How Stripe Sold To Their First Customers

All startups should do un-scalable things to get their first customers.

Good morning! Spirit Airlines announced they’ll be furloughing 270 pilots and demoting 100 more as they prepare to cut flights. There’s an unconfirmed rumor they’ll soon let passengers fly the planes themselves to save on costs. (Jk, we made that part up). If you’ve got a client visit booked on Spirit, you might want to start shopping for backup options… unless you’re cool with a 4-hour delay and a flight attendant casually Googling “how to land an A320”. Now let’s get into today’s Follow Up. 😁 

  • How to wrap up a discovery call 👀 

  • The Hustle: Get Smarter on Business & Tech  💻️ 

  • How Stripe sold their first customers. 🗣️ 

  • The ideal length of an email (backed by data) ✍️ 

  • Sales jobs & a meme 😂

Sales Tip of The Day 💡

When you're wrapping a good discovery call, don’t forget to ask for internal friction.

 “Great convo, let’s book time to dive deeper?”
 “This sounds promising. What usually slows things down after a call like this?”

This uncovers blockers before they become a problem, and lets you plan for them.

Internal blockers will always be there. But you can get ahead of them.

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How Stripe Got Their First Customers (By Doing Something That Doesn’t Scale)

Picture this… You're a startup founder with a product that works.

But you’ve got zero customers. What’s your first move?

For Stripe's founders Patrick and John Collison (yes, they’re brothers), the answer was literally: "Give me your laptop."

Today, Stripe is valued at over $90 billion.

But back in the early days, they had zero customers and an ambitious dream to “increase the GDP of the internet”.

Today, we're breaking down how Stripe's scrappy sales tactics landed them their first clients and what B2B sales reps can learn from their playbook.

The Collison Installation Method

Stripe's founders wasted no time waiting for their customers to come to them.

They went out and found their customers where they hung out.

In the early days, the Collison brothers would go to startup events and pitch other startup founders about trying Stripe. If someone showed even a hint of interest, they ‘onboarded’ them.

As Y Combinator's Paul Graham said, “When anyone agreed to try Stripe they'd say ‘Right then, give me your laptop’ and set them up on the spot.”

One by one, they onboarded new customers.

This ‘technique’ became so legendary at Y Combinator that it earned the name: the "Collison installation."

Most founders and sales reps would email demo links and hope for the best. The Collisons turned every conversation into an impromptu onboarding session. No scheduling. No "let me get back to you." No chance for second thoughts.

The gap between "I'm interested" and "I'm using it" is where deals die.

They eliminated the gap entirely.

Removing Friction and Winning Champions

A massive part of Stripe's early success came from eliminating every possible roadblock for users.

Developers were Stripe's target customers, not CFOs or bankers. And developers felt the pain of clunky payment systems every single day.

The Collison brothers were laser-focused on these technical folks who desperately wanted a simple solution. Instead of using a fancy pitch deck or product list, they basically said, "copy & paste these 7 lines of code and you can start accepting payments by tomorrow."

They sold an outcome and how easy it was to get that outcome.

And by handling the setup for customers on the spot, they eliminated every technical hurdle or objection that would typically kill a deal.

How to use this for your own sales: The easier you make it for customers to say "yes" and start using the product right away, the faster you'll close. This could mean offering hands-on integration help, white-glove onboarding, or a risk-free pilot.

Think about how you can do the heavy lifting for your customers.

Modern buyers are busy and don’t want to spend money on a new product that’s going to require even more of their time.

When you save them time and effort, you make it easier for them to say ‘yes’.

Building Community Through Helpfulness

Stripe (obviously) didn't stop at just a few laptop grabs. If they did, they probably wouldn’t be valued at $90 billy today. 😆 

The Collisons showed up everywhere developers gathered. They attended hackathons, startup events, and networking events. And they weren’t there just to try to pitch and hard close new customers. They'd sit with developers, troubleshoot issues, and write code alongside them.

By being genuine helpers in the community, Stripe earned trust and buzz without a traditional sales pitch.

They also hosted their own events. Monthly "Capture The Flag" hackathons that started in person and later moved online. This further cemented Stripe's reputation among developers.

When an early customer finally got their product live with Stripe, the team often celebrated them and sent swag care packages to say thanks.

This level of personal touch made those first customers feel like part of the Stripe story.

How to steal these tactics for your own sales:

  • Meet your prospects and customers where they hang out.

  • Join their communities, and try to provide value before asking for anything.

  • Celebrate their successes, even when it’s not directly related to your product.

And of course, do things that don’t scale. (:

What's your most 'hands-on' sales strategy?

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