Confidence has become a substitute for competence — and the infrastructure that supports the substitution has never been better. A note on trust, what Dante already knew, and why the people who did the work sleep fine.
I worked with a guy a few years back. We'll call him Sam. Smart enough, decent in a room, knew how to hold a conversation. We were engaged to position his company and raise the investor capital he needed for his growth plan. I know exactly what happened. I know the timeline, the terms, the outcome, and who did what.
What he tells people now is that he built the business and had a successful exit. What actually happened is that he lost the confidence of the investor during the diligence process (the part where someone actually checks) and was forced out of his own company. His partner had to clean up the mess he left behind. There was no successful exit. There was a slow-motion implosion that someone else had to fix.
He tells it with total confidence. Good eye contact, steady voice, the kind of certainty that makes people nod along. And they do nod along. Nobody asks a follow-up question. Nobody picks up the phone to check. They just take it at face value, because the delivery is so smooth that it doesn't occur to them to verify it.
That's the part that gets me. Not that he lies. People lie. It's that nobody is curious enough to check. The confidence is doing all the work. And the competence? That's somebody else's story he's wearing like a suit.
I keep seeing this pattern, and not just in deal rooms. On LinkedIn profiles where the math doesn't add up. On pitch calls where the track record has gaps nobody asks about. On social media, where a 23-year-old with ring lights and a leased Lamborghini is selling you his secrets to building a nine-figure business.
Confidence has become a substitute for competence. And the infrastructure that supports the substitution has never been better.
The confidence is doing all the work. And the competence? That's somebody else's story he's wearing like a suit. — Side Letter No. 003
A decade ago, a fake guru looked like a fake guru. The production was cheap, the claims were obviously absurd, and most people could smell it. That's not how it works anymore.
Today, the tools that make real businesses more efficient also make fake ones more convincing. AI-generated design, professional-grade video editing on a phone, polished landing pages that take twenty minutes to build, testimonials that are either fabricated or purchased. The veneer of legitimacy used to require an actual operation behind it. Now it requires a laptop and an afternoon.
The result is a confidence economy running at industrial scale. The FTC reported that Americans lost $2.1 billion to social media scams in 2025, eight times the 2020 number. More than half of that was investment scams, most of which started with someone posing as a financial mentor, building fake trust through manufactured results. A global audit of 8.7 million influencer profiles found that over 40% showed signs of fraud, and one in three brands admitted they'd unknowingly paid a completely AI-fabricated influencer persona in the past year.
Yuval Noah Harari makes a point in Nexus that's worth sitting with. He traces the history of information networks and finds that more information has never automatically meant more truth. The printing press didn't create an informed public. It created witch hunts. And social media didn't just fail to filter out lies. It actively selects for them. YouTube's own internal research found that outrage drives engagement, and when users stuck to the truth, the algorithm ignored them. The platform's incentives and the liar's incentives are perfectly aligned.
So the cost of manufacturing confidence dropped to near zero. The reach went global. The tools got good enough to fool people who aren't fools. And the algorithms reward exactly the kind of bold, assertive, fact-free content that confidence-over-competence produces best.
That's the supply side. But there's a demand side too, and it starts at the top.
NBC's former head of marketing, John D. Miller, spent 25 years promoting television. In 2024, he wrote an op-ed apologizing for one show in particular. The Apprentice, he said, created a narrative that Donald Trump was a super-successful businessman who lived like royalty. The boardroom viewers saw on TV was a set. Trump's actual boardroom was too old and shabby to show on camera. More accomplished CEOs were too busy for reality television. Trump had plenty of time, loved the attention, and the show painted a picture that wasn't true.
Miller called it fake news that they spread over America like a heavy snowstorm. He said he never imagined the manufactured image would help carry Trump to the White House.
Here's the thing: Trump had filed for business bankruptcy six times. He'd run through casinos, an airline, a vodka brand, a mortgage company, and a string of ventures that opened loud and closed quiet. He created a "university" that settled for $25 million after more than 6,000 students said they'd paid up to $35,000 for courses that were worthless. A New York judge later found that Trump's company had inflated his net worth by billions to get better loan terms. The judge wrote that the frauds "leap off the page and shock the conscience."
This isn't political commentary. This is a case study in what happens when confidence completely decouples from competence and nobody checks. The business record was always there. The producers knew. The people I know who actually did deals in New York real estate, real operators with verifiable track records, saw a carnival barker and wouldn't touch anything he was involved with. But the audience didn't ask. They saw the boardroom set, the assertive voice, the gold-plated everything, and they believed.
The Washington Post counted over 30,000 false or misleading claims during Trump's first presidential term. Six per day in year one. Thirty-nine per day by year four. Andrew Weissmann, in his new book Liar's Kingdom, makes a sharp observation: corporate executives can be sued for lying to shareholders, but there is no legal equivalent when politicians lie to the public. The asymmetry is wild when you think about it. A CEO who inflates quarterly numbers goes to prison. A president who inflates everything else goes to a rally.
And here's where it gets interesting for anyone outside of politics. When deception at that scale and that visibility produces not just survival but the most powerful position on earth, it sends a signal. Every Sam in every deal room, every influencer fabricating credentials, every founder inflating metrics on a pitch deck. They're all operating downstream of a permission structure that says: confidence wins, and nobody's checking. Even Elon, who seems to have decided that saying things loudly enough makes them true, operates in the same current. The lesson cascading down from the top is not just that lying is tolerated. It's that it pays.
So maybe the problem isn't new. Maybe it's permanent.
A CEO who inflates quarterly numbers goes to prison. A president who inflates everything else goes to a rally. — Side Letter No. 003
The Divine Comedy was written more than 700 years ago. Dante's version of Hell descends in nine concentric circles, and the structure isn't random. It's a moral hierarchy. The deeper you go, the worse the sin. The upper circles house sins of weakness: lust, gluttony, greed. Understandable human failures. The middle circle is violence. Murder, tyranny, destruction. Bad, obviously.
But violence is Circle 7. Below it, in Circle 8, Dante placed fraud. And in Circle 9, the very bottom of Hell, he placed treachery. Betrayal of the people who trusted you. Satan himself lives there, frozen in ice, eternally chewing on history's most famous traitors.
Think about that ordering for a second. Dante ranked fraud as worse than murder. Not because he was soft on violence, but because he understood something about what holds civilization together. A violent person destroys a body. A fraudulent person destroys trust. And trust is the mechanism that makes everything else work. Commerce, governance, relationships, deals. Every transaction you've ever done rests on the assumption that the person across the table means what they say.
Harari arrives at the same conclusion from the other direction, seven centuries later. His argument is that trust and truth are the bedrock of functioning societies, and both are degrading. Dante would have recognized the diagnosis. He just would have called it a civilization sliding toward its own eighth circle.
What's changed isn't human nature. People have always lied, exaggerated, and faked credentials. What's changed is the infrastructure. The cost of fraud went down. The reach went up. The tools got convincing. And the most visible figures in public life demonstrated, repeatedly, that the penalty for getting caught is somewhere between nothing and a promotion.
Here's the counterpoint a smart person would raise, and I think you have to be honest about it: it works.
Trump is president. The TikTok guru has four million followers. Sam is still getting meetings. By almost any external metric, confidence-over-competence looks like the winning play. So maybe the real question isn't whether it's wrong. Maybe it's whether it's effective.
Fair. So let's talk about what "works" means.
It works for the person doing it, maybe, for a while. It does not work for the 6,000 people who paid for Trump University and got nothing. It does not work for the people who followed the investment guru's advice with real money. It does not work for the partners, employees, and counterparties downstream of the lies. Confidence-over-competence is a strategy that externalizes all of its costs. The liar profits. Everyone else pays.
But even for the person running the play, here's what I've noticed: they know.
The person manufacturing their credentials isn't building a career. They're managing a story. Every new room is a risk. Every introduction to someone who actually operates in their claimed domain is a potential exposure. They're not resting on their reputation. They're outrunning it. And the experienced people, the ones who've actually done the work, will ask the follow-up question. They always do. It's instinct. And the moment they sense you're hollow, that the story doesn't hold up under any pressure at all, you're done. Not in a dramatic, public way. In a quiet way. They just stop returning your calls. You don't get the second meeting. The referral doesn't come. You never find out why, but you know.
You've built a minefield and now you have to walk through it every day. Every conversation is a potential detonation. Every new contact is someone who might know someone who knows the real story. That's not confidence. That's anxiety in an expensive suit.
That's not confidence. That's anxiety in an expensive suit. — Side Letter No. 003
There's a gym I trained at for years in South Philly, run by a guy named Marco. When you walked in there, nothing from the outside world mattered. Not your degree, not your title, not your net worth. The only thing that mattered was what you could do. And you found out fast, usually in the first thirty seconds of a sparring round, whether your confidence was backed by anything real.
The mat doesn't care about your narrative. The question is whether there's a mat in business, in media, in politics. A place where the performance gets tested against reality. The honest answer is that the mat is getting further away. You can run on manufactured confidence for years now, in ways you couldn't a generation ago. But it never disappears entirely. The timeline varies. The pattern doesn't. They get found out.
And then what? Then they have to sit with a question I can't answer for anyone else: was it worth it? Maybe if they made enough money, they'd say yes. But we know from a lot of data and a lot of lived experience that money doesn't solve the problem that manufactured identity creates. The people who built real things, who did the work, who can point to actual results. They don't seem to ask themselves that question. They sleep fine.
The fix isn't complicated. Ask a second question. Check a reference. When someone's story sounds too clean, too fast, too perfect, do what experienced people do. Follow up. Look at the actual record. Apply the basic smell test that our grandparents used before the internet made it easy to skip.
Competence is boring. It doesn't go viral. It doesn't make for good content. It doesn't attract four million followers. It just compounds, quietly, over years, until the people who did the work are the ones still standing in the room when the stakes actually matter.
The three most underrated principles in professional life are still the same ones they've always been: do what you say you're going to do, show up on time, and say please and thank you. That's not a TikTok video. That's not a framework. That's just the way people who last actually operate.
The people I want in the room when it matters? They're not running the confidence play. They don't need to. Dante's eighth circle has plenty of room. And if you're reading this and recognizing yourself in it, yeah, I know the real story. So does everyone who was actually in the room.