Simon Sinek’s “Start With Why” movement, powerfully articulated in his TED Talk “How Great Leaders Inspire Action,” has become a cornerstone of modern business thinking. It posits that truly great organizations and leaders communicate (and operate) from their core purpose (their “Why”), then their process (their “How”), and finally their products/services (their “What”). This “Why-How-What” approach, Sinek argues, creates a deep, emotional connection with customers. A recent look back at the journey of the once-celebrated t-shirt company Threadless offers a compelling, real-world case study on both the power of starting with “Why” and the perils of forgetting it.

The “Start With Why” Framework: A Quick Recap

Great companies, like Apple under Steve Jobs, define themselves by their purpose. As Sinek highlights, Apple’s communication often followed this pattern:

• Why: “Everything we do, we believe in challenging the status quo. We believe in thinking differently.”
• How: “The way we challenge the status quo is by making our products beautifully designed, simple to use and user-friendly.”
• What: “And we happen to make great computers. Want to buy one?”

Apple’s “Why” transcended specific products, allowing them to extend their brand into music, phones, and more, all while maintaining a core connection with their customers.

Threadless: A Brilliant “Why” Story… Initially

When Threadless launched its screen-printed graphic t-shirt business, it wasn’t just selling apparel. It tapped into a powerful “Why” centered on community, design celebration, and exclusivity.

• Why: “We believe in providing a canvas for great design. Our community is focused on celebrating our individual uniqueness. We create an opportunity to express our unique personalities with a level of exclusivity so we can be ourselves, not a mass-market brand.”
• How: They ran design competitions, fostered a vibrant community of artists and fans, and printed limited runs of winning designs.
• What: They happened to sell cool, unique t-shirts.

Designers loved the validation and exposure. Customers loved the unique, limited-edition nature of the shirts. Threadless became a user-centric design company that celebrated individual expression; a crowning example of crowdsourcing success.

The Cracks Appear: When “Why” Gets Sidelined

Threadless’s original “Why” was potent. The pride of a designer having their work chosen from over a thousand submissions was a powerful non-monetary reward. However, around 2007, responding to pressure from some designers for greater financial reward, Threadless began to shift its model. The prize money increased, but this subtly began to change the motivation from community recognition and exclusivity to financial gain.

This slippery slope continued. By 2014, the reward system was fully profit-driven, with designers retaining ownership and sharing sales profits. In 2015, “Artist Shops” allowed designers to sell directly, effectively eliminating the curated, exclusive nature of the Threadless brand.
As designer “sonmi” commented on their forum at the time: “Changing how artists are paid makes it feel less like a community. Less special.”

What Happened To The “Why”? The Cost of Forgetting

Threadless, in chasing different business models or responding to certain segments, began to act against its original, successful purpose. It eroded the exclusivity and pride for both designers and customers. The brand, once synonymous with unique, “winning” designs, became diluted. They lost touch with the “Why” that built their passionate community, and as a result, that community began to fade. While the company may still operate, its trajectory serves as a cautionary tale.

The Lesson for Your SMB: Start With Why, Align With Why, Execute With Why

The Threadless story offers critical lessons for every Small or Medium-Sized Business (SMB):

1. Define Your “Why” Clearly: What is your SMB’s core purpose beyond just making a profit? What belief drives you? What impact do you aim to have?
2. Embed Your “Why” in Every Decision: Once defined, your “Why” should be the litmus test for all strategic choices, product development, marketing messages, and even your technology investments. As a fractional CIO, I work with SMB leaders to ensure their IT strategy and tech choices are not just functional, but deeply aligned with and supportive of their core “Why” and customer value proposition.
3. Guard Your “Why” Vigilantly: As you grow and face new pressures or opportunities, continually ask: “Does this new initiative, this change in model, this new technology strengthen our ‘Why,’ or does it dilute it?”

Long-term success and brand loyalty are built on this foundation of purpose. Take the time to not only start with your “Why” but to remember it and hold everyone accountable to it in every decision.

What’s Next

If a proposed action, product, or strategy doesn’t align with your core purpose, have the courage to say “no,” even if it seems appealing in the short term. Your “Why” is your North Star.

Is your SMB crystal clear on its “Why”? And more importantly, are your business strategies, operational processes, and technology investments all consistently aligned with that core purpose? If you’re looking for a strategic partner to help you ensure your IT roadmap not only supports but amplifies your “Why,” let’s connect with Succeed Sooner Consulting.