"Do things that don't scale" is excellent early-stage counsel. It means: show up personally, solve problems by hand, build relationships one conversation at a time. The trouble starts when a founder takes that advice to heart at ten customers and then, at fifty, tries to automate the feeling of showing up.
You cannot automate presence. You can only decide where to place it.
Growth creates a reflex: find the bottleneck, remove yourself from it. That instinct is correct for most operational work. It is destructive when applied to trust.
Here is what happens in practice. A founder who personally onboarded the first twenty customers writes a template. The template gets good — warm, specific, well-structured. Then it gets sent four hundred times. Each recipient reads it and feels, accurately, that nobody wrote it for them.
Or a founder records a welcome video. The video is genuine the first time. By the sixth month, it sits in a drip sequence between a feature list and a pricing nudge. It started as presence. It became decoration.
The pattern is always the same. The founder identifies something that worked because it was human, then tries to preserve the output while removing the human. The output survives. The trust does not.
Some founders try a different shortcut. Instead of automating their own presence, they borrow someone else's. Logos on the landing page. Advisor names in the pitch deck. Testimonials from people the prospect has heard of.
Borrowed credibility opens doors. It does not build trust. Trust requires a direct interaction where the other person concludes: this founder understands my problem and will not disappear when it gets hard.
A logo wall cannot deliver that conclusion. Only a conversation can.
The danger is that borrowed credibility feels efficient. It scales horizontally — one logo, a thousand impressions. Real trust scales vertically — one conversation, one deeper relationship. Founders who optimize for horizontal reach often wake up with a wide funnel and a shallow pipeline.
Every product has a small number of interactions where trust is actually formed. Not maintained — formed. These are the moments where a customer moves from "I'm evaluating this" to "I believe these people will take care of me."
For most B2B products, those moments cluster around three points:
The first real problem. Not the onboarding flow. Not the welcome email. The first time something goes wrong or gets confusing and the customer reaches out. How that interaction feels determines whether the customer builds a mental model of "supported" or "alone."
The decision to expand. When a customer considers giving you more scope — more users, a bigger deployment, a higher-stakes use case — they are not reading your documentation. They are asking themselves whether they trust you enough to depend on you more deeply. A founder's voice in that moment changes the answer.
The moment of doubt. Every customer, at some point, wonders if they made the right choice. Maybe a competitor launched a feature. Maybe an internal stakeholder asked a hard question. If the founder is present — not through a drip sequence, but actually present — doubt resolves into loyalty. If the founder is absent, doubt resolves into a quiet evaluation of alternatives.
These moments are rare per customer. That is what makes them protectable. A founder with two hundred customers does not need to be present for every interaction. They need to be present for the six hundred interactions that actually form trust.
The math is more forgiving than founders expect. Two hundred customers, roughly three trust-forming moments each per year: six hundred conversations. Spread across fifty working weeks, that is twelve per week. Twelve real conversations where you show up as yourself, not as a template or a recording or a logo.
Everything else can be systematized. Onboarding can be self-serve. Status updates can be automated. Documentation can replace most how-to questions. Customers do not need you for those. They need you for the moments where they are deciding whether to depend on you.
The founder's job is not to be everywhere. It is to identify the moments that cannot be delegated and then guard them from the efficiency reflex.
"Do things that don't scale" implies a phase. You do unscalable things early, then graduate to scalable things later. That framing hides the real lesson.
Some things should never scale. Not because you lack the tools, but because scaling them destroys the thing that made them work. The handwritten note is not a prototype for the automated email. It is a different act entirely.
Trust scales when the founder stops trying to be present everywhere and starts being present in the right places. Not efficient. Not automated. Present.
That is the work that compounds.
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