Jack Forehand

The S&P 500 is the 1992 Dream Team. Ian Cassel is trying to beat it with a roster of no-name microcaps. "It's Michael Jordan. It's Larry Bird." "It's Nvidia, it's Microsoft, it's Google." "In any given year, I might look like a hero or an idiot." His goal is to beat it over 10 years.

Why can a crowd guess the weight of an ox but get a stock market bubble wrong? "Nobody's really emotionally attached to the weight of an ox." Alex Edmans on what changes when investors' mistakes all point in the same direction: "We actually reinforce each other's biases rather than neutralize them."

PCE inflation rose to 3.6% year over year in September. The risk for a portfolio: stocks and bonds can fall together. In this earlier conversation, Eric Crittenden points to 2022 as a test of an all-weather portfolio: having something that can thrive when both fall, in a size that matters. "All weather to me is simply being prepared for what we know is plausible."

A big loss costs you more than the money you lose today. "If you lose your capital, you're out of the game." "You forego the chance to play in good games in the future." Kris Abdelmessih on keeping enough capital for the next opportunity.

AI data centers aren't just a bet on the chips inside them. "They're extremely valuable, even if the chips wear out." Jay Hatfield argues that scarce land, power access and permits can retain value after the hardware depreciates.

Could your index fund become venture capital's exit strategy? Chris Davis worries that huge private companies could eventually find price-insensitive buyers in index funds. He calls it his "really dark tinfoil hat conspiracy theory."

"The hardest thing for people to do is nothing." "I think our investors expect us to buy something, sell something, do something." "Buy things and hold them for long periods of time and save more." Gregg Fisher on the one lesson he would teach the average investor.

"The returns always come later than people thought." Dan Rasmussen's concern about the AI build-out: spending can outrun the payoff. Kai Wu explains the trap: "That leads to a collective over-investment even if the individual is rational."

Cliff Asness thinks faster markets aren't necessarily smarter markets. "I think most of that is about speed, not about correctly processing information." "I'm old, but I'm not carrier pigeon old. We had Bloombergs and we had phones."

"Cathie and her team, they are good stock pickers." Kai Wu's factor model finds positive stock-picking alpha in ARK. But the portfolio's tilt toward small, unprofitable companies worked against it.

Even an incredibly well-run steel mill can be overwhelmed by its industry. Tom Maher's question for investors: "How much can they make their own weather?" A company's execution matters. So does how much its fortunes depend on the economy around it.

Using AI for free doesn't tell you how much customers will pay for it. "We'll find out about demand elasticity in a hurry" when prices rise, says Jim Paulsen. "I think it's gonna be successful over time. I just don't think it's gonna be nearly as quickly as people are suggesting."

"This isn't wise, but sell everything." Knowing that panic-selling is a mistake doesn't always stop an investor from doing it. Daniel Crosby uses a March 2020 example to explain why understanding risk while calm is different from living with it during a crash.

"Capitalism requires win-win, and we're all taught to think win-lose." Rob Arnott's test for a durable moat: does the company produce something that's worth more to its customers than it charges them?

"The most painful thing is when a client throws the towel in on the bottom." Colin McQueen doesn't just ask whether a portfolio fits his outlook. He asks what it looks like if that outlook is wrong.

"They're companies that got sloppy and lazy 'cause they could grow with very little reinvestment." Alphabet expects capital spending to "increase significantly" in 2027. Aswath Damodaran's earlier warning about Big Tech's move into heavy infrastructure spending: "The way I have to read their earnings reports has to change."

Some investors want their portfolio optimized to the third decimal place. Brian Portnoy thinks the more useful question is whether it fits their goals. "They tend to want the right answers to the wrong questions."

"It always feels awful buying at the bottom, and you're never gonna pick the bottom." Ted Mortonson on a lesson from his mentors: buying from fearful sellers rarely feels comfortable.

"If you feel like something's can't-miss, you probably missed something." Daniel Crosby on why deeper understanding usually brings more humility, not more certainty.

"I think anybody should fire their advisor or a portfolio manager if they're ever told to hang in there." "Stop doing things that are not working and do more things that are working." Ryan Krueger on the one lesson he would teach the average investor.