What we learned about retail marketing from a Rich Roll podcast

One of the strategic practices we heartily recommend to inspire new thinking and spark business growth is to interact with people and content outside of your core area of business. Getting out of your zone of familiarity (your comfort zone) can lead to transformational approaches that solve lingering problems.

We attend multiple conferences each year, interview dozens of executives, and read hundreds of posts from industry sources on LinkedIn. As we sift through what we learn, we find that one-on-one conversations at conference events and personal interviews provide the most candid insights.

Sadly, LinkedIn, the only game in town for digital business networking, is becoming an echo chamber of mutual gratification. While it is a productive promotional tool, its value for thought leadership has degraded. LinkedIn itself has fostered the dilution of thought leadership by adjusting its algorithm to reward superficial posts that generate a stream of vaporous “likes”, while suppressing the value of posts linking to outside content. We hope to see this change in 2025 to make LinkedIn once again a meaningful channel for thought leadership.

Thus, our staff regularly ventures outside of familiar channels to seek out perspectives from other areas of business. A good example of our discovery is an interview we listened to on the Rich Roll podcast with Harley Finkelstein, President of Shopify.  Rich Roll describes Harley as an “entrepreneur who embodies the confluence of commerce and personal growth” and the interview touches on all aspects of retail evolution, including customer loyalty.

Two key points are worth mentioning and we recommend that you listen to the entire interview on your next long run or drive to see the relatives.

The Importance of Brand Empathy for Customers

Harley says that when you look at all the stores across Shopify that are most successful, the ones that stand out are those that have deep empathy for their customers. “There is a tirelessness to the strategy (by successful brands) of having Deep Empathy for your customer. And if you really understand your customer, you do really, really well.”

He tells the story of his niece who stopped going to Starbucks after they changed their rewards program. As he suggests, his niece is not alone. “Some of their customers love coffee, but others believe in the loyalty program so much that, when it changed, it was almost as if Starbucks forgot who they were serving. “

CX and the Future of Retail

Harley says that over the past 10 years, retail has begun to feel “really exciting” again. People care more today about the products they use and are making more intentional selections. Independent modern brands are creating products and experiences to delight these customers. And guess what … Harley notes that when customers feel well taken care of, they become evangelists of that brand.

Customer experience is a differentiating factor for boutique retailers, especially in the DTC space. For example, Tecovas, the boot maker, has a full cocktail bar in every store. The feature is more than a casual gesture to create an interesting in-store experience. It speaks directly to customers as Tecovas remembers their customer’s favorite drinks, giving them a fun reason to return again and again.

As Harley says “They are able to have a one-to-one relationship with their customers, with the customer reciprocating as a result.”

Channel Selection

Rich Roll comments that retail seems to work best “when it is an experience”, and when it has been “event-ized.”  To deliver a richer customer experience, he notes that even the most ardent flagship digital brands are opening physical stores.

Harley goes on to tell the story of his conversation with the founder of cosmetics retailer Glossier, founded as an online DTC brand. When the founder was asked “are you primarily online or offline,” she responded saying “that’s the wrong question, we are everywhere our consumer wants us to be.”

What did we Learn?

You might read this and say, “I knew all of that.” When brands care, they are more successful. When they show empathy to customers, they create evangelists. CX matters if you want to create true customer loyalty. And you’ve got to operate in every channel where your customers want to play.

We knew that too. But the value of the podcast for us was the validation served up for many of our points-of-view by an influential executive who is leading the ongoing growth of e-commerce and general retail. Harley had nothing to sell in this interview (though he never loses sight of his role at Shopify), and it was refreshing to hear his point of view and to listen to new stories that punctuated key points.

Throughout 2025, we will keep looking outside of the Customer Loyalty “core” for wisdom and inspiration. We recommend that you do the same. We all become smarter as a result.