My Early Sales Efforts Were a Disaster

I used to think early-stage sales was supposed to be a chaotic mess. A frantic blur of cold emails, awkward demos, and a spreadsheet that looked more like a graveyard than a pipeline. For my first startup, I thought the "hustle" was the whole point. If you weren't burning the midnight oil on a half-baked pitch, were you even a founder?

Then I realized something: we were all doing it wrong.

The Problem with "Founder-Led Sales"

Most advice about early sales sounds like a locker room pep talk. "Crush your quota," "build a revenue machine," "extinguish the dumpster fire." It's no wonder our first conversations with customers sound like we’re reading from a script written by a hyper-caffeinated sales bot.

The real issue isn't that early sales is hard—it's that we're so blinded by our own solution we forget to listen. We’ve got what I call "Founder Goggles." We’re in love with our product, so we can't stop talking about its features. Your prospect, on the other hand, just wants their problem to go away.

And when your "empathetic" discovery call is just a prelude to a feature dump, people notice.

What Actually Works: Three Shifts That Changed Everything

Instead of trying to force a sale, I learned to focus on three simple shifts that felt more human—and actually got results.

1. Your Goal is Learning, Not Revenue

Instead of trying to hit an imaginary quota, your only job in the first 90 days is to build a playbook. Revenue is just a happy side effect.

I’ve seen founders get their first real traction when they stop trying to sell and start trying to understand. Every conversation becomes an experiment to answer questions like:

• "What words do they use to describe this problem?"

• "What was the final straw that made them look for a solution today?"

• "What's the 'good enough' thing they're doing right now? (Hint: It's usually a spreadsheet)"

These answers are gold. You can’t build good messaging by guessing; you have to hear it from the source.

The key: Your primary KPI for the first 90 days isn't revenue. It's validated learnings per week.

2. Find People Who Are Already Hurting

Your future customers are already online, complaining about the exact problems you solve. They’re in niche communities, professional forums, and subreddits, asking for help. Your job is to go there and listen.

This isn’t about pitching. It's about eavesdropping with empathy.

• Bad approach: "I saw you're struggling with X. My product solves that! Check us out."

• Good approach: "That's a frustrating problem. I ran into something similar and found that [explain the core logic of your solution, without naming your product]. Hope that gives you an idea."

The second approach proves you understand their world. Nine times out of ten, they (or someone else reading) will ask, "Wow, is there a tool that does that?" Now you have permission to talk about what you're building.

The key: Be useful first. You're not looking for leads; you're looking for conversations.

3. Hire a Gardener, Not a Hunter

Eventually, you need to hire your first salesperson. Most founders get this wrong. They hire a slick closer from a big company who is an expert at executing a proven playbook. The problem? You don't have one yet. You have messy notes and a gut feeling.

That kind of hire will fail.

Your first sales hire isn't a hunter who goes out for the kill. They're a gardener. Their job is to take the messy seeds of your founder-led learnings and patiently cultivate them into a repeatable process. They are a systems-builder, not a quota-smasher.

The key: Don't hire a salesperson until you can hand them a one-page document with your best guesses on who to talk to, what to say, and what not to say.

What This Actually Looks Like

Here’s a real example from my own experience:

I was lurking in a professional community for marketers. Someone posted a question about how to manage a workflow that my product was designed for. Instead of dropping a link, I wrote a detailed comment explaining the manual process I used to use before I built a tool for it. I just shared what I knew.

Result: The original poster thanked me, and three other people sent me private messages asking if I knew of a tool that automated that process. I didn't have to pitch anyone. They came to me because I showed them I understood their problem first.

The Long Game

Early sales isn't about growth hacks or closing techniques. It's about becoming a recognized, helpful voice in the places where your potential customers hang out.

This takes time. Weeks, not days. But the payoff is building a company on a foundation of genuine market understanding. When someone has the problem you solve, they don't just find your product—they remember your helpful advice.

Getting Started (Without the Complex Funnels)

1. Pick 2-3 "digital watering holes" (forums, subreddits, communities) where your customers talk about their work.

2. Spend a week just reading. Get a feel for the culture. What do people complain about?

3. Start commenting. Answer questions. Offer advice. Don't mention your product.

4. Keep a running document of the exact words and phrases people use to describe their pain.

5. Be patient and consistent.

That's it. No "sales engines." No "dumpster fires." Just showing up and listening.

The Bottom Line

Early sales works when it doesn't feel like sales. When you're genuinely curious about someone's problems, they'll be genuinely curious about your solution. When you're just there to pitch, they can tell.

The best early-stage sales strategy doesn't feel like a strategy at all. It feels like getting to know people and trying to help.

And that's not something you can find in a playbook—it's just being human.