We hosted our first live event yesterday

Collin Stewart — who has worked with over 1,000 B2B startups — joined us yesterday to talk about the most dangerous moment in a startup's life: when you think you have product-market fit, but you don't.

We don't record these. That's intentional. I've hosted and participated in a lot of sessions like this, and the vibe is different when there's no recording. People sign up–then ghost to await the recording. I get it. I do that all the time.

But if it’s not recorded, guests say things they wouldn't say otherwise. Attendees ask the questions they actually care about — not the ones that look smart for board members who might listen later; the ones they don’t want board members hearing them asking. The important questions.

What you'll find below is what was meant to be shared. It’s as close to a recording as there will ever be. For more, grab Collin's book: terrifyingart.com. We only scratched the surface.

In two weeks, we're hosting another one — this time on AI Video. Hope you can join us live. I’d love to hear what you want to hear about or who you want to hear from. Just reply with questions or suggestions.

Most startups don't die from bad products

They die because they built something people don't want badly enough to pay for.

The product might be great. But that’s not enough.

"People like it" is not PMF. "I can't get people to stop using it and they keep sending me their friends" — that's PMF.

Collin learned this the hard way. His first company, Voltage, was a CRM. He had a real insight. It was just 40% right and 60% wrong. Salesforce was new, but it prioritized managers over salespeople.

Salesforce made CRM a tool for management–not salesperson productivity. That was his insight. That’s what he built Voltage to solve.

But customers wanted Salesforce integration. He said no. The product worked. The market didn't. 1 sale out of 150 conversations.

His next company, Carb, was different. 5 customer development conversations turned into 7 customers — including referrals. He hadn't finished building it.

That's the signal you're looking for.

Customer development is not market research

It's not surveys. It's not a Google Form. It's not asking people if they'd use your product.

It's sitting across from someone and shutting up long enough to hear what's actually painful.

The framework has three stages.

Exploratory. Find problems that score high on importance and low on satisfaction. Ask who else they know with the same problem. That question alone builds your pipeline faster than any outbound sequence.

Focused. You've found the problem. Now narrow who has it worst. Use what you're hearing to tighten the ICP. That's your beachhead.

MVP feedback. Show them something rough. Ask one question: is this 10x better than what you're doing today? Not 25% better. Not "easier to use." Ten times. If the answer isn't an emphatic yes, you're not done yet.

Now — about those first customers.

Collin is running this playbook right now with his new company, Reply Loop. He has 3 users. None of them are paying yet.

That's not a failure. That's the point.

He's being deliberate about who those 3 are. Free access isn't a discount — it's a contract. In exchange for not paying, they give real feedback, stay engaged, and don't ask for features outside the core use case. The wrong free customer is worse than no customer. They pull the product in the wrong direction, consume time, and distort your roadmap.

Once value is established — once they can't imagine going back — then you ask them to pay. And then you ask for referrals.

That's the sequence. Free → feedback → payment → referrals. In that order.

You know you’re onto something if people want to pay you. Or, if you’re not quite there yet, if they ask you when it will be ready or what it will cost. That shows intent.

“I like it” or "I can see how [someone else] would use it” is not intent. Giant red flag.

Here's what most founders miss.

Customer development isn't just for pre-product companies.

If you already have a product — even one with real revenue — you're sitting on an underused asset. Your existing customers will tell you what's broken, what they wish existed, and who else they know with the same problem.

That last part is the pipeline nobody talks about.

Every customer development conversation is a prospecting conversation in disguise. Ask the right questions, get referrals. Get referrals, get customers. Get customers, get more referrals.

Collin is doing this at Reply Loop — using outbound not to sell, but to build signal and expand his network. No ads. No SDR team. No brand. Just conversations, listening, and following the referrals.

It's never too late to go back to this.

Founders with $1M ARR, $5M ARR, who haven't talked to their customers in months. Running campaigns, hiring reps, optimizing sequences — while the ICP drifts, the positioning goes stale, and the roadmap fills up with assumptions.

A week of customer development conversations will tell you more than a quarter of analytics.

Go do it.

I’m going to myself, for Skyp. I’ve got questions only customers can answer:

• How important is finding leads?

• Are new customers more important than getting more out of your existing customer base? People use Skyp for both, but we should probably pick one to focus on.

• Who feels this agentic email pain the most? Big companies? Small? Certain industries?

If you want to talk about it, grab a time–or just reply.

Want to go deeper? Collin's book — The Terrifying Art of Finding Customers — is at terrifyingart.com. Worth your time.

Next session is in two weeks: AI Video. Hit reply — tell us what you want to hear about and who you'd like to hear from.