I was somewhat rebellious as a child and had a bit of a penchant for back-talking or sassing my parents (something that I’ve passed on genetically to my eldest daughter, it seems). Growing up my mother knew how to get through to me - all she had to do was express her disappointment in me.  “Phillip, I know you. I know you didn’t mean that. When you talk back to me it hurts me. Did you mean to hurt me?”

Disappointment. She was disappointed in me. Knowing that, hearing that, used to cut deep. Now, as a parent, I know how deep the disappointment can run - and I have the same kinds of frank conversations with my own children to let them know when I feel disappointed in them. They have yet to retreat to their bedrooms and blast The Cranberries’ “Disappointment” from their Alexa, though. I’m sure that day’s coming.

Re-enactment of the Jackson House, circa 1993


In a heaping mound of disappointment, you’ll often find disdain. In many cases, with enough unmet expectations, you’ll grow distrust, and eventually, resentment. And, seemingly, resentments never seem to vanish on their own. Once you’ve reached the resentment stage it’s time for counseling, recovery, and a healthy dose of self-actualization. Disappointment ultimately leads to distrust.

If you’ll allow me to extend the metaphor, this disappointment, this erosion of trust, is what has happened in the World Wide Web over the past 30 years, accelerating most quickly in just the past 10 years.  Think of this week’s essay as a state of the union on the erosion of trust with consumers.

Without spending more than 3 minutes I came up with a list of some of the stories I could use as the hook for an Insiders post about why our trust is all but gone online: I found an entire site that spots fake Amazon reviews. There’s lots of news this time of year about phony Black Friday pricing strategies. Apparently, Twitter doesn’t know what to do with deepfakes so they’re using a lifeline and “phoning a friend”.

And, finally, Instagram is considering removing likes from the platform. Yes, the very same likes that just 2 years ago they admitted they trickled out to users in a steady stream to keep them coming back for more.

Why would Instagram consider removing likes? Probably because nobody trusts them anymore.

How to Lose a Customer in 10 Days


Remember the movie How to Lose a Guy in 10 Days? In this 2003 rom-com the two protagonists, Matthew McConaughey and Kate Hudson, each plot against each other to win a wager with their respective group of friends. Ben, played by McConaughey, would try to woo Andie (Hudson) to fall in love with him. Andie would attempt to drive him away at all costs, using only the “classic” mistakes women make in relationships.

Neither truly succeeds in the traditional sense. Again and again, they each overcome otherwise uncomfortable relationship dynamics in order to win a bet. He cooks her an elaborate dinner, she names his penis. And so on, and so on.  The relationship is eventually forced apart when their true motives are revealed to each other, in public. Their true motives being financial gain and maintaining status amongst their peers.

Ah, there it is. The tie-in to why a retail newsletter is talking about parenthood dynamics and a 2003 movie with a Rotten Tomatoes score of 42%.

We talk a lot on Future Commerce about customer relationships; and that relationships are built on trust. The word trust here is likely misunderstood. The adage “trust is earned, not given” doesn’t necessarily fit into today’s e-commerce landscape. I have come to the realization that we shouldn’t be talking about trust, necessarily, rather, we should be talking about loyalty.

New thesis: Customers can be persuaded to extend trust. Loyalty is earned, not given.


On Candles and Risks


In a recent Twitter thread I wrote about 5 DTC brands who are selling candles online.

Phillip’s thread on how DTC brands are approaching candle sales online.


Among the 5 brands I reviewed there is are consistent tactics to close the sale:

  • Emotionally-centered copy which attempts to evoke the senses (provided you know what bergamot smells like)
  • A competitive price point, usually with free shipping
  • The ability to share the experience with others, whether through a dinner table setting or by facilitating gifting via the website


It’s fascinating that products in the scent category do so well online. Marcel Proust, in his Remembrance of all Things Past, wrote that a bite of a madeleine recalled childhood memories of his aunt giving him the very same cake before going to mass on a Sunday [1]. The very words “bite of a madeleine” might trigger a memory for you. Words can trigger memories of past experiences.

This is where the brand Homesick, a DTC candle brand which aims to make you nostalgic for your home town, will excel. By capturing your sense of “home” by writing about the things which make you nostalgic for “home”.

It’s brilliant.





By offering free shipping at a low price point they’re asking customers to take a risk. Homesick haven’t yet won the customer loyalty, that will come later. But for now they’re attempting to asail objections - free shipping, free returns.

They’re building some trust to make the first purchase by prominently featuring customer reviews - social proof - that others have taken the chance and loved the smell. They’re offering flexible payments, another common trust-builder.

All of this to overcome your objections to taking a risk on a brand you’ve never heard of, in a category you usually have to smell prior to making a purchase decision. Every single day customers overcome this objection across dozens of other experiential categories - from mattresses to cologne, lotion, even toothpaste.

Our loyalty can be earned by having consistently good experiences. But when we reach a moment of disappointment, cracks begin to appear in the foundations. We can only deceive ourselves so long before a poor experience causes us to lose the trust that free shipping gained.

Loyalty, it seems, isn’t just earned. It’s hard-earned.

The bias for what is familiar is the most important factor for explaining differences in liking for things. People tend to like best what is most familiar. For example, the more listeners hear a piece of music, the more they like it (Margulis, 2014).  Major labels know that frequent airplay is the key to successful record sales. [2]

Shahram Heshmat, Ph.D


Cracks Appear


The cracks in our trust of digital experiences are all around us. Earlier this year I updated my 1Password subscription to the newest version and when I logged in I was surprised to see that I had a number of reused passwords that needed some tending to. If you’re not familiar with the popular password manager they have a premium service that will alert you when you’re reusing your password across multiple services, or when your password was leaked in a security breach.

It turns out I was victim most recently of a data leak due to StockX, the popular sneaker resale marketplace, being hacked back in July of 2019. StockX isn’t alone in the list of services that I use that have been subject to a data breach. Much larger names are on the list:

  • Adobe’s leak revealed, in plaintext, a password that I used many years ago which was shared with other sensitive financial accounts (easily remedied, and no longer the case).
  • Dropbox has a load of information on both my business and private life - from receipts and spreadsheets to pictures of my children.
  • LinkedIn, owned by Microsoft, has the entirety of my work history and professional interaction from the past decade.
  • MyFitnessPal, owned by Under Armor, has years’-worth of biometric data about me.


It’s not just big tech that’s under attack. Retail has had its share of foibles:

An abbreviated list of retail data breaches since 2012


Whether shopping online or in-person customers are taking a risk. As retail professionals, we only have so many tools at our disposal to alleviate the risk, or to earn the trust of the customer.

As you’ve read in prior Insiders essays, growing disappointments is beginning to mount in a backlash towards lenient privacy policies. Customers are beginning to demand sensible approaches to privacy and security in lieu of 20% off. I, too, have grown weary of data surveillance and lack of privacy. I’m tired of every brand having a sameness - both in aesthetic and in the execution of their strategy.

We may not have all the answers but we can start the conversation. Maybe that conversation begins by expressing disappointment and misplaced trust. Maybe that conversation begins with “Brand, I know you. I know you didn’t mean that. When you abuse me as a customer it hurts me. Did you mean to hurt me?”

No limits. No lick-ins. Go ahead with headless commerce. Get the whitepaper from Shopware now.