The Skyp Newsletter
Insights, tips, and strategies for modern AI-powered outreach and sales automation
Insights, tips, and strategies for modern AI-powered outreach and sales automation
The most dangerous moment in a startup’s life is not running out of money.
It’s not a bad hire.
It’s not kicking off a fundraise.
It’s the moment you switch to “sales mode” too early—and kill the momentum you spent months building.
Startups don’t randomly fail. They follow a predictable pattern:
You do the hard customer development work—talk to customers, find a real problem, get the first 10 people to pay…
…and then right at the moment of early traction, you panic.
You hire a sales team.
You bring in marketing to “pour gas on the fire.”
You buy a CRM.
Wrong move. All of it.
I followed that playbook once. It didn’t work out.
Product-market fit isn’t a switch. It’s a multiplier.
Most founders try to scale a sales motion before the underlying PMF is strong enough to support it.
The best indicator you’re ready?
Not a full pipeline.
Not a rep hitting quota.
Referrals.
If customers aren’t pulling others in, you’re probably trying to scale something that still isn’t stable.
Before you touch hiring, “growth,” or systems:
3 → 10 → 30.
Make 3 customers extremely happy.
Then 10.
Then 30.
Your job at this stage isn’t to scale sales.
It’s to go talk to 3 customers.
Collin Stewart has seen this play out more times than he can count. He wrote the book on early GTM—literally: The Terrifying Art of Finding Customers. He took Predictable Revenue from $0 to $1M ARR in 12 months. He built Carb.io from $0 to $1M ARR in just 3. He’s a repeat founder who’s lived every version of this mistake—and figured out how to avoid it.
He’s joining us live, and he’s bringing the full framework.
We’re going deep on:
The customer development funnel
When to actually make the switch to sales mode
What premature scaling looks like before you realize you’re doing it
Join thousands of sales teams using AI-powered email outreach to drive consistent, measurable results.
Get a Demo