The Brand Decision Nobody Has the Guts to Make

An Interview with Joshua Heares, Founder of Porter James

At some point in building a brand, something will sell well and feel wrong at the same time. A product, a partnership, a direction. The numbers say yes. Your gut says no. And every practical argument in the room is pointing at the money.

Most founders take the money. Not because they are greedy. Because they have not built the thing that makes the harder decision obvious. They have not defined, clearly and specifically, what their brand is and is not. So when the moment comes, there is nothing to measure against. Just revenue on one side and instinct on the other. And instinct usually loses.

Joshua dropped a bestselling product six years into building Porter James because it was attracting the wrong customers. It was selling. He dropped it anyway. That decision did not come from courage. It came from clarity. He had spent years building a filter, a specific sense of what the brand was, what it sounded like, who it was for, and where it was going. And the hat did not pass through it.

That filter is what this conversation is about. How you build it, how you protect it, and why the brands that seem to have always known who they are did not get lucky. They just never stopped asking the right question.

Esteban: Give us the brief version of Porter James and where it came from.

Joshua: I finished university, studied business, marketing, advertising, and spent about a decade working in that world. I got to 30 and realized corporate wasn't the path. It wasn't creative in the way I'd been told it would be. I wanted more control over my time, my work, my life. I saw fashion, specifically an ecommerce brand, as a way to do that from New Zealand. To reach a global audience without needing to be somewhere else.

Esteban: New Zealand is genuinely far from everything. Did that feel like a problem or a design constraint?

Joshua: It became a design constraint. Because we knew we couldn't rely on proximity or convenience, we had to eliminate every reason someone in America or Australia might hesitate. Shipping, returns, quality, communication. We asked ourselves every day: what is the friction stopping someone from buying, and how do we remove it? That became a real focus. It still is.

Esteban: Most brands from established markets don't ask that question. They assume the customer will figure it out.

Joshua: Exactly. We couldn't afford that assumption. And I think it made us better at the customer experience than we would have been otherwise.

Esteban: You've grown fast for a brand that doesn't pay for attention. How much of that is product versus everything else?

Joshua: Product is the foundation. We're not a marketing company. We're a product business first. If the product is right, everything else is amplified. If the product isn't right, more marketing just gives you more eyeballs on something people don't actually want. You can compensate with ten times the traffic, but you're still one algorithm change away from it all stopping.

Esteban: You mentioned you've never paid anyone to wear the product.

Joshua: Never. The people who have spoken about us were already following the brand, already buying. Sometimes the biggest creators would purchase something and I'd reach out and say, I appreciate that, can I throw a few more pieces your way? That's it. I've never cold-approached someone and said, here's our brand from New Zealand, can you wear it.

Esteban: Is that creative integrity or is it also a business calculation?

Joshua: Both. If you pay people to promote something, you lose clarity on what the raw potential of your product actually is. When someone chooses to talk about you with nothing in return, that tells you something real. And when you do decide to invest in marketing, you're amplifying something that already works. You're not hoping it works.

Esteban: A lot of founders treat marketing as the fix for a product that isn't connecting.

Joshua: It doesn't fix it. It just costs more. The product has to be the thing.

Esteban: You dropped a bestselling product because it didn't align with where the brand was going. Tell me about that.

Joshua: We had a hat. Sold really well for about eight months. But I started noticing it was attracting the wrong customers. People were buying it because of the logo, not because they connected with what Porter James actually is. And the brand was moving toward something quieter. More refined. The hat was loud in a way that felt off.

Esteban: So you dropped it.

Joshua: Dropped it.

Esteban: That's a hard decision when the revenue is there.

Joshua: It is. But I think about what brand I want to be in five years, not just what's working next season. You can take success now at the expense of success in five years. That's a real trade-off and I think people underestimate it.

Esteban: When did you get to the point where you could make that call without it feeling reckless?

Joshua: It comes with a certain stability. At the beginning, your only job is to find things that move, so you can fund the next round of product. You can't afford philosophy early on. But once you find your best sellers, those fund the foundation. And the foundation is what gives you the flexibility to make decisions for the brand's future, not just its present.

Esteban: You spent six years doing both the creative and the business side. What does that actually feel like from the inside?

Joshua: It's hard. Both parts of the brain compromise each other. You can do both, but only at a satisfactory level until you build a team. And the best advice I received was that founders need to know how to get out of their own way. If you hold on to everything, it costs you the next phase of growth.

Esteban: Where do the mistakes happen most?

Joshua: Product. Because we're a product business first. If I was distracted during a development cycle, it shows up in the product. Maybe something is too cropped and returns are at 15%. Maybe I ordered the wrong categories for American winter and half my sales go soft. These things sound small but at our size they shape the trajectory.

Esteban: And on the financial side, what did you figure out late that you wish you'd understood earlier?

Joshua: Cash flow is not complicated. It just requires awareness. Get a spreadsheet. Map what's coming in. Map what's going out. Know what you owe, know when it's due, know if you have enough to cover it. Most creative founders avoid this not because it's difficult but because looking at the numbers makes reality unavoidable. And reality is uncomfortable sometimes. But the longer you avoid it, the worse it gets.

Esteban: Is it an intellectual problem or an emotional one?

Joshua: Emotional. Definitely emotional. Creatives tense up around money. But at some point you have to decide: is this a business or an art project? If it's a business, the money is part of it.

Esteban: You've been traveling every month, looking at Paris Fashion Week, reading magazines, tracking references. How do you stay inspired without losing your point of view?

Joshua: I heard Rick Rubin talk about this. He described it like a filter. You see everything, you take it all in, but then it has to pass through something that asks: does this align with where I've been and where I want to go? A good creative director keeps that filter tight. You can see those brands that just chase whatever looks cool this week. Their work is all over the place. Whereas the most attractive thing a brand can do is have each body of work look like the last one, only better. A natural progression. Cohesive.

Esteban: That filter also explains why you never did TikTok.

Joshua: Exactly. People told me it would reach more people. I knew in my gut it wasn't the type of content I wanted to make and it wasn't true to how I communicate. So I didn't do it. You have to know what works for you on the product side, the brand side, the marketing side. A strong vision is what guides you through those decisions when the opportunities come.

Esteban: You're still only spending about 10 hours a week designing. That's the part you love most. How do you stay connected to the work when you spend most of your time on everything else?

Joshua: I focus on the moments where I see the impact. Someone who wasn't confident in what they wore puts on something from Porter James and feels good. That's why I do it. Everything else, the finance meetings, the operations, the marketing decisions, is in service of that.

Esteban: And on a longer horizon?

Joshua: New Zealand is losing its best people to Australia right now. The economy is struggling and talented people are leaving. We have twelve people here. Good people who love what they do, who are friends outside of work. Creating that in your own country matters. I never started the business to do that. It just happened. And now it's part of why I keep going.

Esteban: Last question. What did you figure out that you think most brands miss?

Joshua: Tone of voice. Think about what your brand looks and sounds like. Is it more masculine or feminine, more introverted or extroverted, serious or playful? Define that early and let it guide everything: how you write captions, how you shoot content, how you brand a garment. A lot of brands just jump on the next trend and it reads as inauthentic because it isn't true to who they are.

Esteban: And the business effect?

Joshua: The most consistent piece of feedback I've received over six years is that Porter James looks like it's been around longer than it has. I think that's because there's a cohesiveness to the work. It feels considered. And that cohesiveness doesn't just happen because the creative is good. It happens because there's a filter that every decision passes through. That filter is the tone of voice.

There is a moment in this conversation that I keep coming back to. Joshua dropped a hat that was selling well. Not because it stopped working commercially. Because it was working in a way that felt wrong. The customers buying it were buying the logo. And the logo wasn't the point.

That decision is so easy to talk about in retrospect and so genuinely difficult to make in the middle of it. When something is selling, the pressure to keep it is enormous. Every practical argument points in the same direction. The creative argument is harder to defend, especially when you are self-funded and every piece of margin matters. But Joshua made that call because he was thinking five years out, not one season out. And that is a different kind of discipline.

What this conversation is actually about is the relationship between clarity and courage. You cannot make the hard decision without the clear foundation. And the foundation Joshua kept coming back to was tone of voice. Not as a branding exercise. As a decision-making tool. Something every product, every campaign, every partnership either passes through or does not.

The lesson is not complicated. Define what your brand sounds and looks like before you start making decisions. Then let that definition be the thing that says yes or no. Not trends, not what's working for someone else, not what's easiest to sell this quarter. The filter is the strategy. Keep it tight and the work compounds. Let it slip and you get a brand that looks like it's trying to be everything, which is the same as being nothing.