On September 8, 2026, Collective members joined Grant Williams, Dee Smith and Brent Johnson for an hour on one question: who can you actually trust, and what do you do once you accept that the honest answer is almost nobody. This trio and topic were inspired by three separate conversations we had last March: a call with Dee the week the Iran situation broke, a London pub dinner with Grant, and a four-hour roundtable in New York with Brent. Each conversation kept circling the same thing: trust.
Dee Smith is the founder and CEO of Strategic Insight Group, which runs intelligence work for institutional investors, pension plans and private equity firms. Brent Johnson runs the macro fund Santiago Capital and is known for the dollar-milkshake thesis. Grant Williams, the author of Things That Make You Go Hmmm… and a beloved host and interviewer, guided the room. Dee and Brent had never met but their overlapping lenses inspired us to bring them together.
This is the first of three conversations in Vol. 2 of the Collective Roundtable Sessions: live discussions that bring people who joined Collective separately together around a single question. The full recording is free to watch; paid Insights subscribers join Roundtable Sessions live with the opportunity to put their own questions to the room.
Not a paid subscriber yet? Paid subscribers get live access to The Roundtable Sessions, and this is the best moment of the year to join.
Our Summer 2026 offer takes 20% off Collective Insights, and it isn’t an intro rate; the discount is locked in for as long as you stay subscribed.
Summer officially ends at 11:59pm on Tuesday September 22, and so does the offer.
What They Discussed
How Dee approaches information. Dee described the intelligence method his firm uses: gather many small pieces, most of which mean little on their own, look for patterns and anomalies, treat what surfaces as a hypothesis, and test it. He said falsification matters more than verification, and that the hard part is setting your own stake in the outcome aside, which is part of why institutions bring in an outside party. He also offered a tell: if you catch yourself thinking something “can’t be right,” take it as a sign you may not be judging the situation correctly.
Brent on frameworks and what can still be trusted. Brent said the biggest risk to an investor is lying to yourself. His own practice is to take the opposite side of whatever he is told and work out whether it holds, and he cited a line from Michael Lewis’s Liar’s Poker, “you carry the opinion of the last person you spoke to,” as the failure mode of not having your own framework. Even where broad trust has broken down, he said, some things stay reliable: that governments will act to stay in power, that countries will compete, and that investors will act in their own self-interest. Grant added Charlie Munger’s point that if you understand the incentives, you can usually anticipate the outcome.
Investing versus doing the right thing. Brent described a distinction he weighs as a fiduciary: whether something is morally wrong is, in his framing, separate from whether it makes money, and a mandate to grow a portfolio is not the same as taking a moral stand. He said it is something he wrestles with. Dee added that what counts as “right” also shifts over time, noting that practices once accepted are later judged harshly, and that the reverse can be true as well.
Broken promises and the debt underneath. Dee said people tend to experience the moment not as a broken social contract but as broken promises: a deal they kept that others did not. He described asking audiences whether they expect their children’s lives to be better than their own and rarely seeing hands go up, and tied it to roughly $350 trillion of global debt, which he framed as a bet on a future that is always better than the past.
Where they saw hope. Asked where they found reasons for optimism, Brent pointed to a cultural pendulum he believes is swinging back toward the middle, and named AI as a net positive over time. Dee said most problems are solvable with tools that already exist, and that the current willingness to question everything is itself a kind of opening.
What they would watch. Asked for the single most important investment implication of declining trust, neither pointed to the common answer of buying gold. Brent named the Office of Strategic Capital as the institution he expects to move markets most. Dee pointed to security, and to the way supply chains and resources can be used as leverage, citing US and China dynamics as the clearest example.
Notable Quotes
“The absolute worst thing you can do as an investor is lie to yourself.”
— Brent Johnson
“Wrong has absolutely nothing to do with it. It should. You may want it to, I may want it to, but it just doesn’t.”
— Brent Johnson
“Falsification is more important than verification.”
— Dee Smith
“Debt is borrowing from the future to pay for the present. It only works if the future’s always going to be better.”
— Dee Smith
What You Can Walk Away With
* Both described a similar way of working with information: assume what you are handed may be wrong and test it, rather than searching for a source to simply trust.
* Trust has narrowed more than it has vanished. The things that stay dependable are incentives: governments, countries and investors acting in their own interest.
* As trust between states erodes, both watch where the state is directing capital (Brent’s Office of Strategic Capital) and securing resources (Dee’s supply-chain and security lens).
Resources & references
* Liar’s Poker, Michael Lewis. The book Brent is rereading, source of the “you carry the opinion of the last person you spoke to” line. LINK
* “Why Am I Reading This Now?”, Ben Hunt (Epsilon Theory). The framing Grant adapted into “why am I seeing this now.” LINK
* Grant Williams: Things That Make You Go Hmmm…, The Grant Williams Podcast, and the About Time video series. LINK
* The Office of Strategic Capital. Brent has written on it and offered to share his work; you can follow Brent on Twitter LINK
* Dee Smith, Strategic Insight Group. LINK
What’s Next
Two more Roundtable recordings + briefings coming this week:
* The New Rails: Matt Zeigler hosts Kris Abdelmessih, Shaun Martinak and Izabella Kaminska on what tokenization actually changes about markets.
* The Yen at 160: Robert Mullin hosts Vincent Deluard and Louis Gave, recorded in the final hours before the Bank of Japan moved.
Join Us
Not a paid subscriber yet? Paid subscribers get live access to The Roundtable Sessions, and this is the best moment of the year to join.
Our Summer 2026 offer takes 20% off Collective Insights, and it isn’t an intro rate; the discount is locked in for as long as you stay subscribed.
Summer officially ends at 11:59pm on Tuesday September 22, and so does the offer.
Remember, this post is for informational purposes only. For anything investment-related, you should consult a qualified financial advisor who can help assess your individual needs, risk tolerance, and goals.
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