How to Not Suck at Startups #10: How to Get Paid by Your First 100 Users (Without Lying to Yourself)

Let’s rewind for a second.

Ten years ago, I wrote this for independent musicians trying to get paid without selling their souls. What I didn’t realize at the time was that I wasn’t just writing for artists—I was writing for startup founders, too.

See, the starving artist and the early-stage founder are the same archetype. Both are:

• Building something with more heart than capital
• Hoping to be seen in a world where everyone’s yelling
• Struggling with the brutal gap between attention and income

So here’s the truth: most people don’t need 10,000 users to validate their business. They just need 100 people they actually understand. And they need to stop lying to themselves about what those 100 people are telling them.

This piece is about how to do exactly that.

🎯 The Pareto Principle Still Punches

You’ll hear it as the 80/20 rule. In startup land:

• 20% of your users will give you 80% of your feedback.
• 20% of your features will create 80% of your value.
• 20% of your paying users will drive 80% of your revenue.

That’s not a bug. That’s the system.

And it’s why a product that seems to “work for everyone” usually doesn’t work deeply enough for anyone.

In your first 100 users:

• Only 20 will actually engage.
• Maybe 4 will take action.
• Maybe 1 will actually pay.

That 1 person is not just a transaction. They’re a clue. Follow them. They’re your map.

📉 Most Funnels Leak, Not Fail

The old-school marketers used a simple model called AIDA:

• Awareness
• Interest
• Desire
• Action

Founders get stuck in “awareness” hell. They launch on Product Hunt, run ads, post on LinkedIn. But they never ask: Did I earn interest? Did I trigger desire?

Likes and traffic are not product-market fit. Stop counting pageviews. Start asking why no one clicks twice.

📈 Power-Law Kills the Average

Startups are not bell curves. They are power curves. That means your top user will be 10x more engaged than your median one.

Translation: your most vocal early adopter might single-handedly drive the next 50 signups. But they’ll only do it if you’re paying attention to them like they matter.

Most founders average everyone together and build for the middle. But if you're averaging behavior, you're building for nobody.

Build for your top 5 users like they’re royalty. Then use them to scale.

💸 Loss Leaders Are a Power Move

Every startup has something free:

• Your waitlist
• Your demo
• Your freemium tier
• Your time

Don’t get stuck expecting every user to convert on first contact. Give away value that leads to trust. Then give them a reason to come back for more.

A freemium feature isn’t a sunk cost—it’s a signal flare.

Don’t be afraid to offer something for free if it gets you the data, the loyalty, or the case study you need to unlock 10 more paying customers.

💡 ROI Isn’t Revenue. It’s Rhythm.

In music, it’s not about how many songs you release—it’s about whether people come back to hear them again.

In startups, it’s not about how many features you push—it’s about whether the user wants more of what you’re offering.

Before you scale anything, you should know:

• What it costs you to get one real user
• What that user’s worth over time
• What behavior signals intent (not just interest)

If you can’t measure ROI yet, you’re not ready to grow. You’re still proving. And that’s okay.

Wrapping It Up: The First 100 Are Sacred

You don’t need to build for everyone. You don’t even need to scale yet. You need to figure out:

• Who’s actually showing up
• What they’re willing to do next
• And how you can turn that signal into a system

That’s how you go from starving to sustainable.

Whether you’re an indie artist or a scrappy founder: The strategy hasn’t changed—just the context.

So stop refreshing your dashboards and wondering why the world hasn’t noticed you yet. Go find your 100. Get to know them. Serve them well. And build from there.

The rest will come.

Drop a Comment: Got a story about how you got your first 10 users to pay—or a time you mistook noise for traction? Hit reply and share the lesson. We’re all trying to build smarter this year.

How to Not Suck at Startups #9: One Monkey Don’t Stop No Show (But the 100th Monkey Does)—New Year's Edition