Keep the love alive after the first date

Roberto Boi
By Roberto Boi

Winning a new customer is the sprint. Keeping them? That’s the marathon. And where the real money is made.

Last night I came across a quote from Peter Kang that resonated with me:

“If you give someone a free drink once every 20 visits, they’ll love the restaurant. But if you give them 19 free drinks in a row and skip the 20th, they’ll be upset.”

That’s the paradox of adding value in the name of retention.

The “extras” you throw in, a surprise product sample, additional call, a quick tune-up that wasn’t in scope, start as delight, morph into expectation, and end up an “entitlement” the moment you don’t deliver.

Here’s the kicker: every one of those sweet little freebies costs real time and real dollars. After you’ve spent the bulk of the budget (and your team’s energy) getting a customer through the door, losing them over an unspoken expectation is like pouring petrol on a fire and hoping it doesn’t flare.

So how do you strike the balance, whether you run a café, a SaaS platform, a tourism organisation or an e-commerce brand?

  1. Make scarcity your ally.
    A free croissant on a rainy Monday. An unexpected feature unlocked when a user hits their one-year anniversary. A complimentary emergency call-out for a long-time maintenance client. Each lands because it’s rare.
  1. Name the value, every time.
    “We’ve added free next-day shipping this month (normally $12) so our winter range gets to you faster.” When you articulate the what and the why, customers see the gift instead of assuming it was always included.
  1. Rotate the surprises.
    A complimentary consultation this quarter, an exclusive event invitation the next. Variety keeps appreciation alive.
  1. Protect your core offering.
    Never devalue your base service/product with aggressive discounts. An e-commerce brand that regularly takes 50% off everything soon teaches customers that its range isn’t worth the full price. A cafe that offers a complimentary cookie with your coffee every now and then unexpectedly delights. Keep the foundation solid; let “extras” stay clearly separate.

In short, retention isn’t about showering customers with more stuff, it’s about reminding them, at the right moments, why staying with you is still their best move.


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This is taken from the weekly email written by one of our directors, Roberto Boi. Every Thursday he shares observations, ideas and perspectives from the work we’re doing day to day at Dilate. If you’d like to get it delivered straight to your inbox, you can sign up here.

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