Whoever said that entrepreneurship and creativity don’t go together surely hasn’t spent hours agonizing over color and font pairings for their logo. It’s clear now that to be a successful entrepreneur, you’ve got to have a healthy dose of creativity, and that people who score high on the creativity scale can have an even better chance of succeeding. With the opportunity to flex your skills in design, writing, and marketing without the need to invest a ton of money upfront, a dropshipping store might be the perfect first business for creatives.  

Recently I spoke to someone who has done just that. Vasco-San Payo is a Lisbon native who quit his design job at an advertising agency to focus on his dropshipping business full-time.

By leveraging his creativity and design skills he was able to craft a strong brand, helping his store The Lion Chain generate over $170,000 in revenue in its first year. Since then, he’s packed up life in Lisbon and moved to Bali, where he’s living the digital nomad dream.

Here’s how it all happened.

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From Creative Beginnings to Business Ideas

When Vasco San-Payo was a child, his parents thought he would grow up to be an artist. “I started drawing really early,” he says.

But he always knew his love of creation was tied to something more tangible.

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“I think I always had an ambitious mentality. So I want to create something that people would actually like and buy, and that I could make some money out of.”

His passions led him to a career as a designer, working in advertising for some of the world’s biggest brands in Lisbon, Portugal. While working in advertising was a great way to get to create things and get paid for it, he knew that there was only so much freedom he could have working for someone else.

“At some point in my life I just wanted to be my own boss and travel the world,” he says. “So I just started looking for opportunities. I started Googling how to make money online, and how to create an online business.”

This kind of mentality is common amongst both entrepreneurs and creative types, according to serial entrepreneur Jordan French: “Creative people and business owners are generally self-starters that thrive with flexibility. They want the freedom to achieve their goals without others constantly looking over their shoulders.”

When Vasco came across the idea of ecommerce and dropshipping, the business model felt like a good fit. “I looked into ecommerce and I really liked it because I had control of everything. I could design my own website. I could choose and create my own products.”

The Logo That Inspired a Business

Vasco’s created his store, The Lion Chain, around his love of hip hop culture and streetwear.

He sells men’s fashion accessories and clothes, with products that are dropshipped from suppliers found through AliExpress, as well as custom designed print on demand products.

Vasco San-Payo Oberlo Success Story 02

The store’s name and iconic lion’s head logo were inspired by a project from Vasco’s advertising days.

“I worked for one of the big soccer teams in Lisbon. I was working with the advertising team, and they asked me to design a season logo for the next year. So the symbol of the club is a lion, and I designed them this logo, but they didn’t approve it,” he says.

“But I really liked it, and I thought to myself, ‘I wanna use this at some point in my life to create something of mine.’ So I just used it to create The Lion Chain.”

What Makes Dropshipping a Good First Business for Creatives?

When going into business for the first time, there are a million and one things that can go wrong.

But with dropshipping, a good chunk of those potential problems are taken off your hands.

When product development, fulfillment, and inventory control are taken care of by your supplier, dropshippers are left to focus on the things that the customer can see.

This means it’s up to you to focus your energy on marketing your business, with an emphasis on great writing and design.

What creative skills do dropshippers need?

But creativity in dropshipping isn’t just about design and writing – it shows itself in so many other ways.

You’ll be forcing yourself to think creatively from the moment you start tossing around ideas for potential products or niches. In this case, the best ideas often come from connecting two distinct concepts together to create something fresh.

Vasco flexed his creative thinking to combine a profitable product category (men’s clothing and accessories) with a lifestyle and image (hip hop) that he could use to turn into a distinct brand.

Every detail – from his logo to the copy he uses in his ads to his models – reflects this lifestyle and image. Together they work to speak to a very specific kind of person, creating a defined target audience.

Pro dropshipper Yuliya Chernykhovskaya says it best: “The less people you try to speak to, the more people you end up attracting.”

Getting Things off the Ground

Vasco’s not the kind of person to do things in halves. So when he realized he wanted to pursue business and work for himself, he went for it 100 percent.

“I was a little bit crazy. I quit my job and I didn’t have anything. I had €1,500 in my bank account and I invested everything in my Shopify store.”

To begin, things were slow. While he had some experience playing around with Facebook advertising from his design job, for the most part he was going into ecommerce completely fresh. He spent up to 14 hours a day online reading blogs and watching YouTube videos about ecommerce marketing.

“I would say that in my first three months, I was working at least 12-14 hours per day or more. I locked myself at home for those months and just grinded,” he says.

Vasco San-Payo Oberlo Success Story 06

He was so determined to make his store a success that he even sacrificed his grocery budget to make it happen.

“In the first month, I spent around €800 and I didn’t get any sales,” he says. “In February I think I spent the rest of the €1,500 that I had, but I started getting some sales. But even then, I was basically reinvesting all of it and eating ramen noodles every day.”

Although it might not have been very glamorous at the time, it was this desperate situation that Vasco credits with his success.

“I don’t think I ever wanted to quit because this was my only option,” he says. “And that’s a good thing because I had the thought in my head of, ‘I have to make this work, I have no other options.’ It really was tunnel vision.”

After months of scraping by and reinvesting everything back into the business, his fortunes started to change.

“In September it just skyrocketed,” he says. “And that’s when I left Portugal and came to Bali to live.”

Vasco San-Payo generated $183,497 with his store The Lion Chain

Life as a Digital Nomad

When The Lion Chain started to take off, Vasco was ready to realize his dream to live the digital nomad lifestyle. He packed his bags, waved goodbye to friends and family in Lisbon, and got on a plane to Indonesia.

“I worked a lot when I still was in Portugal growing the business. But once it got automated, that’s the moment I decided to go and travel. Creating the Shopify store gave me that opportunity.”

In the eight months since, he’s travelled throughout Southeast Asia, visiting Indonesia, Thailand, Vietnam, Malaysia, Macau, and the Philippines. In between work, he’s spent his time exploring, surfing, and riding motorbikes.

When I spoke to him he’d stationed himself in Kuala Lumpur for a few weeks, to allow himself to focus on work for a while. Soon he’d be back to life in Bali, and back to the surf and sea.


While Vasco acknowledges that he still spends at least 40 hours a week working on the business, the ability to set his own schedule makes all the difference.

“I start when I want and finish when I want. So maybe I wake up at 10:00am, work two hours, then have a four-hour break, then work for another six hours.”

The Difference Is In the Devotion

In Vasco’s opinion, the skills that are needed for dropshipping include a blend between creativity and entrepreneurship.

“It’s a cool business for graphic designers and for anyone that has a business mentality.”

“I’m not good with numbers but I’m still improving and trying to become a better businessman.”

But more than anything, he believes that success lies in persistence and devoting some solid time to working on your business. The ability to work on his business full-time made all the difference, he says. “I think it has to be your only option because I think only when it’s your only option you put the right amount of work in. Because if you take this as a side hustle, I think it’s harder. I think you have to really give 200% for this to work because if you only have 80 or 90%, it’s hard.”

Vasco admits that the advice to keep persisting is nothing new (here are three different successful merchants who agree: #1, #2, #3), but he really believes this is what makes all the difference. And persistence isn’t just key to dropshipping success, it’s the key to all success.

“So when we were young, in my group of friends we were all trying to become rappers in Portugal. We had this one friend who at the start was not as good as us, but he persisted for longer than us. Now he’s one of the top five rappers in Portugal, and he’s basically living the dream,” he says.

“So I think that applies to this business too. So if you really focus and if you put in the time this will work, that’s for sure.”

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