big insider buys don’t always mean super-bullish stuff for people. I’ll have a post on that, but I just thought it was really interesting and wanted to point that out.
Let me switch rapidly here. Let me go to improvement. I’ve been writing and talking a lot about improvement and improving investing. The Ardan Folken podcast [?], number 333, got just absolute rave reviews from people. People really enjoyed us talking about that.
One of the reasons I talk so much about improving is because I’m trying to improve, right? I’ll just give you one thing: I worry it’s very easy to do mindless practice. I’ll give you an example. In grade school, I played a lot of golf with my dad, and that was awesome. We probably went to the driving range 3 to 4 times a week, I probably played a full 18 holes with my dad once a week, and we probably walked 9 holes once or twice a week.
That’s a decent bit of practice. To be honest, I just wasn’t that good. I look back at the amount of time I was putting in during grade school and realize it was mainly time I spent with my dad, which was great. But I look at the amount of time I put into it and think, “Damn, you were pretty bad for how much time you put into golf.”
I’m not saying I needed to be a scratch golfer—I was in 6th through 8th grade—but my peers were much better than me, and I think I was spending as much, if not more, time at the driving range than they were. Or I look at high school, when I probably played an average amount of video games compared with my peers. I kind of look at it and say, “Man, if you were playing an average amount of video games in high school and college versus your peers, you probably should have been better than you were at these games.”
I just look at it and say, “Hey, this was mindless practice. This was mindless time.” Even if you thought you were getting better when you were going to the driving range 3 or 4 times per week, you weren’t really getting better. I think it was mindless.
I’m pointing this out as a personal failing of myself, right? I can look at the pure amount of time I put into something and think of it as spinning my wheels, but it’s not actually improving or getting better. It’s just mindless time. That’s one of the reasons I’ve thought so much about improving and getting better, particularly recently, because I spend a lot of time investing, working on this, and doing the product. I want to make sure that the time I spend investing is driving toward something. It’s getting better. It’s not mindless.
Why do I mention all this? A: I like to rant. I like to talk. Sometimes I think that when I say things out loud, they make more sense than when I’m writing them, which might suggest some failures as a writer.
The reason I mention it now is that I was talking to someone, and they pointed me to an old Todd Combs and Ted Weschler interview. They had been at Berkshire for a year or two, and one of them came out and said, “Look, I’m in my mid-50s, and joining Berkshire and working with Buffett for the past year or two, however long it has been, has been the steepest learning curve of my career. I’m learning so much, but it’s been really difficult, and it’s involved a lot of work.”
I thought that was really interesting. I’m more late 30s than mid-30s at this point, but I don’t consider myself a finished product by any means. I would say that I think about the learning curve and the work curve, and I think it was harder earlier than it is now. It makes me excited that there’s still that much more to learn, and I truly believe that.
But it got me thinking: What about joining Berkshire and joining Buffett pushed the learning curve so high? What were they doing? What specifically was it? Was it the depth of Buffett’s questions? Was there something else? How can I model it? How can I repeat it? How can I use it to make myself better? I have no good answers there—literally none.
I will say that I can use the podcast for this as well. I would suspect one of the things is the depth of questions, but I also think it’s a fine line. I’ve never talked about it in person, but there’s also a fine line that I find myself maybe tiptoeing around too much: What is pushing and what is learning, versus how do you do it without being a completely condescending know-it-all butthole?
Again, I don’t know the answer there, but it’s one thing I’ve really been thinking about. How can I push myself to get better? How can I push the people I talk to a lot to get better? How can I do the latter without being a complete butthole?
People might get better if you yell at them a lot, but you’re just a butthole if you do that. How do you do it in a way that’s collaborative and encouraging? When I look at Berkshire, it does seem like a very collaborative environment, and people do seem to like being there. How do you push each other in a way that everyone feels like they’re getting better and feels happy about it?
That’s a lot of what has been on my mind regarding improvement. I’m always open to suggestions.
If you tell me, “Hey, Andrew, this is something that I do in my investment process that makes me a much better investor, or that I feel has helped me improve,” I’m open to it. For me personally, I think I improve the most when I am writing the most, thinking the most, and putting stuff publicly out. One reason I like these ramblings is that prepping for them helps me clarify my thoughts and deepen my thinking. I tell people all the time that I’ve been writing the blog for 10 years.
I go back and read the stuff I wrote—not just 10 years ago, but 5 years ago and 2 years ago. I’m embarrassed a lot of times, and I’m kind of happy about that. I’m not happy to be embarrassed, but I’m happy that I think the person who was writing and thinking this, if they were doing it today, would write something better, do something better, be better, and think about this better. I feel the same way with a lot of my investments as well.
I’m always trying to improve and always trying to get better. Podcasts—the first podcast I did, I’m just so embarrassed by, but I think I’m still getting better at that. I’m trying to get better, and I’m always open to it. I was not rambling there. I think you can see that.
The last thing I wanted to mention—2 last things. You know what? Let’s save the stuff you change your mind on, because I’m going to go back to Charlie Munger and Warren Buffett. I can save that for next month. I’ll leave you a little tease about the stuff you change your mind on for next month, because we’re running long.
Let me start. I want to end with the last thing, and that’s shitco stocks, meme stocks, whatever you want to call them. There are a lot of them out there. The reason they’re on my mind right now is that if you are paying attention to the markets in September 2025, it is shitco stock season. These things are just going parabolic.
I know short sellers have been borderline despondent recently, and probably with good reason. If you are a company with no revenue, a bad business model, or maybe no business model, high short interest—and this last part is very important—and I don’t own you, because if you’ve got the first 3 and I own your stock, I guarantee you’ve been getting killed. But if you’ve got the combination of the 3 and I don’t own you, your stock has been a rocket ship recently. I’m not going to name any of the stocks, but I’m sure everyone knows many of them and can point to some of them.
I mention that because there are some that are controversial where I understand both sides of the controversy. I could see the bull case, I could see the bear case, and I’m not involved. There are some where I can see the bull case and I’m involved. There are some where I can see the bear case and I’m probably not involved because I’m just not going to short this. But there are 1 or 2 or 7 of these controversial ones where it’s clear to me that the bulls are just insane.
You would normally associate that with retail. You think about some of the retail stocks that went bankrupt and had these cult followings behind them. I normally associate that with retail, but there are 1 or 2 or 7 that, when I look at them, it’s just so clear to me that the technology is a bunch of smoke and mirrors, the company is just completely unserious, they’re hitting the ATM, insiders are selling nonstop, and all this sort of stuff. The stocks have screamed higher. They’re up 5×, 10×, 20×, whatever it is.
I’ll have people reach out to me and talk to me, or I’ll talk to my friends and they’ll be invested in them. It doesn’t even have to be those. There are some controlled companies where I think the management teams are clearly bad actors or their assets suck, and I’ll talk to people and they’ll love them. The point I’m driving at is that there are companies and stocks where I think they’re such clearly bad ideas that sometimes, when I hear people are long them, I’m just like, “I don’t know. I just take the person less seriously.”
I don’t know if I’m like everybody else. I’d hate to be judged by what I do on my worst day. I’d love to be judged by what I do on my best day, but I’d hate it if somebody, in the moment—in rush-hour traffic, I don’t know, whatever—I did something uncharacteristic, and they looked at that one moment and applied it to the entirety of my life. I probably shouldn’t be judging one investor, even if they’re a concentrated investor, based on this one investment that I don’t understand, which for a lot of them has worked out really, really well.
But when I look at that, when I look at being long these companies, I’m just like, “I don’t know how you can be a serious investor and be long this.” I don’t know where I’m going with that, but I’ll talk to these people and I just don’t get it. I don’t know how you think about it if you are a concentrated investor and long 10 companies, and 9 of them you and I can have a good discussion about. We’ve got good points, and I’m learning a lot from you.
Then, on the 10th, you say, “Hey, I’m long this pot of magic beans because I think the magic beans actually sprout a giant beanstalk that grows to the sky. Then we’ll go up to the sky, live with the giants, and get rich off their riches forever.” I’m just like, “No, dude. This is just a pot of magic beans that are actually just beans being sold to you.” All the red flags around this—the insider selling, the ATM issuance, the shady accounting, all of it—you just ignore because the magic beans will grow into a beanstalk. I don’t know how to think about that when I’m talking to other investors and when I’m doing work.
It’s on my mind because some of these—we’re almost done with Q3. You’re going to start getting Q3 letters, or you can go on Twitter and find people taking these crazy victory laps. Retail people went YOLO-long on their AI winner right before the Fed cut, and now they’ve made 100× their money in 24 hours. I guess good for them. I wish I had done that.
But I’m thinking more about the serious people who have made 5-baggers this year on these companies, or who continue to pitch these companies that are controlled companies and aren’t getting this. How do you judge somebody when they’ve got 1 error of omission that, to me, is so glaring and so poor? I don’t know. Maybe it’s a failure of understanding on my end, but it’s something I’ve been thinking about, and I’m going to be thinking about it a lot more as I get hit with people who say, “Hey, I’m up 400% this year because I was long a pot of magic beans that went up quite a bit.” How do you think about them as an investor?
It’s 1 of the reasons Art Folk and I—we talked a lot about this, and I hate to bring it back to that conversation. We talked a lot about how you disaggregate someone’s track record. I think it’s just really interesting.
Okay, ramble, ramble, ramble, ramble, ramble. I am rambling. This has been a lot of fun for me. It is September 20th. I’m looking forward—I think we’ve got a great set of podcasts coming up for you. I’m looking forward to those. I’m looking forward to getting my post up on Elon’s open-market purchase. I’ll include a link in the show notes. As always, you can reach out, love to chat, love to swap thoughts, love to have you help me improve as a podcaster, as an investor, all that sort of stuff. But I really enjoy doing these. I thank you for listening and I’m looking forward to chatting next month. A quick disclaimer, nothing on this podcast should be considered investment advice. Guests or the hosts may have positions in any of the stocks mentioned during this podcast. Please do your own work and consult a financial adviser. Thanks.