First, let’s give the people what they want.
Catch ‘em Fresh
Back when I was living in Seattle, I went on a few months of dates with someone who’d just moved to Belltown from Brooklyn.
Little did I know, this was prime dating strategy: you want to meet people before Seattle’s infamous seasonal gloom sets in. Fresh off the plane, before the rain and sad gets them. Trust me.
It was the kind of carefree dating that feels like a secret gift. He was a great storyteller (not that dating is a competition, but he’d definitely win) and even helped edit my promotion proposal at work.
Very advantageous for me—I assume it was fun for him too. Actually, scratch that. This is my story, and he had a blast. He probably has his own Substack post about me.
His Pants
On one of our date nights (every other Thursday at 6:30), he started grumbling about how Seattle is not New York. I asked for more details, curious how someone smart enough to get poached by Amazon (he was a director of something involving optimization and efficiency) was caught off guard by this revelation.
His biggest complaint? The tailor. Specifically, that Seattle tailors wouldn’t give him a bulk discount when he brought in eight pairs of pants for alterations. He was appalled. Apparently, he needed fresh pants—or suits—for every party or wedding, and to make matters more dire the holidays were approaching, and he is still on his bulk.
Please picture me in this moment, desperately scanning for our server to order another drink while trying to keep a straight face. After all, I really like my standing every-other-Thursday dates, and I really like dating someone that likes talking about work in, a relatable way.
“Oh,” I said, nodding solemnly, pretending to understand the tragedy of losing a 10-15% discount. My brain was screaming with other, far more practical suggestions for saving money, like rewearing pants.
Somehow, I resisted the urge to ask if he’d ever considered washing pants and putting them back on. Instead, I asked what needed altering. I owned a sewing machine, had access to YouTube tutorials, and was willing to undercut the tailor. But Party Pants had very specific (and very elaborate) ideas about how pants should fit his frame. Best not to get involved.
I liked what we had going, I was happy to play my role.
Through cautious questioning, I pieced together that his loyalty to his Brooklyn tailor was rooted entirely in the bulk discount.
Woof.
Pivoting to Loyalty
Let’s zoom out: if you’re only loyal to a service provider for the discount, are you really that loyal?
Discounts, while appealing, are one of the weakest ways to build lasting customer retention. Sure, they attract customers initially, but long-term loyalty requires more. Businesses thrive on repeat buyers—customers who stick around without needing constant incentives. It’s how one great interaction can multiply into five referrals and a lifelong client relationship.
If someone only works with me because I’m running a promo, they’ll likely leave unless I match it next time. It’s a race to the bottom. Compare that to a loyal client who returns for updates every two years and sends five new people my way. That’s where businesses win.
So how do we build real loyalty? Let’s break it down:
Ways Brands Build Loyalty:
Value: Offering the perceived best deal. Think Spirit Airlines: functional, but as soon as you can afford Alaska Airlines, you’re gone.
Trust: Reliability and consistency. You know exactly what you’re getting at chain restaurants. The comfort of predictability builds trust.
Quality: Superior products or services. Patagonia doesn’t just sell gear—they repair it, aligning with values like sustainability. Their loyalty comes from delivering quality and living their ethos.
Culture: A sense of belonging. Apple nails this with its seamless ecosystem and community feel. Green text bubbles, anyone?
I personally, align with the idea of value being ONE reason people work with me, not the ONLY reason. But things like location, access, hours, and market saturation weigh heavier on businesses with physical locations.
Back to Party Pants
For someone in Amazon’s Efficiency Department (not his actual title), I’m sure he ran the numbers on bulk tailoring discounts. But loyalty rooted in price alone is fleeting. In contrast, loyalty built on quality, trust, and culture lasts through recessions, inflation, and new competitors.
And yes, businesses relying on value can still win by excelling elsewhere. What if his tailor offered online scheduling, faster fittings, or a loyalty program? Pairing competitive pricing with convenience and trust could have kept Party Pants happy—even in Seattle.
Where This Leaves Us
The epilogue? Party Pants moved back to Brooklyn, and his tailor retired to the good life. We wish them both well. He knows this story exists, I don’t think he’s read it. Last fall when visited NYC I took a photo of every tailor that I saw in the city and sent him the album, couldn’t resist to which he replied “you play too much.”
(smirk)
This story originally appeared in Weird Magic, Erin’s weekly email newsletter that centers storytelling and candid reflections on life and work. Subscribe below to receive weekly thoughts and musings that you can smirk at your phone while reading.