Fashion Forward - Founder Lessons

Last month was about getting out alive. Pressure, constraint, and the systems that hold when things get tight. It was about staying above the water line when things aren’t going your way.

If you missed last month, dive back in here:

This month were diving into the business of fashion. Taking from the early SAXX days, from our friends in the industry, and how things have evolved. We have so much value on this topic and are excited to bring it to you this month.

If this has meant something to you, share it with someone who should be in the room too. Our referral program is how this grows, not by reach, but by bringing in the right people, one introduction at a time. Ria and I just finished a session with someone today who completed their 20 referrals and I kept thinking how valuable and easy getting 20 referrals is for sharing ideas and time with Ria and I. So do yourself a favour and refer and click the pink link to share.

⏳️ Estimated Read Time: 7 minutes

Was this email forwarded to you? Subscribe here.

The world of design

A lot of this started by looking back at the brands and eras that left an impression early on.

Chip and Pepper, Maui and Sons, Westbeach, No Fear, Hypercolour, Mondetta.

Each of them represented something bigger than the product itself. They were tied to specific environments and cultures, whether that was surf, snow, performance, or just a general sense of energy and optimism at the time.

When you were around it, you didn’t break it down like that. You just wore it and felt connected to something. Looking back, it becomes clearer that the clothing was simply the output of a deeper idea.

I also started thinking about how much influence comes from outside of fashion. The people you’re around, the places you go, even the shows you watch all shape how you see style. Entire looks and aesthetics came out of things like Friends, and they didn’t feel forced or overdesigned. They felt natural to the moment.

There’s also been a newer wave of brands and communities that take a different approach.

Some of our favourites Sporty and Rich, Friends of Felix. They feel more focused, more intentional, and more tied to a specific lifestyle or point of view.

That contrast between older brands, newer brands, and everything in between is where a lot of this thinking started to come together.

When you step back, fashion is one of the most competitive and crowded markets you can be in.

There is constant pressure to create, to release, to stay relevant. New brands are emerging all the time, and attention moves quickly. That environment makes it easy to chase what is working in the moment.

The challenge is that most of those moments are short.

What tends to hold up over time looks much simpler on the surface. It’s consistent, it’s wearable, and it fits into people’s lives without needing constant reinvention. Pieces like flannels, denim, and well-made basics continue to show up year after year because they solve the same problem reliably.

From a business perspective, that creates an interesting tension.

You can build around speed and trend cycles, or you can build around consistency and repeatability. One gives you spikes of attention, the other gives you something that compounds over time.

Differentiation also becomes more subtle than people expect. It’s not always about doing something louder or more complex. In many cases, it comes down to clarity. Knowing exactly who something is for, how it fits into their life, and delivering on that consistently.

That simplicity is harder to execute than it looks, especially in a space where there is constant pressure to do more.

What stands out about fashion is how many different businesses exist within it.

It’s not just about building a clothing brand. There are entire verticals around design, manufacturing, sourcing, and production. There’s retail, e-commerce, and marketplaces. There’s logistics and distribution moving product globally. And then there’s the attention layer, which includes media, marketing agencies, creators, photographers, stylists, and all the people shaping how something is seen and adopted.

You can operate on the product side, the supply side, or the attention side, and each of those paths can be a full business on its own.

Some people are focused on building brands. Others are focused on owning production or controlling supply. Others build distribution channels or own the audience that ultimately drives demand.

And within each of those, there are entire ecosystems tied to sport, streetwear, luxury, and increasingly wellness and lifestyle, each with its own rules and dynamics.

There isn’t a single way to participate in the industry, which is part of what makes it so compelling. The surface looks simple, but underneath it’s one of the more layered and interconnected spaces you can step into.

Not to mention all the education you can receive on each topic. We have close ties to Otis School of design and many other programs. Or the free material you can gain online.

There is a lot happening in fashion at any given time.

The goal isn’t to keep up with all of it. It’s to understand enough to make clear decisions about what actually matters and what doesn’t. This month we are going to bring case studies, interviews with people still in the industry, our perspective on it all, and so much more. We’re passionate about this topic and excited to share it with you all.

More on Fashion:

Finance updates

CRCL REBOUNDING:

After a strong earnings call CRCL has rebounded and got me back in the green.

If you recall my last note on CRCL:

Circle Stock - Well sometimes your early and my decision to purchase circle stock for $130.00 was preceded by a decline in the stock over the next few months to a low of $76.00. approx a 50% loss.

Dollar Cost Average

I invested approx $100,000 in the first purchase at $130. When you like a company and then the company value goes down, if you have the nuts, and more dry powder you can Dollar Cost Average.

What is Dollar Cost Average? Watch this great video walking down wall street.

So I decided to Dollar Cost Average Down and invest another $100,000 at $80.00, so now my total position is $200,000 with a dollar cost average of $100.00 which will help receiver the loss, and hopefully become a win.