The Early Sales Playbook: Why Selling Too Fast Killed My Startup

Hello Predictable Revenue community,

Book update: Book update: We’re rolling into the last few weeks before launch and are closing in on 220 books sold. To make the final stretch special, I’m adding two new pre-sale bonuses — available only until October 27th at midnight.

Cold Email Deliverability Guide — Make sure your emails actually land. A simple, proven checklist to warm up domains, boost deliverability, and avoid spam filters.

Call Review GPT — Paste your call transcript and get one clear, tactical improvement for your next conversation. Your personal AI call coach.

Community update: our last Q&A before the book launch is next week, Friday October 17th at 930am PT. If you’ve already pre-ordered, you’re in. If not, now’s the time. Send me your receipt to get access. I’ll add these two to the pre-order benefits list in the next week.

Onto the newsletter…

Most startups fail not because they can't sell, but because they sell too soon—or worse, too fast.

My second startup went from $0 to $1M ARR in 90 days. Sounds impressive, right? It killed the company.

We proved our hypothesis was correct. The problem was real, the solution worked, and customers wanted it. But I made a critical mistake: I kept selling our shitty MVP. The backend couldn't keep up. Our onboarding was a disaster. And some idiot—me—kept hammering the gas pedal because I wanted to hit $1M ARR as fast as possible.

What happens when you take on more customers than you can serve and deliver a mediocre experience? They churn. And they take your reputation, excitement, and positive word of mouth with them.

Early sales aren't about revenue. They're about proof: proof of problem, proof of value, proof of impact. The goal isn't scale—it's clarity. You're testing your hypothesis of value, and if you get it wrong, no amount of hustle will save you.

Start With the Right Problem: The HILS Test

Find a High-Impact, Low-Satisfaction problem. This is your 10X—the reason someone would risk working with a startup over an established competitor.

Here's how to find it: Ask the magic wand question.

"If there was a problem I could solve for you, what would it be and why?"

Then score it:

• On a scale of 1–10, how important is this to you?

• On a scale of 1–10, how satisfied are you with how you're currently solving it?

You're looking for problems that score 8+ on importance and 4 or below on satisfaction. That's your HILS problem.

But don't stop there. Dig into the impact:

• What happens if this doesn't get solved?

• What's the cost to your organization?

• What's the personal impact on you—career, stress, promotion?

Make sure you can tie the impact to an increase in revenue, a decrease in costs, or a decrease in risk. Write down their answers, we'll come back to them later when we put together the value equation.

Don't chase feature parity with incumbents. Solve one pain 10X better and they'll forgive everything else.

Once you've identified a HILS problem with one customer, validate it with 3–5 more similar companies. Keep this group small so you can stay super hands-on. This stage is about calibration before scale—testing your value hypothesis before chasing volume. You need to prove the problem is real across multiple customers, not just one outlier.

Here's what I should have done with Carb: We had a HILS problem nailed. But we skipped calibration. We onboarded ten customers right away. They told ten more friends, and I onboarded them too. Our onboarding team, software, and infrastructure couldn't keep up. The customer experience suffered—but I kept selling, treating $1M ARR like a scoreboard instead of a signal to slow down. I was either greedy, driven by ego, or just foolish. Likely a cocktail of all three.

Design Partnerships: The One-Month Proof

Never start with a paid pilot. Start with a design partnership.

The goal of a design partnership is twofold: prove that you understood their pain correctly and can solve the HILS problem, and gather metrics on the value you create so you know how much to charge when you get to pricing the pilot.

Keep them short—one month max. These are experiments, not something that's good enough to charge for yet. If you're comfortable charging, you probably waited too long to get the software in front of people.

Treat design partnerships as low-risk, low-pressure experiments for the buyer. Define clear success metrics up front. The goal is to get to a "yes or no" quickly. Either you've proven you understand the pain and can solve it, or you know what to change.

Track everything: time saved, costs reduced, revenue increased, risks mitigated. You'll need these numbers to price your pilot.

What I'll do next time: Keep the first three customers a small, tightly aligned group. Scope the design partnership for a month. If it works, great. If it doesn't, move on to test the next thing. The goal isn't to scale yet—it's to learn quickly.

The Checkpoint I Skipped

Before moving from proof to pilot, pause and ask: Can we deliver a good enough experience to turn these customers into case studies?

If I can't convince my first three customers to do a case study, either I haven't solved their pain well enough, or I picked the wrong design partners. That's the moment to reset—not to scale.

This is the step I missed. Instead of pausing to validate success, I kept adding customers. What looked like growth was actually acceleration toward collapse.

The Value Equation

Remember those impact questions from your HILS discovery? And the metrics you tracked during your design partnership? This is where they come together.

You earn the right to charge once you've proven measurable value. That happens in the pilot stage.

Take the value you measured in the design partnership—whether it's time saved, costs reduced, or revenue generated—and multiply it by 12 months. That's the annual value you're creating.

Now charge 5–10% of that number.

Why so low? Because early pricing isn't about margin—it's about proving ROI and winning trust. If you save a customer $500K a year, charging $25K–$50K makes you a no-brainer. They get a 10X–20X return. You get a customer who renews, expands, and refers.

The math is simple. The discipline is hard. Resist the urge to charge more just because you can.

From Proof to Pilot

Once you've proven you understand the pain and can solve it, move to a paid pilot.

Duration: 1–3 months, with an opt-out clause and automatic rollover into a monthly agreement. Include weekly check-ins with the day-to-day team and monthly check-ins with the economic buyer.

Define success metrics and review them every month. Make "proof of value" explicit. Optimize for fastest time to value, not feature delivery.

During pilots, get as close to the customer as possible. Go onsite if you can. "Hey, I'm going to be in town—can I swing by?" Watch them use your product. Learn what actually matters.

Stop Selling. Start Learning.

After 2–3 design partners, pause new outreach.

Focus entirely on making existing partners successful. The goal: 100% success rate and 2–3 case studies to anchor future sales.

Once you start seeing repeatable success, that's your handoff moment—when it makes sense to begin building a sales motion or team.

The hard-earned truth: If you take on more customers than you can serve well and deliver a mediocre experience, they churn—and they take your reputation with them.

When You're Ready to Scale

Once you have your case studies and proven value, you're ready to run discovery with new prospects. But now you have a weapon: evidence.

Ask the same HILS questions, but pay attention to whether they care about the specific problem you solve 10X better. Not every prospect will. Some will score high on importance but already have a satisfactory solution. Others will care about a different problem entirely.

Your job is to find prospects who light up when you describe the pain you solve. The ones who immediately recognize themselves in your case studies. The ones who've been waiting for someone to finally fix this thing that's been driving them crazy.

Early sales taught you what works. Now you're looking for more of the same—customers who look like your lighthouse accounts, with the same HILS problem, ready to pay for the same 10X solution.

This is when early sales becomes repeatable.

Closing Thought: Early Sales Is an Experiment, Not a Process

Your goal isn't scale—it's clarity.

You're testing your hypothesis of value. Early sales are about learning fast, not selling hard.

If your early customers renew, expand, and refer, you've found traction worth scaling.

As Jerry Seinfeld said, "Pain is just the sensation of experience entering the body." Sometimes, you only learn by living the mistake.

I learned mine at $1M ARR. Learn yours at $0.

Collin

PS - a startup approached me about building my sales methodology into a set of agents. Hit me back with the word “agents” if you’d be interested in having something that would work with your existing systems (crm, email, cal, etc…) but help you follow my sales process.