The Adventures of Dot & Dash

Introduction

Every founder hears the advice: trust your gut. Usually right before someone suggests something risky, expensive, or both.

The truth is more nuanced. The best founders don’t blindly follow instinct, and they don’t wait for perfect data either. They know when intuition is doing real work… and when it needs guardrails.

A useful example comes from outside the tech industry, but it maps nicely onto startup life: independent filmmaker John Sayles.

Sayles built a decades-long career without Hollywood’s traditional funding machine. Not because he couldn’t raise money, but because he didn’t want the wrong kind of money. Instead of chasing investors who would reshape his work, Sayles funded his personal films by taking on commercial screenwriting jobs when needed, then pulled back when he had enough money to fund his projects. He essentially traded easy money for creative control.

That’s not romantic. It’s operational.

And it’s a useful framework for founders navigating growth.

When Gut is the Right Tool

Your gut is the strongest when you’re close to the work. When you’ve talked to customers, shipped products, handled edge cases, and lived inside the problem long enough to recognize patterns before they’re obvious in the data.

This is especially true early on, when dashboards are thin and the market hasn’t fully formed. Some of the most important founder decisions, like product direction, audience focus, and timing, happen before there’s enough information to justify them cleanly.

That’s not recklessness. That’s earned intuition. Earned because you know the context of the problem, and your brain can shortcut the analysis.

Like Sayles choosing stories he believed in even when they weren’t trendy, founders often have to bet on ideas that don’t look great on spreadsheets yet. But if you wait to act until every risk is de-risked, you’re probably already late.

When You Need to Slow Down

Founders tend to get into trouble when they apply gut instinct to things that aren’t creative in nature. Money is a common one.

Sayles was careful about where his funding came from because he understood that money always arrives with expectations attached. The same is true for startups. Capital that pushes you toward the wrong customer, the wrong growth curve, or product compromises you’ll regret later doesn’t just slow you down. It will quietly change what you’re building.

This is where caution matters.

Term sheets, partnerships, and hiring at scale all deserve friction. If something feels off, don’t override that instinct with optimism or urgency. Pressure to move fast is often how “bad money” sneaks in.

A useful rule of thumb: If the decision changes who you’re building for or how you’re allowed to build, slow it down.

The Balance that Actually Works

The founders who scale well tend to follow a pattern:

• Fast intuition for product and vision
• Deliberate scrutiny for money, incentives, and control
• Enough operational discipline to buy themselves time

That last one matters more than it gets credit for. Sayles didn’t preserve his creative freedom by accident. He built a system that allowed him to say no. Founders should do the same.

Trust your gut, but build the business so you’re not forced to trust it under pressure. That’s not playing it safe. That’s how you stay in the game long enough to build something you actually care about.