Friday Haymaker
Grant Williams & Sir Steven Wilkinson: An Interview Summarized
“Though we live in an era of relative peace and comfort, we have settled into a mood of pessimism about the long-term future, fearful that our superpower nation is somehow rotting from within.” -William Strauss
The Grant Williams Podcast - Sir Steven Wilkinson
Two members of Team Haymaker had the chance to spend a couple of days of one-on-one time late last month with our dear friend Grant Williams, (author of the acclaimed newsletter Things That Make You Go Hmmm…). When we asked him who he had interviewed lately that had impressed him the most, he paused briefly and then said, “Sir Steven Wilkinson”. When pressed as to why, he replied it was because the knighted one (much better than being a benighted one) feels the market party can keep on roaring. This was despite articulating a raft of concerns that have been frequently documented in Grant’s work… and our own.
Ironically, or perhaps not so much, we arrived at Grant’s lovely Kiawah Island club just in time to experience a glancing blow from Hurricane Helene, complete with tornado warnings, howling winds, and torrential rain. In his discussion with Grant, Sir Steven didn’t minimize the impending tempest heading our way. Like us, he’s very much convinced we’re in the midst of Strauss and Howe’s Fourth Turning mega-crisis climax, as we discuss below. This is why his bullish views of the next year or two surprised and intrigued Grant and us. It’s our belief our readers will also be fascinated by Sir Steven’s analysis, one of the most lucid and incisive we’ve heard in a very long time. Accordingly, we’ve provided a summary of their conversation.
For those of you looking to add another premium newsletter service to your knowledge inventory, we highly recommend you consider Grant’s TTMYGH, if for no other immediate reason than to avail yourself access to the full Williams/Wilkinson interview (podcast page linked at the end). The summary we’ve provided touches on every major topic these two remarkable gentlemen cover, but as with all such meetings of minds, the texture of conversation is where collaborative brilliance really makes itself known.
UK Politics: A Case of Disillusionment, Not Victory
The discussion kicks off with UK politics, and they don’t mince words about their native land’s predicament. Both Grant and Steven see the recent Labour Party victory not as some grand endorsement of Labour’s leadership but more of a “vomit outcome.” (This might also aptly describe the results of the upcoming U.S. presidential election.)
The public wasn’t cheering for Labour — they were fed up with a Conservative Party that had lost its way. The Tories, who were once about low taxes and tough stances on issues like immigration, had turned into a party that failed to deliver, raising taxes and fumbling key issues. For Steven, this wasn’t about Labour’s success; it was about the public finally saying, “Enough is enough.”
But what’s happening in the UK is just a symptom of a bigger, global problem. Steven argues that liberal democracies, which once seemed invincible, are now creaking under their own weight. The systems that were supposed to be the endgame of political evolution — democracy, free markets, and strong institutions — are starting to break down. The bureaucracies, big corporations, and the banking system have fused together, creating a monster that doesn’t adapt or innovate — it just perpetuates the status quo. And that’s why, Steven says, voters everywhere are feeling disillusioned. They’re trapped in systems that no longer work for them.
The Debt Bomb: Kicking the Can Down the Road
Naturally, they shift to economics, and it’s clear things aren’t looking any better on this front. Steven goes straight to the heart of the issue: debt. We’re in a situation where global central banks have fabricated trillions of dollars, and governments have spent equivalent sums, propping up economies with what amounts to financial duct tape. It’s not sustainable, and Steven doesn’t sugarcoat it. He draws comparisons to the Weimar Republic’s hyperinflation, warning that today’s endless fiscal stimulus is setting us up for something similar. We’re living on borrowed time, he argues, and the bill is coming due.
What’s worse, Steven says, is that money itself has been corrupted. It’s no longer a store of value or a foundation for wealth — it’s just a tool for short-term political fixes. Central banks are manipulating currency to paper over (literally, given the fiat nature of money these days) the cracks in the system. As a result, the middle class — the backbone of society — is being hollowed out. It has lost a significant portion of its savings to government-enabled inflation and the promise of a stable future is disappearing. It’s all part of a broader systemic decay that Steven sees as both an ethical and economic failing.
He refers to Guido Hülsmann’s The Ethics of Money Production to make his point clear: inflating the money supply to meet political needs is more than just bad policy — it’s morally wrong. Big banks, big businesses, and big governments are all in on it, perpetuating a cycle that benefits the few while eroding trust and stability for everyone else.
The Inevitable Crisis: Cycles Coming to a Head
Then, the conversation takes a turn toward historical cycles, and this is where things get really interesting. Steven is a big believer in the idea that history moves in generational cycles, referencing Neil Howe’s The Fourth Turning. According to this theory, history runs in 80- to 100-year cycles, with each “turning” representing a different phase of societal evolution. Right now, we’re in the fourth turning — a period of crisis, where old institutions crumble and society undergoes a radical transformation. The last time we were here? World War II. And Steven suggests we’re barreling toward a similarly intense moment.
The key takeaway? Complacency is the killer. Societies become too comfortable, too locked into old ways of thinking, and they inevitably crack. Steven draws a comparison to businesses: when they stop innovating, they stagnate, and that’s exactly what’s happening now. Today’s world is led by careerists — mediocre leaders and policy advisers more interested in keeping the machine running than in fixing its problems. But the machine is seizing up, and when it finally shuts down, it won’t be pretty.
Steven also brings up other cycles, like the Kondratiev wave and the 18.6-year land price cycle, which suggest we’re heading for a major financial crash. It’s not just society that’s falling apart: the economy is right behind it. All these cycles are pointing to a period of massive upheaval in the mid-2020s, and while it might sound dramatic, history backs him up. We’ve been here before, and we’ll be here again.
In Search of Real Leadership
So, what’s the solution? Leadership, but not the kind we have now. Steven argues we need lateral thinkers, people who can see beyond the narrow, linear thinking that’s gotten us into this mess. He draws a fascinating comparison to Winston Churchill. In his time, Churchill was loathed by the British establishment, but when the chips were down, he was the only one capable of leading Britain through its darkest hour. Churchill’s ability to see the big picture, to connect the dots others couldn’t, made him invaluable in a time of crisis.
Here’s where Steven gets bold: he suggests that, flawed as he is, Donald Trump might be this generation’s lateral thinker. Now, before you roll your eyes, hear him out. Trump, for all his bluster, isn’t a product of the political system, and that’s exactly why he could be the kind of leader who can smash through the entrenched power structures. Steven even speculates that Trump could de-escalate the war in Ukraine by sitting down with Putin, something no establishment politician would dare to do. It’s a provocative take, but Steven’s point is clear: we need leaders who aren’t bound by the bureaucratic and political constraints that have led us into this mess.
What’s Next? A Storm’s Coming
The conversation wraps up with a heavy but honest look at the future. Both Grant and Steven agree we’re heading toward a climactic event; whether it’s war, economic collapse, or a political revolution, something has to give. The systems and institutions we rely on (political, economic, social) are all straining, and the Fourth Turning promises this pressure will eventually lead to a breaking point.
But it’s not all doom and gloom. For one thing, as alluded to in the introduction, Sir Steven contends the financial market boom of the last two years has yet to hit its crescendo. He believes there are too many high-profile pundits out there, like Ray Dalio, warning of the looming reckoning for it to happen. Rather, he believes it will come when euphoria is rampant and the “doomsters” are totally ignored… and discredited. However, he does allow that this is highly likely to make the eventual bear market all the more ferocious.
Yet, Sir Steven argues that out of this destruction will come renewal. Just like past crises have led to periods of rebuilding, this one will too. We’ll see a return to sound money, personal responsibility, and strong institutions… but only after we get through the storm. The key, he says, is to be prepared: mentally, financially, and socially. The people who can see what’s coming, the lateral thinkers who can think beyond the current crisis, will be the ones who lead us through it.
In the end, this interview isn’t just a critique of the current state of the world, it’s a call to action. The systems we’ve relied on for so long are crumbling, and the tropical storm off our shores is building in force. But with the right leadership and a willingness to think differently, we can rebuild. Change is inevitable, how we respond to it is up to us. Like Sir Steven, we are bullish on America’s younger generations to rise to the existential challenge.
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