The importance of being unearnest

In the final scene of Oscar Wilde’s most celebrated play, the protagonist discovers that the lie he’s been telling for years – that his name is Ernest – was accidentally true all along. Wilde’s point lands with a laugh: the difference between a liar and an honest man is sometimes just timing.

Silicon Valley runs on a version of this joke.

Canonical example

The standard account of the visionary-versus-grifter problem goes something like: Elizabeth Holmes knew her technology didn’t work and lied about it; Steve Jobs prophetically anticipated his would work before it did. One was a fraud, one was a visionary, and the market eventually sorted them out. This story is comforting because it implies that liars and visionaries are distinguishable. We just need better due diligence.

But in the early days, both sold futures that did not exist. The later differences are real: Jobs merely pushed engineers past what they thought was possible, while Holmes fabricated lab results and threatened whistleblowers. The early pitches, though, tasted the same: the future framed as slightly more present tense than it actually was. Sometimes a fabrication is there from the beginning. Sometimes it emerges incrementally, as the gap between story and reality refuses to close: from optimistic framing to selective disclosure to active concealment to outright lies.

It’s easy to look back in hindsight and judge what happened. The more interesting questions are forward-looking: today, given the uncertainty inherit in forecasting, how should we evaluate claims about the future, and how should we relate to the people who make such claims? There are, roughly speaking, four ways to sell a future that doesn’t exist yet.

The true believer

In his paper “The Elements of a Scientific Theory of Self-Deception,” the evolutionary biologist Robert Trivers describes the first. His argument is that the most effective deceivers aren’t conscious liars at all. Conscious liars carry what Trivers calls “the stress that accompanies attempted deception,” detectable in their eye movements, vocal quality, even the sweat on their palms. The evolutionary solution is disturbing: believe the lie yourself. If you don’t know you’re lying, those cues vanish. You are, in every way that matters to the people you’re selling to, sincere.

His central claim is that we deceive ourselves to better deceive others. But self-deception is useful twice over: it makes the pitch more convincing, and it sustains the daily grind. The founder who genuinely believes doesn’t have to fight their own skepticism every morning.

In the startup context, this is the true believer. The founder who has genuinely lost the distinction between what is and what they’ve promised. They’re maximally persuasive, to others and, crucially, to themselves. They push through the moment a clear-eyed person would quit, sustain their own conviction through years when nothing works, and make that conviction contagious enough to hold a team together. But they’ve paid for this with the ability to see clearly. Their own story has replaced reality, and when reality shifts, they’re the last to know.

The conscious performer

Wilde understood the second route. His sympathetic characters are deliberate performers who always know they’re performing. Jack knows Ernest is invented, Algernon knows Bunbury doesn’t exist. When Algernon says that “the truth is rarely pure and never simple,” he isn’t confused about which parts of his life are fictional. What Wilde celebrates isn’t the lying but the lucidity: his favorite characters can see that all of Victorian society is a performance, that earnestness is a costume, that identity itself is theater. Their freedom comes not from escaping the charade but from never mistaking it for reality.

The Wildean founder has real advantages. They can adapt, they can stop, they can see when the story isn’t working and change it before it becomes catastrophe. But they pay a different price: they’re less convincing. The person who retains that detachment, who can always see the gap between the pitch and the reality, is the one who hesitates at the crucial moment, who knows too much to be magnetic. They’re running the overhead that Trivers’s self-deceiver has eliminated, and they’re running it all the time: in the pitch, in the team meeting, in their own head at 2 a.m. And in any contest for belief, for capital, for loyalty, they are at a disadvantage.

The low-empathy founder

A third type needs no self-deception at all. The low-empathy founder doesn’t need it to be convincing, because the things that make conscious lying expensive – the anxiety, the guilt, the fear of detection – simply aren’t there in the same way. They can see the gap between pitch and reality with perfect clarity, the way Wilde’s characters can, but it costs them nothing to erase that distance with words. They don’t exhibit stress simply because truth vs lies isn’t an emotionally significant distinction in their minds.

They have the Wildean performer’s strategic awareness and the Triversian true believer’s persuasive force, without the costs of either. They are, to anyone across the table, indistinguishable from someone who genuinely believes. They might even be more convincing, because the true believer’s passion sometimes reads as desperation, while the low-empathy founder’s composure reads as quiet certainty.

The downside here is subtler than for the other two. It’s about team-building. Trust depends on perceived reciprocity: people follow a leader partly because they believe the leader is invested in them, not just in the outcome. When the mask slips, what’s revealed is that the investment was always one-directional. That’s different from a leader who made a bad bet or lost their way. It retroactively reframes every prior interaction, and the recalibration is usually total.

The secret

There is, of course, a cleaner version of all this. Peter Thiel’s famous interview question points the way: what important truth do very few people agree with you on? The founder whose conviction is grounded not in self-deception or performance or indifference, but in genuine private insight: they’ve seen something true that others haven’t seen yet. They have the true believer’s conviction and the conscious performer’s clarity, because they’re not deluding themselves. They’ve found what Thiel calls a secret. Their pitch is honest because it’s backed by real evidence, and their confidence is earned rather than manufactured.

This is the platonic ideal, and almost every founder believes they’re this type. But even this founder is still expressing conviction about an unknowable future, still asking people to commit resources to something that doesn’t exist yet. From the outside, they look exactly like the other three. The distinction between genuine insight and well-placed conviction is real, but it’s only verifiable after the outcome, which means the system still can’t act on it. Even the cleanest category collapses back into timing.

The ratchet

None of these types are stable. A founder who starts with a genuine secret and early success may slide into true belief as the validation accumulates: every round of funding, every customer who signs early, every engineer who quits a safe job to join, is evidence that the story is true. Why keep doubting yourself when the world keeps telling you you’re right? The conscious performer who gets enough reps at lying may pernicously slide towards the low-empathy category as a looser relationship to the truth becomes habitual. The true believer who hits a wall hard enough wakes up into Wildean detachment. Even the low-empathy founder can eventually buy their own myth.

The tech industry drives this fluidity. Success pushes founders toward belief, failure pushes them toward lucidity, and the system rewards whichever posture produces the most convincing pitch at any given moment. The types aren’t personalities but positions, and most founders pass through more than one.

The punchline

So there are four routes through the tech industry’s reality distortion field: believe your own story, know you’re performing, simply don’t care about the difference, or actually know something. When the underlying bet turns out to be winnable, all four look like vision. When it doesn’t, the true believer looks like a fool, the Wildean performer looks like a coward who never committed, the low-empathy founder – if they’ve been careful – walks away clean, and the one with the secret just turns out to have been wrong.

Wilde, characteristically, saw the joke. Jack Worthing spends the entire play pretending to be Ernest, and in the final scene discovers he was Ernest all along. The audience laughs at the coincidence and the pun. But Wilde’s real point is subtler: Jack’s lie turned out to be true, but only by accident. He performed the identity before it was real, and no one could tell the difference – not even him.

The bind

In the tech industry, the same performance is running constantly, at enormous scale, with enormous stakes. And the uncomfortable truth is our moral intuitions don’t map cleanly onto what actually produces progress. The traits we might select for if we were designing ethical people – lucidity, humility, objectivity, a clear-eyed relationship to uncertainty – are precisely the traits the system selects against.

This isn’t a bug to be patched with better vetting or smarter investors. It’s a structural feature of any system that requires committing resources to futures that don’t exist yet. Due diligence, reference checks, technical probing: these all try to distinguish genuine insight from performance, and they help at the margins, but they’re weak signals compared to the conviction itself. And conviction is not just marketing; it’s critical for the actual execution. The founder who believes works harder, persists longer, makes bolder bets, and is, all else equal, more likely to succeed.

How best to proceed then? I’ve come around to something like this: find a real secret if you can, and start there. But don’t expect any of that initial moral clarity to survive contact with the market. And be slow to judge those whose behavior you find distasteful, because for better or worse, it appears to be the cost of innovation: the system that selects for it is also the one that generates the unprecedented material abundance we all enjoy.