Brand-Building Lessons from Sneakers and Streetwear
To me, branding has always felt like a fuzzy, overhyped concept. Marketers and other consumers obsess over branding, but it’s something I never really cared for. However, two amazing books, that I recently read back-to-back, changed my perspective quite a bit.
One was Shoe Dog, a memoir by Phil Knight1, who tells the story of Nike’s suprisingly scrappy beginnings and the other was a gift from my partner called This Is Not a T-Shirt, by Bobby Hundreds2, who recalls how he built The Hundreds from a backyard operation into a streetwear company that made its voice heard, and endures in a challenging market.
Other than a feel-good corporate underdog story and a light, surface-level intro into the fashion world, I didn’t expect much. However, I walked away with a deeper appreciation for branding–not just as a cynical way of selling overpriced products to easily-influenced people, but as a component of strategy that pulls together psychology, storytelling and business. In a way, creating a brand does make the world a bit more interesting (if not better) - it’s about building emotional connections, creating communities, and turning simple stuff into cultural icons that can inspire people.
While Nike and The Hundreds are super different (one is a global sportswear titan and the other is a grassroots streetwear label), they shared common threads when it comes to developing a brand as a moat. And if you’re a business, you should care about this since it is such a powerful driver of pricing and margins.
Based on their stories, they each created this moat through a combination of hustle, credibility and community.
Phil Knight built his brand by embedding himself in the hardcore running world, innovating to improve performance and securing athletes that would make Nike an aspirational brand. Bobby Hundreds, on the other hand, built The Hundreds by embedding himself in street culture, curating careful collaborations and consciously making customers feel like part of a movement.
They both took unconventional (and sometimes questionable) steps to deliver value and reach success, but did so with a lot of admirable heart and courage. Somewhere between Nike’s “Just Do It” philosophy and The Hundreds’ underground vibe is a formula for building a long-lasting brand.
So what did I learn? Let’s jump in.
Nike: Three Little, but Powerful Words
Before I read Shoe Dog, I actually thought Nike had been around forever. Nike has existed from before my birth and naturally I should feel that way. But Knight’s story shattered that illusion, revealing that Nike didn’t start as the empire that we know today (this thought also made me consider how short life is, but considering mortality is a post for another day).
Nike actually started as a bluff. Straight out of business school, Knight flew to Japan and pitched himself as the US distributor for Onitsuka running shoes - the only problem was that “Blue Ribbon Sports”, a name he made up on the spot, didn’t exist as a real company.
That early lie became a catalyst to what Nike has become today. Knight had to earn his brand equity through vision and a willingness to hustle, but balance that with the ability to deliver results. He created the foundation one pair of shoes at a time - importing product and selling directly to athletes at local races, track meets, run clubs, building a base of customers that would eventually influence a larger audience.
Alongside this, his early co-founder Bill Bowerman, a running coach, pushed the boundaries of product innovation, continuing to build credibility among serious runners. He tried all types of crazy experiments in search of a better shoe. At one pivotal point, he poured rubber into a waffle iron to create the first waffle sole, a major breakthrough for high-performance running shoes. Together, they engineered and marketed performance gear for serious athletes, strengthening that aspect of their brand identity.
To reinforce this identity, Bowerman also used his influence as a coach to put their shoes on elite runners. Their big wins included convincing Steve Prefontaine, a running legend, to wear their shoes. Their athlete-first strategy would be solidified, evolving into iconic moves like signing Michael Jordan and launching Air Jordans, then immortalizing this rebel, competitive spirit into the slogan “Just Do It” and inspiring people to push themselves to the limits, much like the athletes they look up to.
However, even a brand like Nike isn’t invincible - if you’ve been paying attention, Nike’s recent headwinds can be traced back to their aggressive direct-to-consumer (DTC) push that began during COVID. While it did boost margins in the short run, this move hurt their relationships with traditional retail partners.
In “This Is Not a T-Shirt”, Bobby mentions that retailers aren’t just distribution channels, but partners that co-sign your product, serve as brand tastemakers that lend credibility and reach to customers. Retailers aren’t just sales channels, but they are also cultural validators - the specialty stores not only sell your product, but also legitimize it in the eyes of consumers.
Besides losing the co-sign effect, there are other operational considerations like having to shoulder more of the supply-chain burdens of returns, shipping, customer service, etc. but we can leave the operational topic for another post.
I actually saw this scenario play out locally in Boston. The last time I walked into a Marathon Sports store, a gold standard of a runner’s shoe store, there wasn’t a Nike Swoosh to be found - only Hokas, ONs, Brooks, Saucony, and Asics. After having read Shoe Dog and really understanding the origin and story of Nike, feeling Phil Knight’s emotion and passion for running, it actually made me a bit sad. At that moment, it felt like Nike’s magic had faded, straying from its roots and, in a way, ghosting the running community that once defined the company.
Nike has felt the real effects of this in slipping margins and flattening revenue growth3. It’s a cautionary tale that even a brand as strong as Nike can drift if it loses sight of the communities and relationships that made it that strong in the first place. Will focusing on hardcore running bring back tremendous growth? Not necessarily, since Nike is a much larger and more complex company than it was when it started - but there is something important about finding a strong, authentic core that inspires people and draws them to the brand.
With the return of the previous CEO, Elliot Hill, and a promise to get back to core sports (running and training), retail partnerships and product innovation, I am hopeful for Nike’s future prospects. The path back will require some humility (backtracking on key decisions) and strategy to get there.
The Hundreds: Creating a Culture of Credibility Through Community
On a smaller scale, The Hundreds continues to survive in the streetwear space (fashion is still a topic that I’m still trying to “get”). Bobby Hundreds built his brand on skate, graffiti and punk culture, focusing on “People Over Product”. It’s less about volume and more about creating communities - people who are willing to queue up for drops and come to the stores even if the products are available online. At its peak, people did this because of the power of the brand’s story - they wanted to be a part of it.
However, the community didn’t appear overnight. Bobby manufactured this momentum and legitimacy before it took off organically.
One of the stories that stood out to me in This Is Not a T-Shirt is how Bobby launched in his first two retail accounts. He convinced an influential boutique to carry a small set of his T-shirts, then used this placement to influence another retailer to stock his T-shirts as well. After doing this, he orchestrated an immediate sell-out by dialing in and asking about the product, as well as getting his friends and family to buy them all. He made The Hundreds “hot”. While the sales were staged, he capitalized on this short term success.
Unlike Knight’s bluff, Bobby’s move was about jump-starting demand, not fabricating a company. Bobby doubled down on the initial spark by building a real community behind this company.
Bobby recognized the dangers of leaning too hard on a single trend. When one of his icons, the Adam Bomb, blew up in a good way, he was careful to not tie everything to that character, even though that’s what partners and customers demanded. He knew that the streetwear world is fickle, and that overexposure can kill a brand.
He was also extremely creative and adopted an air of exclusivity early on. While many other small shops would fight to try to gain the attention of vendors at expos and trade shows, he intentionally kept his product covered up and kicked his feet back to create a sense of rarity to drive up interest. It didn’t work overnight but he committed to this approach (along his other decisions and moves) to drive long term demand.
Consistent with these moves, Bobby’s brand building strategy involved partnering with artists, respected labels and becoming more of a cultural curator. Rather than leaning on collaborations as gimmicks, he treated them as an extension of his brand’s values. While each new partnership brought in new audiences and fresh designs, he reinforced The Hundreds’ authenticity in the streetwear world.
Bobby recognized that credibility is the currency for subcultures like skate and punk, so any misstep - a tone-deaf collaboration, making a brand-damaging move by selling in the wrong stores, could undo his work. His thoughtful partnerships helped The Hundreds grow while many others failed.
Another notable story was Bobby’s retelling of the infamous Gap logo rebrand fiasco - the company panicked and backpedaled when a small set of customers criticized the change. Bobby likened this to a friend who constantly agrees with anything you say and avoids conflict at all cost, desperate to fit in. It’s like a friend who isn’t willing to show you who they are. When a brand acts like this, it can feel flat and uncommitted, losing the respect and loyalty of the audience, generating indifference. Strong brands don’t just chase the audience’s approval, but shapes the culture, and tries to find something that the customer doesn’t even know they want yet.
As the years have passed, The Hundreds, like streetwear itself seems to be at a crossroads. Today, with its products in more mainstream outlets like Zumiez, there is chatter that the brand is straying outside its original promise. Streetwear once thrived on rebellion, but in the latest hype cycle, mainstream brands appropriated its aesthetics, blurring streetwear’s cultural edge. At the high end, streetwear merged with high fashion and became a way for people to show off their wealth, not to express themselves. At the low end, everyone who has a TikTok account and a interest in streetwear saturated the market with similar-looking styles. Now that the hype has died down somewhat, some argue that streetwear has returned to its subculture roots, but that would mean that the market is smaller, fragmented - it seems harder to build a behemoth out of this.
Despite its past success and influential role in millenial streetwear culture, there are signs that the Hundreds might be struggling in the current cycle. Forums, Discord channels and comment boards are quiet or shut down. It’s flagship stores have closed as well. Bobby even briefly alluded to this tension in his book, noting that a lot of core, millenial customers had started aging out (great, now I’m thinking about mortality again). While the brand outlasted many competitors with its diverse operations like printing for other companies and building a strong cut-and-sew process, the Hundreds’ journey is a reminder that building a brand isn’t a once-and-done thing.
The Hundreds had a brilliant run and Bobby seems aware of this need for constant evolution, finding a balance between staying true to your roots and adapting to a changing world.
It may no longer dominate the streetwear conversation as it once did, but its legacy—and its potential to reinvent itself keeps me hopeful, even if it ends up re-emerging as something else.
From a Feeling to Finance: Quantifying Brand Power
Brand is a power that lasts because customers feel something about a business that rises above a product’s specifications or price tags. Once people have locked into this feeling, it secures a strong moat and significantly impacts financial performance. Generally, a brand’s true value lies in its ability to change consumer behavior - it can increase revenues, improve your profit margins and even reduce costs of capital4.
But a moat by itself isn’t worth much if you can’t see it in the numbers. If you zoom right into what a brand does, it lets you charge more (pricing power) and also to sell more (volume) because your buyers believe that you have a business that is special. The proof is in the cash flows, margins, and market share of big brands like Coca-cola, Advil, etc. versus generics.
However, brand value isn’t static and businesses need to continually invest, cultivate, and keep a pulse on the power of the brand or else it can slowly degrade over time due to neglect, cultural shifts, or negative associations.
Doing this turns our intangible perceptions into valuable financial gains and provides a powerful moat to protect the company’s market position.
The Fine Line Between Hustle and Hustler
The whole other layer to this whole branding puzzle is how you jump start this machine in the first place and overcome the “why should anyone care about us?” phase.
Nike did this by bluffing (but delivering) its way into legitimacy, The Hundreds staged its first sell-outs.
However, the hacks really only work if you can back these actions up with substance. Though Knight initially bluffed, he developed a powerful distribution network to move his product, and developed relationships and communities to sustain the business. Bobby Hundreds built a loyal community after the initial placement into key retailers and expanded his capabilities to provide more diverse and better products to market.
Similarly, we see this with tech companies like Uber that subsidized drivers and riders in every new city until it established its network effects (amongst other a bit questionable methods for growth hacking - a lot of interesting anecdotes can be found in The Cold Start Problem by Andrew Chen 5). Uber kept its riders after initial growth-hacky acquisition because it delivered on excellent customer experience, surpassing taxis in convenience.
I was surprised to find how creating a legitimate company can operate more in the gray area than I expected. The way Knight described his accounts payable and accounts receivable processes sounded borderline like a Ponzi scheme at times.
The key thing here is that they were able to deliver on their promises, not just try to sustain a manipulative move. This raises an ethical concern though… Phil Knight and Bobby Hundreds ultimately built the companies they claimed to have but there is some survivorship bias… for every Nike and Hundreds there are hundreds of Theranos and FTXs that are just smoke and mirrors and collapse into chaos.
Does the end result–success–validate the bluff? It’s tempting to say yes because after all, Nike became a global powerhouse. This cold start aspect is a dangerous game, rewarding boldness but only if you are able to back it up quickly - if you fail to do this, you become just another con artist.
Wrapping Up: Strategy and Soul
What I learned is that a brand is more than a logo or a flashy campaign. A good brand transforms an everyday purchase into an emotional connection, a feeling that brings consumers back and compels you to participate in its story. Stories like Nike and The Hundreds show this at different scales but demonstrate how this intangible preference can fuel powerful business returns - they also reveal how walking this tightrope is treacherous and how many have failed in this arena. Even today, Nike and the Hundreds both have to fight to stay relevant in a dynamic environment.
So… what does it mean if you’re working in solutions architecture, sales or consulting? At first, you might not think building a brand is something that matters to you, but I think it’s quite useful to consider.
Brand power extends beyond sneakers and streetwear. It’s actually embedded in every decision customers make–even in B2B and enterprise sales (I recognize this is starting to sound like a LinkedIn-bro post now – I can already see the title: “What Streetwear Taught Me About B2B Sales”– but I’m going to continue down this line of thinking).
Consider how clients respond to names like McKinsey, Bain or BCG (MBB, the Big Three) when trying to develop a strategic plan. You could argue that industry experts in other consulting companies could deliver similar recommendations, but there’s a brand weight behind the recommendation, a co-sign that carries huge influence.
Similarly, in tech, if you’re a Solutions Architect like me, building on AWS, you have the advantage of leaning on a strong brand in cloud computing. So many large customers are powered by AWS or built on AWS and these references carry weight, credibility, and trust. Customers co-publishing success stories is similar in some ways to a sneaker being sold in a top-tier running store, an implicit co-sign.
In both sales and consulting, a brand can act as a sort of borrowed trust. When you walk in, customers might not know you, but they have an expectation based on the company behind you. That brand sets the tone before you even start talking. This opens doors and you can align with that tone, using testimonials, known partners, industry standards to make a point. This puts you in a position to add value and even extend the reach of this borrowed trust. It’s important to remember that overpromising and underdelivering will quickly erode that trust.
Phil Knight walked the line and built Nike. Elizabeth Holmes and Sam Bankman Fried walked the same line, committed fraud and paid a steep price. In the end, people might not remember the bluff… but they will remember whether or not you delivered results.
So, think about how branding applies to what you do, or even how you might be building a brand today. Think long term and about the story you have to tell and how you can consistently deliver on that promise, so that in the long term, you keep those doors open and can create something amazing. So… just do it, but do it thoughtfully and with purpose.