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How Stripe Builds Loyalty with Personalized Gifts

A $50B company still “doing things that don’t scale.”

Hey — It’s Nico.

I know it’s Tuesday. The reason why I’m writing you today is because I’m launching a new series of content. It’s called Behind Tactics 🧠.

Every Tuesday, I’ll be breaking down a specific tactic from a startup. All posts will be super actionable so that you can apply each tactic at your startup.

The tactics will be about raising funds, acquiring customers, hiring talent, and every other thing a startup has to do.

This week’s Behind Tactic is focused on Stripe and how they build brand loyalty by sending personalized gifts to their customers.

Is there any tactic you’d like me to analyze? Let me know.

Can you do a favor for me and give me feedback on this first issue of Behind Tactics? There’s a poll at the bottom of the email.

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The Strategy

Stripe's strategy


Stripe has a pretty unique brand marketing strategy: they send personalized gifts to customers who achieve certain milestones.

This builds a strong relationship between Stripe and its most important customers and conveys to the developer and founder community that Stripe is a brand that cares about their customers.

The result? Customers love Stripe. Community loves Stripe.

The Details

It’s a really unique strategy no other company is doing. While it’s common to send swag, it isn’t to send personalized stuff.

These gifts come in different forms. Frequently, they’re physical products:

  • To celebrate $1M in revenue, they sent a motorcycle-fan founder a helmet with his company’s colors and logo (source).

  • To celebrate $2M in revenue, they sent a tennis-fan founder some tennis balls with his company’s colors and logo (source).

  • To celebrate $3,250 in MRR, they sent a two-Corgi-owner founder a corgi plush and some dog swag (source).

  • To celebrate reaching 150k subscribers, they sent a newsletter writer a rocket sculpture (source).

  • To celebrate a major revenue milestone, they sent a founder two Dumplink rugs similar to her company’s logo (source).

  • As a New Year’s gift, they sent a Samoyed-dogs-fan founder a Samoyed-theme calendar (source).

In some other cases, they send 3D renders:

  • To celebrate $35K in MRR, they sent a founder a 3D render of his yellow Vespa (source).

  • To celebrate $50K in ARR, they sent a founder a 3D render of his boat (source).

And in some others, they send hand-written letters:

  • To celebrate $1M GMV, they sent this founder a personal note and some coffee stuff (source).

  • After tweeting about Stripe’s new product, they sent this guy a surprise letter (source).

  • To celebrate 800 customers, they hand-delivered this founder a letter (source).

As you can see, all gifts were extremely personalized, having references to each customer’s life and company.

In many cases, these gifts are genuinely funny. Stripe’s team seems to be active on Twitter, looking for funny Stripe-related tweets for which they can create gifts around.

  • They sent this founder an oversized check after he tweeted he wanted to build a Stripe plugin giving oversized checks when hitting milestones (source).

  • They sent this founder ice cream after he tweeted Stripe should have a button for ordering free ice cream (source).

  • They sent this founder a Stripe-themed clock after he tweeted that Stripe’s notifications were the best alarm (source).

But my favorite is the gift they sent to the founder of Logology, a failed bootstrapped startup. 

They sent him a custom book telling the story of his business from the beginning to the shutdown (source). A perfect demonstration of how Stripe has empathy for and cares about their customers.

Why I love this strategy: It’s the best example of Paul Graham’s concept of “doing things that don’t scale.”

From Paul Graham’s “Do Things That Don’t Scale” article: "And most importantly, if you have to work hard to delight users when you only have a handful of them, you'll keep doing it when you have a lot."

Should I?

Why This Works

  • Stripe is building long-lasting relationships with its most important customers. It must be hard to move to a Stripe alternative after receiving one of these gifts.

  • Stripe gets exposure in social media. These customers share the gifts with their audience. All of the above tweets got a lot of interactions.

  • Stripe shows people how they care about their customers. If you read the above tweets’ comments, you’ll see how everyone loves Stripe after seeing those gifts.

How to Apply It

You may be thinking only a company of Stripe’s size can apply this strategy. They have a tiny team working on these gifts in their spare time (this is a job post from when they were hiring for it).

However, there are ways to apply it without going crazy. You don’t need to create super fancy gifts. If you check the above examples, the fanciest ones weren’t necessarily the ones with the most impressions. Even simple things like giving free ice cream or a hand-written can work well. It’s more about the time spent on these gifts than what you spend on them.

So here’s what you can do:

  1. Celebrate customer milestones: Add a notification in your CRM for when a customer reaches a key milestone and send them a personalized gift, video, or message congratulating them.

  2. Show empathy: Set up a cancellation customer survey with reasons like “closing down business” or “laying off team.” Send them a personalized “thank you” message for working with you.

But make it authentic and only do it when it feels right. Even at Stripe size, there isn’t an automatic machine sending these gifts; it’s people thinking about what would make the recipients feel great.

Yes, But

It’s not all roses.

  • It’s brand marketing. It barely has any direct impact on sales. It’s a long-term play.

  • You need people and resources dedicated to creating the gifts. But even Stripe does it in a really lean way — 1–3 people do it in their spare time, working alongside independent artists and freelancers.

  • Your customers might not be active on social media, so you might not benefit from them sharing your reward (but word of mouth can still be important).

  • Some customers might be angry they didn’t receive any gift despite being more loyal or more important to your company than others.

Keep Learning

Others Playing It

There’s no company doing it the way Stripe does it, but these are some good examples of other businesses doing similar things.

  • Divvy purchased a billboard to congratulate Lambda, one of its customers, for raising money (source).

  • KFC sent a customer a funny customized painting after he realized why KFC's Twitter account was following the accounts they were following (source).

  • Shopify sends swag in the form of physical products to some of its customers, but they aren’t personalized (source).

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