In fourth grade, Barron Cuadro walked into Sam Goody, a music store at the mall, with his mom beside him. Flipping through the racks of clothes, he found an extra large Snoop Dogg T-shirt.
Taking the shirt off the hanger, he held it up to his body and grinned at his mom.
He didn’t care that it was a few sizes too big, passing just below his knees and hanging well over his shoulders. He was too busy strategizing a way to convince his mom to buy the shirt.
Barron’s mom, however, didn’t share his look of excitement. She shook her head with a hearty laugh and said, “You are not buying that.” To his disappointment, he knew he would have to leave the store without the Snoop Dogg shirt.
The shirt made me feel something. Style is an emotional response to a piece of clothing that you see. As I grew up, I was always really experimental with my style and the stuff I wore.
Decades later, Barron admits that while he wouldn’t choose this shirt from the clothing rack today, it gave him a similar feeling that he now gets when looking at a well-made tie or pocket square.
For Barron, fashion has always given him an outlet for creative expression. Personal style came naturally to him, but he quickly realized that other young professional men had difficulty dressing themselves in a way that felt authentic and presentable.
This led him to start a blog that would later become the catalyst of his business, but before that could happen, he had to recognize the need for his unique skills by immersing himself in the corporate world.
Barron’s Earliest Career Path
During college, Barron landed an internship at CNET, a tech product review company based in San Francisco. He worked as a website developer for two additional years after finishing his internship and graduating from college.
Like many corporate positions, Barron felt like he was living Groundhog Day over and over again when he woke up every morning. After a fifteen minute walk to work, he would start working on web development projects until boredom kicked in. Then he’d walk to the coffee machine for a change of scenery and go back to his desk to answer emails.
Barron remembers watching the clock every afternoon, waiting for 5:00 p.m. to finally roll around so he could go home to unwind. The monotonous rhythm only got worse a year into his job, so he decided to start exploring other career paths in 2008.
He played around with the idea of getting a job at an agency, starting one of his own, or freelancing as a side hustle, but nothing felt like the perfect fit.
He knew he wanted to be a business owner but was unsure of the type of business he wanted to run. As a kid, he and his friends dreamed about opening a brick-and-mortar store or pursuing real estate, but the rise of internet-based businesses in 2009 piqued his interest.
Inspired by Fizzle and Gary Vaynerchuk, Barron felt that starting a blog would be his best step forward. He didn’t intend for his blog to become a business right away, but he regularly imagined what it could grow into down the road.
Although Barron knew a lot about website development, he was more interested in creating a side project that highlighted another skill. He thought back to how many people had asked him over the years for style advice, and a new idea was born.
I grew up with friends and colleagues who would ask me style-related questions, and I never really thought twice about it. But then I realized if these guys have really basic questions about what to wear, there have to be other guys out there who have similar questions.
Already knowing how to develop a website, Barron began writing content for his new blog, Effortless Gent, that would help other men look and feel their best through personal style tips.
He also talked with his now-wife Kate about the blog idea, and she loved it.
In fact, the first thing she noticed about Barron was his personal style. As a fashion designer herself, Kate liked the way Barron was dressed when he approached her during their daily commute on the city train. A year into the relationship, she told him that his seemingly simple outfit helped him make a great first impression.
Hoping to help other men feel that same confidence, Barron set out to create a platform to make style more accessible for the everyday professional.
Launch of Effortless Gent
Knowing that image and perception is important in men’s style, Barron followed the same approach when building his new online platform. To make sure his site reached the level of design and function he wanted, it took Barron two months to fully build.
He created the website on the side of his full-time job at CNET, which proved to be difficult as he started to ramp-up his blog content publishing. After working all day, he would come home to eat dinner with Kate and then work on Effortless Gent from 7:00 p.m. to 2:00 a.m.
While Barron knew he didn’t want to work late night hours forever, he knew the sacrifice in his first year would help him build a solid foundation.
I didn’t know what Effortless Gent was going to be or if it would even be successful, but I wasn’t too worried about that. I just wanted to make sure I got something out there. I figured I would take it one step at a time and see where it would lead.
Sustaining this slow and steady pace, Barron continued to work on the website as he improved the design and attracted more readers. In his first year of blogging, Instagram and Facebook weren’t big traffic drivers, but Twitter helped him build relationships early on.
Instead of focusing on social media marketing, he focused heavily on creating valuable content for his email list. Barron noticed that staying in constant communication with his email subscribers helped him provide better content because many of his ideas were coming directly from what his audience said they needed.
In his second year of blogging, Barron decided to create a small eBook on how to dress stylishly. Before writing a word, he surveyed his email subscribers to see what questions they had about style. These questions helped him create a simple outline for the eBook so he could start writing with confidence.
While writing his eBook, Barron decided to publish a blog post every week to talk about what he was creating and how the process was going. After finishing it and making it ready for purchase at twenty-five dollars, Barron was shocked at how well it sold.
The eBook generated enough money during its launch to encourage Barron to think about quitting his full-time job to pursue Effortless Gent and freelancing full-time.
Quitting His Nine-to-Five Job
Barron didn’t go into the process of creating his first digital product with the goal of quitting his day job, but that’s exactly what happened. With the extra income generated from the blog and eBook sales, Barron was faced with a big decision in his second year of blogging. Was it time to take the leap?
Quitting his job felt less risky because he knew how marketable his skills were as a web developer and designer. After handing in his two weeks’ notice, his boss told him that CNET would have a position open for him if he ever decided to come back.
I didn’t feel like I had too much to lose. I just knew I wanted to go forward and build Effortless Gent. I didn’t really have a specific plan, but I knew that if I could sell this eBook and make $4000 to $5000 in a few weeks, I could continue to market it and create more products that would sell eventually.
Knowing that he had options, Barron took a step toward Effortless Gent and picked up a few short-term freelance gigs to generate a more stable income while he focused more attention on his website.
Surprisingly Lucrative Income Streams
When Barron started his blog, he never considered pursuing brand sponsorships
or affiliate partnerships as a part of his business model. He was always more focused on creating valuable free content on his blog and providing digital products as an upsell.
After launching his first eBook, Barron wrote a few more eBooks priced anywhere between ten to fifteen dollars while also creating an online men’s style course at a higher price point around ninety-nine dollars. Digital products seemed to be a good moneymaker until he began experimenting with other income streams.
Instead of only focusing on digital products, Barron thought about creating a physical product with a fashion line for Effortless Gent. Since Kate is a fashion designer, they both collaborated to create a men’s line called Fifth & Brannan
They worked with various factories and suppliers to make the dream a reality. After testing different styles in the market during their initial launch, Barron found that accessories like ties and pocket squares were the most successful. It’s been one of the most rewarding projects Barron has worked on.
I wouldn’t have done the fashion line if I didn’t have my wife. Selling physical goods is very different from digital products. You have to actually carry inventory, worry about patterns and fabrics, and so many other little details I never would’ve thought about. It was definitely helpful having her as a partner since she has plenty of experience in the fashion design world.
The fashion line was getting off the ground around the same time that Barron and Kate decided to move from San Francisco to New York. As they settled into their new life in New York, they decided to press pause on the fashion line until they could focus more of their attention on it.
Even with taking a step back from Fifth & Brannan, Barron’s blog continued to flourish as more collaboration requests came pouring in. After becoming an influencer in men’s fashion, Barron was perfectly positioned for brand sponsorships. Barron only got serious about brand sponsorships and affiliate partnerships about four years into his business.
As he began working with well-known brands, he created strict guidelines so he was only working with advertisers that were a natural fit with his audience and values.
The biggest income generator for Effortless Gent is now brand sponsorships, making up 80% of his total income. While it may have surprised Barron how lucrative these collaborations could be, he’s now incorporated more sponsored content into his strategy while working with advertisers that he already loves.
The other 20% of Barron’s income comes from digital products like courses and eBooks. Ideally, he would like to create an equal split between the two main income streams while focusing more attention on digital products, which is his main business goal for the next few years.
Barron’s Life and Business Today
Barron is thankful to have those long nights of working until 2:00 a.m. behind him. Now he can take advantage of a more balanced lifestyle.
If he had to describe his lifestyle in one word, he would choose relaxed. He usually starts his days at 7:30 a.m. and goes to the gym before coming home to work. He starts with answering a few emails and talking to his blog editor about what he’s working on that week. He’ll also talk to his agent to see what brand sponsorship collaborations he has coming up.
Much of his time is focused on creating great content for his loyal blog readers. As a writer, he loves staying in his zone of genius. He’s also more focused on design and branding than ever, attributing his visual style as one of the main reasons why he’s been able to differentiate himself.
Rather than sharing his outfit of the day, Barron has carved out a unique niche for himself by catering to men who want a more personal approach to style. Instead of trying to appeal to the masses, he provides valuable content for the readers he already has. This has helped him attract more readers over time.
You can have a profitable online business if you are able to buckle down and know what your strengths are. Just play to those things.
Like many entrepreneurs, Barron still struggles with chasing new ideas, but he’s still focused on doing what he does best. In the next few years, he wants to focus more energy on video marketing and becoming more comfortable on camera. He’s also excited about creating one-on-one and group coaching opportunities so he can test the waters with service-based offerings.
Barron has even bigger dreams for where he wants to take Effortless Gent now that he’s settled into New York. With his supportive wife by his side, he feels as though he can accomplish anything—and do it in style.