I told a founder to kill his best upsell.
He thought I was insane.
The upsell converted at 34%. It added $8K monthly. And it was destroying trust faster than he could rebuild it.
Here's what he didn't see: the upsell worked because customers didn't know they didn't need it yet. Once they figured it out, they felt manipulated. Nobody came back.
High conversion, zero trust.
Because trust doesn't form from big promises. It forms from small, repeated demonstrations of aligned interest.
And most of you are breaking the pattern without realizing it.
In the last email, I told you credibility and trust aren't the same. Competence versus motive.
You got it.
Now here's how trust actually builds: through architecture, not accidents.
Think of trust like a formula:
Consistency × Transparency × Vulnerability ÷ Self-Interest
Most brands max out the numerator. They pile on consistency. They add transparency. They even show vulnerability when it's trendy.
But they forget the denominator.
They never reduce perceived self-interest. So the whole equation stays stuck at zero.
Here's what that looks like in practice:
#1 Consistency without reduced self-interest = predictable manipulation.
You're consistent about upselling. Consistent about pushing upgrades. Consistent about steering people toward your highest-margin offer. Pattern recognized. Trust destroyed.
#2 Transparency without reduced self-interest = honest greed.
You tell them exactly why you're upselling. You're transparent about your margins. Doesn't matter. They still know you're choosing your wallet over their outcome.
#3 Vulnerability without reduced self-interest = performance.
You share your struggles, your failures, your behind-the-scenes. But if every vulnerable moment still leads to a pitch, it's not vulnerability. It's a tactic.
The denominator is where trust actually lives.
You have to reduce perceived self-interest. Not eliminate it — reduce it.
Visibly.
Repeatedly.
Here's what that looks like:
The refund before they ask. You see they're not getting results. You initiate the refund conversation. You lose the sale to prove the point.
The recommendation that isn't yours. They ask for help. Your product could work but another solution is better. You send them there. You lose the deal to prove your motive.
The truth that costs you a sale. They're ready to buy. You tell them they're not the right fit. You walk away from revenue to prove you mean it.
These aren't tactics. They're pattern interrupts.
They recalibrate the trust algorithm in your customer's head. They say: this person will act against their own interest when it matters.
That's the architecture.
The founder with the 34% converting upsell? We killed it. Replaced it with a diagnostic that told 40% of people they didn't need the upgrade yet.
Revenue dropped $3K the first month.
Repeat purchase rate went from 8% to 31% in 90 days.
Because we stopped optimizing the numerator and started reducing the denominator.
Here's what I want you to do: Look at your customer journey. Find the moment where your self-interest is most visible. The upsell. The upgrade. The cross-sell.
Now ask: what could I do here that would cost me something to prove I'm aligned with them?
That's your denominator move.
Reply and tell me where your self-interest is most visible and what you could do to reduce it.
— Shashank