$20 Million in Fashion Sales at 20 Years Old. The Story Of Sunday

An interview with Otto Schiffer

Most people spend their twenties figuring out what they want to do. Otto Schiffer spent his building a brand that is projected to do twenty million dollars in revenue this year. He is twenty years old. He started Sunday when he was seventeen, in his final year of high school, in Melbourne, Australia, selling loungewear into one of the most saturated categories in fashion.

What is interesting about this conversation is not that Otto built something big fast. It is how he thinks. The way he processes information, changes his behavior, delegates before he is ready, and treats money spent on advertising like tokens in a game rather than cash leaving his pocket. That is not a young person's mindset. That is a very specific and deliberately developed way of seeing the world.

He maxed out credit cards to fund a Black Friday inventory order at nineteen because he could see the momentum and did not want to miss the window. He deleted Shopify from his phone because checking sales every hour was destroying his emotional state. He spent eight months releasing products that went nowhere before he found the one that worked, and then he went all in on it. Five products driving the majority of twenty million dollars in one market.

This conversation is about what it actually takes to build something fast. Not the inspiration version. The real one.

Esteban: Twenty million dollars at twenty years old. Two years in. How does someone even get here?

Otto: I think from a young age I was always very interested in being able to make money on my own clock. Seeing money come in from something that did not involve selling my time was always fascinating to me. So I did a lot of reselling and flipping from around thirteen or fourteen. Built up a little capital from that. Then around sixteen I started sourcing blank goods, importing from manufacturers in China, selling on marketplaces. Met a lot of connections through that process. And then it felt like a natural progression to take all of that and build something with real equity behind it.

Esteban: You never had an employed job.

Otto: Never. It was always just things for myself. Flipping, sourcing, and then Sunday.

Esteban: What were the skills that actually transferred?

Otto: Being able to teach myself things. At the start when there is no money to delegate, you have to wear twenty different hats. Design, tax, website, customer service. I had to figure all of it out. And I think the key was getting a working knowledge of everything so that when I could finally delegate, I could actually tell whether the work being done was good or not.

Esteban: Loungewear is one of the most competitive categories in fashion. How did you make Sunday different enough for people to actually care?

Otto: I think differentiation is in the eye of the beholder. I never wanted to tell people this is better. I wanted to show them why and let them arrive at that conclusion themselves. What I invested in was the fit, the fabric, and the craftsmanship. I was incredibly particular about fit. When I got it right I knew it was right. And I think that is what people land into. They feel it.

Esteban: But early days, was it the product or the communication that moved the needle first?

Otto: Honestly neither for a while. The first eight months were nothing. We were releasing products that were just homogenous. Nothing was ours. And then we released a hoodie with our branding on it and it got traction. That was the sign. Something real was there.

Esteban: And then?

Otto: We went sideways for a while. Tried a festival collection. Tried a high fashion women's direction. Both flopped. So I took a step back, went to China, met a new factory, sourced new fabrics, and came back completely recommitted to the loungewear space. Released a new wave of hoodies at the end of March last year and from that point it took off. Most of the revenue has been made in the last year and a bit.

Esteban: How many products are actually driving the majority of revenue right now?

Otto: Honestly five. Maybe five products driving the majority of what we do. Forty SKUs total but five doing the real work.

Esteban: That is extraordinary. The world I come from has brands doing a third of your revenue with a hundred and fifty SKUs twice a year.

Otto: Yeah it is kind of wild when you put it that way. But I think it just comes back to finding what works and going as hard as you can on that thing before anything else.

Esteban: Walk me through the marketing. How much is paid, how much is organic?

Otto: Majority of new customer acquisition is paid. Meta is my thing. That is still basically my only role in the business day to day. But what I love is that the ads are not just driving sales directly. They are building followers, building brand awareness, people are discovering Sunday through the ads and then engaging organically. So it feeds both sides.

Esteban: And returning customers?

Otto: On a daily basis around ten percent. On release days it spikes to thirty eight or forty percent. So on average probably twenty five percent of revenue comes from returning customers. And that compounds significantly over a year.

Esteban: What is the actual skill set behind running paid advertising at this level?

Otto: Three things. Understanding media buying at a real level, not just how to set up a campaign. Being able to read data and find what it is actually telling you. And being a creative, understanding what makes someone stop and engage with an ad versus scroll past it. Then finding the correlation between those two things. A creative with a high click through rate but no conversions is a brand builder. It is bringing new audiences in. A creative with low reach but high conversion is tapping into the warm audience that the brand builders created. You need both and you need to understand what each one is doing.

Esteban: And the budget philosophy?

Otto: I treat it like tokens. Not money. Money to play with, not money to protect. I think that is the only healthy way to look at it. If you believe in your product it should never feel risky. It is an entry fee to make more.

Esteban: What has been the hardest period?

Otto: Growing pains. Getting to a scale we were not ready for from a logistics and customer service perspective. That was probably six months ago. You feel like everything is closing in from all fronts. You are always playing catch up. Customers are unhappy. Reviews are coming in. And because I have built myself so personally into the brand, the criticism hits differently. It becomes personal.

Esteban: How did you work through it?

Otto: Same way everything gets worked through. Persistence, reflection, and then implementation. You figure out what broke. In that case it was logistics and customer service. So you hire for those things and you fix it. And then you build again. I actually think scaling until something breaks is the best strategy because it tells you exactly what needs fixing. You are not guessing.

Esteban: You mentioned deleting Shopify from your phone.

Otto: Yeah. A year ago I was checking it constantly and if sales were not up it would kill my whole mood. It was completely counterproductive. My dad actually compared it to when I first started investing in ETFs at a young age and was checking the portfolio every day. Same pattern. You have to zoom out. Look at things weekly, monthly, yearly. The daily number is just noise.

Esteban: You built in three years what takes most brands seven. What specifically made the difference?

Otto: Risk tolerance. I think some people are not willing to take the risks I was willing to take. I was twenty with no dependants, no fixed costs, nothing to lose in the real sense. So I treated every decision accordingly. The biggest example is probably maxing out credit cards for a Black Friday inventory order last year. Everything was tied up in prior inventory. I could see the momentum. I needed the stock and I did not have the cash. So I went and got it.

Esteban: That is a very specific kind of confidence.

Otto: I think it comes from believing in the product. If you genuinely believe in what you have built, spending money to scale it does not feel like a risk. It feels like the obvious move. The risk would be not doing it.

Closing Reflection

I do not think the lesson from this conversation is about being twenty. Age is not the point. The point is the way Otto thinks about risk, about learning, about what money actually is when you are building something.

He maxed out credit cards for a Black Friday order not because he was reckless. Because he had built enough conviction in what he was doing that the risk calculation was simple. The downside was manageable. The upside was the business. You take the bet.

What I keep thinking about is the product story. Eight months of nothing. Two collections that flopped. A trip to China to reset completely. And then one wave of hoodies that changed everything. Most people would have interpreted those two failed collections as a signal to stop or pivot to something completely different. Otto interpreted them as a signal to go deeper into the one thing the brand was actually built to do. That is not a young person's instinct. That is a very clear sense of what you are building and why.

The lesson is simpler than the number makes it sound. Find the product that is right. Go all in on it. Treat the money as tokens to play with not cash to protect. And do not stop until it works. That is the whole thing.